November 9, 2023 • 48 mins
Web designer, author, and Co-Founder of Week of the Website - Kelsey Gilbert-Kreiling is breaking down barriers with a passion for the people she works with, the clients she serves, and the potential of transforming digital landscapes. Listen in as she talks about building a team of creatives within an environment that invites collaboration and growth.
Kelsey is also a Squarespace expert who is eager to inspire individuals to use technology for empowerment. Her book, "Squarespace from Signup to Launch" is available via Amazon, Bookshop.org, Target, Barnes & Noble, and more. Kelsey's course, "Advanced Squarespace Tools", is available exclusively through SuperHI.
Learn more about the voices in this episode:
Kelsey Gilbert-Kreiling on LinkedIn
Week of the Website | Web Design for Creatives
Michael Messer, Host and Impact Coach
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:06):
What does growth look like in your business in your life as a business owner,
executive or individual,
you can live and lead with intention to create the change you want to see in your community and the world.
Welcome to the Discerning Strategies Podcast,
a place where we can see clearly and act wisely.
(00:31):
Hi,
everybody.
Welcome to the Discerning Strategies podcast.
I am your host,
Michael Messer and this week I am joined by co-founder of week of the website Kelsey Gilbert Kriley.
Week of the website is a Squarespace design agency for creatives with a purpose located in Chicago.
So,
hey,
Kelsey,
how's it going?
(00:52):
Hi,
Michael.
It's great.
I'm so happy to be here.
Hi,
thanks for joining us.
Um Before we get started,
just tell us a little bit about week of the website,
what's going on with you guys there?
Yeah.
So week of the website is my web design agency with my co-founder Mallory.
Um We started,
it'll be 10 years in May,
which is kind of unfathomable to me because how could I have possibly aged 10 years?
(01:17):
But,
well,
congratulations.
More importantly,
you're not a statistic either.
I thank you.
It is,
you know,
what,
we kind of pinch ourselves every day that we're like,
I can't believe that this has been this long.
But,
um,
it's really been a joy.
We,
we started out with the goal of,
you know,
very simply making it easier and less painful for people to build beautiful websites they could use as a tool for their business.
(01:40):
Um,
that's always been something that has felt really important to me And that's started with,
you know,
my,
my co-founder Mallory project managing me building the websites and then eventually grew into something that was much bigger than just the two of us.
So we now have a team of about 20 spread across the country,
but kind of headquartered here in Chicago.
And we do a lot of work for small businesses with our core we of the website product,
(02:05):
but then we also partner with other creative agencies to execute websites for them as like a deliverable of their work for their clients.
And then we work with enterprise scale companies to do like bulk repla projects or more like intense squarespace design builds um on the Squarespace enterprise platform.
(02:26):
So it started from this little idea of building websites should be easier and less painful for people and has now grown into something that's um I don't know,
been really special.
That's awesome.
There's so much that I want to unpack around this.
What you didn't say though,
if you kind of start investigating,
you know,
we,
of the website in general is that you actually describe your company as a design agency for creatives with a purpose.
(02:50):
Yeah.
So what's the purpose?
I think what we are getting at with that is not only that we have,
we have worked with a lot of like nonprofit organizations and very like community driven groups.
That's,
that's just sort of been a part of our DNA as a,
as a company since we started.
Um But what we've identified as we think about who our best clients are,
(03:14):
are there people who come out of the gate with something very intentional that they want to do other than I want to build a business to make money.
Um When we work with clients that have a very clear perspective on what they bring to the world,
we have found that they make the best partners because we can build great websites.
(03:34):
But it's impossible for us to articulate for our clients what they do,
why they do it and what they stand for.
So when we work with creatives who have a real clarity around their purpose and a really clarity around what they are hoping to accomplish.
Um Those are when our websites like they sing,
right?
You,
you can feel that.
So that was kind of how we have defined our like niche,
(03:56):
right?
You are so speaking my language right now because I always talk about intentional business,
intentional,
intentional,
intentional I say that word every day,
100 times a day it feels like.
Um,
but that's exactly what you're saying is exactly the point that I try to go out and take out with my clients,
which is what is the thing that you want to do?
(04:17):
What is your purpose being underneath the profit?
It's so powerful at connecting your business to people,
whether those people are in your business,
your employees,
your contractors,
your customers,
or just people in the community that you wanted to do right by.
Yeah,
definitely.
And I think it's a struggle when people,
(04:39):
I'm sure you feel this in your work as well.
But when people don't have that understanding of like what makes them tick,
it can be really challenging and listen,
I'm not saying that everyone always knows that,
you know,
we,
like I said,
no,
it's a,
it's like a,
it's a journey,
you know,
you go up and down last year after I had my son,
(05:01):
a lot of things changed in terms of like what my role was in our business and my partner and I actually did like a positioning engagement with um a,
a really fantastic consultant who sat us down and asked us very hard questions sometimes until we cried to help us understand like,
what is our,
what is our purpose as a company?
(05:22):
And you know,
for me,
what I got to is like,
the people are the only part of this that I feel truly passionate about the people that we work with,
the clients that we serve.
And so,
um that was something that we,
we need to highlight this.
We have to,
you know,
dig even deeper into this because that's the thing that gives us the most um you know,
(05:44):
connection in our work.
Like websites are just ways that we talk about people online and ideas.
And so,
um identifying that has been really important,
but it wasn't always that way.
Right.
There's the different times where we've had different niches or different goals.
And I think,
um,
if you know that,
then it's much easier for people like me and people like you to help make that dream real.
(06:06):
Yeah,
I love what you're saying is you're actually talking about your purpose,
not just as like something that you stick up in your office and be like,
hey,
this is what we're about,
but it's a strategic value that really is driving your business.
It's part of your own intention within your business.
Sounds like the people.
Yeah,
I think for a lot of people,
uh,
a company that they start becomes just a job that they own.
(06:29):
I,
that's,
that's not something I came up with someone else said that.
Right.
And,
um,
yeah,
I mean,
I think especially over the last five years,
we've all had real reasons to kind of query what the,
the position of work is in our lives.
And,
um,
for me,
(06:49):
if I'm gonna spend,
you know,
eight hours a day away from my,
you know,
from my son,
from my child.
Like,
what is it that I'm doing with my time?
And I think it's become our team and our team's development and growth as they work with clients and then our clients seeing their success once they're done working with us,
that has become the fuel for all of it.
(07:11):
And that's what makes us not feel like a job.
It makes it feel like,
oh,
gosh,
I'm so glad that I've spent the last decade of my life working on this because every day that I get to collaborate with one of our contractors,
um you know,
see them grow in their skill set,
match them with our clients to take on jobs that really push them and excite them.
Like that's the best,
right?
(07:32):
That's awesome.
So I know,
you know,
you,
you talked about employees and people are really important to you and you mentioned that you work a lot with contractors.
Tell us a little bit about how you think about managing a workforce and growing a business over 10 years with a contracted workforce.
We started out with um like really coming from the company of one mindset.
(07:56):
Um Paul Jarvis is,
was a longtime collaborator of my husband's and so got a chance to be familiar with his work very on in my like entrepreneurial journey.
And I remember reading it and being like,
yeah.
No.
Yeah,
totally.
Like this is what I want to do.
But also it's a company of two because I have a business partner.
But with web design and development,
we very quickly realized that in order to serve the kind of clients that we wanted to serve to,
(08:20):
you know,
have a life that we've,
that each wanted to have like the minute you add another person that multiplier becomes a little bit more complicated.
And as we grew,
and as our company grew,
we realized that like Mallory and I were needed for other responsibilities outside of just project,
managing web design and building websites.
And so we very trepidatious stepped into working with contractors.
(08:46):
Um And I say that because it was like hard for me to imagine taking a client through the sales process and then being like,
ok,
and now you're going to work with someone else.
Um I,
I think people don't like that and they,
they want to really understand who they're working with.
So we were hesitant to become an agency even though we were always called agency.
It was kind of funny.
Um And once we did what we realized was it would be very,
(09:11):
very hard for us to scale our team size with a business that says seasonal as web design.
And when I say seasonal,
I don't mean like we get a Christmas rush,
but we do have like really significant ebbs and flows mostly based on like when people's attention is available for projects outside of their core work.
(09:33):
Um And so,
and bringing on contractors,
but really wanted to do it in a different way.
Um,
I had worked freelance before I had,
I'd been in contracting roles prior to my work here and I just felt like it always felt a little tough.
It was like I was brought in to build it to,
to solve a problem but not to be a part of like an ongoing solution.
(09:57):
And um even though we knew we were going to need to be able to build our team and that kind of ebb and flow with projects,
we also wanted to do it in a way that felt like we were really investing in our team as a team.
Um And also giving them the freedom to like work on the projects they want to work on.
I'm not trying to like lock anyone down to just do my work.
Um Sometimes that's not what they want to do.
(10:18):
So I also wanted to figure out we also want to figure out a way to really honor the like super creative and independent spirit of the collaborators who worked with us while also creating a place where they wanted to come and be on week of the website projects.
Yeah.
And you're actually,
you're talking about the importance of building culture,
even with people that are not actually on the permanent payroll Yeah.
(10:41):
Yeah,
we've been talking about that a lot because you could see,
I'm in an office and,
um,
I worked from home until a year ago last year and when,
at the time,
my business partner and her dog were actually living with me,
my husband and our son and we also host a nanny share in our place.
So eventually I was like,
(11:02):
ok,
guys,
we cannot make this work.
Like we can't have three adult human beings working from home,
one nanny,
two kids and a,
a dachshund in the same like townhouse,
we need an office.
So uh we ended up taking an office space that's like right around the corner um in Wicker park in Chicago and we've had to move offices three times,
(11:24):
Michael because people want to come in and work like this is a very rare day that there's no one here.
Um But we like started off with like a two person office and then maybe two people come in and we have an extra desk.
We have like five people who regularly come into work because they like it here.
So like,
oops.
So OK,
so I have to go here now.
(11:45):
Like there's all of this chatter about return to the office,
remote work.
There's the proponents,
the detractors,
like people have very strong feelings around this.
You've done both for significantly and in a significant way.
What is your thought on this whole thing?
I mean,
make it fun,
make it,
make it worthwhile for people to be there.
(12:07):
Like if you,
if the culture is really like at your core and what you really care about is people being in person and collaborating.
Like this is not a plug.
They don't pay us,
I pay them,
but we work out of an industrious office.
They take such good care of us.
There's coffee,
there's food twice a day,
like it's a lovely space.
(12:28):
It's beautiful.
But the best part is,
is like when,
especially when um Alex,
one of our developers is here,
like we turn around and just like talk things out constantly.
She'll be like,
hey,
what do you think about this or do you have any code that can do this?
And it feeds both of us.
That's our personalities.
I'm quite extroverted.
(12:48):
She is as well.
We're both really curious people,
but I think like insisting that people come into the office,
you're not gonna get what you want from that.
So just,
just offer people the things that they feel incentivized by and trust people to make good decisions for their own working needs and they'll do what they need to do to be successful when it comes to work.
(13:11):
I don't think that there's like that big of a group of people who are like I am here to absolutely betray what I brought,
what I told this team,
I was gonna bring to them and I am gonna be a drain on the system.
If they're coming in with that mindset,
there's probably a reason that should be,
like,
investigated,
but I don't think it's a big enough thing to,
like,
force a bunch of people into an office of that problem,
(13:32):
this whole quiet quitting thing.
Right.
You have to be like,
what's broken in your organization.
That this is a concern,
right?
Like,
because people wanna get ahead,
they want to provide for their families.
Like I,
I,
you know,
um but you said a word that I think is really important here that people don't talk about enough,
which is trust.
(13:52):
Yeah,
you have to trust people to do and show up,
right?
So how do you like you've got,
you just said you have like 20 people all over the country that are collaborating every single day across all of these different projects.
I mean,
you've launched over 700 websites.
(14:12):
It's a lot.
OK.
So a lot of volume is coming to your office.
How do you create trust when everybody is,
is dispersed like that?
Yeah,
I think first of all,
you wanna be really clear on the types of things you're hiring for people hire for hard skills,
(14:39):
but it's so much harder to teach people how to be trustworthy and good communicators open,
vulnerable and brave than it is to teach them squarespace,
right?
Like I have a book,
I can teach you how to build on squarespace.
Even I have a video course,
I can teach anyone to use the Squarespace platform.
(15:00):
Um I can't teach that sense of collaboration and curiosity.
I had this one guy,
I had a conversation with one time and was explaining our week of the website process,
which is like quite intensive.
You basically work with our team for over the course of five days to build a custom website that we then launch within 10.
(15:24):
And part of that is that we are showing our work from day two.
Like you get a link to the site in progress on the second day of your engagement and you get to see the designer work on it until it's ready to launch.
And I,
I just thought of that as like,
that's just like a really,
I don't know,
just like a really open way to build and it felt like a good way to get ahead of like time wasted on design that didn't work.
(15:49):
And this one other founder,
he's like,
God,
that's so brave.
Like it's really hard to show unfinished work.
And I think that's one of the things that our team is just so comfortable doing because we try very hard to start every engagement by like thanking the client for their hard work,
thanking them for the effort that they've put into preparing.
And then also telling them like we are showing up to this engagement with the genuine goal and expectation of building you a site.
(16:18):
You're really really happy with.
Sometimes we're gonna have to say no to things that you have ideas for because it's not doable in the time that we have or it doesn't serve the goal that you have told us as your objective at the beginning of the process.
And we're going to ask that you trust that we are here with your best interests at heart.
And if we all engage on that level of like,
(16:39):
I trust that when you give me feedback,
it's because you also want the project to be great,
then that depersonalizes it,
right?
That means our designers are able to show up pretty like,
you know,
transparently and be like,
what do you think of this design if you don't like it?
That's OK.
But I have to know,
you know,
so that trust trickles down.
Well,
you're talking also about leading with your values and in a sense like,
(17:02):
you know,
those values in,
in like open communication and the spirit of collaboration,
you're actually bringing this creative with a purpose into that value space and almost self selecting around that,
which is exactly what you're supposed to be doing.
Your values,
attract the clients you want to work with.
(17:23):
And that's what actually the results in a website in 10 days.
I also will say I do a lot of the I now do most of the all of the enterprise sales process and then um a good part of oversight for our like core business sales and pro partnership sales.
And we are extremely selective when it comes to clients who we we will work with based on you can have whatever kind of project you want.
(17:54):
But I feel very protective,
not in a patronizing way,
but like,
I'm not gonna put our teammates in the line of someone who's not going to be a good collaborator for them.
Like I would rather leave money on the table and say thanks but no thanks to working with a client who isn't aligned with our values because my clients come and go and as much as we lead from a spirit of like the client,
(18:24):
the reason why the client is asking for something,
there's a good reason like I can't get more Alex's Shelley's Susan's and it's like I can't get more of those people but clients are gonna come and go.
And so for me being really protective of our team and choosing to take on projects that align with our resource,
(18:47):
align with our values as a company means that we can create a more positive environment for them to work in.
So they still want to keep building websites for us,
right?
Yeah,
that like what I'm hearing you say is like,
it's about reciprocity like it's not in the in the reciprocity goes beyond.
OK?
You 1099 contractor are going to get a paycheck based on this project based work.
(19:10):
You're talking about you creating a space where they feel protected where they can create and,
and serve in the way they need to do it.
Um And not have to worry about that.
That's part of the culture,
right?
Yeah.
Yeah.
I mean,
we,
we kind of say like,
listen,
we know you could go build squarespace websites for yourself,
for your own clients.
Here's the part that we want to take care of finding the project,
(19:33):
selling the project contracting,
the project project,
managing the project and you know,
client relationships so that they can show up and the project manager can manage the project in terms of like getting content together,
timelines,
things like that,
the developer can take that information,
work with the client and build a site that's really,
really great and there's an external,
(19:54):
not external,
but like there's a third group here who deals with the other stuff that can sometimes I think get in the way of the creative process.
I don't think you can go through as a designer and deal with a client like paying late and then also feel really good about putting your heart behind their work,
you know.
So I think that that's become like a really nice um balance of responsibility.
(20:17):
But I also think like that kind of circle back,
you mentioned trust and it takes an immense amount of trust for us to be like,
all right,
we got this client for you for us,
for all of us.
And their project is really special.
Here's what we want you to do.
Like we always come into it with the best of intentions and then people are human and things happen.
(20:39):
The only way that we have been able to keep this train running is that we talk about projects when they go,
right,
we applaud them when they go.
Right.
And if for some reason they go wrong,
then we lean into open communication as a team where we just sit down and we talk about it.
I think one of the most toxic things in creative and in,
(21:03):
in,
you know,
client based work is not knowing where you stand.
And I never want that for my team.
I never want them to feel like they can't raise an issue of how a project's been sold or,
you know,
what client expectations are,
we have those reviews.
And we also do like monthly stand ups with the P MS and with the devs to just say like this is like open talk time,
(21:26):
what are you seeing,
what's going on with the process?
What adjustments need to be,
make made?
And our team actually like,
leads those changes because they are the ones on the ground,
right?
Like we're figuring out the mechanics of money and process and on boarding and all of that stuff.
Um But they're the ones who can tell us what it's like when they're,
they're building it.
And so because we have created that environment of transparency with them.
(21:50):
Um It's my hope II I,
you know,
I can't,
I can't promise this,
but they don't feel afraid to come to us with a question or a concern about a project.
And I feel the same way that if I feel like something's going on,
I can come to them and say,
hey,
what's happening with this?
And they know it's not being me being like what's happening with this answer wrong or I'm going to kick you out like that's not the vibe.
Well,
(22:10):
yeah,
so there's so much good stuff that you're talking about,
right?
Like uh you know,
part of the trust is like people want to be heard.
And so like you're giving,
you're holding space for people to actually have two way communication and that's not actually going to work if you're like,
(22:30):
you're just talking at somebody and like,
oh,
we have our monthly meetings.
Well,
did you elicit any feedback?
Uh No,
I just gave them the information very different than what you're talking about.
Yeah,
I have found that in those conversations.
I it is if I want that,
(22:51):
if we want that kind of feedback,
you have to start with questions and then people will start opening up.
So you can't just be like,
how do you think this is going and then wait for people to speak?
Like,
what I've found is that we ask,
I,
I'll come in with specific questions that maybe I'm like seeing a little of friction around or things that keep bubbling up to me on slack that I see.
(23:13):
And I'll be like,
hey,
feels like I'm seeing a trend here.
What's going on with like this part of this?
What do we think is causing this?
What do we think is behind this?
And,
you know,
then we can have that open conversation.
Money is always a huge part of this co like issue.
I think a lot of people view contractors as this kind of like disposable way to get things done for us.
(23:42):
They're a really essential part of our business.
And so we are very transparent with the team about like when we price a project,
here's,
here's what it breaks out to,
right?
Like here's the percentage of the project that goes to the designer.
Here's the percentage of the project that goes to the developer.
Here's the payout schedule,
here's what you can expect for this.
(24:02):
If it's a larger project,
if we differ from that margin,
we just tell them like when I'm pricing things out that are new for us,
that has been one of the best parts of having a team member in the office is I'll just turn around and be like,
Alex say,
hypothetically and she'll be like,
oh,
great.
I can't wait to hear where this is going,
you know,
and I'll be like,
(24:22):
this is what you're gonna do.
This is what the project would be.
This is what it would entail.
This is,
you know,
da da,
da da.
This is what I'm thinking of for developer payout.
How does that feel based on these factors?
And then she'll tell me it feels high,
it feels low,
it feels appropriate.
And I think like I have my numbers and data points in my computer that I can use to get us to like information,
(24:48):
but having the ability to talk to team members and get their sign off so that I know we're walking into a project on equal footing that is like hard earned,
but so appreciated because I wanna be able to look at someone and be like,
do you feel underpaid for this and have them be like,
yeah or no,
this feels good.
Well,
(25:09):
I have to say like that is an incredibly brave stance to take as a,
as a small business owner because so often,
right?
Like there's a lot that comes up when you own your own business.
Like how much am I going to make?
Like it?
Like all of this,
like you want to take care of your team,
you wanna take care of yourself too,
you want to have a business that you can reinvest in.
Um And so it's so refreshing to actually hear someone say,
(25:32):
let's core a division of the games generated by this project that it's win,
win.
Yeah,
there is no way we could do it without them.
I think if you,
I don't know how to express this,
(25:52):
but like,
I feel an immense sense of responsibility to our team and a like really intense level of gratitude for what they have allowed us or helped us build.
Um I wish I could give everyone on my team like a full time,
you know,
high salary job that they could just like hang their hat on and,
(26:15):
and not worry about ever again.
That's not a financial reality for us.
And so I think the best,
next,
best thing that we can do is create a space that they feel like they are a true collaborator in.
Um And that kind of goes back to like the purpose.
I don't think that my purpose in this world is to build websites.
(26:37):
I think that my purpose in this world is to build teams of people and to mentor them into their own creative like entrepreneurship,
the way that I've been able to do that is through this agency.
And like,
that's the part that I really get out of bed for.
(26:59):
Um And I think like it,
when you think about it from that perspective,
it's not hard.
Of course,
it's like an ongoing conversation we have between myself and our financial people of like,
well,
you could do X,
you could charge this and you could cut your margins to your team or you could offshore,
you could do this,
this and this and it's like,
(27:19):
ok.
Sure.
Yeah,
I could do all that.
But like,
is that the business I wanna run again?
It's,
it's around your intention and you're connecting your intention directly to your purpose.
The thing,
that's cool about what,
what I hear you say is that you were very clear about where,
where the limits of what you could do were like,
(27:40):
you couldn't bring on 20 people salaried.
So,
instead of just being like,
well,
I guess we can't do it.
I'm going to take all these contractors and we're going to just exploit,
exploit,
exploit.
You sat down and you thought,
how can I make this win,
win?
Like where do we,
how do we create value for everybody in this relationship?
That must have taken a minute,
(28:02):
like you've been in business for 10 years like this employee value proposition,
which I think is very cool because you're really talking about giving your contractors a reason to show up and be their best self.
But that must have developed over time.
Like what was the journey to get to the point that you're at now where you can kind of look back and say,
(28:23):
ok,
these are the things that seem to be important and that actually matter in terms of developing the human capital of my office.
Yeah.
Uh I mean,
that is the fun thing about a journey,
right?
Looking back on it,
there's stuff that you experience,
you just,
you never knew.
Um And and we certainly have had like ups and downs and challenges building this out.
(28:46):
I also want to stress that like at no point,
have I done this alone?
Having my business partner here with me?
Um We are so close and very different but also like in lockstep on um on our team and what we want this place to be.
So I think like,
(29:07):
it's been fun to do that with someone else because I get to share that experience with someone and be like,
yeah,
we're doing this,
we're imperfect and we're probably gonna mess it up but we're doing it.
Um I think this is really silly but we have a very active slack and our slack.
(29:27):
We,
we kind of don't kick people out when they have like moved on to other roles.
And it's become this really amazing community of designers and developers who are always in collaboration.
So like no matter what projects people are working on,
(29:48):
there's always this sense of like,
I am a part of a team who is there to help and support me.
So we invest heavily in resources to support our developers,
whether those are like design tools or um you know,
plugins or whatever,
we,
we want them to have those resources to pull from.
And there's like an interesting part of that,
which is that we have this,
you know,
(30:08):
these,
this resource bank of like agency license tools that folks can use and what comes out of that is that they end up talking to each other about like,
hey,
have you used this plug in?
How was it like,
what did you do it on?
Oh,
this site is cool.
So like that community I think has felt that like that friendship that folks have developed from,
(30:29):
that has felt like it's become its own little sense of like power behind the designer and PM community at our company.
Um So having that very open communication through Slack has been a huge part of our,
our growth in that area.
Um I think we've like hit the right size teams for both of those things,
(30:52):
both of those groups and I think like,
we've had times where we've had too few developers and they're feeling really overworked or too many people and they don't feel like they're getting enough business.
So being really mindful that we're like staffed appropriately for the volume of projects that we're working on has also been really important and then also like tools that we've built out for them to share their ongoing availability has also been really good.
(31:15):
Yeah,
it's like a million little things that stack up.
Yeah,
I know it,
the little things make all the difference,
right?
Uh What's interesting though is that when you talk about community,
it just occurs to me like you actually not just have a team of engaged employees,
but you kind of have evangelists when they go out and they meet other creatives who are,
like,
I actually have a really great situation going on right now with week of the website and it's good energy like that helps attract people to you when you need it.
(31:44):
I,
I feel like if our team was out there and like when they talk about their work with week of the website that they had a little,
like I work for this company and I can't believe it's what I get to do.
Um And I can't believe these are the people I get to work with.
Like,
that's the dream.
You know,
we just got a box.
One of our team members is in Hawaii.
(32:06):
And uh we've been working on this massive project for like a very large um nonprofit organization in the US that is,
we're essentially relat 60 of their websites from various platforms to squarespace.
And it's been a massive team effort.
Like,
it's,
I think there's probably 12 different people who have worked on it in some capacity and it's become like a very fun,
(32:33):
you know,
micro community like project based.
But like we got a box of treats from Hawaii from Susan,
you know,
a couple,
like a couple weeks ago to our office with a lay and it was just like,
I wish,
I wish I could be there in Chicago with you.
I miss you guys,
you know,
when people are in town in Chicago,
they'll come in and work for the day in the office and it's just like,
(32:55):
what a joy that,
that is the outcome is that people want to feel close to the hub of that.
Um Yeah,
I mean,
it's like one of the things I'm the most proud of in my whole life is,
is getting to work with these like,
truly wonderful,
wonderful people.
Um And seeing them grow so much throughout their careers,
it's phenomenal.
(33:16):
No.
So I think what you're,
you're,
it's,
you're saying something really inspiring,
which is like,
you know,
so many people don't have this experience with any kind of work,
like whether they're like a salaried employee or a contractor.
That was me iiii I worked for a really long time for organizations that I just didn't feel like I was in the right place with.
(33:40):
Yeah,
what would you say to other small business owners that really want to create that for their,
for their people?
Like what's a piece of learning or a piece of advice that you're like,
focus on that?
Um I think that people have very small,
(34:02):
sometimes can have very small world mindsets when it comes to their team.
I had a couple of really uh um I don't know how,
I don't know what the right word is,
but I would say like,
not great working situations before.
Uh we found a week of the website and I also had one like,
really outstanding manager when I was hosting at a restaurant in Chicago and I will never forget that every time someone left to a new job,
(34:32):
that manager,
um his name is Avi Rath N Kumar,
he's um in the restaurant and hotel hospitality,
uh executive space.
Now he would get out a bottle of champagne.
She,
he would pour a glass for everyone who was on uh working that night and he would toast them to the next thing that they did.
And I thought,
(34:53):
you know,
no matter what that person,
what their experience was working,
even if they were like the most mediocre,
you know,
person on the floor,
that competence and humility to think his team for what they had brought to the table and to congratulate them on what came next.
(35:17):
I remember leaving and think thinking,
you know,
I'd work for that guy any time doing whatever because I felt that trust and I felt like that appreciation and you can't fake it.
I think for people who want to work with contractors or want to work with employees of any kind thinking of them as some level of partner and um not family because that's gross and toxic and weird.
(35:48):
Not,
that's not it.
That's not it.
We,
we actually joke about that all the time.
I'll be like,
I'm so grateful.
Thank you so much.
Like you are a really special part of this community but not a family because that's weird.
Work isn't family.
Work is work.
Um But I think like that humility of understanding the people that are working with you are working with you.
(36:10):
Like you can think of it as someone working for you and that's gonna set up a weird dynamic.
But like if you can think about your collaborators as collaborators,
then those choices don't feel hard anymore because you might make a choice that feels unbalanced towards someone who works for you.
But would you make that same choice for someone that you think of as working with you?
(36:33):
And I think that that's something that feels like very infused in this approach.
And it's like,
because we work with contractors,
I think we've kind of backed into that as um uh overall mindset even for folks that are full time with us.
Um that like,
how do we create the best environment for us to work together?
(36:54):
It's like an easy solution to a lot of those problems that feel hard.
Well,
when I do culture work with organizations and we talk about trust because trust is like the the foundation for building culture,
right?
There's,
there's two pillars to trust that you just talked about,
which is compassion and connection and like just the simple act of your,
of your former manager,
(37:14):
like effectively,
not just thinking but celebrating somebody's contribution.
Yeah,
they see scene,
they feel connected,
right?
That build trust with you.
Yeah,
my,
my challenge to people listening to the podcast is like,
think about in your own organization.
How do you bring compassion and connection to your employees every day?
(37:35):
Let me ask you this because I know it comes up and since you're a digital marketing expert,
I am going to use this opportunity to,
to maybe uh solicit some free advice to folks.
I work,
I work,
I work,
I work with a lot of organizations um that are kind of doing some of the work that you're talking about,
(37:57):
which is leading with purpose,
leading with your values trying to connect into the community.
And I'm always telling them,
tell your story um particularly about your community impact and the impact that you want to see.
What advice would you give to businesses that wanna connect in their community as far as like talking about their journey telling stories?
(38:20):
Yeah,
it can be so powerful to hear about your story from the people whose lives you've touched.
And I will say like,
I'm kind of not,
I,
we have historically not been great about this.
Like we'll finish a project and we'll be like,
OK,
we hope you had a really great experience.
(38:41):
Why?
Because it,
because we don't want it to feel like we did this work for you.
Now give us a good testimonial that we can use for social proof.
Um That,
that's always felt complicated to me.
But what I have found especially over the last couple of months is that people like to share details of their experiences and when they've had good experiences,
(39:05):
they want to tell other people about it.
When you're very in your own journey and your own purpose.
As an entrepreneur,
as someone who's working with a purpose driven company or a nonprofit,
it can be very hard to see what your impact is from the inside.
And I think getting in the habit and getting comfortable,
comfortable asking for specific feedback from the people who you work with to tell that story can be really helpful and very um like ego resetting because we have the things that we tell ourselves about what we are trying to do and then we have what we are actually doing.
(39:41):
And I think sometimes this part of what you're actually doing can tell that story even more profoundly than you sitting down for hours and hours trying to write it out or,
or create a digital representation of that.
So getting in the habit of asking people about the specific impact your work has had on them and letting them tell your story can be very,
(40:02):
very useful I think.
And then also being restrained in telling that story,
tell enough to get people excited and interested and ask,
asking questions but not so much that they have nothing to say to you.
We're actually doing that on our own website right now is we've kind of erred on the side of like we're gonna give you every detail because that's my personality where I just want to know everything and then I can make a choice but for some people that can be really overwhelming.
(40:27):
So finding that middle ground between too much and not enough.
Um I think when it comes to story storytelling,
especially online giving people a little bit of space to fit curiosity and around your message can be really helpful.
Yeah,
particularly in social media,
you want the engagement,
right?
Solicit the question like,
(40:47):
oh,
that's interesting.
Let me know more about that.
Yeah,
perfect.
One of the things I tell like in the context of a lot of my clients,
like they want to work with,
like I say a community partner,
like a nonprofit,
they're trying to find something that they or a partner that they can collaborate with,
that really feels good for them just as an entrepreneur.
And what I always say is,
(41:08):
you know,
tell stories.
You don't have to be perfect at social impact work as a business,
just be,
be vulnerable about it.
Let people know why you're doing what you're doing.
And then exactly you said,
don't make yourself the main character,
make it about the organization that you're trying to work with.
They're the heroes of the story.
Everything else will come back to you for the people that are resonating.
(41:30):
Yeah,
I mean that,
that is so endemic right now.
There is this,
I think it's like a natural expression of the kind of creator economy is that the influencer and the things that they share becomes the product.
But if you're a service driven business,
as much as I'm sure people would enjoy hanging out with me and Mallory,
(41:50):
we have a great time.
We're not the thing people are buying like you are not here to get a Mallory Kelsey doll in your life.
Uh You are here for a really good website and you're here because what we have created is a really phenomenal process that leverages the talent and creativity of a remarkable team.
(42:11):
And the outcome of that is a website.
And so I think figuring out a way that,
you know,
our own little pieces of Mallory and Kelsey Magic are infused in our business is important because people want to know there's a person behind it.
But at a certain point,
like it can't just be about you as a person,
it has to be about what you are able to help other people accomplish with your help.
(42:34):
Um And I think especially now with like the education entrepreneurship that's happening.
It can be so easy for people to mistake like an individual sparkle for something that they can teach you or something they can do for you or with you.
And so I think that that like the more that you can distinct,
(42:55):
I what it is that you help people accomplish in partnership with them,
the easier it is for them to imagine themselves doing that work with you because they don't have to then imagine being you.
They can just imagine.
Oh,
what am I like with Michael's support?
What am I like with a week of the website website client recently?
She's like,
I was hoping that some of your cool would rub off on me.
(43:16):
But what actually happened was that I got a website that was perfectly representative who I actually was and that was what I needed all along.
And I was like,
why would you do that to me?
No,
I'm crying.
It's all about the authenticity people.
It needs to be.
Yes.
Yeah.
Um But you actually are helping people,
like you mentioned,
you know,
you've got a book,
(43:38):
the course that is geared at helping people do some of the stuff that you're doing.
Yeah.
Yeah.
So this like spirit of education has always been a part of week of the website.
Uh We didn't even have like a support team for seven out of the,
you know,
9.5 years.
We've been around because we were so hell bent on getting people to use their own websites.
(44:02):
So we had this like training portal.
We would do training with folks when we launched their websites and fortunately slash unfortunately,
our clients got to the point where they were like we appreciate that,
but also we are too busy.
Can you please just do it for us?
Um But that desire for people to feel comfortable using a tool like Squarespace,
which was initially built as a diy tool to build,
(44:26):
edit and own their own sites has never left.
So I had a publisher reach out to me um about a year ago in November and ask if I would be interested in writing a book about Squarespace.
And um I said yes,
but I don't want to write just a guide.
Like Squarespace has this amazing um learning and education center and their support site.
(44:50):
So I was like,
we don't need to replicate that.
So what I did was I ended up creating a guide for either um small business owners or independent,
you know,
entrepreneurs or earlier stage designers to understand how to build a website using Squarespace.
Um So each chapter goes through not just like here's mechanics of how you do it,
but from a designer and a design agency's perspective,
(45:14):
here is how we approach this topic,
right?
So,
like,
here's how you write an outline for your site content.
Here's how you find design,
you know,
resources,
here's how you build out a blog and here's why.
Um And then I got to do the best part of it all which was interview all of these other scores,
spaces,
entrepreneurs about their areas of specialty.
(45:34):
And it was like,
I felt so sneaky because I was just like,
I just get to talk to all these people who are so influential in my own career.
And um so yeah,
that's squarespace from sign up to lunch,
it came out,
um,
about 2.5,
3 months ago and it's been,
um,
wonderful.
I've gotten some really great student feedback and it just warms my heart.
So that's quite an accomplishment.
(45:56):
Like writing a book.
You can check that off the bucket list.
Right.
I know.
I,
I actually have a big stack of them in my office right now because I have to send them out to my collaborators.
But it's like on days when I'm feeling a little low,
I'll just be like,
you know what?
At least I wrote a book,
please n out a book.
That,
that is awesome.
So I really appreciate your time,
(46:18):
Kelsey.
This was awesome.
Um Check out squarespace from start up to launch.
That's your book.
What Last Pearl do you want to leave with folks in terms of anything that we talked about today?
Good question.
I think building a team has been the most fulfilling part of my career as someone who is a creative turned entrepreneur.
(46:38):
And if you have the chance to do that,
you should and if you have the chance to do it in a way that feels like it really uplifts your work as a collaborative environment and community.
I think you should do it.
It's not gonna be perfect.
Not every day is gonna be sunshine and rainbows.
You're still gonna have tough conversations with your team members.
(46:59):
You're still gonna fall short some days.
You're still gonna need them to,
to do more.
Um,
but I think going into it with that sense of like,
humble appreciation for what they bring to your organization,
what they bring to your work.
Um People feel that like when it's there and then when it's real,
your clients will feel it,
your team will feel it and you'll be able to put your head down at the end of the day and think like,
(47:22):
oh,
man,
I'm trying to do something a little different here and that is immensely rewarding.
Ah,
I love that.
Thank you so much.
Thank you,
Michael.
All right,
join us on our next episode for now.
We'll sign off on a discerning strategies podcast.
Thanks.
(47:42):
You can find Michael Messer at discerning strategies.com.
Set up a free 20 minute consultation,
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(00:31):
Hi,
everybody.
Welcome to the Discerning Strategies podcast.
I am your host,
Michael Messer and this week I am joined by co-founder of week of the website Kelsey Gilbert Kriley.
Week of the website is a Squarespace design agency for creatives with a purpose located in Chicago.
So,
hey,
Kelsey,
how's it going?
(00:52):
Hi,
Michael.
It's great.
I'm so happy to be here.
Hi,
thanks for joining us.
Um Before we get started,
just tell us a little bit about week of the website,
what's going on with you guys there?
Yeah.
So week of the website is my web design agency with my co-founder Mallory.
Um We started,
it'll be 10 years in May,
which is kind of unfathomable to me because how could I have possibly aged 10 years?
(01:17):
But,
well,
congratulations.
More importantly,
you're not a statistic either.
I thank you.
It is,
you know,
what,
we kind of pinch ourselves every day that we're like,
I can't believe that this has been this long.
But,
um,
it's really been a joy.
We,
we started out with the goal of,
you know,
very simply making it easier and less painful for people to build beautiful websites they could use as a tool for their business.
(01:40):
Um,
that's always been something that has felt really important to me And that's started with,
you know,
my,
my co-founder Mallory project managing me building the websites and then eventually grew into something that was much bigger than just the two of us.
So we now have a team of about 20 spread across the country,
but kind of headquartered here in Chicago.
And we do a lot of work for small businesses with our core we of the website product,
(02:05):
but then we also partner with other creative agencies to execute websites for them as like a deliverable of their work for their clients.
And then we work with enterprise scale companies to do like bulk repla projects or more like intense squarespace design builds um on the Squarespace enterprise platform.
(02:26):
So it started from this little idea of building websites should be easier and less painful for people and has now grown into something that's um I don't know,
been really special.
That's awesome.
There's so much that I want to unpack around this.
What you didn't say though,
if you kind of start investigating,
you know,
we,
of the website in general is that you actually describe your company as a design agency for creatives with a purpose.
(02:50):
Yeah.
So what's the purpose?
I think what we are getting at with that is not only that we have,
we have worked with a lot of like nonprofit organizations and very like community driven groups.
That's,
that's just sort of been a part of our DNA as a,
as a company since we started.
Um But what we've identified as we think about who our best clients are,
(03:14):
are there people who come out of the gate with something very intentional that they want to do other than I want to build a business to make money.
Um When we work with clients that have a very clear perspective on what they bring to the world,
we have found that they make the best partners because we can build great websites.
(03:34):
But it's impossible for us to articulate for our clients what they do,
why they do it and what they stand for.
So when we work with creatives who have a real clarity around their purpose and a really clarity around what they are hoping to accomplish.
Um Those are when our websites like they sing,
right?
You,
you can feel that.
So that was kind of how we have defined our like niche,
(03:56):
right?
You are so speaking my language right now because I always talk about intentional business,
intentional,
intentional,
intentional I say that word every day,
100 times a day it feels like.
Um,
but that's exactly what you're saying is exactly the point that I try to go out and take out with my clients,
which is what is the thing that you want to do?
(04:17):
What is your purpose being underneath the profit?
It's so powerful at connecting your business to people,
whether those people are in your business,
your employees,
your contractors,
your customers,
or just people in the community that you wanted to do right by.
Yeah,
definitely.
And I think it's a struggle when people,
(04:39):
I'm sure you feel this in your work as well.
But when people don't have that understanding of like what makes them tick,
it can be really challenging and listen,
I'm not saying that everyone always knows that,
you know,
we,
like I said,
no,
it's a,
it's like a,
it's a journey,
you know,
you go up and down last year after I had my son,
(05:01):
a lot of things changed in terms of like what my role was in our business and my partner and I actually did like a positioning engagement with um a,
a really fantastic consultant who sat us down and asked us very hard questions sometimes until we cried to help us understand like,
what is our,
what is our purpose as a company?
(05:22):
And you know,
for me,
what I got to is like,
the people are the only part of this that I feel truly passionate about the people that we work with,
the clients that we serve.
And so,
um that was something that we,
we need to highlight this.
We have to,
you know,
dig even deeper into this because that's the thing that gives us the most um you know,
(05:44):
connection in our work.
Like websites are just ways that we talk about people online and ideas.
And so,
um identifying that has been really important,
but it wasn't always that way.
Right.
There's the different times where we've had different niches or different goals.
And I think,
um,
if you know that,
then it's much easier for people like me and people like you to help make that dream real.
(06:06):
Yeah,
I love what you're saying is you're actually talking about your purpose,
not just as like something that you stick up in your office and be like,
hey,
this is what we're about,
but it's a strategic value that really is driving your business.
It's part of your own intention within your business.
Sounds like the people.
Yeah,
I think for a lot of people,
uh,
a company that they start becomes just a job that they own.
(06:29):
I,
that's,
that's not something I came up with someone else said that.
Right.
And,
um,
yeah,
I mean,
I think especially over the last five years,
we've all had real reasons to kind of query what the,
the position of work is in our lives.
And,
um,
for me,
(06:49):
if I'm gonna spend,
you know,
eight hours a day away from my,
you know,
from my son,
from my child.
Like,
what is it that I'm doing with my time?
And I think it's become our team and our team's development and growth as they work with clients and then our clients seeing their success once they're done working with us,
that has become the fuel for all of it.
(07:11):
And that's what makes us not feel like a job.
It makes it feel like,
oh,
gosh,
I'm so glad that I've spent the last decade of my life working on this because every day that I get to collaborate with one of our contractors,
um you know,
see them grow in their skill set,
match them with our clients to take on jobs that really push them and excite them.
Like that's the best,
right?
(07:32):
That's awesome.
So I know,
you know,
you,
you talked about employees and people are really important to you and you mentioned that you work a lot with contractors.
Tell us a little bit about how you think about managing a workforce and growing a business over 10 years with a contracted workforce.
We started out with um like really coming from the company of one mindset.
(07:56):
Um Paul Jarvis is,
was a longtime collaborator of my husband's and so got a chance to be familiar with his work very on in my like entrepreneurial journey.
And I remember reading it and being like,
yeah.
No.
Yeah,
totally.
Like this is what I want to do.
But also it's a company of two because I have a business partner.
But with web design and development,
we very quickly realized that in order to serve the kind of clients that we wanted to serve to,
(08:20):
you know,
have a life that we've,
that each wanted to have like the minute you add another person that multiplier becomes a little bit more complicated.
And as we grew,
and as our company grew,
we realized that like Mallory and I were needed for other responsibilities outside of just project,
managing web design and building websites.
And so we very trepidatious stepped into working with contractors.
(08:46):
Um And I say that because it was like hard for me to imagine taking a client through the sales process and then being like,
ok,
and now you're going to work with someone else.
Um I,
I think people don't like that and they,
they want to really understand who they're working with.
So we were hesitant to become an agency even though we were always called agency.
It was kind of funny.
Um And once we did what we realized was it would be very,
(09:11):
very hard for us to scale our team size with a business that says seasonal as web design.
And when I say seasonal,
I don't mean like we get a Christmas rush,
but we do have like really significant ebbs and flows mostly based on like when people's attention is available for projects outside of their core work.
(09:33):
Um And so,
and bringing on contractors,
but really wanted to do it in a different way.
Um,
I had worked freelance before I had,
I'd been in contracting roles prior to my work here and I just felt like it always felt a little tough.
It was like I was brought in to build it to,
to solve a problem but not to be a part of like an ongoing solution.
(09:57):
And um even though we knew we were going to need to be able to build our team and that kind of ebb and flow with projects,
we also wanted to do it in a way that felt like we were really investing in our team as a team.
Um And also giving them the freedom to like work on the projects they want to work on.
I'm not trying to like lock anyone down to just do my work.
Um Sometimes that's not what they want to do.
(10:18):
So I also wanted to figure out we also want to figure out a way to really honor the like super creative and independent spirit of the collaborators who worked with us while also creating a place where they wanted to come and be on week of the website projects.
Yeah.
And you're actually,
you're talking about the importance of building culture,
even with people that are not actually on the permanent payroll Yeah.
(10:41):
Yeah,
we've been talking about that a lot because you could see,
I'm in an office and,
um,
I worked from home until a year ago last year and when,
at the time,
my business partner and her dog were actually living with me,
my husband and our son and we also host a nanny share in our place.
So eventually I was like,
(11:02):
ok,
guys,
we cannot make this work.
Like we can't have three adult human beings working from home,
one nanny,
two kids and a,
a dachshund in the same like townhouse,
we need an office.
So uh we ended up taking an office space that's like right around the corner um in Wicker park in Chicago and we've had to move offices three times,
(11:24):
Michael because people want to come in and work like this is a very rare day that there's no one here.
Um But we like started off with like a two person office and then maybe two people come in and we have an extra desk.
We have like five people who regularly come into work because they like it here.
So like,
oops.
So OK,
so I have to go here now.
(11:45):
Like there's all of this chatter about return to the office,
remote work.
There's the proponents,
the detractors,
like people have very strong feelings around this.
You've done both for significantly and in a significant way.
What is your thought on this whole thing?
I mean,
make it fun,
make it,
make it worthwhile for people to be there.
(12:07):
Like if you,
if the culture is really like at your core and what you really care about is people being in person and collaborating.
Like this is not a plug.
They don't pay us,
I pay them,
but we work out of an industrious office.
They take such good care of us.
There's coffee,
there's food twice a day,
like it's a lovely space.
(12:28):
It's beautiful.
But the best part is,
is like when,
especially when um Alex,
one of our developers is here,
like we turn around and just like talk things out constantly.
She'll be like,
hey,
what do you think about this or do you have any code that can do this?
And it feeds both of us.
That's our personalities.
I'm quite extroverted.
(12:48):
She is as well.
We're both really curious people,
but I think like insisting that people come into the office,
you're not gonna get what you want from that.
So just,
just offer people the things that they feel incentivized by and trust people to make good decisions for their own working needs and they'll do what they need to do to be successful when it comes to work.
(13:11):
I don't think that there's like that big of a group of people who are like I am here to absolutely betray what I brought,
what I told this team,
I was gonna bring to them and I am gonna be a drain on the system.
If they're coming in with that mindset,
there's probably a reason that should be,
like,
investigated,
but I don't think it's a big enough thing to,
like,
force a bunch of people into an office of that problem,
(13:32):
this whole quiet quitting thing.
Right.
You have to be like,
what's broken in your organization.
That this is a concern,
right?
Like,
because people wanna get ahead,
they want to provide for their families.
Like I,
I,
you know,
um but you said a word that I think is really important here that people don't talk about enough,
which is trust.
(13:52):
Yeah,
you have to trust people to do and show up,
right?
So how do you like you've got,
you just said you have like 20 people all over the country that are collaborating every single day across all of these different projects.
I mean,
you've launched over 700 websites.
(14:12):
It's a lot.
OK.
So a lot of volume is coming to your office.
How do you create trust when everybody is,
is dispersed like that?
Yeah,
I think first of all,
you wanna be really clear on the types of things you're hiring for people hire for hard skills,
(14:39):
but it's so much harder to teach people how to be trustworthy and good communicators open,
vulnerable and brave than it is to teach them squarespace,
right?
Like I have a book,
I can teach you how to build on squarespace.
Even I have a video course,
I can teach anyone to use the Squarespace platform.
(15:00):
Um I can't teach that sense of collaboration and curiosity.
I had this one guy,
I had a conversation with one time and was explaining our week of the website process,
which is like quite intensive.
You basically work with our team for over the course of five days to build a custom website that we then launch within 10.
(15:24):
And part of that is that we are showing our work from day two.
Like you get a link to the site in progress on the second day of your engagement and you get to see the designer work on it until it's ready to launch.
And I,
I just thought of that as like,
that's just like a really,
I don't know,
just like a really open way to build and it felt like a good way to get ahead of like time wasted on design that didn't work.
(15:49):
And this one other founder,
he's like,
God,
that's so brave.
Like it's really hard to show unfinished work.
And I think that's one of the things that our team is just so comfortable doing because we try very hard to start every engagement by like thanking the client for their hard work,
thanking them for the effort that they've put into preparing.
And then also telling them like we are showing up to this engagement with the genuine goal and expectation of building you a site.
(16:18):
You're really really happy with.
Sometimes we're gonna have to say no to things that you have ideas for because it's not doable in the time that we have or it doesn't serve the goal that you have told us as your objective at the beginning of the process.
And we're going to ask that you trust that we are here with your best interests at heart.
And if we all engage on that level of like,
(16:39):
I trust that when you give me feedback,
it's because you also want the project to be great,
then that depersonalizes it,
right?
That means our designers are able to show up pretty like,
you know,
transparently and be like,
what do you think of this design if you don't like it?
That's OK.
But I have to know,
you know,
so that trust trickles down.
Well,
you're talking also about leading with your values and in a sense like,
(17:02):
you know,
those values in,
in like open communication and the spirit of collaboration,
you're actually bringing this creative with a purpose into that value space and almost self selecting around that,
which is exactly what you're supposed to be doing.
Your values,
attract the clients you want to work with.
(17:23):
And that's what actually the results in a website in 10 days.
I also will say I do a lot of the I now do most of the all of the enterprise sales process and then um a good part of oversight for our like core business sales and pro partnership sales.
And we are extremely selective when it comes to clients who we we will work with based on you can have whatever kind of project you want.
(17:54):
But I feel very protective,
not in a patronizing way,
but like,
I'm not gonna put our teammates in the line of someone who's not going to be a good collaborator for them.
Like I would rather leave money on the table and say thanks but no thanks to working with a client who isn't aligned with our values because my clients come and go and as much as we lead from a spirit of like the client,
(18:24):
the reason why the client is asking for something,
there's a good reason like I can't get more Alex's Shelley's Susan's and it's like I can't get more of those people but clients are gonna come and go.
And so for me being really protective of our team and choosing to take on projects that align with our resource,
(18:47):
align with our values as a company means that we can create a more positive environment for them to work in.
So they still want to keep building websites for us,
right?
Yeah,
that like what I'm hearing you say is like,
it's about reciprocity like it's not in the in the reciprocity goes beyond.
OK?
You 1099 contractor are going to get a paycheck based on this project based work.
(19:10):
You're talking about you creating a space where they feel protected where they can create and,
and serve in the way they need to do it.
Um And not have to worry about that.
That's part of the culture,
right?
Yeah.
Yeah.
I mean,
we,
we kind of say like,
listen,
we know you could go build squarespace websites for yourself,
for your own clients.
Here's the part that we want to take care of finding the project,
(19:33):
selling the project contracting,
the project project,
managing the project and you know,
client relationships so that they can show up and the project manager can manage the project in terms of like getting content together,
timelines,
things like that,
the developer can take that information,
work with the client and build a site that's really,
really great and there's an external,
(19:54):
not external,
but like there's a third group here who deals with the other stuff that can sometimes I think get in the way of the creative process.
I don't think you can go through as a designer and deal with a client like paying late and then also feel really good about putting your heart behind their work,
you know.
So I think that that's become like a really nice um balance of responsibility.
(20:17):
But I also think like that kind of circle back,
you mentioned trust and it takes an immense amount of trust for us to be like,
all right,
we got this client for you for us,
for all of us.
And their project is really special.
Here's what we want you to do.
Like we always come into it with the best of intentions and then people are human and things happen.
(20:39):
The only way that we have been able to keep this train running is that we talk about projects when they go,
right,
we applaud them when they go.
Right.
And if for some reason they go wrong,
then we lean into open communication as a team where we just sit down and we talk about it.
I think one of the most toxic things in creative and in,
(21:03):
in,
you know,
client based work is not knowing where you stand.
And I never want that for my team.
I never want them to feel like they can't raise an issue of how a project's been sold or,
you know,
what client expectations are,
we have those reviews.
And we also do like monthly stand ups with the P MS and with the devs to just say like this is like open talk time,
(21:26):
what are you seeing,
what's going on with the process?
What adjustments need to be,
make made?
And our team actually like,
leads those changes because they are the ones on the ground,
right?
Like we're figuring out the mechanics of money and process and on boarding and all of that stuff.
Um But they're the ones who can tell us what it's like when they're,
they're building it.
And so because we have created that environment of transparency with them.
(21:50):
Um It's my hope II I,
you know,
I can't,
I can't promise this,
but they don't feel afraid to come to us with a question or a concern about a project.
And I feel the same way that if I feel like something's going on,
I can come to them and say,
hey,
what's happening with this?
And they know it's not being me being like what's happening with this answer wrong or I'm going to kick you out like that's not the vibe.
Well,
(22:10):
yeah,
so there's so much good stuff that you're talking about,
right?
Like uh you know,
part of the trust is like people want to be heard.
And so like you're giving,
you're holding space for people to actually have two way communication and that's not actually going to work if you're like,
(22:30):
you're just talking at somebody and like,
oh,
we have our monthly meetings.
Well,
did you elicit any feedback?
Uh No,
I just gave them the information very different than what you're talking about.
Yeah,
I have found that in those conversations.
I it is if I want that,
(22:51):
if we want that kind of feedback,
you have to start with questions and then people will start opening up.
So you can't just be like,
how do you think this is going and then wait for people to speak?
Like,
what I've found is that we ask,
I,
I'll come in with specific questions that maybe I'm like seeing a little of friction around or things that keep bubbling up to me on slack that I see.
(23:13):
And I'll be like,
hey,
feels like I'm seeing a trend here.
What's going on with like this part of this?
What do we think is causing this?
What do we think is behind this?
And,
you know,
then we can have that open conversation.
Money is always a huge part of this co like issue.
I think a lot of people view contractors as this kind of like disposable way to get things done for us.
(23:42):
They're a really essential part of our business.
And so we are very transparent with the team about like when we price a project,
here's,
here's what it breaks out to,
right?
Like here's the percentage of the project that goes to the designer.
Here's the percentage of the project that goes to the developer.
Here's the payout schedule,
here's what you can expect for this.
(24:02):
If it's a larger project,
if we differ from that margin,
we just tell them like when I'm pricing things out that are new for us,
that has been one of the best parts of having a team member in the office is I'll just turn around and be like,
Alex say,
hypothetically and she'll be like,
oh,
great.
I can't wait to hear where this is going,
you know,
and I'll be like,
(24:22):
this is what you're gonna do.
This is what the project would be.
This is what it would entail.
This is,
you know,
da da,
da da.
This is what I'm thinking of for developer payout.
How does that feel based on these factors?
And then she'll tell me it feels high,
it feels low,
it feels appropriate.
And I think like I have my numbers and data points in my computer that I can use to get us to like information,
(24:48):
but having the ability to talk to team members and get their sign off so that I know we're walking into a project on equal footing that is like hard earned,
but so appreciated because I wanna be able to look at someone and be like,
do you feel underpaid for this and have them be like,
yeah or no,
this feels good.
Well,
(25:09):
I have to say like that is an incredibly brave stance to take as a,
as a small business owner because so often,
right?
Like there's a lot that comes up when you own your own business.
Like how much am I going to make?
Like it?
Like all of this,
like you want to take care of your team,
you wanna take care of yourself too,
you want to have a business that you can reinvest in.
Um And so it's so refreshing to actually hear someone say,
(25:32):
let's core a division of the games generated by this project that it's win,
win.
Yeah,
there is no way we could do it without them.
I think if you,
I don't know how to express this,
(25:52):
but like,
I feel an immense sense of responsibility to our team and a like really intense level of gratitude for what they have allowed us or helped us build.
Um I wish I could give everyone on my team like a full time,
you know,
high salary job that they could just like hang their hat on and,
(26:15):
and not worry about ever again.
That's not a financial reality for us.
And so I think the best,
next,
best thing that we can do is create a space that they feel like they are a true collaborator in.
Um And that kind of goes back to like the purpose.
I don't think that my purpose in this world is to build websites.
(26:37):
I think that my purpose in this world is to build teams of people and to mentor them into their own creative like entrepreneurship,
the way that I've been able to do that is through this agency.
And like,
that's the part that I really get out of bed for.
(26:59):
Um And I think like it,
when you think about it from that perspective,
it's not hard.
Of course,
it's like an ongoing conversation we have between myself and our financial people of like,
well,
you could do X,
you could charge this and you could cut your margins to your team or you could offshore,
you could do this,
this and this and it's like,
(27:19):
ok.
Sure.
Yeah,
I could do all that.
But like,
is that the business I wanna run again?
It's,
it's around your intention and you're connecting your intention directly to your purpose.
The thing,
that's cool about what,
what I hear you say is that you were very clear about where,
where the limits of what you could do were like,
(27:40):
you couldn't bring on 20 people salaried.
So,
instead of just being like,
well,
I guess we can't do it.
I'm going to take all these contractors and we're going to just exploit,
exploit,
exploit.
You sat down and you thought,
how can I make this win,
win?
Like where do we,
how do we create value for everybody in this relationship?
That must have taken a minute,
(28:02):
like you've been in business for 10 years like this employee value proposition,
which I think is very cool because you're really talking about giving your contractors a reason to show up and be their best self.
But that must have developed over time.
Like what was the journey to get to the point that you're at now where you can kind of look back and say,
(28:23):
ok,
these are the things that seem to be important and that actually matter in terms of developing the human capital of my office.
Yeah.
Uh I mean,
that is the fun thing about a journey,
right?
Looking back on it,
there's stuff that you experience,
you just,
you never knew.
Um And and we certainly have had like ups and downs and challenges building this out.
(28:46):
I also want to stress that like at no point,
have I done this alone?
Having my business partner here with me?
Um We are so close and very different but also like in lockstep on um on our team and what we want this place to be.
So I think like,
(29:07):
it's been fun to do that with someone else because I get to share that experience with someone and be like,
yeah,
we're doing this,
we're imperfect and we're probably gonna mess it up but we're doing it.
Um I think this is really silly but we have a very active slack and our slack.
(29:27):
We,
we kind of don't kick people out when they have like moved on to other roles.
And it's become this really amazing community of designers and developers who are always in collaboration.
So like no matter what projects people are working on,
(29:48):
there's always this sense of like,
I am a part of a team who is there to help and support me.
So we invest heavily in resources to support our developers,
whether those are like design tools or um you know,
plugins or whatever,
we,
we want them to have those resources to pull from.
And there's like an interesting part of that,
which is that we have this,
you know,
(30:08):
these,
this resource bank of like agency license tools that folks can use and what comes out of that is that they end up talking to each other about like,
hey,
have you used this plug in?
How was it like,
what did you do it on?
Oh,
this site is cool.
So like that community I think has felt that like that friendship that folks have developed from,
(30:29):
that has felt like it's become its own little sense of like power behind the designer and PM community at our company.
Um So having that very open communication through Slack has been a huge part of our,
our growth in that area.
Um I think we've like hit the right size teams for both of those things,
(30:52):
both of those groups and I think like,
we've had times where we've had too few developers and they're feeling really overworked or too many people and they don't feel like they're getting enough business.
So being really mindful that we're like staffed appropriately for the volume of projects that we're working on has also been really important and then also like tools that we've built out for them to share their ongoing availability has also been really good.
(31:15):
Yeah,
it's like a million little things that stack up.
Yeah,
I know it,
the little things make all the difference,
right?
Uh What's interesting though is that when you talk about community,
it just occurs to me like you actually not just have a team of engaged employees,
but you kind of have evangelists when they go out and they meet other creatives who are,
like,
I actually have a really great situation going on right now with week of the website and it's good energy like that helps attract people to you when you need it.
(31:44):
I,
I feel like if our team was out there and like when they talk about their work with week of the website that they had a little,
like I work for this company and I can't believe it's what I get to do.
Um And I can't believe these are the people I get to work with.
Like,
that's the dream.
You know,
we just got a box.
One of our team members is in Hawaii.
(32:06):
And uh we've been working on this massive project for like a very large um nonprofit organization in the US that is,
we're essentially relat 60 of their websites from various platforms to squarespace.
And it's been a massive team effort.
Like,
it's,
I think there's probably 12 different people who have worked on it in some capacity and it's become like a very fun,
(32:33):
you know,
micro community like project based.
But like we got a box of treats from Hawaii from Susan,
you know,
a couple,
like a couple weeks ago to our office with a lay and it was just like,
I wish,
I wish I could be there in Chicago with you.
I miss you guys,
you know,
when people are in town in Chicago,
they'll come in and work for the day in the office and it's just like,
(32:55):
what a joy that,
that is the outcome is that people want to feel close to the hub of that.
Um Yeah,
I mean,
it's like one of the things I'm the most proud of in my whole life is,
is getting to work with these like,
truly wonderful,
wonderful people.
Um And seeing them grow so much throughout their careers,
it's phenomenal.
(33:16):
No.
So I think what you're,
you're,
it's,
you're saying something really inspiring,
which is like,
you know,
so many people don't have this experience with any kind of work,
like whether they're like a salaried employee or a contractor.
That was me iiii I worked for a really long time for organizations that I just didn't feel like I was in the right place with.
(33:40):
Yeah,
what would you say to other small business owners that really want to create that for their,
for their people?
Like what's a piece of learning or a piece of advice that you're like,
focus on that?
Um I think that people have very small,
(34:02):
sometimes can have very small world mindsets when it comes to their team.
I had a couple of really uh um I don't know how,
I don't know what the right word is,
but I would say like,
not great working situations before.
Uh we found a week of the website and I also had one like,
really outstanding manager when I was hosting at a restaurant in Chicago and I will never forget that every time someone left to a new job,
(34:32):
that manager,
um his name is Avi Rath N Kumar,
he's um in the restaurant and hotel hospitality,
uh executive space.
Now he would get out a bottle of champagne.
She,
he would pour a glass for everyone who was on uh working that night and he would toast them to the next thing that they did.
And I thought,
(34:53):
you know,
no matter what that person,
what their experience was working,
even if they were like the most mediocre,
you know,
person on the floor,
that competence and humility to think his team for what they had brought to the table and to congratulate them on what came next.
(35:17):
I remember leaving and think thinking,
you know,
I'd work for that guy any time doing whatever because I felt that trust and I felt like that appreciation and you can't fake it.
I think for people who want to work with contractors or want to work with employees of any kind thinking of them as some level of partner and um not family because that's gross and toxic and weird.
(35:48):
Not,
that's not it.
That's not it.
We,
we actually joke about that all the time.
I'll be like,
I'm so grateful.
Thank you so much.
Like you are a really special part of this community but not a family because that's weird.
Work isn't family.
Work is work.
Um But I think like that humility of understanding the people that are working with you are working with you.
(36:10):
Like you can think of it as someone working for you and that's gonna set up a weird dynamic.
But like if you can think about your collaborators as collaborators,
then those choices don't feel hard anymore because you might make a choice that feels unbalanced towards someone who works for you.
But would you make that same choice for someone that you think of as working with you?
(36:33):
And I think that that's something that feels like very infused in this approach.
And it's like,
because we work with contractors,
I think we've kind of backed into that as um uh overall mindset even for folks that are full time with us.
Um that like,
how do we create the best environment for us to work together?
(36:54):
It's like an easy solution to a lot of those problems that feel hard.
Well,
when I do culture work with organizations and we talk about trust because trust is like the the foundation for building culture,
right?
There's,
there's two pillars to trust that you just talked about,
which is compassion and connection and like just the simple act of your,
of your former manager,
(37:14):
like effectively,
not just thinking but celebrating somebody's contribution.
Yeah,
they see scene,
they feel connected,
right?
That build trust with you.
Yeah,
my,
my challenge to people listening to the podcast is like,
think about in your own organization.
How do you bring compassion and connection to your employees every day?
(37:35):
Let me ask you this because I know it comes up and since you're a digital marketing expert,
I am going to use this opportunity to,
to maybe uh solicit some free advice to folks.
I work,
I work,
I work,
I work with a lot of organizations um that are kind of doing some of the work that you're talking about,
(37:57):
which is leading with purpose,
leading with your values trying to connect into the community.
And I'm always telling them,
tell your story um particularly about your community impact and the impact that you want to see.
What advice would you give to businesses that wanna connect in their community as far as like talking about their journey telling stories?
(38:20):
Yeah,
it can be so powerful to hear about your story from the people whose lives you've touched.
And I will say like,
I'm kind of not,
I,
we have historically not been great about this.
Like we'll finish a project and we'll be like,
OK,
we hope you had a really great experience.
(38:41):
Why?
Because it,
because we don't want it to feel like we did this work for you.
Now give us a good testimonial that we can use for social proof.
Um That,
that's always felt complicated to me.
But what I have found especially over the last couple of months is that people like to share details of their experiences and when they've had good experiences,
(39:05):
they want to tell other people about it.
When you're very in your own journey and your own purpose.
As an entrepreneur,
as someone who's working with a purpose driven company or a nonprofit,
it can be very hard to see what your impact is from the inside.
And I think getting in the habit and getting comfortable,
comfortable asking for specific feedback from the people who you work with to tell that story can be really helpful and very um like ego resetting because we have the things that we tell ourselves about what we are trying to do and then we have what we are actually doing.
(39:41):
And I think sometimes this part of what you're actually doing can tell that story even more profoundly than you sitting down for hours and hours trying to write it out or,
or create a digital representation of that.
So getting in the habit of asking people about the specific impact your work has had on them and letting them tell your story can be very,
(40:02):
very useful I think.
And then also being restrained in telling that story,
tell enough to get people excited and interested and ask,
asking questions but not so much that they have nothing to say to you.
We're actually doing that on our own website right now is we've kind of erred on the side of like we're gonna give you every detail because that's my personality where I just want to know everything and then I can make a choice but for some people that can be really overwhelming.
(40:27):
So finding that middle ground between too much and not enough.
Um I think when it comes to story storytelling,
especially online giving people a little bit of space to fit curiosity and around your message can be really helpful.
Yeah,
particularly in social media,
you want the engagement,
right?
Solicit the question like,
(40:47):
oh,
that's interesting.
Let me know more about that.
Yeah,
perfect.
One of the things I tell like in the context of a lot of my clients,
like they want to work with,
like I say a community partner,
like a nonprofit,
they're trying to find something that they or a partner that they can collaborate with,
that really feels good for them just as an entrepreneur.
And what I always say is,
(41:08):
you know,
tell stories.
You don't have to be perfect at social impact work as a business,
just be,
be vulnerable about it.
Let people know why you're doing what you're doing.
And then exactly you said,
don't make yourself the main character,
make it about the organization that you're trying to work with.
They're the heroes of the story.
Everything else will come back to you for the people that are resonating.
(41:30):
Yeah,
I mean that,
that is so endemic right now.
There is this,
I think it's like a natural expression of the kind of creator economy is that the influencer and the things that they share becomes the product.
But if you're a service driven business,
as much as I'm sure people would enjoy hanging out with me and Mallory,
(41:50):
we have a great time.
We're not the thing people are buying like you are not here to get a Mallory Kelsey doll in your life.
Uh You are here for a really good website and you're here because what we have created is a really phenomenal process that leverages the talent and creativity of a remarkable team.
(42:11):
And the outcome of that is a website.
And so I think figuring out a way that,
you know,
our own little pieces of Mallory and Kelsey Magic are infused in our business is important because people want to know there's a person behind it.
But at a certain point,
like it can't just be about you as a person,
it has to be about what you are able to help other people accomplish with your help.
(42:34):
Um And I think especially now with like the education entrepreneurship that's happening.
It can be so easy for people to mistake like an individual sparkle for something that they can teach you or something they can do for you or with you.
And so I think that that like the more that you can distinct,
(42:55):
I what it is that you help people accomplish in partnership with them,
the easier it is for them to imagine themselves doing that work with you because they don't have to then imagine being you.
They can just imagine.
Oh,
what am I like with Michael's support?
What am I like with a week of the website website client recently?
She's like,
I was hoping that some of your cool would rub off on me.
(43:16):
But what actually happened was that I got a website that was perfectly representative who I actually was and that was what I needed all along.
And I was like,
why would you do that to me?
No,
I'm crying.
It's all about the authenticity people.
It needs to be.
Yes.
Yeah.
Um But you actually are helping people,
like you mentioned,
you know,
you've got a book,
(43:38):
the course that is geared at helping people do some of the stuff that you're doing.
Yeah.
Yeah.
So this like spirit of education has always been a part of week of the website.
Uh We didn't even have like a support team for seven out of the,
you know,
9.5 years.
We've been around because we were so hell bent on getting people to use their own websites.
(44:02):
So we had this like training portal.
We would do training with folks when we launched their websites and fortunately slash unfortunately,
our clients got to the point where they were like we appreciate that,
but also we are too busy.
Can you please just do it for us?
Um But that desire for people to feel comfortable using a tool like Squarespace,
which was initially built as a diy tool to build,
(44:26):
edit and own their own sites has never left.
So I had a publisher reach out to me um about a year ago in November and ask if I would be interested in writing a book about Squarespace.
And um I said yes,
but I don't want to write just a guide.
Like Squarespace has this amazing um learning and education center and their support site.
(44:50):
So I was like,
we don't need to replicate that.
So what I did was I ended up creating a guide for either um small business owners or independent,
you know,
entrepreneurs or earlier stage designers to understand how to build a website using Squarespace.
Um So each chapter goes through not just like here's mechanics of how you do it,
but from a designer and a design agency's perspective,
(45:14):
here is how we approach this topic,
right?
So,
like,
here's how you write an outline for your site content.
Here's how you find design,
you know,
resources,
here's how you build out a blog and here's why.
Um And then I got to do the best part of it all which was interview all of these other scores,
spaces,
entrepreneurs about their areas of specialty.
(45:34):
And it was like,
I felt so sneaky because I was just like,
I just get to talk to all these people who are so influential in my own career.
And um so yeah,
that's squarespace from sign up to lunch,
it came out,
um,
about 2.5,
3 months ago and it's been,
um,
wonderful.
I've gotten some really great student feedback and it just warms my heart.
So that's quite an accomplishment.
(45:56):
Like writing a book.
You can check that off the bucket list.
Right.
I know.
I,
I actually have a big stack of them in my office right now because I have to send them out to my collaborators.
But it's like on days when I'm feeling a little low,
I'll just be like,
you know what?
At least I wrote a book,
please n out a book.
That,
that is awesome.
So I really appreciate your time,
(46:18):
Kelsey.
This was awesome.
Um Check out squarespace from start up to launch.
That's your book.
What Last Pearl do you want to leave with folks in terms of anything that we talked about today?
Good question.
I think building a team has been the most fulfilling part of my career as someone who is a creative turned entrepreneur.
(46:38):
And if you have the chance to do that,
you should and if you have the chance to do it in a way that feels like it really uplifts your work as a collaborative environment and community.
I think you should do it.
It's not gonna be perfect.
Not every day is gonna be sunshine and rainbows.
You're still gonna have tough conversations with your team members.
(46:59):
You're still gonna fall short some days.
You're still gonna need them to,
to do more.
Um,
but I think going into it with that sense of like,
humble appreciation for what they bring to your organization,
what they bring to your work.
Um People feel that like when it's there and then when it's real,
your clients will feel it,
your team will feel it and you'll be able to put your head down at the end of the day and think like,
(47:22):
oh,
man,
I'm trying to do something a little different here and that is immensely rewarding.
Ah,
I love that.
Thank you so much.
Thank you,
Michael.
All right,
join us on our next episode for now.
We'll sign off on a discerning strategies podcast.
Thanks.
(47:42):
You can find Michael Messer at discerning strategies.com.
Set up a free 20 minute consultation,
clarify your goals,
scale your business,
amplify your impact,
discerning strategies.com.
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