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August 20, 2025 • 53 mins
In this episode, Joel Palathinkal engages with Brynne Kennedy from Impact VC to discuss her career journey and the significance of connection points in professional growth. They delve into strategies for new fund managers on fundraising and building relationships with limited partners (LPs), addressing the importance of fund materials, follow-up, and scheduling etiquette. Brynne shares insights on constructing a sales team, utilizing LinkedIn for hiring, and defining the characteristics of early-stage salespeople. The conversation explores marketing's supportive role in sales, effective communication, and nurturing. They also cover demand generation, growth marketing, and offer life advice, including incentives for pipeline and deal generators.
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Episode Transcript

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(00:00):
Yeah, and from a materials perspective, I thinkit's critical to have really three things.

(00:06):
The teaser, so it can be a one or a two pager,but something that can capture people's
attention and as I say, get them on the phone.
People want to default to email, people arebusy, get them on Zoom to get the full story to
build the relationship or get them, now thatthings are opening up, more get them to a

(00:27):
coffee, right, so
you can
forge that connection.
So that's really the purpose of the teaser.
Welcome to The Investor, a podcast where I,Joel Palafinkel, your host, dives deep into the
minds of the world's most influentialinstitutional investors.
In each episode, we sit down with an investorto hear about their journeys and how global

(00:51):
markets are driving capital allocation.
So join us on this journey as we explore theseinsights.
Okay, awesome.

(01:12):
All right, I think we are live.
So Brynn Kennedy, thanks so much for coming onthe show.
I really appreciate this.
We do this a couple of times a week.
Meet new friends, have people come on the show,talk about their story of how they broke into
venture capital.
Hope you guys can bear with me with my scratchythroat.
But Brynn, welcome to the show.

(01:34):
Just a quick intro on Brynn, she'll go a littledeeper, but she's a venture partner at Impact
Venture Capital and also a managing director atArchibald Venture.
So actually have collaborated with her on acouple of interesting deals with Impact Venture
Capital, and I'm excited to learn about all theother things you're working on.
So thanks for coming on the show.

(01:54):
Excited to just hear your story.
So maybe we can start with, I know you did astint in Congress as well.
So would love to hear everything and learnabout your story from the beginning.
We all have gotten into venture through our ownpaths.
Sometimes it's a much crooked path than it isstraight, but we all end up there at some

(02:18):
point.
So we'd love to learn your story, where you gotstarted, and how you ended up where you are
now.
Great.
Well, first of all, Joel, thank you for doingthis and sharing everyone's stories, and thank
you for having me on today.
I have had a diverse career to date, which issomething that I think brings great
perspectives to investing.

(02:40):
And I think the theme across my career is I'vealways looked at innovation as a force for
good, that entrepreneurs and technology cansolve big problems and do good for society.
And I really have focused on the intersectionof private capital, public policy, and

(03:01):
entrepreneurs to make those things happen.
So I started my career in investment bankingand private equity, had the opportunity to work
all throughout Asia, so saw things from thefinancing side.
After living around the world, I realized thatthe relocation market was really archaic, so I
started a business that at that time was calledMoveGuides when I was in business school in

(03:25):
London and ended up running that business forabout a decade.
We morphed from a relocation business to a fullHR technology platform for remote, mobile and
distributed work over the years.
So great run, raised 110,000,000 in venturefunding through the journey, led the
acquisitions of two companies, a big strategicrebrand and grew the business through the scale

(03:50):
up phase to operations across more than 100countries and offices on three continents.
So that was a great journey and started to getinvolved more politically on the policy side of
things, innovation policy, technology policy,the education and workforce training and
infrastructure that goes into that, sort of onthe advisory side as a CEO.

(04:14):
And then I thought, hey, there's not that manypeople in Congress and in the government that
come out of operating backgrounds, have livedthese things, are working on the future
innovations for society, so I should bring thisperspective into the government and really push
for policies that extend economic opportunityto more people, so more startup hubs, more

(04:37):
companies started and funded by women, peopleof color, people from non traditional sort of
entrepreneurial backgrounds and the governmentand the private sector working productively
together to solve problems in society.
So I ran for Congress, I actually did not win,so it was an uphill battle about a 12

(04:57):
registration advantage for the other party, Iknew it was going to be a challenge, but we
raised some really, really important issues,the technology policy side, but also
bipartisanship, both of which are things thatI'm very proud of.
So that finished in 2020 in that election andnow since then I spend my time working with and

(05:22):
advising venture capital funds and then doingmy own investing and advisory work through
archival ventures through my own portfolio ofcompanies, which has been really great.
And then I also have some policy activitiesthat I do as well.
That's great.
Yeah, I really appreciate that story.

(05:43):
One thing that I'm thinking about as you tellme this is just the connection points as you
pivot in your career.
So for me, I have similar transitions where Iworked for the Department of Defense, did some
entrepreneurship for a while and then brokeinto VC.
So with me looking back, I can see someconnection points.

(06:03):
So what are the connection points that you seebeing in banking, those quantitative skills?
And then how do you see that tying together,those superpowers that you had from banking to
entrepreneurship to public policy, and now intoventure capital?
Obviously, with running for Congress, I'massuming you probably have to raise a lot of

(06:25):
money.
So I'm assuming your experience being anentrepreneur, raising money, storytelling, what
are some of the connection points or skill setsthat you've seen kind of evolve and translate
to complement your journey?
That's a great question.
And I think the fundraising point is a reallycritical one.

(06:46):
Often joke socially that I spend my liferaising money to the extent that, you know, my
university, I went to Yale and I was an athletethere and we're building out the Yale Women's
Athletic Network.
And I said, I'll do anything for this groupexcept fundraise because I spend my entire life
fundraising and then they said, Oh, thank you.
We'll put you down for ahead of fundraising.

(07:07):
Was like, Wait, what?
Yeah, I mean, is a tool.
It's a skill that's important because it allowsfor the deployment of capital into things that
are productive for society.
I think on the investment banking and privateequity side, I sort of learned early in my
career the fundamentals of finance and alsojust of being a professional and a

(07:31):
businesswoman.
I was a history major in college, so thatfoundational experience was very important for
me.
And then in my business, fundraising is justreal lifeblood, got to manage cash and pay the
bills as an entrepreneur, so raised a lot ofmoney there.
It was about seven rounds of financing from theseed round through a series C plus and that

(07:56):
enabled us to grow the business, buy othercompanies, consolidate the industry, drive best
in class growth and then in politics you raisea lot of money as well unfortunately that's
still our political system so spend a lot of mytime doing that and then the funds I'm working
with, two of the funds are now out raisingmoney, Impact Venture Capital where I'm a

(08:20):
venture partner which is an artificialintelligence focused fund based in California.
We invest across The US but we are based inCalifornia and we are currently raising a
$100,000,000 fund too and I also advise a fundbased in The UK called Eight Dimensions
Ventures which is a health and wellness focusedfund.

(08:43):
We call ourselves ESG plus plus because weapply the Eight Dimensions framework, which is
a scientific methodology that looks at wellnessof people and planet to score our investment
opportunities.
So top venture returns, but ensuring that theinvestments we do also do good for people and
planet.
So

(09:03):
those themes are really prevalent.
I think in order to raise money or in order tobuild a business or in order to bring people
together behind you in a campaign or as anentrepreneur, you do need to be able to tell a
story to show passion to excite people becausewhether it's a startup or it is a campaign,

(09:25):
it's a lot of work.
Often you're paid in other ways than a bigglossy cash salary and that is a critical,
critical skill and I often joked in my campaignlike it literally was like another startup.
Mean, so many of the activities were the sameas starting a business and then raising funds

(09:46):
even though I'm more operating on the part timeadvisory right now, it's still another
entrepreneurial experience.
Any advice you have for first time fundmanagers to build relationships with LPs?
I think we can both agree.
And I always say this, too.
I think sales is the most important skill.

(10:11):
Find Whether a life partner, whether you'retrying to get a job offer and be the best
candidate, I always believe sales is superimportant.
But we've been talking about kind of theseemerging managers coming in and then people
that are on fund too.
What are some tips that you would give kind oflooking back on just fundraising as a whole,
maybe in general as an entrepreneur?

(10:33):
And then what are the differences that you'veseen on the fund side with fundraising and just
kind of really building relationships with LPs?
Yeah, that's a great question.
I mean, it's really interesting and good toanswer your question directly, but just a
slight tangent.
I spend a lot of my time on the advisory side,and this is both through the funds I work with

(10:55):
and then on the direct side, working withentrepreneurs who often have a great idea, a
great technology and capital behind it.
If we look at the world today, there's a lot ofcapital and there's a lot of great ideas and
there's a lot of great entrepreneurs.
I think the companies that succeed reallyfigure out how to take those things and build a

(11:16):
go to market and a growth plan.
Who buys it?
Who's our ideal customer?
What's the staging of this?
How do we fund this through the journey?
How do we set the milestones to drive theinvestment conversation.
That is actually the same for funds, There's alot of people raising funds, there's a lot of
people with great ideas, great theses for theirfunds, There's not a lot of people that know

(11:39):
exactly how to position their fund, how toarticulate that in the market, have a plan,
execute that, and then ultimately bring in thecapital and close the funds.
So the advisory work that I do now really hitson those two areas.
It was my expertise as an entrepreneur.

(12:00):
I led all of the sales in our business and thego to market growth fundraising, strategic
activities.
My co founder was leading our product andengineering and operational organizations.
So that I think is just an absolutely criticalskill, whether you are raising a fund or you

(12:21):
are building a company.
And what I find so interesting is I have somany companies that come to me asking to
contribute that expertise.
And I also have so many funds that come to mesaying, Oh my gosh, we just put all this money
into all these companies.
We need a go to market plan, which is aninteresting question of chicken or egg.

(12:45):
So that I I just want to hit on that becausethat's what I'm seeing so prevalently in the
market today.
I think with respect to building thoserelationships, relationship building,
stakeholder management, sales has a lot ofthemes, whether you're an investment banker,
you're a politician, you're an entrepreneur anddoing enterprise sales, or you're a GP raising

(13:11):
a fund.
And I think it starts with, this is going tosound very basic, but it starts with research.
Like, am I talking to the right people?
What have they done in the past?
Why would they care about this, etc?
Then it goes with building a relationship.
You can't just pick up the phone and asksomeone for money.

(13:33):
I always advocate a direct introduction,whether you're a CEO or raising a fund, my
experience has been it's incredibly rare that acold outreach results in anything.
It's a direct introduction, it's meetingsomeone at a conference and nurturing that
relationship or through an existing network,it's spending a lot of time on your LinkedIn
feed and figuring out who knows whom and whocan make that introduction.

(13:55):
And then I think it really is down to having acompelling thesis for your fund that
differentiates you in what is very much acrowded marketplace today of people rising
funds and then down to back to that point ofhow do you then position that idea, how do you
make the materials, how do you articulate that,how do you drive the process from an execution

(14:17):
and data management perspective And all ofthose things contribute to successful
fundraising and incidentally also successful goto market plans and sales and any other aspect
of a business, whether it's at the seed stageor the theory seed stage.
Any best practices for the layers of thecollateral and then the follow-up?

(14:42):
Because I've spoken to a lot of people thathave been in our emerging manager program and
obviously sometimes you start with like a onecheater, maybe you have an abbreviated deck,
then you have a detailed deck, you have adiligence deck, and then there's a cadence for
kind of like follow-up and finding interest.
So any tips that you give your clients as faras kind of the cadence and maybe the high level

(15:08):
layers of information because you obviouslydon't want to give them the whole data room the
first day.
You want to give them maybe a teaser, onesheeter.
I guess the cadence that I expressed with justthose different layers, that resonate well with
some of your strategies that you'verecommended?
Or are there other ideas that you have as faras just kind of providing the materials?

(15:30):
Yeah, from a materials perspective, I thinkit's critical to have really three things.
The teaser.
So it can be a one or a two pager, butsomething that can capture people's attention
and as I say, get them on the phone.
People wanna to default to email, people arebusy, get them on Zoom to get the full story to

(15:53):
build the relationship or get them, now thatthings are opening up, more get them to a
coffee, right?
You can
forge that connection.
So that's really the purpose of the teaser.
And then the second thing is a deck.
I very much advocate for doing the work to makeyour deck as concise and clear as possible and

(16:15):
then having a lot of supporting information inthe appendix.
Most people should get it in advance of thefirst meeting for a pre read.
Most people are very busy.
Most people aren't going to flip through 15 or20 slides.
The best practice is 10 to 15, and then you canreference a lot of data or a lot of supporting
information in the appendix.

(16:36):
And then the third, and I think the deck is themost important piece of this, really doing the
work on that.
And then the third piece, which again is themost important, so I probably said that
incorrectly, but the deck is more importantthan the teaser.
Then you have the data room and that is all ofthe information about the fund, the fund model,
the bios of the GPs in more detail, informationon prior investments if that exists or what's

(17:02):
in the pipeline if it's a newer fund andeverything that goes around that so that an
incoming LP can get confidence in the GPs andthe quality of thinking and materials and get
confidence through their due diligence inmaking an allocation to the fund.
But it's really important, I think, to do thework in advance of those things, refining the

(17:27):
thesis of the fund.
I think that this is often overlooked in thismarket.
I mean, there are so many people raising fundsthat sort of go like this.
The startup space is really hot.
I've been a great finance person or I've beenan operator.
I'm going to raise a fund.
And that just isn't good enough in a marketwhere so many people are competing for capital

(17:48):
and so many existing funds are pulling up theirtimelines for raising new funds.
So I think having a thesis, whether it is likein the case of Impact Venture Capital, where
I'm a venture partner, our thesis is AI isgoing to transform the world, it's already
doing that and applying it to financehealthcare and cyber security is an area where

(18:14):
we can build really big companies and generateoutsized returns for our LPs.
Like that's a very cogent focused thesis.
I do an emerging technology tied to specificindustries.
In the case of Eight Dimensions Ventures, it'sthe health and wellness industry is a
$4,500,000,000,000 industry.
It's three times the global pharmaceuticalmarket and investing in health and wellness

(18:37):
will do good for people and planet.
Big businesses do good.
And so developing that and then making thematerials that position that I think is really
critical in a market in particular wherethere's competition for capital.
I've got another question for you.
So just kind of a minor question.

(18:57):
This is more around etiquette And I'm onlybringing it up because it came up in our
accelerator, in our emerging manageraccelerator.
So I give everybody my link to Calendly, likeeven LPs.
And I love it because I magically see thecalendar show up.
So I don't really think too much of a formalityabout it.
But I've seen a few emerging managers actuallyhandle scheduling with LPs a little

(19:20):
differently.
They'll actually just manually try to find thetimes that work for LPs and they'll kind of
just manually do it on the calendar I don'tknow what your thoughts are on that.
Is it bad to just give everybody your Calendly?
Because it kind of is an inconvenience when yougot to use somebody else's Calendly, right?
Because you got to like match up their calendarwith yours.

(19:42):
So any thoughts on that or does it matter?
Just wanted your opinion.
It's an interesting question.
It's funny that you bring this up.
I was just thinking about this yesterday with abusiness that I advised that does enterprise
sales that is operating in this way.
To be honest, I've never done that.
I am, I guess, maybe old school.
It it does take a phenomenal amount of time toschedule stuff.

(20:04):
I feel
like I've been in
my day doing scheduling and miss my incredibleassistant, Sophia, who was my right hand and
dearest friend for many, many years at Topiaso, so much every day.
But my viewpoint is everyone is looking for areason to say no.
I mean, that's, I think the lens, it's a littlebit of a pessimistic lens, but that's the lens

(20:28):
that you have to look at sales, politicalfundraising, fund fundraising with.
People are busy, A, very, very busy, andthey're looking for a reason to say no to you.
No, I don't want to take a meeting.
No, I'm not going to invest in your fund.
So your job as someone raising money or doingsales, raising a fund is to make it as easy as

(20:51):
possible for them to say yes.
So not give them any out, any canned statementthat they can say back to you.
So my perspective is that I would personallynot use Calendly or not advise people to
because I think that that just creates abarrier to your point, they have to go in.

(21:11):
They're clicking out.
The burden of scheduling, you know, rather thanjust saying copying Sally and she'll organize
it or copying my assistant Joe and he'llorganize And I think that that's just one thing
to be cognizant of.
Also, there is a little bit of a generationalaspect to this perhaps, so I think depending on

(21:36):
who you're talking to, it may be more or lessaccepted, but I just assume that going with
what people are comfortable with in the massesis a more seamless course of action.
This may have changed, you know, people aregetting more adopted or adopting Calendly more,

(21:59):
getting more comfortable with it, but I just,again, always try to reduce barriers and make
things as easy as possible and as sort ofstandard operating procedure as possible for
LPs.
And if you don't have an assistant, I guessmaybe just in clear bullets, just list your
time slots that are available and ask.
And I know it's so simple to like, but I'mmaking it more complicated, but is it, when you

(22:23):
do it, let's say you don't have an assistant,right?
So you just ask them for the time slots thatthey're available for and then you just kind of
book a time or do you give them your time slotsas well?
What I typically do is say, like to schedule acall, I'm available these times next week.
And then Monday, x to y eastern time, Tuesday,x to y, and just go down and say, is there a

(22:49):
time that works for you?
I mean, that's one way to do it.
The other way is just to depending on how fullyour calendar is or how much of a priority the
person you're emailing with is to just say,please suggest sometimes that work for you and
then you are the one that fits that in.
Yeah, think the earlier one is less burdensomefor them because they don't have to hold those

(23:14):
spots.
So I think they can just kind of look at theircalendar really quickly and respond in the
email versus Calendly like noted earlier,you're kind of clicking out from the
experience.
And I know we're spending too much time onthis, but it's these minute details that I
think people pick up on.
And it's something that I've been recentlynoticing.

(23:34):
So thanks for sharing your opinion on that.
Sure.
I got another question switching gears on theentrepreneurial side because I'm thinking about
this too.
I've been studying sales and enterprise, B2Bsales specifically.
So the question for you is, when is a good timeto maybe hire your first sales rep and what are

(23:57):
some things that you would recommend as far askind of choosing the talent, testing them to
make sure they're a good fit?
Any thoughts on that as far as just pickingsales talent and the timing of when you should?
Is there a certain revenue number that youshould aim for to kind of hire like a full time
sales rep versus a part time sales rep?

(24:17):
Any thoughts on that?
It's a great question.
And I am smiling because I spent the vastmajority of my life doing enterprise sales
myself and then building up a Salesforce.
So I have many thoughts on that.
And it's funny, because when I stepped down asCEO of Topia, I was like, wow, I never want to
do enterprise sales again, you know, likebegging at the end of the quarter, some large

(24:40):
company to sign a contract.
And then when I started my campaign, I didn'treally realize how similar the dynamics were,
except you're just begging an individual tomake their contribution by the end of the
quarter, and then I just realized, oh, you'regoing to be doing this for a while in different
domains.
So when you start a company, I believe thefounder should be doing the majority of sales

(25:07):
in the early years, principally up to about amillion dollars of ARR, annual recurring
revenue.
That varies a little bit depending on theprofile of the founder, right?
If the founder is the CTO and very technicallyoriented, there may be a co founder who's doing

(25:27):
the go to market side, or there may be a VP ofsales or a senior level person that's been an
early hire that can drive the go to market sidewhile the founder is building the product, but
for the most part the founder needs to beinvolved and be the chief salesperson for the
beginning phase.
I would say that's up to a million ARR give ortake and up to a seed round.

(25:51):
It's critical to know the market.
You get really important feedback in the earlydays that goes back into the product.
You can then credibly go to investors and say,have product market fit.
I've been doing the sales, here's what I'veheard, here's how I've iterated, here's where
we are and therefore fund my seed round.

(26:13):
So that's kind of my viewpoint on that.
The other side of this is then you start tohire account executives or a VP or director or
whatever it is that you decide to hire firstand to some extent I think that depends on what
else the founder needs to do, how senior thathire is, how involved the founder is going to

(26:38):
stay, what their skill sets are, whether yousort of hire account executives first to get to
two or three of them before then hiring a VP,or you hire the VP and say, go hire all of the
account executives.
I hired two account executives first, fairlyjunior, and then hired a VP and said, okay, go
own this, because there is a point where youshould be doing an interview, but there is a

(27:03):
point where you can't be building a salesorganization.
Yeah.
Is LinkedIn a good place to find talent?
Just create a job posting?
Yeah, think LinkedIn is a good place.
I mean, I would also just be, again, consciousof the competition in the market.
It's always hard to hire recruiters becauseit's a big cost early on, etcetera, but

(27:26):
enterprise sales productivity models work suchthat any day that you delay your hiring
massively impacts your revenue model, so Ithink balancing the cost that you would pay a
recruiter versus the hours you would spend onLinkedIn and the risk of being off of your
revenue plan from a productivity model is animportant conversation.

(27:47):
So that's one thing.
I think in terms of profile early on, the mostimportant thing is that the salespeople you
hire will do lead generation and pipelinebuilding as well as sales and are motivated by
that and are motivated by a very big territory.
There are salespeople that expect to, and Iwould say the majority of them, expect to start

(28:11):
with a pipeline, expect to have a salesdevelopment rep or some kind of inbound
marketing handing them leads and expect to havea defined territory.
That is one type of salesperson.
That type of salesperson does not succeed in anearly stage business.
You need people who will hustle, you needpeople that are excited by having a blank

(28:35):
canvas and literally building things inSalesforce as they go building their own
pipeline, cold calling are humble enough to dothe work that an SDR may be doing in a later
stage business and be a part of sort ofbuilding that up and nimble enough to sort of

(28:56):
grow through the company.
There are salespeople that are really good inthe early days that don't like that later stage
because they like territories and blankcanvases and get excited by the demand gen.
There are salespeople that hate the early daysand like later, and then there are those that
can go through the whole journey and sort of benimble through the phases of the business.

(29:18):
So that I think that is the most importantthing to diligence in the early interviewing.
I can't tell you the number of salespeople Ihired early on who could not do.
The lead gen side hated it, hated not having apipeline, hated cold calling and they were good
salespeople but they were just more appropriatefor a stage where there was more pipeline, more

(29:42):
infrastructure.
Yeah, I mean there's the closer and thenthere's the pipeline.
So when you have somebody that's doing the Theycan do both.
My judgment, and this is me being new to sales,but my judgment is maybe the people that are
more junior, they're not as good sales reps andthey're not closers.

(30:03):
But what you're saying is if you find the rightperson, there could be people if you motivate
them and they love your mission, they couldactually do both.
But does that take away from their time ofclosing?
Essentially, you want to have 10 meetings a dayand just out of those 10, maybe close two or
three of them.
What's kind of the split?

(30:28):
Do they budget maybe a couple of hours a weekto build a pipeline?
Or is it half of the week that it takes time todo that?
Or what have you seen as far as kind of thebreakout when you have those roles that do kind
of the full stack?
And then does that save some money on marketingas well?
Or do you still need marketing to complementthat?

(30:49):
I think it depends on the stage of the businessand the type of business, whether you're doing
more mid market SME type sales, which is highervelocity, lower deal sizes, or you're doing
true enterprise $200,000 ASP plus longer salescycles, more stakeholder management, more
nurturing.

(31:11):
Personally ascribe to the philosophy that everyaccount executive up till the business is like
50,000,060 million dollars ARR should be doinga portion of their time in lead generation.
I do not believe in salespeople that sit backand wait for things to come to them and only
close.
There are people who do believe in that.

(31:32):
It's a little bit more of an school viewpoint.
I believe in people with heart, with hustle,that are builders, especially in a startup and
I think that culture is really important.
Those percentages shift through the years, soyour first account executive could potentially
be spending for the first six months greaterthan 50% of their time, 50%, 60%, 70% of their

(31:56):
time building a pipeline, doing demandgeneration, etcetera, because that's what's
required when you walk in with no pipeline.
But I think in a steady state, we always saidthey should be spending 30% of their time doing
pipeline generation and 70% of their time lateron in the cycle nurturing and closing.

(32:18):
The other model as you get larger, and it'simportant to build this early on, is you do
need to build concurrent to hiring accountexecutives who can do demand and generation or
lead generation in addition to the actual salescycle is you need to start hiring some sales
development reps.

(32:39):
These are people out of college typically whoare hitting the phones, scheduling meetings in
certain businesses.
They should be able to get through the demophase.
In certain businesses they'll grow to be ableto sell deals under $100,000 That was sort of
our barometer also or sort of the career pathis to get to that.

(33:01):
But as you build that up, eventually you'llpair an account executive with one or two SDRs
who are feeding them leads in addition to theown demand generation that they are doing but
in Etopia when I was CEO, we never acceptedthat as account executive regardless of how

(33:24):
senior he or she was, was just going to sitthere and wait for the SDR to give them leads.
They each had a map of target accounts, theSDRs were a little bit easier to navigate, but
the account executive would still have a listof like twenty, thirty target accounts.
I mean, these would be the largest businesseson the planet and they would need to figure out

(33:45):
how to penetrate them, but they would still bedoing that.
And walk me through, if you can, if you'reallowed to, maybe your interview process.
So is it like Jordan Belfort where it's like,hey, sell me this pen or is it what do you
expect them to do when you're trying to hiretalent?
Do they do kind of a practice pitch?

(34:06):
Is it like a paper that they write or somethinglike that?
But I guess what are some ways that you canidentify that talent and just evaluate if
they're a good hire or not?
Well, first of all, there's multipleinterviews.
So I think there's different screening orqualifying questions at different stages in the
interview process.

(34:29):
But I think thematically, the sort of threestages are, does this person have the sort of
skills and experience that this role requires?
That's like basic level.
What have they done in the past?
How do they think about selling?
How do they approach pipeline building?

(34:49):
How do they approach pipeline management?
How do they approach navigating if it's anenterprise business, navigating an enterprise
account and doing stakeholder management?
What sales processes have they used in thepast?
How do they approach qualifying leads or not?
Is there a methodology they use like MedPick orone of those sales methodologies?

(35:10):
So that's just sort of like what level ofsalesperson are they?
And a lot of that can be taught, but justtrying to get a sense of sort of level and
where they are on that journey.
Then I think the second phase is what can't betaught, which is the heart and the hustle.
And those are more behavioral or sort of valuestype questions.

(35:34):
I always liked the question of what's thehardest thing you've ever done and why?
Because sales is hard, A lot of it reallysucks.
There's just no other way to say it, especiallyin the early days.
You're calling people that disproportionatelysay no.
I mean, fundraising is a thing, right?
You're calling people that disproportionatelysay no to you.

(35:54):
Some of them do that in nice ways, some of themdo that in not a very nice way, you're pounding
the pavement metaphorically on and on and on,even when you might be working a big deal and
excited about it, you get to the end andsomeone says no, and then you eventually get a
great deal on the door.
This is not for the faint of heart and you needto test for grit and tenacity and how are they

(36:20):
going to handle it when the ninety ninth personsays in a really rude way, no.
Are they going to say and how do they managethat as a person?
One of the frameworks that I often use, which Iactually read years ago in a Daniel Pink book
about a, he was like a vacuum salesman that hehad profiled in the book that is this ratio of

(36:42):
three good for one bad.
So you know, and these are not like big things,but you know, you're talking to someone that
says no to you, like say, give someone acompliment in the office, hold the door open
for someone, like send your mother a nice textmessage, three things for every one difficult
conversation that as like a human keep you upand happy.

(37:04):
So just getting a sense of how they navigatedifficult situations and their values is the
second phase.
And then the third is, and by that point theyshould know about the business, we always have
people make a presentation and do a mock salesmeeting.
And with that, you can test a few things, youcan test presentation skills and communication

(37:29):
skills, you can test how much they care, likehow much effort they put into the presentation,
but you also can test how much they've listenedthrough the course of what at that point will
be many interviews about what the business doesand whether they can articulate that back to
you.
Sure.
And I mean, obviously if they got the job, Ialways think being the best candidate in an

(37:55):
interview process is a sale too.
So I mean, just that whole package of delivery.
The follow-up, you can even observe thefollow-up when they follow-up about the
opportunity, how they package that messaging,all that stuff too.
So that's all really helpful feedback.
I liked your comment about just offsetting thenegativity with a couple positive statements as

(38:16):
well.
So it was really helpful.
And then I'd say the final thing with sales isreally just communication and nurturing.
So with nurturing, what are some tools that youthink people should have in their back pocket?
Is it blogs as well?
Like, should they share some literature or isit really just kind of a follow-up?

(38:38):
It's probably a balance I'm assuming with beingtoo aggressive versus just slowly checking in.
You don't want to check-in with them like threetimes in the same week, but maybe once a week
or something like that.
I'm not sure for like B2B sales.
Are there any cadences or patterns that you'veseen for nurturing and follow-up?

(38:59):
Well, it's where marketing and sales need towork closely together.
So it's a very difficult and somewhat unfairsituation for a salesperson to be in where the
only thing they have to say all the time in thecycle is, hey, just checking in, what are the
next steps?
Or, you know, have you reviewed yet?
That is not going to be successful.

(39:20):
So this is where, depending on the stage of thebusiness, the founder and the marketing
department need to be creating collateralmaterials, events, updates that the salesperson
can then share through to the prospect,inviting them to webinars that the company may

(39:41):
be hosting, sharing news, press releases offunding rounds, press releases of product
launches, sharing updates on new products thathave shipped.
In the case of a SaaS platform that are goingto be pushed live, but just giving the prospect
a heads up or sharing the release notes thatmight be published from a public viewing

(40:03):
perspective, sharing white papers or blog postswithin the business, the salesperson is going
be writing any of that stuff, so you needsomeone early on in marketing that can be
producing content to surround the earlysalespeople.
My recommendation is to hire a marketingmanager level person that is a jack of all

(40:27):
trades.
We have this exceptional one named Sean Atopia,I think he's even still there, who was just
integral to growing our US business and couldwrite blog posts, write product notes, write
white papers, write a lot of different thingsand work very closely with the account

(40:49):
executives.
That's really what you need and then you growthe marketing department in tandem with the
business growth going forward.
Yeah, no, it's a good point.
Because I mean, I think there's a couple ofdifferent flavors of marketing.
There's product marketing, there's brandmarketing, and then the content marketing is a
big piece.
So I think to your point, having somebody thatcan kind of do a lot of those things in the

(41:11):
beginning and be scrappy is helpful.
And then did you guys ever hire like a brandmarketing person?
Because I feel like that's probably more for amature business where they really wanna rethink
the strategy, they wanna do a rebrand, if theywanna really rethink the logo.
What are your thoughts on how that falls intokind of the marketing stack?

(41:31):
Yeah, mean, it's an important aspect of it.
And it depends on, to some extent, who thefounder is and the different stages of the
business when you might want to hire that.
But I think the important fundamental thing isthat a brand marketer is very different from a
demand generation marketer.

(41:51):
I personally believe that marketing should beoriented towards revenue in the early days and
that the marketing people that are hired in theearly days should be very closely aligned with
sales to drive pipeline generation.
Remember, you need really a minimum of 3xpipeline coverage to hit your number.

(42:16):
That's a lot.
You're not going to get there with just SDRs,just some account executives with Hustle and
Hart who are doing their own pipelinegeneration or just marketing, doing demand
generation, all those things.
And the magic of the early business is gettingthat machine working.
That's what any series A investor is going tolook for.
It's like, where are you on that journey?

(42:38):
And then any Series B investor is going to lookfor, okay, do the economics of that work, do
the economics of the interplay between demandgeneration, the cost of sales, the size of
those sales and the term of those contracts, dothey work?
Does the cost of acquisition and the long termvalue work?

(43:00):
And if that machine works, then you just putmore money into it and it scales.
So that I think, and that is not an easy orshort process, right?
Getting that machine working, buying themilestones to the fundraising is a big process,
right?
So my belief is that the important thing is tofocus on that in the early days, and then once

(43:24):
you get the machine working, then you can say,okay, let's rebrand or let's focus on the
branding aspect.
That's not to say that you can have like reallyimmature branding or bad materials, so you know
you need someone that can do that, butcorporate marketing or corporate branding, I
think can come a little bit later.
There are some caveats to this,
depending on

(43:44):
the business, but I think that thematically,that's generally the way to look at it.
And then when it comes to growth marketing, isthat also a function that the jack of all
trades would manage to like the paidacquisition as well?
Or do you think that should be a dedicatedresource?
So when I say growth or demand generation,that's what I mean.

(44:06):
I think you're calling it growth marketing.
Just call it demand generation.
Demand generation, yeah.
There's different aspects to that.
I mean, I think the first hire should be ableto do sort of a jack of all trades growth
marketer, demand generation marketer, you cancall it everyone.
And then content also along But with that as

(44:27):
that person should be able to create content tounderstand Salesforce and work with the sales
leadership or the whom founder, whomever'sdoing it at that point to sort of drive some of
the pipeline metrics, etcetera.
Demand generation is a particular skill, ittends to be very quantitative, it tends to be

(44:47):
very systems driven today, eventually are goingto need to hire someone who's familiar with
HubSpot or Marketo or whomever you're using,set up all of those systems, can look at the
metrics and really get the machine going againin the terms of the true pipeline generation,

(45:10):
demand generation machine.
And there is going to then be a content focusedmarketer that works with that person to create
the materials to put into that machine, right?
But you've got to get to that point.
So in the early days, the jack of all tradesmarketers should be able to sort of touch on
all of those things, right?

(45:31):
Well, get basically up to speed with HubSpot orMail chimp or Constant Contact or whatever
you're using in the early days, sort ofunderstand or have the capability to understand
the metrics side of the business, buteventually those two things are going to split
so that you can get a really sophisticated andproper demand generation machine going.

(45:54):
That's great.
Well, thank you so much.
I know we're out of time here.
Look, this was amazing.
Think just your insights into sales and tyingthat into fundraising as emerging managers or
people on Fund two is really helpful.
So thanks for all that wisdom and all yourinsights on entrepreneurship and being a fund
manager.

(46:16):
Always ask this at the end.
I always ask for just a piece of life advicethat you've carried with you that you'd like to
share with us or anything that you have kind oflooking back.
It could be a quote, it could be just a pieceof advice from a mentor.
Would love that.
And then if anybody has any final questions,I'll shout those out as well.
But anything that you'd like to leave us withwould be great.

(46:38):
Oh, gosh, he threw that at me.
Let me think about that.
One thing that a coach in the past or afacilitator in the past said, and then another
CEO who happens to be a female CEO of one ofthe largest energy public companies in America,

(47:03):
she was incredible, also encouraged me to see,is the notion that all people and circumstances
are your allies.
So I think we can, fundraising or in any sortof business, sometimes come at things with a
defensive posture, sometimes take feedback ortake no's or take whatever it is negatively,

(47:29):
but to be able to just reframe that and say,okay, what can I learn from this?
And this person is not out to get me in like apersonal context, but this person is giving me
a gift that I can learn from and that I can useto further my goals is a really important
principle.
That's really helpful and I think part of salestoo, was probably implied is just having a

(47:55):
positive attitude.
So I think this also piggybacks off of theother nugget that you gave us earlier.
If you get a no, try to do three nice things.
So I think that positivity, especially in salesand fundraising is super important.
And that one really, really, really works.

(48:15):
If you're feeling super down, just pick up thephone and call an old friend and just say, hey,
I was just thinking about you and I wanted totell you.
There's something about, like, we receivepositivity back from people as humans that
really reframes your perspective.
Or even just like, when you're going to lunchor pick up your smoothie, like, say thank you

(48:36):
so much.
I hope you have a nice day to the person at thecatch register.
Like most people don't say that they just likegrab their smoothie and tap their card and run.
And people are really appreciative of that.
Sure.
That's really helpful.
So we got one question.
Do you have like maybe thirty seconds for areally quick one?
So Deji just wants any tips on incentivizingpipeline generators or deal generators.

(48:59):
So I guess, obviously, commission.
Any tips on just the commission split or justcompensation to keep them still hungry and
excited.
And one tip that I will say, I learned this ina video that I watched recently.
Some people say to hire two sales reps at thesame time so that there's always a competitive

(49:20):
spirit.
But anything else that you have, any nuggets onyour years looking back and building a sales
team to incentivize them?
So I think it depends on what you're talkingabout.
I mean, for SDRs, they should typically be paidon meetings booked.
And then for account executives, they should bepaid on revenue generated.

(49:45):
And for demand generation people, they shouldhave a pipeline, marketing contributed pipeline
target that they're paid on.
I am not a fan.
You may hear different views from other people,but I am not a fan of having a very complex set
of metrics like account executive, this muchpipeline generation, this much at this stage,

(50:05):
this much business close.
The reality is they're not closing business ifthey're not generating a pipeline.
So that is for me, I just keep the targetssuper simple, like what are we trying to get
to?
We don't really care how you close business.
Maybe you don't need 3x pipeline coverage.
You probably do, especially when you get toscale, but in the early days, you may not when

(50:26):
there's no one else in the market.
So I don't really care how you get there, justclose the business, hit the number, and then if
they exceed the number, then having really,really aggressive accelerators.
I learned the sales methodology of really,really paying people for performance, like
outsized accelerators.

(50:47):
It can be expensive for the business, but ifyou have salespeople in your business making a
million dollars a year off of a 200 ks basesalary, like everyone wants to work at your
business, that person's going and telling allhis buddies or her friends that they're doing
really well.
It goes through having very, very aggressiveaccelerators and it does pay dividends.

(51:10):
So when you say accelerators, just be generouswith their commission payouts.
Is that what you're saying?
Yeah, mean, in the enterprise side, the typicalstructure is 50% of the comp is base and 50% is
variable tied to hitting their targets, theirquotas.
Once they hit the quota and start exceeding it,then having a pretty exponential increase in

(51:33):
the comp that they can make past that tied tostages at which they accelerate it.
Yeah, and to your point, that's important, too,because to your point, in the big cities like
New York and San Francisco, there's anothergreat company right across the street that'll
pay them like $20 more.
So being generous will kind of keep them there.

(51:55):
And it's going to be more expensive for you tohave to hire a new person and go through the
whole process again.
Yeah, mean, most people are gonna negotiate fora higher comp base and then expect another 50%
of that in variable and then somewhat take theaccelerators with a grain of salt.
I mean, will be different in a later stagebusiness, but in the early days when there's no

(52:18):
proof points, that's in my experience how mostpeople evaluate offers where I believe you want
to get to as an entrepreneur or a CEO or aboard member is the lowest.
And I don't want say this from a negativeperspective because people should be paid
fairly, but the most reasonable base salarywith a very, very aggressive outperformance

(52:43):
plan.
Sure.
That was really helpful.
Well, hey, Brian, thanks so much for beinggenerous with your time and really good
spending time with you.
And I hope you have a great week and hope tocatch up soon in person at some point.
Thank you so much.
You have a very good day, Joel.
And thank you so much for having me on.
Thank you.
If anyone wants to follow-up, you can follow meon Twitter Brynn Speak, connect me on LinkedIn,

(53:09):
BrynKennedy or reach me on Bryn.
Kennedygmail dot com.
Great.
Have a good one.
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