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May 26, 2025 45 mins

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On todays episode, we talk with Rick Collins, Vice President of Demand Generation at ConnectWise, to explore his unconventional yet inspiring journey from IT to marketing operations and ultimately into executive marketing leadership. Rick shares how he transitioned from managing systems to driving demand, the pivotal career moments that shaped his path, and the leadership lessons he’s learned along the way. Whether you're early in your marketing ops career or looking to break into leadership, this conversation is packed with valuable takeaways on navigating transitions, building trust, and expanding your influence.

Tune in to hear:

  • Rick’s unique career path from IT and QA into marketing operations and eventually to a VP role in demand generation.
  • How to leverage technical and relational skills to create career mobility within marketing.
  • The importance of curiosity, relationship-building, and challenging assumptions—internally and externally—for leadership growth.
  • Insights into managing through organizational change, including private equity acquisitions and team restructuring.
  • Tips on transitioning from managing ICs to managing other managers, including the importance of communication, presentation skills, and executive alignment.

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Episode Transcript

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Speaker 1 (00:01):
Hello everyone, welcome to another episode of
OpsCast brought to you byMarketingOpscom, powered by all
the MoPros out there.
I'm your host, michael Hartman,flying solo as Mike is right in
the thick of Spring Fling 2025,the inaugural one, and then
Naomi's tied up and so we aregoing to power through.
So joining me today to shareabout his career journey is Rick

(00:23):
Collins.
Rick is currently VicePresident of Demand Generation
at ConnectWise.
Rick started his career in IT,eventually as the head of IT CRM
and more with United Way ofCentral Ohio.
When he joined ConnectWise, hepivoted to a role as a Senior
Marketing Systems Analyst.
Since then, he has moved intoleadership roles within
marketing operations and theninto his current role of vice

(00:44):
president of demand generation.
So, rick, thanks for joining metoday.

Speaker 2 (00:47):
No, thanks for having me.

Speaker 1 (00:49):
So this is going to be fun.
So we talked before and I lookforward to sharing the story
with everybody who's listeningbecause we want to get into this
conversation.
But I think a lot of what wasreally intriguing and what I
think I reached out to you to beon is I think it was
interesting that your path wentthrough marketing operations

(01:09):
into a more general marketingleadership role, and I think a
lot of people are alwaysthinking about, like, if I'm in
marketing ops, what's the nextstep and what's the next step of
that?
And I think it hasn't alwaysbeen clear and sometimes there
hasn't been a lot of belief thatyou could move into more of a
general marketing leadership one.
So I think that's part of why Iwas curious.

(01:30):
So why don't you maybe talkthrough your career I did a very
high level right.
Talk through your career in alittle more detail.
Know that one of the things I'malways interested in is if
there are like pivotal momentsor decisions or people that had
maybe an outsized impact in youknow the trajectory and
direction of your career yeah um, no happy to uh and uh yeah um.

Speaker 2 (01:55):
Is marketing ops marketing right?
Is that where we're going to go?

Speaker 1 (01:59):
down.
Oh no, no, we we've coveredthat.
But yeah, if you want to gothere, we can no, I'm kidding,
I'm kidding, um, I've seen themall.

Speaker 2 (02:07):
Uh, they've been fun dialogue, uh, no, I, you know I
was I was never.
I never saw myself kind ofgoing down into an it path, even
though most of my career waskind of down it I was.
I was more of a.
It was an internationalbusiness and spanish major.
At college I thought I wasgoing to be, I don't know, an
importer, exporter or somethingrelated to like business within

(02:27):
Latin America and, uh, doingsomething related to that.
Really didn't have it mappedout.
It was just kind of a.
You know an aspect of where Ithought I'd go.
And when I graduated collegemany, many years ago, um, I uh
started to try to find out wheream I going to land?
What is this going to look like?
I just happened to find myselfin IT and was pretty good at it.

(02:48):
I picked up systems really well.
I was able to understandapplications.
I was in QA is where I started,and so even what you're talking
about, what pivotal momentsthat year and a half that I had
in a telco in QA is.
I was working directly withdevelopers, I was testing
systems, systems.
I was learning um automation.

(03:09):
I learned how to do lightcoding.
Um, I was that I didn't have acomputer, uh, at my house
growing up.
I wasn't one of those peoplewho was like super into it.
I just kind of picked it up.
I I guess it just fit for me,um, and so I kind of parlayed
that into my next role and I wasimplementing software for a
software company.
So I got kind of my first tasteof SaaS.

(03:31):
This is like the early 2000s.
It's a much different world,but it was a lot of moving from
mainframe computers to clientserver-based applications,
computers to client server-basedapplications.
And so I got into SQL andreally was kind of liaison
between the tech and business.
And so that's where I kind offound my niche.

(03:53):
Was I fit well, kind ofbalancing and understanding the
business world and being able towork with non-technical users
and people, people.
A lot of the people I wasworking with at that time in
that role was, uh, countygovernment, uh employees, and so
a lot of um, a lot of peoplehave never used a mouse before

(04:15):
uh and transitioning them from a, you know, green screen
mainframe computer.
Some of the listeners probablydon't even know what that is but
oh, I do, yeah, I'm sure you doright.
Uh, so they were going from hp3000, these old old school
mainframe, uh, green screenapplications, and moving them to
a client server basedapplication.
And so I was training them, Iwas implementing the software.
Um, I would have to remote intotheir machines, uh, at times,

(04:39):
and they'd have to.
You know, is the modem pluggedin?
Try this, it's all that kind ofstuff, um, and and really
that's just highlights kind ofthat um, that bridge that I kind
of served between the technicaland the non-technical, because
then I was working directly withthe developers.
Hey, here's what we're seeingon the ground, here's the areas
that we might need to do.
I was building the databases, um, we'd have a local copy of the

(04:59):
database, and so I would setthings up based on the
requirements of the the user, soit was a lot of that, which I
definitely took that into once Igot into a more marketing role
and kind of leveraging thatbusiness impact and
understanding the impact and theend user aspect of things, and
so when I got to.
United Way.

(05:19):
I was over IT, I had multipleroles throughout the software
company.
I was over IT, I had multipleroles throughout the software
company.
And then when I went to UnitedWay, it was really kind of a it
was sort of marketing ops beforewe knew what marketing ops was.
But it was a little more thanthat because it was kind of it
was a CIO essentially with anoutsourced IT company, a managed
service provider kind of tookcare of the day-to-day IT.

(05:42):
And I just looked at, you know,looked at holistically, but a
big part of it was building outum crm and marketing uh
automation platform and so washeavily involved with the, the
worldwide organization of unitedway, trying to build a, a
common um donor managementsystem powered by salesforce uh.
And so got very heavy on themarketing side, decided I wanted

(06:06):
to move to Tampa.
It was too cold in Ohio, I'm aBuckeye, and so decided my wife
and I were like let's go to thebeach and start over.
And so when I found ConnectWise, found a role there in
marketing ops didn't know whatmarketing ops was really, but
the way it was described, theway the role was described, it's

(06:26):
like, yeah, that's kind of me.
I remember talking to the CMOat the time.
He's like we're kind of lookingfor a unicorn, someone who
understands tech really well andcan dive into the systems and
the process but can understandthe users and work with the
business on sales and marketing,and I'm like, well, well, let's
kind of feel like that you'redescribing me um and so kind of

(06:47):
fit.
Well, uh, and and I saw a lotof upside there and so you know
I was, I was a one-man, uh,marketing ops person didn't mean
we didn't have those functions,some of the functions that
eventually came under me undermarketing ops we had email,
right, we had, uh, cms, uh andkind of the, the front end web
dev and that kind of stuff.
We had some project management,but this is like 2017.

(07:10):
So, marketing tech I don't knowwhat Scott Brinker's slide was.
It probably was not more than1,000 at that time.
It was small, so it just hadn'tbecome a reality.
But I think I joined at theright time time and it was kind
of the explosion and theformalization of marketing ops.
And so I, you know, proved myvalue pretty quickly and kind of

(07:33):
made the case.
I I'm the one who approachedthe CMO about formalizing
marketing ops into a team.
He, he, aligned with that and sowe started to kind of build
that out and build out a teamfrom there and we acquired
companies got acquired by pe, soa lot of things, uh, it's kind
of good timing as well as umjust the the landscape changing

(07:55):
so I guess I think it's a couplethings that so first, like
three things that came kind ofcaught my attention in that like
one.

Speaker 1 (08:02):
So first off, my wife .
We were talking about thisright before we got on.
She's involved with nonprofitsworld and so I am now, because
of that, becoming familiar withSalesforce's version for
nonprofits.
It's a lot of the same things,but there are certain things
that are different.
It's an interesting learningexperience, but it transfers

(08:25):
right.
So that's like another thing,right, like I can help.
I can still help her when she'strying to like, I need a report
that does this right, I canfind my way around.
Um, I think it's interestingthat you came out of college
without a like what would belike typical, like a computer
science or engineering typedegree, and you ended up in that
role.
It reminds me of when I firstgot out of college, because I

(08:47):
did, I came out of anengineering school and sort of
uh, something adjacent tocomputer science, and so I
started at price waterhouse inthe consulting practice, and one
of the things they did is theysent um new, new hires off to
learn like how to, how to codethe way they do it right, how to
do it projects.
And I remember in my cohort this, this one woman who really

(09:10):
stood out to me, who, like mostof us, had some sort of at least
experience with computers, andyada, yada, this one girl, she,
um, sorry, one woman, she was,had been a, she was a religion
major at Duke, and I rememberjust being like, oh, she is
going to struggle, but shedidn't, and it really sort of

(09:31):
changed my viewpoint.
Like that, I think there's thisjust because somebody's got on
paper right what looks likesomething that doesn't make me
make a match, like there areother characteristics are
important.
She knew how to think, she knewhow to learn, she had to ask
good questions, like all thosethings applied, and I suspect
you probably had something likethat as well, right?

Speaker 2 (09:51):
Yeah, you know, I think a lot of people in
marketing ops and in marketingin general is we talk about kind
of the curiosity, and I thinksomeone who is naturally curious
and who wants to go deeper andunderstand, I think that's.
I look for that when I'm hiringpeople, whether it's for
marketing ops or rev ops or ageneral marketing role in demand
gen.

(10:11):
I think that just sets peopleapart.
When they do that.
I think it can drive so muchinnovation and digging.
I definitely had that and Ilearned it at times, but I also
kind of had that.
It was a little bit that and Ium, I learned it, um, at times,
but I also kind of had that.
It was a little bit innate.
And so I remember, you know,early in my career, uh, going to
a developer and you know, acustomer had an issue and so,

(10:34):
hey, here's, here's the issue,that describing what's going on,
it's like, oh, you, you know,did you check this?
Uh, no, I didn't check that.
We need to check that.
Did you check this?
And so he's kind of giving melike, here's the way to solve,
to try to narrow down anddiagnose what's wrong, and so
it's almost like, all right, Ican do that.
So then I started to back intothings and then you know, if it

(10:54):
was a store procedure, fix andsequel, like all right, show me
how you did that.
And it's like not just taking.
I haven't heard a storyprocedure in so long, Wow, Going
way back right, I'm older thanI look.
But that was kind of what tookme down this path of I'm not
just going to wait for somebodyto answer it, I'm going to find

(11:15):
the solution myself and I'mgoing to learn how to do these
things.
And so I really started thatjourney early on in my career
and that kind of fueled me as I,that journey early on in my
career and I that kind of fueledme as, as I advanced up into
two different roles as well.

Speaker 1 (11:30):
So the.
So I said three, that's two.
Two.
The third thing that wasinteresting to me is the story
about how you ended up atconnect wise.
In that did you say it was theCEO or the CMO that that
described like what they werelooking for as a unicorn the CMO
, yeah.
So I think it's interestingthat, um, like what do you think
that?
What do you think happened thathelped him see that you even

(11:52):
though on again, on paper youdidn't look like you would
probably be a match, that thatgave him a confidence, that
would, that would work yeah,it's a good question, I think so
.

Speaker 2 (12:01):
I interviewed with man I feel like 10, 11 people
there.
It was a I remember goingthrough a barrage of interviews
and it was digital marketing.
It was their web developresource, their internal
development resources, all theirVPs of marketing him that.
There were a ton of differentaudiences that I was

(12:23):
interviewing with.

Speaker 1 (12:23):
That's a huge number.

Speaker 2 (12:25):
I know it was a lot of people.
Wow, it was, uh, it was anintense interview process, um,
and and I think they hadinterviewed I what I'm pretty
sure if they uh, if I rememberright, this was a while ago, it
was eight years ago, um, butthey had been through a ton of
people and every person theywould interview they were either
too technical and didn'tconnect with the business side,

(12:46):
or they weren't technical enoughand they at least from the
interview process, they feltlike they were kind of lacking
in one area too much that theydidn't think they could pull it
off.
And so I guess I blended thatmix pretty well I was able to
connect with the more dev heavyor IT technical resources and
then with the business side.
I was really able to connectwith the more dev-heavy or IT
technical resources and thenwith the business side.
It was really able to connectthere.

(13:07):
And so I think that heunderstood that and saw and said
I think this is the person thatwe're looking for, that kind of
fills, both of those roles and,ultimately, what he had a
vision for I think that a lot ofthis credit to him.
He had a vision for what therole could be and what he was
looking for.
And yeah, the rest is historythat's great.

Speaker 1 (13:28):
So in that transition period, um, yeah, it's so like
you were a team of one, so maybeyou had some connections to
people who had other sort ofskills that you could lean on as
well.
But like what, um, can you talka little more specifically
about maybe skills from yourprior experience that you were

(13:49):
able to leverage as you moved itfrom I don't want to call it,
maybe it's general, it kind ofsupport to the marketing domain?

Speaker 2 (13:58):
yeah, I mean the troubleshooting, uh,
troubleshooting skills, uh, itwas like immediate um, I think
that.
And then requirements, uh likeunderstanding requirements, high
level requirements and how tohow to challenge, um, a vendor
or, uh, an external resource.
I think those are two stories II can remember uh vividly that
were maybe the first month thatI started.

(14:20):
So, um, lead routing, leadmanagement, was a big um issue.
That that we were strugglingwith at the time had a lot of
complex rules, had a homegrownsystem, and so I spent probably
my first few weeks, monthsreally understanding the system
and how it worked.
And then I remember we had anexternal group that was bringing

(14:43):
in a tool like a partnermanagement tool that they wanted
to implement.
We had a homegrown CRM system,a homegrown lead management
system.
At the time we weren't onSalesforce or Marketo like we
are now, but they wanted tocreate a custom integration.
And so I went to this meetingwith our head of internal
development and they had sentover some requirements ahead of

(15:05):
time.
So I read through otherrequirements and then build out
like, all right, here's thequestions I have that this is
how our system works.
How are you going to do this?
And kind of just not.
I don't think it was anythingtoo crazy, but it was just kind
of like I understand how oursystems work and the month that
I've been here for the most partand here's what I think we're

(15:30):
going to need to do for howyou're trying to connect with us
.
It's different than Salesforceand having a lead object, a
contact object and a companyobject like those types of
things, and being able to showthat knowledge.
I think that helped like okay,this guy knows what he's talking
about to our internaldevelopment lead and that those
relationships I think I think myrelationship building was
something I really pried myselfin and really kind of
concentrated on and trying tobranch out into different

(15:51):
aspects of the company.
So I think that was one.
The second scenario is we havemultiple products or multiple
business unit company and one ofour products has a try.
It's more of a PLG motion.
We didn't call it PLG back thenbut yeah, you get into a trial
and you get trial nurture andthen you convert to purchase.
We were having trial issues.

(16:12):
The trial was not working andnobody could really diagnose
what was going on From a productstandpoint.
Yeah, so like signing the formyou know, nobody knew.
Is the form Nobody knew, is theform wrong?
Why are we having issues?
It was basically a prospectwould call into sales and say,
hey, I can't get the trial towork, something's wrong.

(16:34):
And somebody a web resourcewould go on the page and say,
nope, works for me.
And then it was like that's it.
They're crazy, there'ssomething wrong.
And so somehow it ended up.
They're like hey, rick, here,here's a project I want you to
work on.
And so I got really deep intoit and just kind of the
troubleshooting skills we talkedabout earlier, like using some

(16:55):
of the technical resources,talking to the sales team what
are they telling you?
And then starting to diagnosewhat, um, what was going on.
And all of a sudden it was myproject and now I owned making
sure that the trial would work.
What are we going to do toensure that the trial is
available and working at alltimes?
And we mentioned we had a lotof homegrown systems at the time
and so it wasn't like let me goto the Marketo community and

(17:17):
see if anybody else has had thiserror.
This is our own system trying todiagnose and work with Dev, and
so I think those are two earlyscenarios that earned a lot of
trust in the company for me andwith my boss and the CMO and
then the rest of theorganization.
So I think I kind of parlayedthat into into a few different
things.
And then you know he was reallybig on what.
What can we bring?

(17:39):
How can we really advanceourselves from back then a lead
scoring model that we didn'treally have?
How can we advance this?
How can we engage with sales alittle bit better, get a tighter
connection with sales?
And I had been working veryclosely with the donor
management team in my United Wayyear, so very different

(18:01):
nonprofit, but it's still sales.
So I had those strongrelationships.
I think those kinds of things Itried to to use and that you
know that that relationship andtrust that I was gaining with
sales to to help them.
So, like I am an, I'm aresource, I'm a value add to you
, not just somebody trying tothrow something down your throat
.

Speaker 1 (18:20):
Yeah, I think it was interesting, I was, I was gonna,
I have a follow-up for you, notjust somebody trying to throw
something down your throat.
Yeah, I think it wasinteresting, I was going to, I
have a follow-up for you, but Iwas, you just kind of touched on
it.
Like, the ability to build Iwould call it trusted
relationships, right?
Is, I think, an important skillthat I think a lot of,
especially people in early intheir career, are maybe not as
comfortable with.
And I think one of the nuancesthere like I do a lot of
coaching and one of them I do Ihave to work with people on

(18:44):
regularly is use the wordchallenge.
Right, you just like challengevendors, I think.
I think sometimes you have todo that internally as well,
right, with people who have abigger title than you, right and
like, is that something thatyou like?
Did you also challengeinternally in this process, like
and like?
We could talk about how you didit if you want, but I mean, I

(19:06):
know how I would approach it.

Speaker 2 (19:08):
Yeah for sure.
We had a weekly meeting withour head of digital, our head of
internal development, our headof web development and there
were a few other kind of VPs ofmarketing in there and I got
pulled into it and and thatessentially all we were doing
was kind of challenge,challenging things, and I I got

(19:29):
comfortable very quickly withthat group.
But I, you know, I formedrelationships initially to try
to understand and kind of tookmore of a let me understand
first before I try to challengeanything.
But once I felt like I had agood grasp you know two months
in which that's hard to say,like nobody knows that a company
of size in two months but Ifelt like I had a decent

(19:49):
understanding that I could startto, to push back on things and
question things.
My, I'm not like a in your facetype of person, that's just not
my personality.
So I think more, uh, I usequestions to try to challenge
things.
So tell me more about that.
Why do you think that way?
Or why should we approach itthat way?
If we look at some of the databehind that is you know, things

(20:15):
like that are all leveraged datato try to show like, hey, you
know, it's not a bad idea.
Here's what I was looking at.
Is there a reason this wouldn'twork?
That's kind of the approachthat I've typically taken and
certainly was not afraid to dothat.

Speaker 1 (20:32):
This was eight years ago, so my memory is failing in
terms of an example, but I thinkthat's how I approached it.
Have you always beencomfortable with when you get
challenged as well?

Speaker 2 (20:39):
Yeah, I'm very much a show me, prove to show me, you
know, prove to me.
It won't work, then let's do itLike I, and there's no sacred
cows in my world.
Um, I'm very much, uh, in favorof um.
You know, if someone has a goodidea and my idea is not right,
tell me why and let's talk aboutit.
And okay, let's try differentapproach.

(21:02):
So, um, I'm sure I did, I I'm Idon't remember an example of it
, but we definitely uh yeah, I'mdefinitely not afraid of that I
, I, I try to do the same thingand think about it in terms of
team leadership stuff.

Speaker 1 (21:16):
But I had somebody work for me who I can't remember
what the details were, but wewere working on a problem.
We were going into ourone-on-one which normally I let
them set the agenda, but thisone we, we had a specific thing
we were trying to work throughand I came into it with a like I
think this is what we should do, mindset and um, this other,
the person who worked for me,really like challenged that and

(21:38):
had a different idea and um,convinced me that that was the
better one and that's what wewent with.
And my first reaction was tocelebrate right and go tell my
boss like, hey, this is a goodday.
You know, this personchallenged me, was right, fought
for it, and that's what we didLike to me, that's a good thing.

Speaker 2 (21:58):
Absolutely no, I think.
I mean, I think you're spot on.
I think people are especiallyearly in their career.
Oftentimes someone can be uhuncomfortable with that, like
this is, and and I invite thechallenge, uh for my team now
right, like, um, I want them topush back to like guys.
This is what I'm seeing, thisis what I think like tell me I'm

(22:18):
wrong.
I like, like I'm okay with that, and I feel like we do have um
a a culture at connect wise thatthat invites that Um.
I do think, as a leader, uh, ina role that I'm in, that I need
to like welcome that.
And and again, you're, you saidcelebrate.
I think that's a great way to toapproach it, like we should
celebrate when someone pushedbacks and doesn't doesn't give,

(22:42):
give in, just because I have abigger title than them and said
we should do this and when theyknow that's not right, they just
do it, then we're all worse off.

Speaker 1 (22:52):
If that's the case, so I think that's a really good
point.
Yeah, 100%.
So you started as a team of oneand then at some point you saw
that it actually could besomething more, or needed to
have something more, and youwent and pitched the idea of
growing the team.
What was that process like?

(23:18):
I mean, I'm going to expectright there's, you are going to
have to come up with some sortof business case for maybe not
an ROI, but some sort of likereasoning that people could sink
their teeth into and go, yes,we need to do this.
So what was that like and howdid it go from there?

Speaker 2 (23:38):
Yeah, and there's a few things that were happening
in the business that helped.
I would advise anybody who'skind of looking at their career
there's.
Certainly you control a lot ofthat, but the state of your
business and the externalfactors that are happening
within the business.
The opportunity has to be thereand the timing was right for me
.
We had just gotten acquired byprivate equity so we were on a

(24:00):
move to move off of ourhomegrown systems onto
Salesforce and Marketo.
We had just acquired anotherpretty large company too.
So like the multiple thingswere happening within the
business that were kind ofdriving the need to change the
structure that we had.

(24:20):
So I think those were part ofit.
Now I had started talking to myCMO about it before then.
Back then we were pretty heavySerious Decisions users and
really got involved prettyheavily with them.

Speaker 1 (24:35):
Well, that's interesting just by itself.
I mean Serious Decisions.

Speaker 2 (24:37):
clients are usually really big enterprises, yeah
right and we talked a lot aboutour maturity.
How do we get moreoperationally mature?
What are the things we need todo?
How do we put the?
I mean just think of the demandwaterfall, the old school
demand waterfall that existedback in the day.
We were heavy, I don't knowadvisors to that, or that was

(25:01):
kind of where we took things.
Well, I leveraged a lot of theirresources on marketing ops and
here's what a marketing ops rolewould look like, here's what a
team structure would look like.
So I had some help on thatfront for sure, um, but I use
that as kind of a guide and Ithink, um, you know, I was able
to um show some wins that wewere having just by having this

(25:23):
formalized under our marketingops umbrella that me plus a few
others, and the combination ofthe acquisition, the private
equity, as well as just some ofthe wins that we had able to
make a case like, hey, what ifwe formalize this?
Here's what it would look like,what are your thoughts?
And I think he was open to itpretty quickly.

(25:43):
So it wasn't like it took a tonof convincing that I had to
build out a huge business case.
It was more.
This is the structure that wedo it in.
And here's what, especiallywhen I was hiring that new role,
so we formalized some existingroles.
So the email team came under me, which was under a different
team, was under digital before,and so we kind of formalized it.
That way, Project managementcame under me.
But then I need a role in netnew role that does not exist

(26:07):
today to just scale what I'mdoing, and it really was just
another person.
And tech drove that a lot too.
We were expanding our techstack pretty significantly, as
pretty much everybody was in2018, 2019.
And so that I think that droveit a lot.
Like, hey, if we're going toacquire any type of tech, we
need a strategy around it, ofcourse, but we also need someone

(26:29):
to optimize it, not just be anadmin to add users, but really,
how are we going to leveragethis to its fullest?
And I think that drove thebusiness case even more.
If we're going to spend$100,000 on a tool, it makes no
sense to just not have anybodyown it, because if nobody owns
it.
Nobody, nobody's going to use itand we're just going to have um

(26:52):
shelfware yeah, vaporware,shelfware, whatever you want to
call it right, yeah, so it'sinteresting to me.

Speaker 1 (26:56):
Um, it totally makes sense that there were sort of
external factors or you knowcatalysts, that you know.
When the time was right, itmade sense.
But I I don't want ourlisteners or audience to to walk
away from us thinking, oh, Ineed some sort of external thing
to happen, because you alsotalked about, you started
conversations, I don't know whatwas it, months, you know maybe

(27:18):
it was months in advance.

Speaker 2 (27:19):
yeah, it was before it actually came together.

Speaker 1 (27:22):
Yeah, yeah, yeah, and I think that's a really good
lesson to learn, because youknow, one of the things that
I've tried to do when I've triedto like pitch something big and
maybe not an organizationalchange, but maybe a big project
that's in that new thing is, bythe time it becomes like you

(27:42):
need the formal decision to say,yes, you can go.
You know, do I want that to bea no brainer right?
All the work that goes intoahead of that is really, really
important, so that you don'twant surprises when you get to
the formal discussion aboutapproval.
Right, you want all the headswho are going to have to nod yes
or already on board.

Speaker 2 (28:01):
Yeah for sure.
No, I think you're spot on.
I mean, you don't want to waittill an external factor.
And then like, hey, I see it, Ithink you know I was pretty
factor.
And then like hey, I see it, um, I think you know I, I was
pretty, uh, proactive and justlike, all right, I see an
opportunity here.
I, I chatted with some of therelationships that I had within

(28:21):
the organization.
Like, hey, I feel like there'sa need here.
Am I off on that?
So I approached it that way islike, tell me if I'm missing
something.
So, relying on some of thoserelationships I had and I, you
know I had good buy-in and goodrelationships that could tell me
, no, you're, you're crazy.
You shouldn't do that, becausehere's why, um, I didn't get
that.
I, I got support, and so Ithink that helped too.

(28:43):
Um, but I, I had a reallystrong relationship with our CMO
.
I think I was able to to showvalue that that I was able to
provide and I hate saying I,because it was really a we.
It was not me doing this on myown.
There were other people veryinvolved in this.
But I think, centralizing thatand just kind of the expansion

(29:04):
that we were going to.
Back then we were calling itdigital transformation.
We were able to show somereally good value from the
digital transformation effort.
That made sense to start toexpand and then, once we got one
person, it was just like oh wow, bit of data.
And then they need more andthey keep asking and they don't
know how they lived without it.
Before.
It was kind of that where westarted to do some things and we

(29:44):
saw how valuable it was so nowwe need more, and to do more we
needed to scale.

Speaker 1 (29:49):
Yeah, I don't know about you, but one of the things
I've struggled with before iswhen I see that there's a need
and it seems so glaringlyobvious to me and that I don't,
then when I get, when I didn'tfollow that practice I just
described of like preparingahead of time with all the
people, I would get into theformal thing, and then I get all
this like resistance orquestions or whatever, and it

(30:11):
was because I hadn't done thelegwork of helping.
There's two ways, right,there's two, two parts of this,
and one is me helping them seethe same thing and, b, helping
me understand, uh, why theymight like, because of their
perspective, right, why theymight see it not as big a need
as I do.

Speaker 2 (30:32):
Yeah.

Speaker 1 (30:33):
So it can help you refine the way you communicate
and tell the story.

Speaker 2 (30:43):
Definitely.
I think you you touched onsomething really important is
like try to uh, try to determineor um predict what pushback you
might get.
How are they going to um toreact?
What are the questions youmight get asked?
What, what are the holes inyour uh, your approach?
And then see if you can findthe reasons why ahead of time,
so that you're already preparedlike, hey, that's a good
question.
I thought about that and here'swhy I think this still makes
sense.

(31:03):
For you know, whatever thereason is um, and and it's I
mean go back to like traditionalmarketing, um, um, it's persona
based.
So this persona, the CRO, isgoing to say this and this is
why cause this is what he or shecares about the CMO is going to
think this way.
The head of your demand genteam is going to think this way.

Speaker 1 (31:23):
And the CFO is getting a whole nother
perspective the CFO.

Speaker 2 (31:25):
Absolutely.
If your CFO is involved there,you better start talking CAC and
and you know cost pereverything and understanding
that if you're going to get onthat route and really being
intentional, I think you youcalled it out like you know do
the homework ahead of time sothat you're ready for those
conversations.

Speaker 1 (31:41):
Well, and and and maybe the one thing I would add
to that is don't I mean, if youfeel like you can't put yourself
into those shoes cause youdon't know that, be humble and
go.
Oh yeah, go ask for that input,right, and just, I've got this
idea.
Um, because I think every timeI've done that, because I would
be afraid to do that in the past, or like unsure, like why do I

(32:04):
bother these people?
I found that most people, ifyou have, if you've put some
thought into it right and you'renot're not coming in totally
random, unless or if you set itup as hey, I've got an idea I
just want to bounce off of youand it's like an open-ended
conversation that, like, you'regoing to like people, they want
to, they want to help.

Speaker 2 (32:22):
No, I think you're the way you approach those
conversations.
I don't think I've ever had aconversation like that where
somebody was like no, screw you,like move it on Right it's.
It's a really good way to do it, and I think people are more
than happy to um, to have thatconversation and to to give you
feedback when it comes to that.

Speaker 1 (32:43):
Yeah, absolutely, I think that's.
That's so true, all right, soshow you at some point I can't
remember exactly when, butyou're now in this role out of
DemandGen About two years ago,two years ago.

Speaker 2 (33:03):
So I went from individual contributor on
marketing ops one person tosenior manager, to a director,
to a senior director all inmarketing ops and so build a
team from me to, essentially at15 at the end, when I was still
in marketing ops, at 15 at theend, when I was still in working
ops.
And then our head of demand genleft, our VP of demand gen left,
our CMO approached me and saidhey, I would like you to
consider taking over demand genand was not necessarily the

(33:23):
career path I had laid out.
I was like I don't know if Ireally see myself as a demand
gen leader.
Okay, let's talk about it.
And so we talked about it.
And so we talked about it andsaid, all right, let's, I'll do
it for 90 days.
Um, and then after 90 days,when I decide I don't want to do
this anymore, um, you know, ifyou, if you decide you like I'm
not doing well with it and it'snot the right role, or if I

(33:45):
decide that this is not theright fit for me, um, I would
like to be able to reconsider,like going back or what are we
going to do.
And so we agreed like that's,that's the right approach.
Um, and uh, here I am, twoyears later still doing yeah 90
days times.
Uh, whatever the exactly rightto 24 months, right?

Speaker 1 (34:05):
um, yeah, that's interesting.
So it was, um, it was a kind ofa mutual decision, but it
actually started from your CMO,is that right?

Speaker 2 (34:16):
Yeah, it was definitely not my idea.
So she was in town and wantedto have breakfast and so I'm
like, yeah, sure, let's havebreakfast.
So she's like I know the VP ofDemand Gen put in his
resignation.
I was like oh crap, oh right,okay, what are we going to?
do like you know, trying tothink like, who could we find?

(34:37):
And she's like, well, I want totalk to you about that.
But I was like, well, who doyou have in mind?
And she's like, how about you?
And I was like, what do youmean?
How about me?
Why would I do this?
And so, yeah, it was, it was agood conversation.
It she was she.
She's awesome.
She's not here anymore but she,you know, really intentional
about career pathing and careerplanning and what, where do you,
how do you want to approachyour career and what's your next

(35:00):
step?
And kind of thinking about that, especially with her direct
reports and leadership team, butreally for the whole marketing
team.
And so she, I know she was veryintentional about that for me
and, talking through what I know, she was very intentional about
that for me.
And talking through what youknow, do I want to go down the
traditional RevOps route andtake on more of a, a leader of
RevOps?
So, going from marketing ops toRevOps, do I want to be a CMO?

(35:21):
Do I?
You know what's the right pathand I've always been.
I always feel like there's twokinds of paths that people take
in their career Some who knowexactly what they want to do and
they are like I'm going thereand I'm aiming to that target
and I, every decision and rolethat I take, is aimed for that.
And then others are like Ireally like what I do.
I'm ready to do more, but I'mnot really sure what that is and

(35:42):
when the opportunity presentsitself like yep, that sounds
good.
I'm going to move and I'mcertainly more of the latter.
I've never been like I want tobe a CMO and that's all I want
to do, and I'm going to keepgoing there.
If you told me, you know, 20years ago, 30 years ago, I said
CMO.
I didn't know what a CMO doesright it certainly wasn't the
path or anything like that, butit just you're the opportunist,

(36:02):
not the planner.
Yeah, I think that's a goodsuccinct way of saying it.

Speaker 1 (36:07):
Yeah, I, I, I think there's a little bit of that in
me as well.
So now MarketingOps doesn'treport to you, right, correct.
How is that now, where you'rekind of a I can't believe I'm
going to use this word internalcustomer of theirs?

Speaker 2 (36:23):
Yeah, no, it's a good call.
So when I moved over,MarketingOps reported to me for
those 90 days.
When I moved over, marketingops reported to me for those 90
days and then, fairly soon after, we had a separate marketing
ops, separate sales ops,separate customer success ops
teams.
We brought into a formal kindof go-to-market ops team, merged

(36:50):
it all together, centralizedeverything.
We soon after that decided tojust go rev ops instead of go,
instead of go to market ops,sales ops, marketing ops
together.
So that's how it's been sincethen.
Um, I won't say it's been easy.
I think, um, some of the beingembedded in marketing, I think
it can work in other cases.
I would always start there Likeyou can, any a company can can
have a centralized RevOpsfunction, it can be fully

(37:12):
functioning work rate and acompany can have a dedicated
marketing ops function.
It could be horrible and notwork well and I think a lot of
it's involved with the peopleand the, the approach that
people take.
I think it we have beenchallenged, I think from a
resource perspective and I thinkjust getting that kind of like

(37:33):
not letting sales consumeeverything which can you know
that's?
a tendency that I think a lot ofpeople have seen right.
Sales consumes all theresources because the CRO is who
everybody is looking towards todrive the business, because
that's where bookings come from.
So it certainly has been achange and a challenge.
I have to be pretty proactivewith kind of pushing to be a

(37:55):
little more proactive on theirside of where.
Before I think we saw a littlebit more of that.
Where we're embedded inmarketing, we were looking at
the data a lot more closely.
We're in the systems day to day.
We're partnering together alittle bit more closely.
I'd say in the past four monthsthree, four months it's gotten
a lot better.
We've really been intentionalabout making some strides there.

(38:16):
We still have some gaps, so Ithink it's different.
I think the good is that I can.
you know, I know the systems andI know the data, and so I will
get into the data when I need toand you know if I'm not in a
lot of meetings, which is allthe time yeah, my, my, uh, my
role or my uh day-to-day hasshifted a lot, but, um, I can

(38:38):
find some of those and then callthose out to them and and, um,
and look at it that way, I thinkthe other thing maybe that, um,
I have some empathy for whatthey go through and where
they're at, and so I try toconvey that to them, but also to
my broader team.
Like you know, somebody isfrustrated with a lack of
response or whatever it might be.

(38:59):
I can be like, well, let megive you a little context.
Here's why it's not as simpleas just they click a magic
button and it's done.
Here's all the steps that theyhave to take, and so, like, I
agree, it's frustrating, buthere's why that, um, maybe
that's the case.
Or here's how we can be alittle bit more, uh, descriptive
and give them the full scope ofwhat they need to do.

Speaker 1 (39:20):
I, I'd say like help them, help us right, absolutely
like if.

Speaker 2 (39:23):
If we can help give them these answers, then they're
going to be able to respondquicker.
That kind of.

Speaker 1 (39:28):
Yeah, uh, you just touched on like the way the
nature of your day-to-day workor week-to-week work has changed
since you've gotten into into.
It's probably changed fromgoing from an individual
contributor to managing peopleright, and now you're managing
other managers.
So, like, what are the big?
What are the big things that,um, you've you've had to like

(39:52):
learn to be more effective, butand maybe I think we've talked
to a number of people who arelike managers of people, which
is great.
I'm curious about that.
But I'm also like we haven'ttalked to a lot of people who
are managers of other managersand in my experience, that's got
its own set of sort ofadditional nuances.
That, um, because you thinkyou're like coaching a person,
about how to coach anotherperson, sometimes right things

(40:13):
like that.
So like what, what are the kindof the skills that you've had
to kind of really um, invest ingetting better at in your new
roles?

Speaker 2 (40:23):
yeah, I I would say, if you so, someone that is
managing just managers, um,versus somebody that is managing
managers and individualcontributors, that's probably
the hardest.
The latter is.
Managing managers andindividual contributors, that's
probably the hardest.
The latter is just because andit just depending on the scope
and the skillset of theindividual contributor and the
managers, when you're having togo both sides, it gets really

(40:46):
tricky because you have to get alittle bit more tactical and
more into the weeds and it'sthat is probably the most
challenging aspect of as youmove up in the career is, like
you're, you know I'm in meetingsall the time with our cmo, our
cro, our uh head of rev ops, andyou know, last night I was in
meetings with our cfo and our c?
Uh, our ceo, and so you're thethe level of discussion that

(41:08):
we're having and the I'mproducing a lot of information
and reporting and PowerPointdecks and that kind of thing.
Like it's a very executivelevel summary, like here's, I
have to distill all thisinformation that's happening in
a, two slides and tell yousimply, succinctly here's what
is happening, here's the trend,here's what we need to do about
it, and I might get five minutesof your attention, because you

(41:29):
got a thousand other things todo, right.
But, then if I have to go to anindividual contributor and talk
through like here's, here's theemail that you need to send in
the list that we need to get, solet me help you get to that,
that is very challenging and soI I don't have that now.
I have had that um where I hadkind of a combination of the two
Um.

(41:50):
I think that the focus itreally is like the managing up,
managing down and the level ofcommunication, that what, how
detailed you get, how you rollup the information.
So I think what I have to donow a lot is take eight
different, nine differentsources of information and what
people are telling me's what'shappening.

(42:11):
Here's what I'm seeing in mydifferent channel or my area.
Summarize that try to see thetrends.
Okay, so if I, um, if I takeyou know this thing happening,
all right, so roughly 80 of thestuff is this, and so if we
focus on that, we can change 80of the business.
So we're going to focus thereand trying to take all that
information, distill it down sothat I can show the trends and

(42:33):
talk to my boss, talk to our CRO, talk to the rest of the team.
Here's where we need to put ourfocus on, here's what we're
doing about it.
Trying to get in front of that,I think, is where I spend
probably most of my time.
It's probably 60 or 70% of mytime is in building, uh,
building presentations and boarddecks and that kind of thing,

(42:53):
as well as in meetings andtalking through, like, the
trends and how we're going tofix things.
And then the other time isspent with my leaders and just
uh, working with them and andhelping them.
I have an amazing leadershipteam that, uh, they're easy to
to lead because they're reallygood, um, and so I I think we
have a really good team.
I'm, of course, biased, but Ido think that that helps and it

(43:14):
makes my life a lot easier.

Speaker 1 (43:16):
Yeah, that's great.
Yeah, I mean I wish we had moretime, because I would love to
go deeper in a lot of that.
Unfortunately, we're going tohave to probably wrap it up here
, but, Rick, thank you so much.
It's been interesting and Ithink it's going to be really
helpful for a lot of people whoare out there listening or
watching.
If folks want to, you know, isit okay if they reach out to you

(43:38):
or follow you?
What's the best way for them todo that?

Speaker 2 (43:42):
Yeah, LinkedIn is probably the easiest path.
If you're not connected with meon LinkedIn, send me a message
or just send a connectionrequest.
It's Rick Collins.

Speaker 1 (43:52):
Reference the podcast .
How about?
How about that?

Speaker 2 (43:54):
yeah, there you get reference the podcast.
Um, if you, I I've uh spoke atuh masa palooza in uh in the
fall, or I guess it was thewinter that was the fall sale it
was in november, right, um, Itold I told people that were in
the session that I spoke at,like, if you have a sales title,
just reference that you werehere, because I get a lot of

(44:14):
sales outreaches.
And so now I love my salespeople, but I get so many
outreaches I typically won'taccept it, because if I'm going
to get pitched right away thenyeah, that's not really what I'm
looking for.
But so if you do have that,I'll still connect with you.
If you let me know that youheard me on the podcast.

Speaker 1 (44:28):
There you go.
Awesome.
Well, I appreciate it.
Um well, which means they alsolistened all the way through,
which is great.

Speaker 2 (44:34):
There you go, that's right.

Speaker 1 (44:35):
Yeah, Um, yeah.
Well, great Rick is, it wastime to let tough on.
I'm so glad we were able tomake this work.
I appreciate it, Um, so anyway.
So, yeah, to our, to ouraudience.
Again, thank you for uhsupporting us.
Uh, thank you for your ideasfor guests and topics and, as

(44:56):
always, if you have a suggestionfor a topic or a guest or want
to be a guest, reach out toNaomi, Mike or me and we'd be
happy to talk to you about it.
Until next time, Bye everybody.
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