September 2, 2025 • 38 mins
Paul Williamson is a seasoned go-to-market leader and advisor best known for helping Plaid scale from $3M to $300M ARR. As Head of Revenue, he built and evolved Plaid’s go-to-market roadmap across product-market fit, upmarket expansion, and new verticals. With deep experience aligning GTM with product, he now advises founders on sequencing bets, building forward-compatible roadmaps, and scaling revenue organizations with intention.
Discussed in this Episode
- Why GTM roadmaps should be “forward-compatible”
- Iteration cycles in GTM vs. product roadmaps
- Early lessons from Plaid’s rudimentary qualification process
- Recognizing high-value clients vs. anti-patterns in inbound leads
- How daily standups created fast GTM learning loops
- Shifting from PLG to sales-led motions with SDRs and routing
- Sequencing GTM expansion: fintech → enterprise FSIs → embedded fintech
- Compensation design mistakes and their impact on sales behavior
Episode Highlights
00:00 — Why GTM roadmaps should be built “forward-compatible”
01:53 — How Plaid iterated through 9–10 GTM versions in the first year
05:12 — Plaid’s early qualification process: 4 simple questions
07:28 — Why most inbound leads weren’t equal—and how Plaid spotted patterns
10:01 — Using daily standups twice a day to refine GTM qualification
14:32 — How Plaid’s GTM roadmap evolved from monthly to yearly cycles
20:46 — Moving beyond partnerships to diversify top-of-funnel channels
24:53 — Scaling into enterprise financial institutions with tailored product needs
27:09 — Entering phase three: embedded fintech with customers like Tesla
30:00 — Compensation design mistakes that slowed deals and created risk
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
The way that we build a go-to-market roadmap is that
we want our roadmap to beforward compatible.
Something today that we buildinto the business is something
that we would then want to buildon top of as we go over time.
What's the actual problem thatwe're solving for the customer
and where does that fit in termsof like the value for them?
Speaker 2 (00:19):
Thank you A quick word from a tool that we use.
(00:41):
Harmonic helps you spot thebest startups before anyone else
.
We use it at GTM Fund, as dotop investors at USV and Insight
and go-to-market teams atNotion and Brex.
The platform tracks millions ofstartups and lets you search
with simple filters or naturallanguage.
In seconds you get founderbackgrounds, traction and market
data all in one place.
At GTM Fund, we even have acompany-watchless Slack channel
powered by Harmonic.
(01:02):
Company watch the Slack channelpowered by Harmonic.
Their website is harmonicai.
Get two free sessions withtheir team to help you structure
the perfect searches if you usethe link in the show notes.
Most startups obsess overbuilding the perfect product
roadmap, but few treatgo-to-market with the same
intentionality.
Paul Williamson joined Plaid at$3 million in AR and helped
scale it to $300 million bybuilding and evolving a
(01:22):
go-to-market roadmap that servedas the blueprint for growth.
In this episode, paul shareshow he first built that roadmap,
how it evolved throughproduct-market fit and upmarket
expansion, and why every founderneeds to treat go-to-market as
intentionally as product.
You'll learn how to sequencethe right bets at each stage,
avoid over-engineering too earlyand use simple rituals to keep
go-to-market aligned as youscale.
(01:44):
All right, let's get into it,paul, welcome to the podcast.
Speaker 1 (01:48):
Thanks for having me, Sophie.
I've really been lookingforward to getting on.
Speaker 2 (01:51):
It's a pleasure.
Well, I want to get started,because most founders obsess
over a product roadmap and oneof the things that you advise
startups around is to alsoobsess over a go-to-market
roadmap For everyone listening.
Can you explain what exactly ago-to-market roadmap For
everyone listening?
Can you explain what exactly ago-to-market?
Speaker 1 (02:07):
roadmap is yeah, absolutely.
I first really kind ofencountered or started thinking
about this concept around abouteight, nine years ago when I
joined Plaid in 2017.
Since working at Plaid, I'vebeen working with over a dozen
different startups across anumber of different spaces and
I've started to see a little bitof a trend in terms of the
importance of building ago-to-market roadmap.
(02:28):
So, quite simply, similar to aproduct roadmap, a go-to-market
roadmap is really sort of adocumented and outlined
structure about how ago-to-market leader whether it's
marketing, sales, customersuccess, all of those functions
combined want to think aboutbuilding out the structure to
(02:49):
the go-to-market organizationand really thinking about
putting that information andthat detail down on paper and
kind of documenting and clearlyoutlining how we essentially
want to go from where we aretoday to where we want to be in
the future relative to the waythat our go-to-market function
ultimately works.
Speaker 2 (03:06):
And what stage does it make sense to be starting
this?
Should founders be creatingtheir go-to-market roadmap at
the earliest stage?
Should they wait till they'vegot their first pivotal
go-to-market hire?
What makes sense?
Speaker 1 (03:18):
I think, especially for founders, they're often
going through sort of afounder-led sales motion in the
very early days.
I actually don't think thatthere's probably a lot of need
for them to start to build aroadmap and things like that at
that point.
But especially as companies arestarting to transition from a
founder-led sales motion andkind of going into an actual
go-to-market-led sales motion, Ithink that that's a really
(03:40):
really important thing forcompanies to be doing and
particularly like the thing thatI would encourage go-to-market
leaders to think about isgo-to-market really as a product
.
It's actually a key feature ofthe way that a company needs to
operate, so treating it like aroadmap item within the business
is a really important thing.
Speaker 2 (03:59):
And how would iteration cycles function with a
go-to-market roadmap?
Very similarly to a productroadmap.
Speaker 1 (04:05):
I think a lot of people talk about sprints and
things like that from anengineering perspective and a
sprint might be two weeks orfour weeks or six weeks or
whatever that structure might be.
In some cases, when you'redoing early go-to-market work,
you actually want to think aboutyour kind of go-to-market
roadmap in short, incrementalbursts.
From that standpoint, forexample, when I first joined
(04:27):
Plaid back in 2017, we had avery rudimentary sales
organization at that point andwe really thought about version
0.1 of our go-to-market when Ifirst arrived and we really
thought about iterating on thatgo-to-market structure
consistently over the course ofthe year.
In the first 12 months that Iwas there, we probably went
(04:47):
through nine to 10 differentsort of subversions of what
go-to-market and ourgo-to-market motion would look
like, because our business atthat point in time necessitated
the need to kind of rapidlychange and rapidly evolve the
way that we essentially approachgo-to-market.
Now, over time, as a businesscontinues to kind of scale, as a
(05:10):
business continues to mature,you might not be doing it with
that same level of maybe monthlycadence in terms of the change
or update, and the windowbetween essentially version
changes of your business willprobably start to get longer as
the business kind of gets morescalable, more consistent, more
repeatable, which is a goodthing, right, like we want to
see a business continue to kindof find structure.
(05:33):
We wanted the business to findpatterns inside the organization
.
But what we really want to bethinking about and one of the
things that I talk a lot withfounders about is that the way
that we build a go-to-marketroadmap is that we want our
roadmap to be forward compatible.
Something today that we buildinto the business is something
(05:54):
that we would then want to buildon top of as we go over time.
A lot of people, from atechnical standpoint, kind of
talk about when product is builtit's backwards compatible.
Does the thing that we'rebuilding now work with the
things that we've already built?
And you could probably applythat concept, but I prefer to
kind of talk about it as likewe're going to continue to kind
of build on the foundation thatwe've got.
(06:14):
Each iterative version shouldbe an enhancement or an
improvement on the things thatwe've done before.
Speaker 2 (06:23):
Okay, so you use this go-to-market framework at Plaid
and clearly it works.
You headed up revenue there,took it from 3 million to 300
million.
Let's break down how youactually applied that roadmap.
You've mentioned a few thingsnow.
So you join at 3 million.
What was the state ofgo-to-market and how did you
actually outline that roadmap?
Speaker 1 (06:41):
When I joined Plaid, as you mentioned, we were doing
about 3 million in ARR.
At the time.
We had approximately about 100clients who were working with us
at that point in time and, bythe way, we had some amazing
clients in those early daysVenmo, robinhood, acorns, like
household names now from aFinTech perspective.
But when I walked in the door,we had two things that we were
really fortunate about is thatwe built a product that was
(07:04):
really valuable for people.
That was part one, and part twois we actually had a fairly
good amount of inbound that wascoming into our business today
because we were solving a prettyimportant problem that hadn't
really been solved that wellbefore.
However, to call ourgo-to-market motion in those
early days sophisticated wouldbe a massive overstatement.
(07:24):
When I first turned up and wehad a couple of founding
employees working ingo-to-market at that point in
time, for example, ourqualification process was really
rudimentary.
We asked four questions, and itfeels laughable to talk about
these four questions now, butthe four questions that we asked
were have you downloaded ourAPI keys?
(07:45):
Have you read our technicaldocumentation?
Where are you at in terms ofyour build out of your
application?
And the fourth part was likewhen do you expect to go live?
That was qualification for usin the early days and obviously
most people would probably laughat that level of qualification
and, looking back, we do as wellbut the thing is that was what
(08:05):
felt was the right approach forus at the time.
But what we weren't reallyseeing, what we weren't starting
to understand, is what's theactual problem that we're
solving for the customer andwhere does that fit in terms of
the value for them.
From that perspective and I'lltalk about one big thing as I
said, we used to have a lot ofinbound, that perspective and
(08:25):
I'll talk about one big thing asI said, we used to have a lot
of inbound.
Often like hundreds of inboundson a weekly basis were coming
into us, and that was because webuilt some strategic referral
partnerships in the early dayswith people like Stripe and
Douala, and so we had quite aneffective top of funnel flow
coming into the business.
But the thing about that isthat, of the hundred leads that
we were getting a week, a lot ofthose leads were not equal.
(08:46):
However, our behavior in termsof the way that we were working
with those prospective clients,we were treating all of those
opportunities as equal.
And so what we were looking forin the early days is just
starting to recognize patternsin the business good patterns
for us, and then theanti-patterns.
What are the things that wedon't see a lot of value in?
(09:06):
And the example for us in thoseearly days is, of the 100 leads
that were coming in a week, 90of those were payment partner
referrals, as I mentioned withStripe and Douala, and what was
happening in that instance isthat those prospective customers
were thinking about ACH, sobank-to-bank money movement, as
(09:28):
an additive feature to theirpayment stack.
At that time, ie, hey, wealready take credit card and all
these other things, of whichcredit card might have
represented 95% of the moneymovement volume that they needed
for their business.
And then ACH was this small,fractional component of what it
is that mattered to theirbusiness.
(09:49):
And so what we recognize islike that's an anti-pattern,
like that wasn't a good patternfor us to go invest significant
time, energy and effort into.
So we had to ask ourselves aquestion of like do we want to
spend time on that opportunity,on a client like that?
(10:09):
In fact, the answer for us wasthat this is actually a much
better client to actuallyreroute back to a PLG motion
because that was actually goingto be the most effective
strategy for us, both in termsof how our product worked and
operated, but also that was themost cost-effective way for us
to acquire those customers.
And what we needed to get to aquicker understanding of is hey,
there was probably about 10really important prospective
(10:31):
clients that were coming throughfor us in those early days that
wanted us.
Ach was the core funding reasonfor them to be using Plaid and
they wanted to do other, moreenriched services validate the
person's identity on the otherside, maybe understand things
like how much money they had intheir account so that they
wouldn't have an NSF or anoverdraft if they were doing
(10:52):
things like funding their Venmoaccount or funding a trading
account like Robinhood andthings like that, and so, again,
it was one of those thingswhere we could have become very
enamored with the hundred leadsthat were coming in every week
and try to treat everyoneequally, but what we quickly
realized is like we couldn't andwe shouldn't be treating
everyone equally, because ourprospective clients were not
(11:14):
equal in terms of the value thatthey would receive from the
platform, from us, and also thevalue that we could then invest
back into working with thoseearly prospective customers.
Speaker 2 (11:26):
How did you think about evaluating that value?
Speaker 1 (11:28):
Yeah, I'd love to tell you that we were that
sophisticated in the early days.
Honestly, for the first I thinkthree to four months that I was
in the business, we essentiallydid a morning stand-up and an
afternoon stand-up, andparticularly as we started to
add more people into thebusiness, it became even more
important for us.
And so really what we weredoing in the early days is that
(11:50):
we were manually looking forpatterns inside the business and
what worked or what wouldn'twork.
And what we started to seequite clearly early on was like
there was a clear delineationbetween these high value, high
impact clients and, like lowvalue, the customers who thought
that what Plaid could do wasaccretive to their business but
(12:10):
not essentially the core to whatit is that they wanted to do
inside their business.
And it was great, like weactually would get to the end of
the day and literally we wouldtalk through nearly every single
deal that we'd gone through aqualification process on.
And particularly because wewere also making real time
changes to the way that we weredoing qualification, it was also
(12:31):
a good check-in point for us tosay, okay, cool, hey, this like
V0.1 of our qualificationprocess.
Is it working?
What would we change Like?
Why would we change it?
Is there an extra question thatwe should add tomorrow?
Is there a different way thatwe'd phrase the way that we
would ask that question tomorrow?
And then we'd also then recountwho had what calls, what did
(12:52):
they do, what did we find out onthose calls during the course
of the day.
That was really a great way forus to recognize that, again, we
weren't that sophisticated ofproduct feedback loops and all
that kind of stuff, because,again, we were still really
early in terms of our processand I know that the team was
probably quite sick of me, likerunning a daily standup twice a
day for the first three or fourmonths.
(13:12):
But it was also an amazing wayfor me to learn the business,
but also for the team to startto recognize as well what were
good prospective clients andwhat were less good prospective
clients.
We obviously wanted everyone tobe building on Plaid, but there
were just prospects that weknew that we should be spending
more time with than less andeffectively we shouldn't be
treating everyone equallybecause of the value that
(13:33):
represented to us and also thevalue that we represented to
them as well.
Speaker 2 (13:39):
Makes sense, and this is around 2017, you mentioned
You're running these stand-upstwo times a day.
How many people are in thecompany overall in these early
days?
So Plaid?
Speaker 1 (13:49):
yeah, plaid was about 50 people in those early days
total, by the way.
So that was go-to-marketengineers, all that kind of
stuff exactly.
And for me on the go-to-marketside we had two initial kind of
founding AEs in the business andwe had two people on the
account management customersuccess side at that point.
(14:09):
And then we started to add acouple of people to the team
particularly we added two SDRs,pretty much all almost
immediately to really become aninitial filter for us for those
kind of hundred new prospectsthat were coming in, because it
was really a good opportunityfor us to start to then route
where that prospective customershould go.
Is that something that shouldbe sales-led, is that something
(14:30):
that should be product-led andbeing really prescriptive
ultimately in steering where aprospect should go?
Because there were also in somecases we couldn't do as good a
job as what the product couldpotentially do for a certain
segment of customer.
But there are also places wherewe as a sales-led motion or a
go-to-market-led motion, wecould do an inordinately better
(14:51):
job than what the product coulddo from that standpoint and so
we kind of like wanted to.
It was human-based routing.
At that point Again, we didn'thave this amazing level of
sophistication, at least at thispoint in time, which sounds
like quite rudimentary rightcompared to where people are
today in terms of revenueoperations and revenue
engineering.
But it was the right thing forus to do at the time and it got
(15:12):
us really, really close to thebusiness.
It got us really close to theuse cases and it helped us get
really close to the customer andwhere the value was for the
business.
Speaker 2 (15:22):
Did you have a go-to-market plan, a roadmap,
outlined at this point, or wasit going through this motion,
where it created the inspirationfor writing a go-to-market
roadmap?
Speaker 1 (15:36):
Yeah.
So I think one of the thingsthat I learned, especially early
on in terms of my work with thetwo co-founders of Plaid, zach
and William, is that and this isnot just a Plaid-specific thing
, this is a nearly every tech,early-stage tech startup thing
(15:58):
is that VCs invest in highlytechnical founders who are going
to build technical productsright, which is fantastic.
Really, really smart peoplehave found a way to technically
solve quite a unique problem,and the thesis of VC is like
let's go invest in those peopleand it's a great thesis and I'm
not saying that that thesis isbad, but obviously, in more
often than not, those foundersthat get invested into often
(16:19):
have very little understandingabout go-to-market.
The reason why this kind ofconcept of a roadmap became
important is because I alsoneeded to take Zach and William
and subsequently other foundersafter this through the process.
They actually did want to knowabout what it is that we were
building, why were we buildingthese things, but it actually
made it a lot easier for me toultimately communicate what was
(16:43):
our plan, why it was importantand what we needed to build next
, and really essentially in theearly days, we were making that
plan on a month-by-month basis.
Hey, we just implemented thisnew qualification framework.
We're seeing really positivesignal about it.
Okay, the next thing that we'reactually going to go build
around us is a little bit moresophistication in terms of how
(17:03):
we price.
Now that we've gotten better atqualifying our prospective
customers, we understand thevalue that we're creating for
them.
We probably need to get alittle bit better about how we
price how we write a proposalfor someone, because we also
wanted to really make sure thatwe were tying what it is that we
did to the value that was beingcreated at those companies as
(17:25):
well, and it meant that we justwould kind of continue to build
into the sophistication overtime and again.
Like I said, in the early days,we were literally going month by
month.
We would like get towards theend of the month and I was like
mini brief about what theroadmap would look like for the
next month and month over monthin that first year and then in
(17:50):
our second year it was reallylike hey, every other month we
would be kind of talking aboutlike what was going to come up
on the roadmap next, and by ourthird year it was like kind of
like a quarterly roadmap.
Fourth year it was a halfyearly.
Fifth year it was kind of halfyearly as well.
Sixth year, we were reallythinking about what the roadmap
looked over a 12-month timeperiod because obviously
go-to-market had continued toget larger over that time.
As I said, we were founded andwe had about four people when I
started.
By the end it was close to 200in the go-to-market organization
(18:13):
and so it's very hard to beoperationally changing things
month over month with that manypeople.
Like the impact that that wouldhave on the business is
actually probably quite negativethe speed of change at that
point.
But it really resonated and itwas really important for us in
those early days to have a realrapidity of change.
And the great thing is, by alsodocumenting these things it
(18:36):
kind of kept me a little bit incheck too, of like, hey, am I
investing in and putting theeffort into the right things at
this point in time?
I think most go-to-marketleaders when they start inside
an early stage business and Ihear this from formal colleagues
who've all entered into kind oflike going from like large tech
(18:56):
and into early stage startupthere's often this like
paralysis because there's justso many things that could
potentially be done in a periodof time and it actually gave me
real clarity of thought aboutbeing focused on what was
important at that moment for usas a business.
(19:17):
It wasn't about taking theplaybook that I knew and
superimposing that into thebusiness that I was in.
The playbooks that I've knownand learned and had an
appreciation for over the courseof my career are really just
it's just information that I'vegot and I need to work out
whether the things that I'velearned and experienced before
(19:39):
are applicable to the situationthat I'm in today.
It's not about taking the thingthat I was at and dumping that
on top of the business, becauseI think overly building process
in the early days of companiesis nearly as risky as no process
and there's that really healthybalance that you need to have
(20:01):
and I think go-to-marketleadership probably feel this
most acutely out of anyone isreally making sure that we're
building appropriately for thestage of company that we're at
and we're not overbuilding.
In fact, you probably want tofeel like you're just always a
little bit behind in terms ofyour go-to-market structure
relative to the rest of thecompany, rather than too far
(20:22):
ahead.
I think if you're too far aheadin terms of the infrastructure
that you've built into thebusiness, then you've probably
overbuilt and over-structuredthe organization and you're
probably running a costinefficient go-to-market
organization.
But you're probably alsoimposing way too much structure
inside the business.
That will actually be a netnegative for the business, not a
(20:44):
net positive.
Speaker 2 (20:45):
So it sounds like go in parallel to the rest of the
company in terms of finding thathappy medium of sophistication.
Speaker 1 (20:53):
Yeah, a super, super healthy balance.
Speaker 2 (20:55):
Yeah, and so to super tactical question.
But to not create overlyprocessed areas as you build
this out, how are you actuallycommunicating this to the team,
to founders?
If someone were to listen tothis and say I'm going to create
a go-to-market roadmap, whatwould you recommend they do for
actually sharing that anddisseminating the information?
Speaker 1 (21:17):
Look, I think today, anything like a G-Doc all the
way through to kind of Notion orsomething, so something that is
, by the way, completelyaccessible to everyone inside
the organization is the beststart, and we shouldn't hold
these things private, right?
We should be actually gettingthese out and exposed to the
team.
So I think it's a reallyvaluable exercise, not only for
a go-to-market leader todocument it, but also have it be
(21:40):
presentable, because I thinkonce you start to talk with
people and you start toarticulate what it is that
you're building and you startsharing and you're also willing
to actually receive feedback onthis stuff, it will also make
you a way better leader in theprocess, and I think one of the
great things about that bydocumenting and publicly sharing
this stuff as well is that youthen start to take the rest of
the company along with you inthat journey, and this I think
(22:03):
was very, very impactful for usat Plaid in that journey, and
this I think was very, veryimpactful for us at Plaid and
again I've seen this in terms ofthe dozen plus organizations
that I've spent time withadvising over the last few years
is that then the rest of thecompany also gets really, really
bought into the investmentsthat you're making and why, and
they become, quite honestly, amuch better partner for you in
that process, because they cansee what it is that you're
(22:25):
building and you know it's notthis black box of go-to-market
stuff.
In fact, you know I thinkthat's what a lot of early stage
founders fear when they bringtheir first external
go-to-market hire into thebusiness is, you know, this
person's joining from X company.
They're going to come in,they're going to impose their
will on our organization.
(22:48):
We're more engineering focused,we're more product focused in
the things that we do and Ithink, by being really
transparent with the things thatyou're building, being really
clear and making it accessibleto anyone who's interested in
finding that out, I think that'sa really great place to start.
But again, particularly, Ithink the key there is get it
documented, start sharing andreally see this as an
(23:10):
incremental improvement.
I'm a really big believer inmaking today just a little bit
better than we did yesterday.
That's the way that we shouldtreat this kind of concept of a
go-to-market roadmap as well.
How are we improving today overthe things that we did
yesterday and making smallincremental improvements and
changes progressively over many,many years inside an
organization?
Speaker 2 (23:32):
But if you ask anyone within an organization, they
know the product roadmap, theyknow what's coming.
It sounds like it should be theexact same on the go-to-market
side.
If you ask anyone whetherthey're on the technical side,
go-to-market side, everyoneshould have a clear idea of what
that roadmap is.
Speaker 1 (23:52):
Yeah, completely agree, because I think one of
the things sales teams andgo-to-market teams always clamor
for is the product roadmap.
We need it because we need it tosell and we need it to do these
things.
But then, conversely, if thego-to-market organization is
doing things that people don'thave any context of, they don't
have an understanding of andappreciation of, then they won't
be able to be as involved orpositively impacted by that.
(24:12):
And the thing that we found atPlaid particularly is, as we
started to share this more withpeople, the head of engineering,
jean Denis, and I would spendeven more time together kind of
aligning how product releasesand updates would be coming out.
Where does that fit now interms of our roadmap?
So we really saw this as a veryunifying function for us inside
the business and in a lot ofcases I think it was one of the
(24:36):
reasons not the only reason, butone of the reasons why we were
not only able to accelerate thegrowth the way that we did, but
it got us to a much, much faster, much better operating place
and a much better operatingcadence as an organisation.
Speaker 2 (24:51):
That is fantastic, and you had the first stage at
Plaid where you were iterating.
You were having these stand-upstwice a day.
What came after that?
As you started to move awayfrom all the inbounds and really
double down on the high-qualityprospective accounts.
Speaker 1 (25:10):
One of the things that became important for us as
we started to recognize who themost high-value clients for us
were.
Then the question then becamewhat do we need to do to seek
out more of those really highvalue clients for us?
And so then we started to thinka lot more about what is our
acquisition strategy, what isour distribution strategy for us
inside the business.
(25:32):
We had a very positive impactfrom some early product
partnerships that I mentioned,but what we needed to start
thinking about is okay, cool, weneed to start to diversify our
top of funnel.
And what does that look like?
What are the other channels forus from an acquisition
standpoint?
Should we do more things from apartnership perspective?
(25:53):
And this was, by the way, forus in the early days, it was
partnership referral, notpartnership selling.
We got to partnership sellingmuch, much later in the journey
for us at Vlad, but we reallythen started to think about what
do we need to do to go startgenerating better high-quality
top of funnel.
Let's get more committed tofield marketing.
(26:14):
Let's commit more in terms ofour SEO.
Let's start to get into things,our SEO.
Let's start to get into thingslike pay.
Let's start to get into thingslike outbound, and so we really
wanted to then go to startdiversify the things that we did
from a top of funnel activityfor us, and that was a really
critical thing.
But it was only once we couldsee really clear repeatable
(26:35):
patterns for us in the businessthat it then made sense for us
to go and invest into theseother channels, because we knew
that if we put a dollar in thetop of the funnel from that
standpoint, then the likelihoodthat it would precipitate into
revenue for us was pretty high.
We were moving out of this kindof like very random but amazing
(26:55):
stage for the business and justbringing in more structure,
creating more repeatabilityinside the business, and once
you see that repeatability,that's a really, really good
sign for us to then start toinvest in scale.
Speaker 2 (27:10):
Incredible as you scaled and started to create
that repeatability top of funnel, would you say that accelerated
your focus on a different typeof customer than all your
inbounds.
So it sounds like you shiftedall your inbounds to more of a
PLG motion.
You're building out more ofthat sales led motion, including
the two BDRs you hired.
Speaker 1 (27:30):
Yep, yeah, exactly.
So you know we went through aseries of really interesting
stages in terms of kind ofPlaid's go-to-market motion and
our areas of focus of thebusiness.
In the very early days we werea fintech ourselves, working
with other fintechs, and look,that was a very fast-growing,
(27:51):
rapidly expanding part of themarket.
There were literally hundredsof new fintech applications
being built every year andpeople starting to bring in
inside these fintechs like thekind of data that Plaid could
provide to really deliver on aunique product experience.
But what we also thought aboutover time is like, obviously,
(28:11):
like fintechs will not be theonly customer for us here at
Plaid and you know what doeslike the next phase of growth
look like for us as a company.
And we had sort of like twomajor customer categories that
we kind of thought about afterthe early stage FinTech.
The first of that was kind oflike going up market in FinTech
(28:32):
or financial services that wasto go into like the more
traditional banks and wealthorganizations and things like
that, so starting to work withlarge financial institutions
customers.
The large financialinstitutions were a big part of
the data network that we wereproviding, but there was also
real value in what we couldactually provide the traditional
financial services businessesas well.
You know, because they had, youknow massive businesses around.
(28:56):
You know savings and accountopening and funding to loan
originations like whether it wasunsecured or secured mortgages
and home equity lines of credit.
So we really wanted to start tomove up market.
But in that sense, what we alsoknew is that the likelihood of
those traditional financialinstitutions coming inbound to
us were very, very low.
(29:17):
But we really then understoodwhat our value proposition was.
We knew who we needed to go tomarket with and we knew who we
needed to target, and so we gotreally really clear about who
they were from a prospectivestandpoint and we started to get
more focused on outbound fieldmarketing and other things like
that to really go driveourselves into that audience.
(29:38):
And so that was phase two forus as a company, which was
really exciting.
It's a very, very slow process,at least at that time, selling
into the large enterprise banksand financial institutions, but
it was one that we committed to.
About two years after I started.
Kind of late 2018, kind ofgetting into early 2019 was when
we really started to kind oflate 2018, kind of getting into
early 2019, was when we reallystarted to kind of focus on that
(30:00):
, because not only was itimportant for us to start to
diversify, we also had a productthat was ready to sell into
that market and into that space,because the largest of
enterprises especially financialinstitutions and wealth and
things like that they had veryspecific needs from us as a
company.
They wanted uptime andavailability, they wanted
service level agreements, theywanted a lot more enterprise
(30:22):
reporting and insights, theywanted things like SSO and
rules-based access control andall these other things that in
the early days of us, when wewere working with a fintech,
those things didn't reallymatter, to be perfectly honest.
So we needed to not only evolveand change the way that we did
our go-to-market, our productalso actually needed to evolve,
(30:42):
and this was the other big thingabout having a roadmap relative
to our go-to-market motion.
I could then talk about ourroadmap and say, look, we are
now going to start to focusabout going upmarket and we're
going to need these things tobecome a reality of our product
for us to be successful.
And so then it became abi-directional conversation
between go-to-market andengineering about what we needed
(31:05):
from a product perspective.
And then the third market forus that we went after is we went
from fintech, as I said, intotraditional financial
institutions.
We then went into what we wouldcall this embedded fintech stage
, which were companies thatweren't fintechs and companies
that weren't financialinstitutions, but they wanted to
bring in a financial elementinto the product that they were
(31:28):
offering.
And a really amazing examplethere are like the major
telecommunications companies,they wanted to actually stop
taking things like credit cardpayments.
They wanted to move from creditcard into ACH and make a
fundamental shift, by the way,in terms of the way that they
got paid by their consumers.
Or another really great examplefor us in that instance was
Tesla was an early client on theembedded fintech side, and so
(31:52):
what was really interestingabout them is they are building
one of the most modern vehiclesin the world, but your down
payment and things like that foryour Tesla was by check.
So this is the most modernvehicle in history today, but
they were using a paymentinstrument from the 1700s.
It was a really funny branddissonance that was happening
there, and so we had companiesthat wanted to make the
(32:14):
financial element and elementsof their product be more akin to
the way that, like their moderntech, their modern stack, their
modern products were there andthat was really like the next
phase of growth for us, as wetruly moved out of just purely
servicing fintechs and financialinstitutions but moving into
this kind of like concept ofembedded fintech.
Speaker 2 (32:34):
What kind of AR inflection were you at where it
made sense to go into this phasethree, this embedded tech?
Speaker 1 (32:41):
We were scaling pretty rapidly at that point, so
we were probably around aboutthe 100 to 150 million in ARR
where that became quiteimportant for us.
Obviously, we'd grown very,very rapidly with our fintechs
and also with traditionalfinancial institutions at that
point, but that was when itbecame a really important part
(33:01):
and that has become one of thecore things of the business
today for Plaid, which is reallyexciting.
Speaker 2 (33:06):
Super exciting and what were some of the biggest
challenges that you faced?
Obviously, a lot went right intheir journey, scaling $3
million to $300 million.
What were some of the biggestchallenges throughout that?
Speaker 1 (33:23):
Oh, we got probably just as many things wrong as we
did.
People talk a lot about thecompensation plan, the
compensation structure for theirteams, but one of the things to
really think about when you'rebuilding the right kind of
compensation structure is alsothe impact that it actually has
on the way that your teams sellto your customers as well.
We made a really big mistake inthe early days, particularly as
we were moving into, like ourenterprise business.
We had a commission and payoutmodel that worked really well
(33:47):
for high, rapid, high growth,short sales cycle SMB clients.
You know often, you know peoplewere signing a 20K, 50k, 80k
order form, but they werehappening pretty rapidly.
We were closing deals in thesame day to less than 45 days
and we had a great compensationplan that really worked and was
(34:09):
quite reflective andrepresentative of our SMB
business that we were.
But as we started to move intothe upper market, our
compensation plan really thensaid hey, the way that you would
be compensated is essentiallyon the initial structure of the
deal.
What it actually meant was thatour sales teams were actually
keeping a deal open for a lotlonger period of time than what
(34:30):
we would have liked.
So what did we do.
We had incentivized in terms ofour structure for the team to
keep a deal open for longer.
So that meant that a deal wasessentially quote unquote on the
street for a lot longer than itneeded to be, because the way
that our compensation structurereflected that was like hey, we
would pay you out on the initialstructure of the deal.
So what it did is like our AEswere actively delaying and
(34:53):
trying to find not just thefirst use case but the second
and the third and the fourth usecase to make that initial deal
as big as possible, becausethat's what our compensation
plan was incentivizing them todo.
That was such a fundamentalmistake for us because it
actually meant that our dealswere staying out there a lot
longer than we would haveexpected because people were
(35:14):
trying to supersize these things.
And so what it did is that itjust created way more surface
area for us to make a mistake inthe sales cycle.
It often meant that ourcompetitors would actually
become involved in the salescycle, so we actually created
more competition for ourselvesin that process and we
essentially were just creatingmore risk in terms of getting
deals done, and so that, for me,is probably one of the standout
(35:35):
mistakes that I made, alongwith like hundreds of other
mistakes that we made over thecourse of the six years that I
was there.
But that was probably one ofthe biggest ones and we needed
to go make that change.
And once we recognized thatthat problem existed, we made a
wholesale change to the way thatour compensation structure
worked.
In fact, we ran differentcompensation structures based on
(35:57):
the different roles that we hadinside the business, because
that's what the businesswarranted.
We couldn't build a structurethat was just one size fits all.
Speaker 2 (36:08):
And that's great advice for anyone really
building out their teams too isto think about whether a blanket
process makes sense, whether itmakes sense to build them in
silos a little bit more.
Speaker 1 (36:17):
The key there is really don't over-engineer the
process.
For us, when we were thinkingabout our go-to-market motion,
we really wanted to keep thingssimple, and I think that that's
a really important thing,especially in a rapidly changing
, rapidly evolving environment,and I think that would probably
apply not just for Plaid, butlike many, many high growth
startups that are out theretoday.
Speaker 2 (36:39):
Great advice.
And, paul, are there any booksthat have made the biggest
impact on your career?
Speaker 1 (36:46):
Yes, I mentioned before thinking about improving
the business and making todayjust a little bit better than we
did yesterday.
I've always talked about thisconcept for a really long period
of time and it wasn't until Iread this book and I read it a
couple of years ago.
It was a book by James Clearcalled Atomic Habits, so
essentially like how do you gobuild repeatable habits inside
(37:07):
the business?
It really really resonated withme.
I think I had sort of likearticulated versions of that
kind of concept for a reallylong period of time, but it
really really hit home for mepersonally.
In fact, we actually got Jamesto come to our revenue kickoff
in 2021, I think it was, yeah,2021 or 2022.
(37:30):
And we already spent time withthe entirety of the Plaid team
and that, for me, was reallyimpactful.
And I'll give you a second one A, because I was a contributor to
this book, but B I think it's afantastic one.
So Index Ventures actually is afantastic VC, but they're also
a fantastic publisher and theyactually wrote a book a couple
of years ago and released it andit was called Scaling Through
Chaos and I think it's a reallyimportant book for not only
(37:53):
founders to read.
It's largely directed atfounders, but I think it's also
really important forgo-to-market people to read this
, largely because it will helpget you into the mind of what it
is like to work with a founder,some of the pressures and the
challenges and issues that theyface daily, and kind of like
where our role as go-to-marketleadership should fit relative
to founders.
So I think that that's animportant kind of like industry
(38:15):
read for anyone.
That's an important kind oflike industry read for anyone.
Speaker 2 (38:18):
Great recommendations there.
We'll drop them in the shownotes and both fantastic reads.
I think the James Clear one Iactually got notes of earlier in
your conversation around justfocusing on being 1% better
every day and thatincrementality mindset.
Well, paul, this has beenfantastic.
Really appreciate the time,appreciate you sharing all of
these insights and your journeyat Plaid.
(38:39):
Where can people find you ifthey want to get in touch or
follow your journey?
Speaker 1 (38:42):
Best place to find me is on LinkedIn.
Speaker 2 (38:46):
Brilliant.
That will also be in the shownotes, Paul.
Thank you so much to all ourlisteners.
Thank you for joining us and wewill see you next week.
Speaker 1 (38:54):
Thanks, Sophie.
The way that we build a go-to-market roadmap is that
we want our roadmap to beforward compatible.
Something today that we buildinto the business is something
that we would then want to buildon top of as we go over time.
What's the actual problem thatwe're solving for the customer
and where does that fit in termsof like the value for them?
Speaker 2 (00:19):
Thank you A quick word from a tool that we use.
(00:41):
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(01:02):
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Get two free sessions withtheir team to help you structure
the perfect searches if you usethe link in the show notes.
Most startups obsess overbuilding the perfect product
roadmap, but few treatgo-to-market with the same
intentionality.
Paul Williamson joined Plaid at$3 million in AR and helped
scale it to $300 million bybuilding and evolving a
(01:22):
go-to-market roadmap that servedas the blueprint for growth.
In this episode, paul shareshow he first built that roadmap,
how it evolved throughproduct-market fit and upmarket
expansion, and why every founderneeds to treat go-to-market as
intentionally as product.
You'll learn how to sequencethe right bets at each stage,
avoid over-engineering too earlyand use simple rituals to keep
go-to-market aligned as youscale.
(01:44):
All right, let's get into it,paul, welcome to the podcast.
Speaker 1 (01:48):
Thanks for having me, Sophie.
I've really been lookingforward to getting on.
Speaker 2 (01:51):
It's a pleasure.
Well, I want to get started,because most founders obsess
over a product roadmap and oneof the things that you advise
startups around is to alsoobsess over a go-to-market
roadmap For everyone listening.
Can you explain what exactly ago-to-market roadmap For
everyone listening?
Can you explain what exactly ago-to-market?
Speaker 1 (02:07):
roadmap is yeah, absolutely.
I first really kind ofencountered or started thinking
about this concept around abouteight, nine years ago when I
joined Plaid in 2017.
Since working at Plaid, I'vebeen working with over a dozen
different startups across anumber of different spaces and
I've started to see a little bitof a trend in terms of the
importance of building ago-to-market roadmap.
(02:28):
So, quite simply, similar to aproduct roadmap, a go-to-market
roadmap is really sort of adocumented and outlined
structure about how ago-to-market leader whether it's
marketing, sales, customersuccess, all of those functions
combined want to think aboutbuilding out the structure to
(02:49):
the go-to-market organizationand really thinking about
putting that information andthat detail down on paper and
kind of documenting and clearlyoutlining how we essentially
want to go from where we aretoday to where we want to be in
the future relative to the waythat our go-to-market function
ultimately works.
Speaker 2 (03:06):
And what stage does it make sense to be starting
this?
Should founders be creatingtheir go-to-market roadmap at
the earliest stage?
Should they wait till they'vegot their first pivotal
go-to-market hire?
What makes sense?
Speaker 1 (03:18):
I think, especially for founders, they're often
going through sort of afounder-led sales motion in the
very early days.
I actually don't think thatthere's probably a lot of need
for them to start to build aroadmap and things like that at
that point.
But especially as companies arestarting to transition from a
founder-led sales motion andkind of going into an actual
go-to-market-led sales motion, Ithink that that's a really
(03:40):
really important thing forcompanies to be doing and
particularly like the thing thatI would encourage go-to-market
leaders to think about isgo-to-market really as a product
.
It's actually a key feature ofthe way that a company needs to
operate, so treating it like aroadmap item within the business
is a really important thing.
Speaker 2 (03:59):
And how would iteration cycles function with a
go-to-market roadmap?
Very similarly to a productroadmap.
Speaker 1 (04:05):
I think a lot of people talk about sprints and
things like that from anengineering perspective and a
sprint might be two weeks orfour weeks or six weeks or
whatever that structure might be.
In some cases, when you'redoing early go-to-market work,
you actually want to think aboutyour kind of go-to-market
roadmap in short, incrementalbursts.
From that standpoint, forexample, when I first joined
(04:27):
Plaid back in 2017, we had avery rudimentary sales
organization at that point andwe really thought about version
0.1 of our go-to-market when Ifirst arrived and we really
thought about iterating on thatgo-to-market structure
consistently over the course ofthe year.
In the first 12 months that Iwas there, we probably went
(04:47):
through nine to 10 differentsort of subversions of what
go-to-market and ourgo-to-market motion would look
like, because our business atthat point in time necessitated
the need to kind of rapidlychange and rapidly evolve the
way that we essentially approachgo-to-market.
Now, over time, as a businesscontinues to kind of scale, as a
(05:10):
business continues to mature,you might not be doing it with
that same level of maybe monthlycadence in terms of the change
or update, and the windowbetween essentially version
changes of your business willprobably start to get longer as
the business kind of gets morescalable, more consistent, more
repeatable, which is a goodthing, right, like we want to
see a business continue to kindof find structure.
(05:33):
We wanted the business to findpatterns inside the organization
.
But what we really want to bethinking about and one of the
things that I talk a lot withfounders about is that the way
that we build a go-to-marketroadmap is that we want our
roadmap to be forward compatible.
Something today that we buildinto the business is something
(05:54):
that we would then want to buildon top of as we go over time.
A lot of people, from atechnical standpoint, kind of
talk about when product is builtit's backwards compatible.
Does the thing that we'rebuilding now work with the
things that we've already built?
And you could probably applythat concept, but I prefer to
kind of talk about it as likewe're going to continue to kind
of build on the foundation thatwe've got.
(06:14):
Each iterative version shouldbe an enhancement or an
improvement on the things thatwe've done before.
Speaker 2 (06:23):
Okay, so you use this go-to-market framework at Plaid
and clearly it works.
You headed up revenue there,took it from 3 million to 300
million.
Let's break down how youactually applied that roadmap.
You've mentioned a few thingsnow.
So you join at 3 million.
What was the state ofgo-to-market and how did you
actually outline that roadmap?
Speaker 1 (06:41):
When I joined Plaid, as you mentioned, we were doing
about 3 million in ARR.
At the time.
We had approximately about 100clients who were working with us
at that point in time and, bythe way, we had some amazing
clients in those early daysVenmo, robinhood, acorns, like
household names now from aFinTech perspective.
But when I walked in the door,we had two things that we were
really fortunate about is thatwe built a product that was
(07:04):
really valuable for people.
That was part one, and part twois we actually had a fairly
good amount of inbound that wascoming into our business today
because we were solving a prettyimportant problem that hadn't
really been solved that wellbefore.
However, to call ourgo-to-market motion in those
early days sophisticated wouldbe a massive overstatement.
(07:24):
When I first turned up and wehad a couple of founding
employees working ingo-to-market at that point in
time, for example, ourqualification process was really
rudimentary.
We asked four questions, and itfeels laughable to talk about
these four questions now, butthe four questions that we asked
were have you downloaded ourAPI keys?
(07:45):
Have you read our technicaldocumentation?
Where are you at in terms ofyour build out of your
application?
And the fourth part was likewhen do you expect to go live?
That was qualification for usin the early days and obviously
most people would probably laughat that level of qualification
and, looking back, we do as wellbut the thing is that was what
(08:05):
felt was the right approach forus at the time.
But what we weren't reallyseeing, what we weren't starting
to understand, is what's theactual problem that we're
solving for the customer andwhere does that fit in terms of
the value for them.
From that perspective and I'lltalk about one big thing as I
said, we used to have a lot ofinbound, that perspective and
(08:25):
I'll talk about one big thing asI said, we used to have a lot
of inbound.
Often like hundreds of inboundson a weekly basis were coming
into us, and that was because webuilt some strategic referral
partnerships in the early dayswith people like Stripe and
Douala, and so we had quite aneffective top of funnel flow
coming into the business.
But the thing about that isthat, of the hundred leads that
we were getting a week, a lot ofthose leads were not equal.
(08:46):
However, our behavior in termsof the way that we were working
with those prospective clients,we were treating all of those
opportunities as equal.
And so what we were looking forin the early days is just
starting to recognize patternsin the business good patterns
for us, and then theanti-patterns.
What are the things that wedon't see a lot of value in?
(09:06):
And the example for us in thoseearly days is, of the 100 leads
that were coming in a week, 90of those were payment partner
referrals, as I mentioned withStripe and Douala, and what was
happening in that instance isthat those prospective customers
were thinking about ACH, sobank-to-bank money movement, as
(09:28):
an additive feature to theirpayment stack.
At that time, ie, hey, wealready take credit card and all
these other things, of whichcredit card might have
represented 95% of the moneymovement volume that they needed
for their business.
And then ACH was this small,fractional component of what it
is that mattered to theirbusiness.
(09:49):
And so what we recognize islike that's an anti-pattern,
like that wasn't a good patternfor us to go invest significant
time, energy and effort into.
So we had to ask ourselves aquestion of like do we want to
spend time on that opportunity,on a client like that?
(10:09):
In fact, the answer for us wasthat this is actually a much
better client to actuallyreroute back to a PLG motion
because that was actually goingto be the most effective
strategy for us, both in termsof how our product worked and
operated, but also that was themost cost-effective way for us
to acquire those customers.
And what we needed to get to aquicker understanding of is hey,
there was probably about 10really important prospective
(10:31):
clients that were coming throughfor us in those early days that
wanted us.
Ach was the core funding reasonfor them to be using Plaid and
they wanted to do other, moreenriched services validate the
person's identity on the otherside, maybe understand things
like how much money they had intheir account so that they
wouldn't have an NSF or anoverdraft if they were doing
(10:52):
things like funding their Venmoaccount or funding a trading
account like Robinhood andthings like that, and so, again,
it was one of those thingswhere we could have become very
enamored with the hundred leadsthat were coming in every week
and try to treat everyoneequally, but what we quickly
realized is like we couldn't andwe shouldn't be treating
everyone equally, because ourprospective clients were not
(11:14):
equal in terms of the value thatthey would receive from the
platform, from us, and also thevalue that we could then invest
back into working with thoseearly prospective customers.
Speaker 2 (11:26):
How did you think about evaluating that value?
Speaker 1 (11:28):
Yeah, I'd love to tell you that we were that
sophisticated in the early days.
Honestly, for the first I thinkthree to four months that I was
in the business, we essentiallydid a morning stand-up and an
afternoon stand-up, andparticularly as we started to
add more people into thebusiness, it became even more
important for us.
And so really what we weredoing in the early days is that
(11:50):
we were manually looking forpatterns inside the business and
what worked or what wouldn'twork.
And what we started to seequite clearly early on was like
there was a clear delineationbetween these high value, high
impact clients and, like lowvalue, the customers who thought
that what Plaid could do wasaccretive to their business but
(12:10):
not essentially the core to whatit is that they wanted to do
inside their business.
And it was great, like weactually would get to the end of
the day and literally we wouldtalk through nearly every single
deal that we'd gone through aqualification process on.
And particularly because wewere also making real time
changes to the way that we weredoing qualification, it was also
(12:31):
a good check-in point for us tosay, okay, cool, hey, this like
V0.1 of our qualificationprocess.
Is it working?
What would we change Like?
Why would we change it?
Is there an extra question thatwe should add tomorrow?
Is there a different way thatwe'd phrase the way that we
would ask that question tomorrow?
And then we'd also then recountwho had what calls, what did
(12:52):
they do, what did we find out onthose calls during the course
of the day.
That was really a great way forus to recognize that, again, we
weren't that sophisticated ofproduct feedback loops and all
that kind of stuff, because,again, we were still really
early in terms of our processand I know that the team was
probably quite sick of me, likerunning a daily standup twice a
day for the first three or fourmonths.
(13:12):
But it was also an amazing wayfor me to learn the business,
but also for the team to startto recognize as well what were
good prospective clients andwhat were less good prospective
clients.
We obviously wanted everyone tobe building on Plaid, but there
were just prospects that weknew that we should be spending
more time with than less andeffectively we shouldn't be
treating everyone equallybecause of the value that
(13:33):
represented to us and also thevalue that we represented to
them as well.
Speaker 2 (13:39):
Makes sense, and this is around 2017, you mentioned
You're running these stand-upstwo times a day.
How many people are in thecompany overall in these early
days?
So Plaid?
Speaker 1 (13:49):
yeah, plaid was about 50 people in those early days
total, by the way.
So that was go-to-marketengineers, all that kind of
stuff exactly.
And for me on the go-to-marketside we had two initial kind of
founding AEs in the business andwe had two people on the
account management customersuccess side at that point.
(14:09):
And then we started to add acouple of people to the team
particularly we added two SDRs,pretty much all almost
immediately to really become aninitial filter for us for those
kind of hundred new prospectsthat were coming in, because it
was really a good opportunityfor us to start to then route
where that prospective customershould go.
Is that something that shouldbe sales-led, is that something
(14:30):
that should be product-led andbeing really prescriptive
ultimately in steering where aprospect should go?
Because there were also in somecases we couldn't do as good a
job as what the product couldpotentially do for a certain
segment of customer.
But there are also places wherewe as a sales-led motion or a
go-to-market-led motion, wecould do an inordinately better
(14:51):
job than what the product coulddo from that standpoint and so
we kind of like wanted to.
It was human-based routing.
At that point Again, we didn'thave this amazing level of
sophistication, at least at thispoint in time, which sounds
like quite rudimentary rightcompared to where people are
today in terms of revenueoperations and revenue
engineering.
But it was the right thing forus to do at the time and it got
(15:12):
us really, really close to thebusiness.
It got us really close to theuse cases and it helped us get
really close to the customer andwhere the value was for the
business.
Speaker 2 (15:22):
Did you have a go-to-market plan, a roadmap,
outlined at this point, or wasit going through this motion,
where it created the inspirationfor writing a go-to-market
roadmap?
Speaker 1 (15:36):
Yeah.
So I think one of the thingsthat I learned, especially early
on in terms of my work with thetwo co-founders of Plaid, zach
and William, is that and this isnot just a Plaid-specific thing
, this is a nearly every tech,early-stage tech startup thing
(15:58):
is that VCs invest in highlytechnical founders who are going
to build technical productsright, which is fantastic.
Really, really smart peoplehave found a way to technically
solve quite a unique problem,and the thesis of VC is like
let's go invest in those peopleand it's a great thesis and I'm
not saying that that thesis isbad, but obviously, in more
often than not, those foundersthat get invested into often
(16:19):
have very little understandingabout go-to-market.
The reason why this kind ofconcept of a roadmap became
important is because I alsoneeded to take Zach and William
and subsequently other foundersafter this through the process.
They actually did want to knowabout what it is that we were
building, why were we buildingthese things, but it actually
made it a lot easier for me toultimately communicate what was
(16:43):
our plan, why it was importantand what we needed to build next
, and really essentially in theearly days, we were making that
plan on a month-by-month basis.
Hey, we just implemented thisnew qualification framework.
We're seeing really positivesignal about it.
Okay, the next thing that we'reactually going to go build
around us is a little bit moresophistication in terms of how
(17:03):
we price.
Now that we've gotten better atqualifying our prospective
customers, we understand thevalue that we're creating for
them.
We probably need to get alittle bit better about how we
price how we write a proposalfor someone, because we also
wanted to really make sure thatwe were tying what it is that we
did to the value that was beingcreated at those companies as
(17:25):
well, and it meant that we justwould kind of continue to build
into the sophistication overtime and again.
Like I said, in the early days,we were literally going month by
month.
We would like get towards theend of the month and I was like
mini brief about what theroadmap would look like for the
next month and month over monthin that first year and then in
(17:50):
our second year it was reallylike hey, every other month we
would be kind of talking aboutlike what was going to come up
on the roadmap next, and by ourthird year it was like kind of
like a quarterly roadmap.
Fourth year it was a halfyearly.
Fifth year it was kind of halfyearly as well.
Sixth year, we were reallythinking about what the roadmap
looked over a 12-month timeperiod because obviously
go-to-market had continued toget larger over that time.
As I said, we were founded andwe had about four people when I
started.
By the end it was close to 200in the go-to-market organization
(18:13):
and so it's very hard to beoperationally changing things
month over month with that manypeople.
Like the impact that that wouldhave on the business is
actually probably quite negativethe speed of change at that
point.
But it really resonated and itwas really important for us in
those early days to have a realrapidity of change.
And the great thing is, by alsodocumenting these things it
(18:36):
kind of kept me a little bit incheck too, of like, hey, am I
investing in and putting theeffort into the right things at
this point in time?
I think most go-to-marketleaders when they start inside
an early stage business and Ihear this from formal colleagues
who've all entered into kind oflike going from like large tech
(18:56):
and into early stage startupthere's often this like
paralysis because there's justso many things that could
potentially be done in a periodof time and it actually gave me
real clarity of thought aboutbeing focused on what was
important at that moment for usas a business.
(19:17):
It wasn't about taking theplaybook that I knew and
superimposing that into thebusiness that I was in.
The playbooks that I've knownand learned and had an
appreciation for over the courseof my career are really just
it's just information that I'vegot and I need to work out
whether the things that I'velearned and experienced before
(19:39):
are applicable to the situationthat I'm in today.
It's not about taking the thingthat I was at and dumping that
on top of the business, becauseI think overly building process
in the early days of companiesis nearly as risky as no process
and there's that really healthybalance that you need to have
(20:01):
and I think go-to-marketleadership probably feel this
most acutely out of anyone isreally making sure that we're
building appropriately for thestage of company that we're at
and we're not overbuilding.
In fact, you probably want tofeel like you're just always a
little bit behind in terms ofyour go-to-market structure
relative to the rest of thecompany, rather than too far
(20:22):
ahead.
I think if you're too far aheadin terms of the infrastructure
that you've built into thebusiness, then you've probably
overbuilt and over-structuredthe organization and you're
probably running a costinefficient go-to-market
organization.
But you're probably alsoimposing way too much structure
inside the business.
That will actually be a netnegative for the business, not a
(20:44):
net positive.
Speaker 2 (20:45):
So it sounds like go in parallel to the rest of the
company in terms of finding thathappy medium of sophistication.
Speaker 1 (20:53):
Yeah, a super, super healthy balance.
Speaker 2 (20:55):
Yeah, and so to super tactical question.
But to not create overlyprocessed areas as you build
this out, how are you actuallycommunicating this to the team,
to founders?
If someone were to listen tothis and say I'm going to create
a go-to-market roadmap, whatwould you recommend they do for
actually sharing that anddisseminating the information?
Speaker 1 (21:17):
Look, I think today, anything like a G-Doc all the
way through to kind of Notion orsomething, so something that is
, by the way, completelyaccessible to everyone inside
the organization is the beststart, and we shouldn't hold
these things private, right?
We should be actually gettingthese out and exposed to the
team.
So I think it's a reallyvaluable exercise, not only for
a go-to-market leader todocument it, but also have it be
(21:40):
presentable, because I thinkonce you start to talk with
people and you start toarticulate what it is that
you're building and you startsharing and you're also willing
to actually receive feedback onthis stuff, it will also make
you a way better leader in theprocess, and I think one of the
great things about that bydocumenting and publicly sharing
this stuff as well is that youthen start to take the rest of
the company along with you inthat journey, and this I think
(22:03):
was very, very impactful for usat Plaid in that journey, and
this I think was very, veryimpactful for us at Plaid and
again I've seen this in terms ofthe dozen plus organizations
that I've spent time withadvising over the last few years
is that then the rest of thecompany also gets really, really
bought into the investmentsthat you're making and why, and
they become, quite honestly, amuch better partner for you in
that process, because they cansee what it is that you're
(22:25):
building and you know it's notthis black box of go-to-market
stuff.
In fact, you know I thinkthat's what a lot of early stage
founders fear when they bringtheir first external
go-to-market hire into thebusiness is, you know, this
person's joining from X company.
They're going to come in,they're going to impose their
will on our organization.
(22:48):
We're more engineering focused,we're more product focused in
the things that we do and Ithink, by being really
transparent with the things thatyou're building, being really
clear and making it accessibleto anyone who's interested in
finding that out, I think that'sa really great place to start.
But again, particularly, Ithink the key there is get it
documented, start sharing andreally see this as an
(23:10):
incremental improvement.
I'm a really big believer inmaking today just a little bit
better than we did yesterday.
That's the way that we shouldtreat this kind of concept of a
go-to-market roadmap as well.
How are we improving today overthe things that we did
yesterday and making smallincremental improvements and
changes progressively over many,many years inside an
organization?
Speaker 2 (23:32):
But if you ask anyone within an organization, they
know the product roadmap, theyknow what's coming.
It sounds like it should be theexact same on the go-to-market
side.
If you ask anyone whetherthey're on the technical side,
go-to-market side, everyoneshould have a clear idea of what
that roadmap is.
Speaker 1 (23:52):
Yeah, completely agree, because I think one of
the things sales teams andgo-to-market teams always clamor
for is the product roadmap.
We need it because we need it tosell and we need it to do these
things.
But then, conversely, if thego-to-market organization is
doing things that people don'thave any context of, they don't
have an understanding of andappreciation of, then they won't
be able to be as involved orpositively impacted by that.
(24:12):
And the thing that we found atPlaid particularly is, as we
started to share this more withpeople, the head of engineering,
jean Denis, and I would spendeven more time together kind of
aligning how product releasesand updates would be coming out.
Where does that fit now interms of our roadmap?
So we really saw this as a veryunifying function for us inside
the business and in a lot ofcases I think it was one of the
(24:36):
reasons not the only reason, butone of the reasons why we were
not only able to accelerate thegrowth the way that we did, but
it got us to a much, much faster, much better operating place
and a much better operatingcadence as an organisation.
Speaker 2 (24:51):
That is fantastic, and you had the first stage at
Plaid where you were iterating.
You were having these stand-upstwice a day.
What came after that?
As you started to move awayfrom all the inbounds and really
double down on the high-qualityprospective accounts.
Speaker 1 (25:10):
One of the things that became important for us as
we started to recognize who themost high-value clients for us
were.
Then the question then becamewhat do we need to do to seek
out more of those really highvalue clients for us?
And so then we started to thinka lot more about what is our
acquisition strategy, what isour distribution strategy for us
inside the business.
(25:32):
We had a very positive impactfrom some early product
partnerships that I mentioned,but what we needed to start
thinking about is okay, cool, weneed to start to diversify our
top of funnel.
And what does that look like?
What are the other channels forus from an acquisition
standpoint?
Should we do more things from apartnership perspective?
(25:53):
And this was, by the way, forus in the early days, it was
partnership referral, notpartnership selling.
We got to partnership sellingmuch, much later in the journey
for us at Vlad, but we reallythen started to think about what
do we need to do to go startgenerating better high-quality
top of funnel.
Let's get more committed tofield marketing.
(26:14):
Let's commit more in terms ofour SEO.
Let's start to get into things,our SEO.
Let's start to get into thingslike pay.
Let's start to get into thingslike outbound, and so we really
wanted to then go to startdiversify the things that we did
from a top of funnel activityfor us, and that was a really
critical thing.
But it was only once we couldsee really clear repeatable
(26:35):
patterns for us in the businessthat it then made sense for us
to go and invest into theseother channels, because we knew
that if we put a dollar in thetop of the funnel from that
standpoint, then the likelihoodthat it would precipitate into
revenue for us was pretty high.
We were moving out of this kindof like very random but amazing
(26:55):
stage for the business and justbringing in more structure,
creating more repeatabilityinside the business, and once
you see that repeatability,that's a really, really good
sign for us to then start toinvest in scale.
Speaker 2 (27:10):
Incredible as you scaled and started to create
that repeatability top of funnel, would you say that accelerated
your focus on a different typeof customer than all your
inbounds.
So it sounds like you shiftedall your inbounds to more of a
PLG motion.
You're building out more ofthat sales led motion, including
the two BDRs you hired.
Speaker 1 (27:30):
Yep, yeah, exactly.
So you know we went through aseries of really interesting
stages in terms of kind ofPlaid's go-to-market motion and
our areas of focus of thebusiness.
In the very early days we werea fintech ourselves, working
with other fintechs, and look,that was a very fast-growing,
(27:51):
rapidly expanding part of themarket.
There were literally hundredsof new fintech applications
being built every year andpeople starting to bring in
inside these fintechs like thekind of data that Plaid could
provide to really deliver on aunique product experience.
But what we also thought aboutover time is like, obviously,
(28:11):
like fintechs will not be theonly customer for us here at
Plaid and you know what doeslike the next phase of growth
look like for us as a company.
And we had sort of like twomajor customer categories that
we kind of thought about afterthe early stage FinTech.
The first of that was kind oflike going up market in FinTech
(28:32):
or financial services that wasto go into like the more
traditional banks and wealthorganizations and things like
that, so starting to work withlarge financial institutions
customers.
The large financialinstitutions were a big part of
the data network that we wereproviding, but there was also
real value in what we couldactually provide the traditional
financial services businessesas well.
You know, because they had, youknow massive businesses around.
(28:56):
You know savings and accountopening and funding to loan
originations like whether it wasunsecured or secured mortgages
and home equity lines of credit.
So we really wanted to start tomove up market.
But in that sense, what we alsoknew is that the likelihood of
those traditional financialinstitutions coming inbound to
us were very, very low.
(29:17):
But we really then understoodwhat our value proposition was.
We knew who we needed to go tomarket with and we knew who we
needed to target, and so we gotreally really clear about who
they were from a prospectivestandpoint and we started to get
more focused on outbound fieldmarketing and other things like
that to really go driveourselves into that audience.
(29:38):
And so that was phase two forus as a company, which was
really exciting.
It's a very, very slow process,at least at that time, selling
into the large enterprise banksand financial institutions, but
it was one that we committed to.
About two years after I started.
Kind of late 2018, kind ofgetting into early 2019 was when
we really started to kind oflate 2018, kind of getting into
early 2019, was when we reallystarted to kind of focus on that
(30:00):
, because not only was itimportant for us to start to
diversify, we also had a productthat was ready to sell into
that market and into that space,because the largest of
enterprises especially financialinstitutions and wealth and
things like that they had veryspecific needs from us as a
company.
They wanted uptime andavailability, they wanted
service level agreements, theywanted a lot more enterprise
(30:22):
reporting and insights, theywanted things like SSO and
rules-based access control andall these other things that in
the early days of us, when wewere working with a fintech,
those things didn't reallymatter, to be perfectly honest.
So we needed to not only evolveand change the way that we did
our go-to-market, our productalso actually needed to evolve,
(30:42):
and this was the other big thingabout having a roadmap relative
to our go-to-market motion.
I could then talk about ourroadmap and say, look, we are
now going to start to focusabout going upmarket and we're
going to need these things tobecome a reality of our product
for us to be successful.
And so then it became abi-directional conversation
between go-to-market andengineering about what we needed
(31:05):
from a product perspective.
And then the third market forus that we went after is we went
from fintech, as I said, intotraditional financial
institutions.
We then went into what we wouldcall this embedded fintech stage
, which were companies thatweren't fintechs and companies
that weren't financialinstitutions, but they wanted to
bring in a financial elementinto the product that they were
(31:28):
offering.
And a really amazing examplethere are like the major
telecommunications companies,they wanted to actually stop
taking things like credit cardpayments.
They wanted to move from creditcard into ACH and make a
fundamental shift, by the way,in terms of the way that they
got paid by their consumers.
Or another really great examplefor us in that instance was
Tesla was an early client on theembedded fintech side, and so
(31:52):
what was really interestingabout them is they are building
one of the most modern vehiclesin the world, but your down
payment and things like that foryour Tesla was by check.
So this is the most modernvehicle in history today, but
they were using a paymentinstrument from the 1700s.
It was a really funny branddissonance that was happening
there, and so we had companiesthat wanted to make the
(32:14):
financial element and elementsof their product be more akin to
the way that, like their moderntech, their modern stack, their
modern products were there andthat was really like the next
phase of growth for us, as wetruly moved out of just purely
servicing fintechs and financialinstitutions but moving into
this kind of like concept ofembedded fintech.
Speaker 2 (32:34):
What kind of AR inflection were you at where it
made sense to go into this phasethree, this embedded tech?
Speaker 1 (32:41):
We were scaling pretty rapidly at that point, so
we were probably around aboutthe 100 to 150 million in ARR
where that became quiteimportant for us.
Obviously, we'd grown very,very rapidly with our fintechs
and also with traditionalfinancial institutions at that
point, but that was when itbecame a really important part
(33:01):
and that has become one of thecore things of the business
today for Plaid, which is reallyexciting.
Speaker 2 (33:06):
Super exciting and what were some of the biggest
challenges that you faced?
Obviously, a lot went right intheir journey, scaling $3
million to $300 million.
What were some of the biggestchallenges throughout that?
Speaker 1 (33:23):
Oh, we got probably just as many things wrong as we
did.
People talk a lot about thecompensation plan, the
compensation structure for theirteams, but one of the things to
really think about when you'rebuilding the right kind of
compensation structure is alsothe impact that it actually has
on the way that your teams sellto your customers as well.
We made a really big mistake inthe early days, particularly as
we were moving into, like ourenterprise business.
We had a commission and payoutmodel that worked really well
(33:47):
for high, rapid, high growth,short sales cycle SMB clients.
You know often, you know peoplewere signing a 20K, 50k, 80k
order form, but they werehappening pretty rapidly.
We were closing deals in thesame day to less than 45 days
and we had a great compensationplan that really worked and was
(34:09):
quite reflective andrepresentative of our SMB
business that we were.
But as we started to move intothe upper market, our
compensation plan really thensaid hey, the way that you would
be compensated is essentiallyon the initial structure of the
deal.
What it actually meant was thatour sales teams were actually
keeping a deal open for a lotlonger period of time than what
(34:30):
we would have liked.
So what did we do.
We had incentivized in terms ofour structure for the team to
keep a deal open for longer.
So that meant that a deal wasessentially quote unquote on the
street for a lot longer than itneeded to be, because the way
that our compensation structurereflected that was like hey, we
would pay you out on the initialstructure of the deal.
So what it did is like our AEswere actively delaying and
(34:53):
trying to find not just thefirst use case but the second
and the third and the fourth usecase to make that initial deal
as big as possible, becausethat's what our compensation
plan was incentivizing them todo.
That was such a fundamentalmistake for us because it
actually meant that our dealswere staying out there a lot
longer than we would haveexpected because people were
(35:14):
trying to supersize these things.
And so what it did is that itjust created way more surface
area for us to make a mistake inthe sales cycle.
It often meant that ourcompetitors would actually
become involved in the salescycle, so we actually created
more competition for ourselvesin that process and we
essentially were just creatingmore risk in terms of getting
deals done, and so that, for me,is probably one of the standout
(35:35):
mistakes that I made, alongwith like hundreds of other
mistakes that we made over thecourse of the six years that I
was there.
But that was probably one ofthe biggest ones and we needed
to go make that change.
And once we recognized thatthat problem existed, we made a
wholesale change to the way thatour compensation structure
worked.
In fact, we ran differentcompensation structures based on
(35:57):
the different roles that we hadinside the business, because
that's what the businesswarranted.
We couldn't build a structurethat was just one size fits all.
Speaker 2 (36:08):
And that's great advice for anyone really
building out their teams too isto think about whether a blanket
process makes sense, whether itmakes sense to build them in
silos a little bit more.
Speaker 1 (36:17):
The key there is really don't over-engineer the
process.
For us, when we were thinkingabout our go-to-market motion,
we really wanted to keep thingssimple, and I think that that's
a really important thing,especially in a rapidly changing
, rapidly evolving environment,and I think that would probably
apply not just for Plaid, butlike many, many high growth
startups that are out theretoday.
Speaker 2 (36:39):
Great advice.
And, paul, are there any booksthat have made the biggest
impact on your career?
Speaker 1 (36:46):
Yes, I mentioned before thinking about improving
the business and making todayjust a little bit better than we
did yesterday.
I've always talked about thisconcept for a really long period
of time and it wasn't until Iread this book and I read it a
couple of years ago.
It was a book by James Clearcalled Atomic Habits, so
essentially like how do you gobuild repeatable habits inside
(37:07):
the business?
It really really resonated withme.
I think I had sort of likearticulated versions of that
kind of concept for a reallylong period of time, but it
really really hit home for mepersonally.
In fact, we actually got Jamesto come to our revenue kickoff
in 2021, I think it was, yeah,2021 or 2022.
(37:30):
And we already spent time withthe entirety of the Plaid team
and that, for me, was reallyimpactful.
And I'll give you a second one A, because I was a contributor to
this book, but B I think it's afantastic one.
So Index Ventures actually is afantastic VC, but they're also
a fantastic publisher and theyactually wrote a book a couple
of years ago and released it andit was called Scaling Through
Chaos and I think it's a reallyimportant book for not only
(37:53):
founders to read.
It's largely directed atfounders, but I think it's also
really important forgo-to-market people to read this
, largely because it will helpget you into the mind of what it
is like to work with a founder,some of the pressures and the
challenges and issues that theyface daily, and kind of like
where our role as go-to-marketleadership should fit relative
to founders.
So I think that that's animportant kind of like industry
(38:15):
read for anyone.
That's an important kind oflike industry read for anyone.
Speaker 2 (38:18):
Great recommendations there.
We'll drop them in the shownotes and both fantastic reads.
I think the James Clear one Iactually got notes of earlier in
your conversation around justfocusing on being 1% better
every day and thatincrementality mindset.
Well, paul, this has beenfantastic.
Really appreciate the time,appreciate you sharing all of
these insights and your journeyat Plaid.
(38:39):
Where can people find you ifthey want to get in touch or
follow your journey?
Speaker 1 (38:42):
Best place to find me is on LinkedIn.
Speaker 2 (38:46):
Brilliant.
That will also be in the shownotes, Paul.
Thank you so much to all ourlisteners.
Thank you for joining us and wewill see you next week.
Speaker 1 (38:54):
Thanks, Sophie.
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I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Ruthie's Table 4
For more than 30 years The River Cafe in London, has been the home-from-home of artists, architects, designers, actors, collectors, writers, activists, and politicians. Michael Caine, Glenn Close, JJ Abrams, Steve McQueen, Victoria and David Beckham, and Lily Allen, are just some of the people who love to call The River Cafe home. On River Cafe Table 4, Rogers sits down with her customers—who have become friends—to talk about food memories. Table 4 explores how food impacts every aspect of our lives. “Foods is politics, food is cultural, food is how you express love, food is about your heritage, it defines who you and who you want to be,” says Rogers. Each week, Rogers invites her guest to reminisce about family suppers and first dates, what they cook, how they eat when performing, the restaurants they choose, and what food they seek when they need comfort. And to punctuate each episode of Table 4, guests such as Ralph Fiennes, Emily Blunt, and Alfonso Cuarón, read their favourite recipe from one of the best-selling River Cafe cookbooks. Table 4 itself, is situated near The River Cafe’s open kitchen, close to the bright pink wood-fired oven and next to the glossy yellow pass, where Ruthie oversees the restaurant. You are invited to take a seat at this intimate table and join the conversation. For more information, recipes, and ingredients, go to https://shoptherivercafe.co.uk/ Web: https://rivercafe.co.uk/ Instagram: www.instagram.com/therivercafelondon/ Facebook: https://en-gb.facebook.com/therivercafelondon/ For more podcasts from iHeartRadio, visit the iheartradio app, apple podcasts, or wherever you listen to your favorite shows. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com
The Joe Rogan Experience
The official podcast of comedian Joe Rogan.