Product Marketing Adventures

Moving upmarket to Fortune 1000 accounts isn't just about great products—it's about building trust with complex buying committees. Kevin Gough joins us as one of the most creative problem solvers in product marketing, from launching Google Cloud products to leading category-defining efforts at Okta, Asana, and Grammarly. Today he's sharing how he built trust strategies that opened enterprise doors and helped Okta beat Microsoft at their own game.

Kevin reveals his approach to mapping each stakeholder's unique trust requirements—treating trust like a product with features and proof points. We explore Okta's "trust ecosystem," including their genius microsite showcasing uptime data and compliance documentation usually buried in legal folders. This wasn't transparency theater; it was demonstrating trust with actual receipts that transformed market perceptions.

The magic happened when Kevin mobilized the entire go-to-market team around trust, transforming it from marketing message to company-wide mission. His approach proves platform storytelling isn't about louder claims—it's about earning trust one stakeholder at a time, proving even Microsoft-sized giants become beatable when you get trust right.


LINKS

Rippling (messaging critique): https://www.rippling.com/ 

Connect with Kevin:

LinkedIn: https://www.linkedin.com/in/kevingough/ 

Connect with Elle:

LinkedIn: https://www.linkedin.com/in/elle3izabeth/ 

What is Product Marketing Adventures?

Product Marketing Adventures is the only PMM show that goes beyond theory and into the real execution of product marketing. In each episode, experienced product marketers co-host two segments of the show: first a case study example of their work, followed by a messaging critique of companies we admire. Listeners enjoy a fun conversation packed with practical guidance to leverage in your product marketing career.

Elle: In the world of

B2B, moving up, market

means landing larger,

more complex customers.

Think like Fortune 1000 or

Global Enterprise accounts.

These deals are

often high value.

High stakes and come with

really long sales cycles,

and they're really complex

with multi-threaded

buying committees.

And in my experience, from

scrappy startups to scaled

enterprises, cracking into

that world is never easy.

It takes way more than

just a great product.

It takes trust.

Which brings me to our topic

for today, how to build

trust with that upmarket

segment to unlock growth.

With that, it is my

pleasure to welcome

Kevin Goff to the show.

Kevin is one of the

most creative problem

solvers in the product

marketing community.

He was the first.

PMM for what's known today

as Google Cloud, where

he launched game changing

products like Google

Workspaces and Chromebooks

for business and education.

Since then, he's led

category defining efforts

at companies like Okta,

Asana, and Grammarly, helping

each one to rethink how

they show up in the market.

and build trust

with customers.

And before all of that,

Kevin actually stepped out

of college to start a digital

accessibility compliance

company, which went on to

be acquired by KKR in 2022.

Oh and fun fact, he also sang

on the Edward Scissor Hands

movie soundtrack as a kid,

Kevin, I'm thrilled

you're here.

Welcome to the show.

Kevin: Thanks so much El

excited to, to dig in.

Elle: Yeah, likewise.

A little bummed.

We're not digging into

the Edward Scissor

hands experience.

We'll have to chat

about that another time.

Kevin: I know.

Well, maybe this will be a

good voice warmup for me.

Know.

Elle: I love it.

All right.

Well, let's dive right in.

I can't imagine anyone would

not know this, but just

to keep listeners up to

speed, can you give a brief

overview of Okta for us?

Kevin: Sure.

So Okta makes it easy

to sign into all your

workplace applications.

Uh, it keeps them secure

and makes sure the right

people have access to

the right applications.

Elle: Awesome, thanks.

So, Okta of course is part

of the, the case study that

we'll be discussing today.

So, with that, that the

topic that we'll be diving

into around that case study

is, building trust with

the upmarket segment and.

I'll just say this isn't

a fluffy brand topic that

I think a lot of, uh,

marketers may think it is.

So for the first segment of

the show, let's talk through

that case study a bit more.

What was going on at Okta

when you realized you

needed to completely over

all the messaging and the

go-to-market strategy for

that upmarket segment?

Kevin: Yeah, definitely.

So, so first off, you know,

it's funny, we're, we're on

a product marketing show,

but, uh, this, you know,

is not a product, right?

Trust is not a product per se.

but it, it is something that.

We, our kind of insight

was we need to market

trust the concept just

like we market a product.

So some of the same

tools and techniques.

And so to, to walk you

through what you said, uh,

Okta was doing great in the

bid market, uh, but we were

trying to move up, up market

to really sell to those large

enterprises, and Microsoft

was our, our main competitor.

They had, you know,

20 year relationships.

They had earned credibility.

some people had built their

careers on it, and so our

deals were stalling because

our target, uh, customers.

Uh, really weren't willing

to make the jump to a

relatively new vendor, so we

really had to gain the trust

of the buying committee.

And, what we did was really

a, a holistic approach.

So this was a company-wide

initiative that was

something, everything

from brand to sales.

but the question was how

can product marketing

contribute to it?

and so that's where,

where we came in and we

could walk through some

of those activities.

And ultimately the goal was

really how do we uplift, uh,

conversions across the funnel.

we actually did a before

and after, measurement

of brand trust scores.

So how do we improve those

and then increase win rates

against Microsoft specifically

in that enterprise category.

Elle: I love that.

So, man, talk about going

up against a Goliath like

Microsoft is huge and while

Okta of course now has a

very respectable brand and

really strong recognition in

the market, I could imagine

how back then not, not that

that was that long ago, but.

Could have been pretty hard

if you're trying to win

with those big enterprises.

and you mentioned so much

that I wanna dig into, you

talked about how it was a

holistic approach and it was

a company-wide initiative.

Um, and you didn't just slap

on, you know, hey, we're

secure some kind of badge.

Right?

you went so much

deeper than that.

It sounds like you tackled

this from like product sales,

marketing, and potentially

even, you know, analysts and

so many different angles,

all while staying consistent

on a current narrative.

So I wanna dig a little

bit deeper on how

you landed on this.

I guess, like, what was

part of that analysis for

assessing the situation?

Like why did you, why

trust was the main core

value that you wanted to

anchor on as a company?

Kevin: Yeah, certainly.

Well, you know, I think it

was, it was looking at, at our

sales data and uh, what we saw

was we had a superior product.

Uh, if you, if you even

did kind of side by

side comparisons, uh,

people preferred our

product capabilities.

but we saw just our win

rates were not where

we wanted them to be.

We also did some market

research and understood

sentiment analysis of Okta

compared to Microsoft, and

we also looked at some of

the, claims that competitors

were making in the market.

Claims about uptime

or compliance.

And we recognized that we

weren't really, at parity,

uh, with some of these

claims, even though maybe

our product could deliver

the same amount of compliance

or same amount of uptime.

Uh, so it was really looking

at both market signals,

but also looking at the

state of our product.

And we really felt our product

was ready for the enterprise.

So how do we, uh,

make market perception

match market reality?

Elle: Got it.

Okay.

And it sounds like, multiple

members of the team and

potentially even third

parties, you did so much

analysis and it's analysis

from sales and feedback

from sales, looking at

your win rates, all of

that told a story that.

Hey, we have our

product can do this.

Our product can solve the

problem that the customer has.

We just need to step up to

the plate so that they can,

rely on us for the long

haul like they can with a

big beast like Microsoft.

Kevin: Right.

There was, I mean, there

was kind of a, a vendor

consolidation, right?

People wanted to choose

a few strategic vendors.

So our idea was how could

we, we be one of the top

five vendors that someone

chooses to have a, a long

term and hopefully million

dollar, uh, relationship with.

Elle: Yeah.

Right.

Absolutely.

So when you think about

it with your team, then

focusing on the, I guess,

product marketing's role

moving forward, you, you have

this very, uh, compelling

assessment with all this

data and the team across the

entire, when I say the team,

I mean the entire company

is rallying around this.

What was, I guess, the

task at hand just for

product marketing, I guess?

How did you get started?

What was the big

question in your mind?

Kevin: Well, really it

circles back to thinking about

trust as a product, right?

So if we were to market a

product, if we were gonna

go to market with a product.

What are the components of

an amazing product launch

or, product messaging and

taking that, you know,

something that's very

tangible, like product

marketing and applying it to

something that's a little bit

less tangible, like trust.

So really it starts just

like when you're, starting

to market a new product

with thinking about the

buying committee and who

are you actually trying

to sell to, and what do

they actually care about.

That was, that's true

for products, but it

was also true for trust.

So different members of the

buying committee, which we

had mapped out, you know,

from engineering to product

to finance and compliance, we

realized they had different,

uh, values or different

things that they cared about.

When you talked about

the concept of trust.

Elle: Got it.

Okay.

I wanna talk more about the

buying committee process.

and I feel like it's worth

thing again, when you thought

about product marketing's

role and looking at this

non-tangible thing like trust.

Looking at it as a product

like what's required,

that dedication to, I

guess, like redefining

that experience from the

customer's perspective

and how the customer may

experience what trust.

looks and feels like.

So, I would love to now

turn this into a playbook

and, you know, say that

I'm a PMM facing, you

know, some kind of like.

You know, maybe it's like

late stage friction or trying

to move up market, whatever.

and I've done that research

and benchmarking that

big assessment that maybe

you've done or done in

partnership with various

folks across the team.

and now I'm realizing I need

to build out a go-to-market

strategy and some messaging

around some key value, you

know, whether that's trust or

quality or even authenticity.

Um, like where do I start?

What's step one?

It sounds like.

Mapping some something.

You, you started to talk

about buying committees, but I

don't wanna get too far ahead.

Like what, what's step one?

Kevin: Sure, certainly.

So, so I really think it

is about, you know, we

all talk about ICP and the

firmographics and personas,

but it's really understanding

as you move up market,

especially to the enterprise,

there's a broader set of

people in the buying committee

as compared to mid-market.

So one, we were

really expanding.

Our, our buying committee,

it might have been different

layers within the IT team,

not just the directors,

but the VPs and the CIOs.

It was also expanding,

uh, cross-functionally.

So you had chief compliance

officers, for example, you

had chief legal officers.

You had very sophisticated

procurement teams.

So first we had to kind

of map out this broader

set of buyers and then

that contextualization.

So I'll just give you

a couple examples.

When we talk about trust

for the product team,

they actually cared

about uptime guarantees.

So they cared that the

product was gonna be

up 99.99% of the time.

So if they had a big

spike in traffic on their

brand new Uber competitor,

that they wouldn't lose

any of those signups.

So, you know, that was their

kind of definition of trust.

Whereas the engineering

team actually cared about

APIs and API documentation.

And let's say if we move from.

Version 1.2 of the API

to 1.4, that it wouldn't

break any of their code or

any of their integrations.

So that's what they

meant by trust.

And so we've came to

realize that different

stakeholders really had

different metrics for trust.

So we really had to

contextualize that kind

of fuzzy concept in a

lot of specificity for

the various stakeholders.

Elle: Yes.

And what you're saying

makes a lot of sense too.

'cause I think, earlier in

our conversation, just a few

minute moments ago, as we were

talking about, well, what does

it mean to move up market?

And, um, you know,

what that challenge

is, you mentioned that.

in the upmarket segment,

these companies are

really looking for like

consolidation and they're

looking to get more with

these like, you know, this

idea of like best of breed.

And, and I know we're gonna

get into more of that a

little bit later, but, what

you're saying, it makes a

lot of sense now then to

dig deeper into this more

complex, sophisticated

buying committee.

and looking at it from

each perspective of.

How, how does this person

think about trust and

what about this person?

it makes a lot of sense.

Okay, so let's say as

A-P-M-M-I am, you know,

on this journey and I've

accomplished step one,

I've done all of the

mapping and analysis on

that buying committee.

What's next?

What's step two?

Kevin: Yeah.

So step two I really

think is, is creating,

uh, I call it like a trust

ecosystem or your ecosystem.

Around your organization,

so you've all had seen the

cliche of like a used car

sales person saying, Hey,

trust me, or something like

that, you The reality is your

brand, your, you know, your

statements can only go so far.

So, you need to start

to develop and cultivate

these third party proof

points or very data

grounded proof points.

so an example would be a

product level proof point.

So we launched a, an updated

trust.okta.com site that

had historical information

about our uptime and had

an updated guarantee.

I think it was.

Three nines instead

of two nines.

And even that uptime

guarantee was something

that, uh, we had to actually

go to bat for internally.

So we had to talk to the

engineering team, we had

to talk to the legal team.

We had to talk to the finance

team because there were some

risks in terms of service

level agreements, and we

might have to credit back.

Some amount of the purchase

price if we didn't actually

meet those uptime guarantees.

So product marketing, we

really need to make the

case that this would help

increase sales and move up

to the, into the enterprise

to offset any financial risk

or legal risk that we might

be exposing by being more

specific in our, even our

uptime, uh, for example.

Elle: Yeah.

Got it.

It's so helpful.

So there's all kinds of

different validation points

from, you know, maybe third

parties that you can look at.

I love by the way, and I know

we're this too, we're gonna

get into more later, but,

building out a separate site.

To house all this strong

validation that you're,

that you're building, makes

a lot of sense and Right.

It's, it's that, trying to

say without saying like,

don't just take it from us.

Like, don't just

take my word for it.

Okay, so once you get that

validation going, how do you

take all that work that you've

done with the persona and

the buy team and put it all

together in a story that's,

you know, backed by evidence,

you know, in addition to that,

all that third party data and

like, you know, even bringing

customers into the net mix,

like what's the next step?

Kevin: Yeah, so you, you

know, you raised a good point.

So I'd say it's, it's

more than just you

providing that proof.

It's things like any third

party certifications you have,

you think of FedRAMP or HIPAA

type of certifications that we

also had to kind of advocate

as product marketing to get,

it's brand associations.

So we actually.

Forged some partnerships

in, in collaboration with

partner marketing with other

companies who are actually

competing with Microsoft.

So you think of Box or Slack

or Zoom, I think we called

ourselves the Velvet Alliance.

Right.

and we were kind of the

best of breed and so we

also got some validation

of way if someone used

Zoom and they liked.

Maybe they'd wanna use Okta.

So that also helped in that

kind of trust ecosystem.

and then I'd say step three is

not just those third parties,

but really how to get your

customers engaged and really

kind of trying to tie, your

trust points that you're

trying to, demonstrate with

some of the business outcomes.

That your customer

actually cares about.

So not about efficiency,

but really about those

business outcomes and how

they're really trusting

you to help deliver

those business outcomes.

Elle: I love that.

I love that.

So it's, there's so many

opportunities for the third

party component, but then

taking what the customer,

what's meaningful to the

customer, and framing ev all

of your capabilities and,

you know, the differentiator

of your product rather than

starting with that, starting

with, well, what's really

meaningful to our customer

and their business and what

they're trying to achieve.

and we did that a

lot at Cisco as well.

across the company, or at

least across marketing, we

always frame everything that

we're doing around business

outcomes for the customer.

so I can attest that that is

a very, uh, effective strategy

from a PMM perspective.

Okay.

So bringing it back to

our step-by-step process.

We've got mapping and

contextualizing, we've got

the, the buyer team, we've got

building out the, validation

points, you know, maybe

that's with third parties

and, you know, maybe it's

with, you know, metrics

that you can provide with

the, you know, like you

gave the uptime example, and

then we have the bringing

customers on board, getting

them engaged, and really

framing the story around,

you know, their business out.

Comes, I guess like as

you're thinking about all

of this, and especially

with like the validation

with third parties and

customers, we'd be remiss if

we didn't talk about analysts.

So tell me, what role do

analysts play in all of this?

Kevin: Sure, certainly.

Well, as you, as you move

up, market analysts are

increasingly critical.

Uh, large companies, uh, one

maybe don't have the time to

evaluate all the different

vendors in an ecosystem,

and so they look to their.

Hopefully well paid

analysts to do some of

that vetting for them.

And there's a little bit of

risk mitigation honestly,

too, where you can say, Hey,

I made this choice because.

Gartner or Forrester also put

them in the leaders quadrant

of the Magic Quadrant.

Um, so there's a little bit

of bias towards that as well.

So I'd say analyst is

definitely a long game.

my strategy that I've found

that works well and also

I think works well for

the analyst is you both

wanna listen and share.

So analysts do have a broad.

Based insights into a market.

They're talking with

all of your competitors.

They're talking with

all of your customers.

So they can share a lot of

insights in terms of product

roadmap, differentiation,

even things like messaging.

They can say, well,

this message is dead.

People aren't

interested in that.

Um, so I always wanna

listen and learn from them

up front, but I'm also, to

be honest, always planting

little seeds, even in those

listening sessions to try

to tease out those core

bits of differentiation.

That we have, against a, a

competitor, especially one

like Microsoft, where they've

probably had a long-term

lucrative relationship with

a Microsoft type vendor.

So, I'd say it's a long game

in terms of changing vendor

perception, but one of the,

the tricks, or I've tips, I

would say, is really focus on

trying to get a question or

two, that you can influence

in one of the magic quadrants.

So, For example, for Okta,

we really did a great

job with integrations.

We had literally thousands

of integrations, which made

it very easy to sign in to

all these new cloud apps.

And that was something that

we were much, much better

than our competitors on.

So we were successful in

getting that question in one

of the magic quadrants, and

that really helped to improve

our score and our perception.

And ultimately we

became a leader in

the access management,

uh, magic quadrant.

Elle: That's so strategic.

So, I totally agree.

The Magic Quadrant, strategy

from a vendor perspective,

it starts way before you

actually get the questionnaire

from Gartner, um, or you

know, magic Quadrant or

whatever, equivalent other.

Um, yeah.

IDC.

Yeah.

all of them.

And I think it's so strategic

to think about plant when,

when you plant those seeds

and the way that you were

able to do it with your

differentiators, so that

you ended up getting your

differentiator as a question

on the questionnaire as

just really smart thinking.

okay.

So it sounds like step four

would've been like building

out that analyst strategy,

which maybe you should I, from

a timeline perspective, now

that I'm thinking about this.

You know, some of these

things are happening

in parallel, right?

It's not like you do

one check, then you do

the other one check.

Like you have to be

thinking from a timing

perspective, some of these

things are happening.

You know, I. either earlier on

in the process, I can imagine,

for example, like planting

those seeds with Gartner.

It's an ongoing strategy.

You just have to make Sure.

all that goodness that

you're doing in the first

few steps with like,

mapping out the buyer team

and building out, um, the

validation and the, and the

customer objectives, right?

Like you're bringing that into

the analyst strategy, right?

Like is that kind of what

you guys did at Okta?

Kevin: Yeah.

Well, I, you know, honestly,

I think it became a year long

initiative for us because

there are things, I mean,

you think of some other

long lead times like to,

to do the uptime guarantee.

Engineering needed to

do a little work, to

get the certifications.

We actually had to apply

and get audited for, you

know, SOC type two or HIPAA

or

FedRAMP.

so I think that there

is, of course, there's

some quick wins.

I think the customer stories,

like, you know, a JetBlue case

study that says they trust us

with a thousand flights a day.

That's something you can

do, you know, in a month.

Whereas some of these other

things are longer lead time.

So I wouldn't say don't start

until you have everything,

but I think it's probably

gonna be a little bit more of

a, of a rolling thunder, um,

as you're rolling this out.

Elle: Yeah.

Yeah.

Helpful tip.

Okay, so, once you get all

of this strategy in place

and you're, you have some

of those quick wins as well

as, you know, the long term,

uh, plan all in place, what

does this look like from

a customer's perspective?

Kevin: sure.

So, you know, I think

really to make this or

any initiative successful,

it's about how to deputize

the entire go-to-market

organization so you're

kind of getting the same

message across all surfaces.

I mean, very explicitly

and visually, we

redid our website.

We, we chose some really rich

purples, you know, and kind

of financial services type

imagery that said, Hey, you

know, trust us we're serious.

But it was also about, uh,

the sales team and giving

them a trust playbook, you

know, with a specific assets

and collaterals around

compliance that they could

actually present to customers.

it was partnering with the

customer success team as well.

So how can we give the

customer success team

information around these

enhanced capabilities that

might drive improved renewal

rates or expansion into areas

of the business that they

hadn't quite been comfortable

trusting Okta, uh, previously.

So, um, that I think was

part of the success was

everyone was kind of a trust

ambassador for the company.

Elle: I love that everyone was

so involved and when you do

that, especially earlier on as

I, it sounds like you guys did

this with building out the,

the go to market strategy.

Everyone got to, I guess, like

see that plan as it was coming

to fruition and I'm, I would,

be willing to assume that.

Even take part in shaping it.

So then as you go and,

and do that, step five

of, to use your words,

deputizing, the entire

go-to-market organization.

It's not the first time

they're seeing or hearing

it as in, I don't know about

you, but I've certainly

experienced, um, I would

say even mistakes that

I've made, like not looping

sales in early enough when

I'm building a strategy

and then I go to do some

sales enablement and they're

like, whoa, whoa, whoa.

Hang on.

And then I get great feedback,

but it's feedback I should

have and wish that I gotten,

would've gotten earlier on.

Um, so it's, it's good then.

cause then by the time

you go and launch, they're

eager, willing, and they

have an appetite for

this great content that

you're putting together.

Like that playbook, that the

trust playbook you mentioned,

which sounds really cool.

Um, and helpful for the team.

Kevin: Yeah.

Well, I think, I think

what was, particularly,

uh, important there was

showing the, the other

cross-functional partners

metrics that would be

meaningful to them that we

could move, or we believe

we could move with this.

So corporate marketing and

customer marketing, it was

brand perception we could

move that we believe we could

move, um, lead generation

and conversion rates.

And win rates in, uh,

the enterprise market.

So that meant our enterprise

sellers were more engaged and

we believe we could improve

renewal rates as well by this

in the enterprise segment.

So that meant our customer

success team was engaged.

'cause the metrics we

thought we could move were

aligned with the metrics

that they were gold upon.

so there was a symbiotic

relationship there.

Elle: Yeah.

Okay.

And can you talk a little bit

more about the microsite that

you, um, or the, the Okta

team built, I guess, like

what was the goal of that

microsite and what kind of

content did you put on there?

I know earlier in our, in

our chat you mentioned, um,

that you put some of that

validation content on there.

What else was, did

you use that site for?

Kevin: Sure.

So I mean, I'd say the, some

net new aspects of it was one,

the kind of visual dashboard

of our uptime over time.

So it was literally

a heat map.

You know, where you saw

green and yellow and red and

hopefully not a lot of red.

Right?

Uh, that kind of said,

Hey, we're being, it was

a transparency, so we're

being transparent with

you over six months.

And so you can actually be

confident that what we're

claiming is actually, what

we're, what we're delivering.

So that was one.

The second was kind of fun is

we actually had increasingly

been hiring security

researchers and regional chief

information security officers.

So we use this as a, a

launchpad for publishing

security research to

improve our thought

leadership and credibility.

Elle: That is so smart.

Kevin: Yeah.

Yeah.

And then the, the third one,

which was kind of low hanging

fruit, and I actually think

a lot of companies might have

this, is there was a lot of

documentation that we had to

go through for these various

certification processes.

You know, SOC type two

or HIPAA or FedRAMP, and

typically that lives in

some shared folder, and

if some customer asks for

it, you send it as a PDF.

Um, so it, you don't get a lot

of marketing value from it.

But we actually put that

all online and so we had

a whole compliance section

and so it enabled us to

be much more front footed

and those questions and

conversations earlier.

Customers could discover

it themselves or sales reps

could just kinda link to

it and it just, once again,

it forced kind of that we

were buttoned up and the

transparency to remove

friction in the process.

Elle: that's the exact

word I was gonna use.

Transparency.

It's like you removed all

the blockers that typical

B2B intentionally puts there.

Kevin: Mm-hmm.

Elle: So for customers or

prospective customers to

get all this information

and do some of the diligence

themselves upfront, I

mean, even when I'm doing

buying for marketing tools.

I wanna do as much research

I can before I have to pause

my own buying process to wait

to talk to a salesperson, to,

for them to do their pitch.

And then we go back and forth.

Like, I just wanna do as

much diligence on my end as

I can to make my shortlist.

Before I go forth

having some engagements.

So it's helpful, to, arm

your prospective customers

with that information so

they can get it themselves.

Um, and then the other

thing that you mentioned,

that strategy that you did

of hiring these, you know,

security experts to author

some content it all helps

to build that trust that

you're trying to achieve.

So I just wanted to call that

out as, Being really helpful.

Very cool.

Yeah, Okay.

So quick recap on

everything, you know,

we talked about so far.

so step one, we talked

about, um, mapping out

the buying committee

and like contextualizing

around the buy team.

Um, you talked about step

two of, building out the

validation points, and

that could be everything

from your own product

validation to third parties.

Um, step three, you

talked about, tying

everything to mm-hmm.

Business outcomes for your

customers, and then step four.

having an analyst

relations strategy and

then step five to, deputize

the go to market org.

And all of these steps

maybe, you know, are

happening in parallel.

So not necessarily a one

after the other type of thing.

But, uh, a lot

of goodness here.

And I guess like the one

thing that I don't know

if we talked about yet is.

When all this is said and

done, you know, you're, you're

in the, you've got your story

in the market, you've got

this brilliant microsite up.

what are the metrics that

you use to make Sure.

that a strategy like

this is working?

Kevin: Sure.

So we had, we had done a

brand study, so we were

able to do a measure of, of

increased in brand perception.

So that's kind of

the top of the funnel

as much as anything.

we were also able to

measure, uh, win rates.

So increased win rates

specifically against

Microsoft or other.

Competitors in the

enterprise segment.

Also, we saw a, an uplift

in those renewal rates in

the enterprise segment,

so we weren't losing

deals back to Microsoft.

And then we were looking at a

lift in pipeline, specifically

in the enterprise segment.

So really, uh, it was, uh,

initiative that, as you said,

it was multi-threaded, but

was able to deliver on a

number of different dimensions

across the, the buyer journey.

Elle: Yeah, I could imagine

being part of a team and

as you're doing maybe team

check-ins or you know, a

road show or of some sort

on some of the results.

Maybe it's even like

a company all hands.

I could imagine the

celebration when you see

some of those, all that hard

work that everyone had been

working towards for so long.

Payoff, that's,

that's really awesome.

Okay, so final question for

you on this topic, Kevin.

So for any PMM out there

who's trying to move their

product up market, and maybe

they're focusing in on some

non-tangible value like

trust, what's one piece of

advice that you have for a

PMM who's in that situation?

Kevin: I think it was really

the unlock was, uh, getting

much more specific on the

buying committee and really

contextualizing this idea of

trust or really any product

feature to have it be specific

to either the KPI or the

strategy or the value that

that specific member of the

buying committee was pursuing.

And so that allowed us to

really be crisp in terms of.

The value that we were gonna

deliver to them on trust.

And it also kind of created

these new work streams with

collaborative partners like

engineering, with like sales,

like, uh, customer success

that enabled us to expand

the initiative beyond just

being a, a product marketing

initiative or marketing

initiative to truly a, a

company-wide initiative.

Elle: Yeah.

Yeah, I think so too.

So, and I really appreciate

how you and the team thought

about what trust looks like

across that buyer team, and

it made it so, so much more

personal and more genuine when

you do it that way, versus

just applying to what you want

trust to be and then slapping

it across all the content.

You know, it sounds like

from the very beginning.

You, you, when I say you,

I mean you and, and the

rest of the Okta team.

Um, you know, you did all

this research around really

understanding like what

are, what signals gave

customers that confidence

to move forward and what

proof they needed to do that.

it's.

Obviously speaks that

it was very successful

by doing that approach.

and you didn't just throw

some, you know, generic

trust signals into the mix

either again, like, not

just like slapping a badge

on a, on, on the website.

You actually built something

that's personal and human.

Um, so I love that.

It's, it's really helpful

and appreciate you taking

the time to walk us

through this playbook.

Alright.

Okay, so closing out that

segment and moving on to.

the next, next segment

of our show is the

messaging critique.

Okay.

So this is where we as product

marketers get to analyze real

world market or messaging.

And the fun part is,

Kevin, you might guess

get to pick the company.

so before we get started,

I'm gonna walk through,

um, some quick round rules.

So.

You're gonna tell us what

the company is that we're

going to analyze today.

and then once we do that,

we're, you're gonna walk

us through the messaging.

Um, you're gonna tell me

one thing that you're loving

about the messaging, something

that stood out about the

product, and then you're

gonna tell me something that

you wish the PMM would've

done differently as they were

building out that messaging.

And then finally.

We're gonna do a quick

fun brainstorm around how

could this PMM take it,

uh, to the next level,

how, you know, maybe they

could create, um, some fun

content or a new creative

campaign, something that

the PMM could think about.

it's all about

refining our craft.

No negativity.

Just a thoughtful,

constructive critique.

So let's get into it.

What is the company that you

would like to analyze today?

Kevin: Yeah, so the

company I wanna look

at today is rippling.

It's kind of an everything in

one tool for small businesses.

It does hr, IT financial

things like spend

management, payroll.

So I think it's

interesting because

it's kind of a platform.

But the buyers are

pretty different.

Typically a HR person versus

an IT person, versus a finance

person, they really have

to try to reach a really

diverse set of buyers.

But for a system or a

tool that's, that pitches

itself as all in one.

Elle: Yeah, you really

distinct buyers that,

that you mentioned, right?

Like you, I think you said

it, hr, finance, those are

very distinct buying centers.

Um, okay.

So for those of you

who wanna follow along,

check out rippling.com.

It's R-I-P-P-L-I-N g.com.

okay, so tell me

about their messaging.

Like right off the bat.

No, I guess just starting at

like with their head, header

and subheader, what are

you seeing here and what's

working and not working?

Kevin: Yeah, so their, their

header is, employees get

more done with rippling.

And here's what I like about

it, is they're not, because

they have such a diverse

set of buyers, they're not

trying to get something that

touches every single buyer.

They're talking about the end.

Consumer, which

is the employee.

So hr, it, finance, ultimately

they in some ways have

to be in service of the

employee, and if they can

help the employee get more

done, then that delivers

value across the business.

So I like how they've kind

of thread the needle where

this is something that

all three of those buyers

probably wanna have happen.

Elle: Yeah, so it's kind

of like uniting these very

distinct buying centers

around one common goal.

and I heard this, maybe I

heard it from a different

guest on my show, I can't

remember, but I heard this

one time where you can

tell how good a product is

by like when you take it

away from your end user.

And how they react to

you taking it away.

Like Slack is an

example of that.

Like when you take away the

like, like every employee

is not the buyer of Slack

as an example, but if you

take that tool away from

them, they're gonna be

really bummed about it.

So applying that same

similar idea here.

Obviously I don't, I've

never used rippling.

I'm not really sure, you

know, not speaking on it from

that perspective, but the

idea is that like uniting

all of these different

buying centers around.

giving a tool that

employees appreciate

or like, ideally right,

they're getting more done.

that's maybe a good, a good

way to test how effective

that tool is and, you

know, so a definitely

consideration for those

different buying centers.

so you like that

aspect about it.

Okay.

And what's something

that maybe the PMM could

have done differently as

they were building out

some of their messaging?

Kevin: Sure.

So it's interesting just

looking at the site itself.

There are many calls

to action, which is see

rippling, uh, get a demo.

All of those drive

to a reg form.

So to me, it's really clear

that this site is owned by

demand gen, you know, it's,

it's designed to perform,

you know, and so in some

ways you kind of see like.

The org chart when you look

at a website and sometimes

it's very brandy and

sometimes it's very producty.

Well, this one is very,

uh, revenue marketing and

that, I mean, this is a

hypergrowth company, so,

and it's also SMB, so the.

Cost per acquisition is

key to the profitability

of the product.

So I get it.

what I would love to see as

just a visitor of the site

is surfacing a little bit

more of the interactivity

and engagement, you know,

a little, just a little

of a teaser demo or,

uh, a teaser quote from,

an existing customer.

just something that kind

of, I'd say humanizes.

The product a bit more

is I think, um, what I'd

love to see on the site.

Elle: I completely agree,

and I was thinking that

as you were saying, so for

example, on their website

here, they've got this

great headline, this really

strong message, employees

get more done with rippling.

And then on the side they

have a stat, like right next

to that they have a static

image and it's, I think

it's a replication of what

their product looks like.

and that's not bad.

in fact, I like seeing what

the product looks like.

I liked product imagery.

I just think they could

have done, there's, um, so

much more opportunity with

that real estate to tie the

imagery directly back to

employees getting more done.

And maybe they're trying

to show that with.

Showing the, you know,

they've got talent benefits,

like it spent, payroll,

like all in that one image.

So maybe they're trying

to show an all-in-one.

In my opinion, it's a little

too much and it makes the,

it makes your customer,

your ICP have to work a

little too hard, I think,

to make that connection.

So I would like, I would

like to see them maybe just

some brainstorming around

how could they make it easier

for visitors of the site or

their ICP to make it easier

for them to, to draw the

connection with whatever

imagery they use with that.

really strong, you know,

messaging that they have.

So, curious what you think

about like the imagery?

Kevin: Yeah, I mean, I, you

know, I, I'd love to see if,

if their site supported it.

I mean, that could

be an animated gif.

It could be a little.

Carousel, it could be

something that kind

of has some action or

activity around it.

Uh, because the workflows

are interesting.

I mean, you see enrolling in

benefits assigning a computer

or assigning a corporate

card, you know, once you,

once you zoom in two, two

times and you see some of

the capabilities, you're

like, oh, this looks good.

So I think that surfacing

these workflows in, uh, an

engaging fashion and maybe

a couple of these workflows.

I think could really,

um, kind of add a little

bit more specificity, uh,

to the, to the product.

Elle: I completely agree.

I think some kind of like

animated gif or something that

showed like a process, cause

as you're saying it, like,

like showing it as a story,

would be really effective.

I do love that they have

all the, the proof points,

with all of the, um.

You know, star ratings

that they have.

Um, so that's really

effective too.

And they've got great customer

stories on here as well.

Um, so what's something that

the PMM could consider to

take it to the next level?

Kevin: You know, I would be

curious about how they use

this landing page, because

part of me says maybe there's

a bunch of microsites that

they've created for it,

for hr, for, uh, you know,

so maybe there's a whole

play of you're actually

targeting specific ICPs.

Bringing them to an IT

or an HR specific landing

page, having more specific

messaging, and then kind

of over time expanding

into these other areas.

So I would be curious

about their land and expand

strategy and maybe go deeper

on, um, some more targeted

microsites or landing pages,

specific to those buyers.

Elle: Yeah.

You know, when I click,

I clicked on each one

of those CTAs, those

call to actions for each

of the buying centers.

And it looks like it

has a special one,

and the others don't.

There's just like immediately

looks and feels different

and the, the actual URL

is different as well.

So it's really interesting.

I wonder if something that,

as you're saying is kind

of the strategy, but maybe

there's another way that

they could be thinking

about it, as you said, to

take it to the next level.

very cool.

Any thought, any quick, like,

last thoughts on rippling?

Kevin: Well, you know, the

other thing I like that it,

it was, it was pretty popular

a while back, but I, I'd say

it's fallen out of favor,

but I like that they have

that what's new at rippling?

Uh, carousel.

I, I think if you have enough

news, uh, that if people

are coming back to the site

or have a little time to

explore, I do like how they're

surfacing the latest and

greatest it's case studies.

It's, it's launches and

so this also just gives

honestly PMM surface area

to do a little bit of of

promotion while keeping the

site fresh, without having

to do an entire site redo,

which can be time consuming

Elle: Yes.

Oh my gosh.

I know.

and hard, just, um, hard

for a PMM to try to get,

even if you will, you know,

update messaging for example.

Or you have a new creative

story to tell and you want

it featured on the site.

Oh my gosh.

Could take forever

take, especially getting

it on a homepage.

So yeah, that's a

really good call out.

okay, cool.

Well, hey, rippling,

pmms great work.

We like your strong messaging

and we've got some ideas for

you if you're open to it.

alright, so that concludes the

messaging critique segment.

So Kevin, there's one thing

I wanna do before we go.

I like to make space for

what I call a moment of

gratitude on the show, um,

because in product marketing.

None of us get here alone.

We always learn

from each other.

Definitely building on

each other's work and

we're all better for it.

So before we wrap up, I

wanna say a genuine thank

you for your time and effort.

you know, all the preparation

that went in on your side

ahead of this show and

sharing your, playbook

on, Okta and all the time

and insights you shared.

Thank you so much.

I really, really

appreciate it.

Kevin: Thanks.

It was a lot of fun.

Al,

Elle: Yeah, of course.

And I would love to now turn

it over to you who's maybe

one or two pmms, who's made

a real impact on your career.

This is a great time to give

them a little shout out.

Kevin: Sure.

I definitely have a,

a, a few outs, um,

from across my career.

Wanna give a shout out

to Jeremy Milo From my

time at Google, he was,

instrumental in helping me

think about kind of zero

to one product marketing.

So I think we launched

13 different products

during my time there.

And so really just building up

that muscle of understanding

the ICP and taking it to, to

market and figuring out what

channels to sell it through.

I wanna give a shout out to

Ed Sama from my time at Okta.

Ed is, is kind of

a master craftsman.

Of product marketing.

Uh, he has a blog that's

taught me a lot, but also

we work together closely.

So kind of all of the, the

fine tuning of the craft,

especially around pricing

and packaging, which I

think is something that's

increasingly important as,

especially with AI workloads

and cloud workloads.

We're kind of innovating

new ways to price and

package offerings.

And then, uh, Puja, Ramani

from my time at Asana.

And this was a really fun one.

We were, we're trying to

figure out the product-led

sales motion, which kind of

takes the best of product-led

growth and sales-led growth

and combines 'em together,

in innovative ways.

So I really enjoyed my time

working with her on that.

Elle: I love it.

You really had some

amazing mentors, uh,

across your career.

That's awesome.

and this is my last

question for you, I promise.

Where else can we

access your expertise?

Is it best to find

you on LinkedIn?

Kevin: Sure.

Uh, happy, happy

to have a chat.

I always like talking to

people, starting companies,

so if you ever want a, an

hour of, of free time, uh,

to riff, I'm, I'm all for it.

Elle: That's awesome and

very generous of you, um,

as is with all the rest of

the effort and time that

you've already given us.

So thank you so much.

Um, and thank you PMM

listeners for coming on this

adventure with us today.

I hope this episode leaves

you with inspiration to

take and the next step

of your own journey.