Lead cross-selling like a Gusto PMM

Elle: You've heard the

phrase timing is everything.

That definitely rings true

for today's conversation

on cross-selling.

You know, when you're trying

to figure out the right

moment to tell a friend about

something new, that's exactly

what cross-selling feels

like in product marketing.

It's not about pushing

more products, it's about

recognizing when a customer's

ready to level up, when

their needs are evolving

and you can offer something

that genuinely adds value.

And when you get that timing

right, you're not selling.

You're helping them

evolve their business.

Few people understand how

to get that timing right,

like today's guest, Leah

Bright head of benefits

product marketing at Gusto.

I could not be more excited

to bring Leah on the show.

And let me tell you guys

why I've been following

her career like a fan girl,

um, for a long time, ever

since I discovered her a

MA content on share Bird.

where she was named a top

100 product marketing mentor

for three years in a row, and

it's no surprise why, she's

not just incredibly sharp.

She's so generous

with her knowledge and

always willing to share,

help other pmms grow.

Her content is among some

of the best that I've seen.

And her love for marketing

started early, like really

early at just 15 years old.

She competed in a statewide

marketing competition

hosted by Deca, and I'm sure

you guessed it, she won.

And that passion has

a teenager has only

grown since then if

you've worked with her.

You know, Leah moves fast.

She's a productivity

powerhouse who somehow manages

to be three steps ahead.

While also pulling

everyone else forward.

I'm so excited for you guys

to hear how she approaches

cross-selling with heart

precision and serious results.

Leah, welcome to the show.

Leah: Thank you, Elle, for

such a wonderful introduction.

I am thrilled to be here.

Hi listeners.

I am Leah, and as El said,

I get the privilege of

leading the benefits product

marketing team here at Gusto.

Elle: Yay.

Okay, so on that note, tell us

a little bit more about Gusto

for some of our listeners who

may be new to the company.

Leah: Yeah, you bet.

All right, so Gusto is a

platform that helps over

400,000 small businesses

by simplifying payroll.

Benefits and hr. So Gusto is

a very mission-driven company,

and we are all united through

our shared passion for SMBs.

Small businesses are so

central to the fabric of

our economy and they're

integral in our communities.

And Gusto exists to help

take work off of their

plates with an intuitive

and stress-free platform.

And we just really focus

on freeing up their time

so that they can focus

on their passion that got

them into starting their

business in the first place.

Elle: Awesome.

Yeah, I, my mom was a small

business owner, so I feel like

I grew up with that lifestyle.

And Gusto specifically, I

would say long time fan.

I remember years ago seeing

an ad somewhere, probably

LinkedIn, and I just felt

like from a B2B content

perspective, it was so

fresh and so compelling

and such a fun brand.

so I'm really

excited to dig in.

To our content today.

so the first segment

of our show, starts

with a case study.

and this case study is, in

particular of how you and

your team led a successful

cross-sell program at Gusto.

So can you tell us a little

bit more about what was

happening at Gusto when you

realized this was something

that had to be a priority?

Leah: Yeah, you bet.

So some customers at Gusto

adopt the full platform,

payroll benefits, and HR from

the jump right when they join.

But for many others,

they start using Gusto

when they're quite small.

And so they join us for

payroll and then as they grow,

they encounter new challenges

with running their business.

And those are challenges

that oftentimes Gusto

can help solve for them.

These are things like being

able to offer, easy to use,

affordable benefits to their

hardworking team as they

hire more team members on to

run their growing business.

So we think about the

customer journey and know

when they are likely to need

additional products through

a customer readiness score.

And we have a growing number

of customers that we could

see would really get a

lot of value by providing

benefits, employee benefits

to their employees, but had

not yet started doing so.

And at the same time, we

were looking to create more

scalable marketing motions and

supplement some of our kind of

more manual one-off campaigns

with automated campaigns

that would send at the moment

in time that a customer was

exhibiting, interest or a

need for a particular product.

so I need to figure out what

were all of those moments?

What were the key triggers

in the customer journey

that we could use as a

signal for their readiness

to offer health insurance?

And then I worked with a

really highly cross-functional

team to identify and

size out those audience.

Instrument the triggers,

create all the content

for these campaigns and

then build them out.

So, uh, we had a really big

brainstorm and we narrowed

in on five key triggers,

and then we built out those

campaigns to cross sell

health insurance into our

existing customer base.

We launched this campaign and

we started monitoring results.

We knew it was gonna

take a little while

for the data to bake.

Uh, just given that it

generally takes a customer

between one to three months

to purchase health insurance,

it's a huge investment

for a small business.

and so we really needed

to give those businesses

time to kinda mature

through, that sales cycle

and we saw great results.

So after that time period,

we established that.

We hit nearly a 20% lift

in lead creation for

the treatment group.

The treatment group was

those that received that

automated triggered nurture

series versus the holdout

group that didn't get any

automated emails at all.

Um, so that was a huge moment

for us to get that 20% lift.

Elle: Awesome.

Wow.

So something you said here

that really stands out

to me, and I wanna unpack

it a little bit with you.

So, you talked about

using a customer readiness

score to time, that

cross-selling motion.

And, you know, I think

that's such a perfect

example of a customer-centric

strategy, which is so vital.

To who we are as pmms, right?

personally I have not

been exposed to a ton of

cross-selling campaigns.

Most of what I have seen in my

career has been around selling

solutions or bundles, you

know, maybe at the same time

over a particular product.

So I'm curious in

your experience.

is that like a different

segment of customers?

Like in terms of selling for

the right time to cross sell?

Like is versus selling a

solution all at the same time?

Like where does the readiness

like come into play there?

Leah: Yeah, it's a great

question because we look

at their readiness score,

uh, which of course these

algorithms, they're always

evolving and they're learning

and they're never perfect.

Uh, but they're getting

better every day and we have

really fabulous data science.

Scientists that think about

this problem all the time.

and so we use that to signal

to us that yes, the customer

is ready and then we can layer

other things on top of it.

We can layer on moments in

time throughout the year that

they're most likely to buy.

We can layer on hand raising

signals that maybe aren't as

emphasized in the customer

readiness algorithm and score,

but that we know signify

that like, yes, this customer

is raising their hand, they

are expressing interest.

Um, so I would say, yeah,

we, we do view that as kind

of a key entry criteria to

say, Hey, if your, customer

readiness score isn't

above a certain threshold,

we're not gonna try to

cross sell you that product

because there's probably a

different solution out there.

That's part of our,

our solution set.

That's a better fit for

you at this moment in time.

So maybe you're not

ready yet to offer health

insurance, but maybe it's

the best moment in time for

us to offer you something

like business insurance.

You've just hired that

first employee, and so you

need workers' comp to be

compliant with your state

mandates for the first time.

so yeah, we, we really

do look at that as a,

a threshold barrier.

We want customers to get

across to know that yes,

this is gonna be a great

fit product for them.

Elle: Awesome.

Awesome.

Okay, so what I wanna do

now is, in your brief

synopsis of, kind of what

we're gonna get into today.

maybe let's break that

down for our PMM listeners

out there who, they're

in the midst of trying to

figure out this whole cross

cross-selling strategy and

maybe feeling a little lost

and are getting inspired by.

Your story.

So you mentioned a number

of different activities that

you, um, led throughout that

entire process, starting with

this, customer readiness.

So talk to us a little bit

more about like step one,

step two, step three, and

I guess like just kicking

it off with step one.

Let's explore that,

that first step that a

PMM would have to take.

tell us more about

how we'd get started.

Leah: Yeah, you bet.

Uh, so one of the first things

that we did was looking at

what are those key triggers?

And so we got probably

about 15 different

cross-functional stakeholders

in a room together.

So these are.

Product managers, these

are salespeople, these

are operations people.

Uh, these are data scientists.

These are people that in one

capacity or another, work with

these customers or their data

on a daily basis and know a

lot about these customers.

But each of us bring a

really different lens

and perspective to it.

And so we find that getting

that highly diverse,

cross-functional stakeholder

group is key to getting

that full customer journey

and getting kind of those

deep insights from all

the different angles.

And that group brainstormed

what could all the

triggers really be, uh,

that would indicate that

it's the right moment in

time for that customer.

And then we layered that on

top of things that we already

know about our customers,

pain that they're experiencing

as they grow, hiring new

employees, trying to retain

that top talent, in, you know,

sometimes a competitive job

market, just depending on the

industry and the geography.

Elle: Got it.

Okay.

So part of identifying

that customer readiness is,

figuring out the, signals

or triggers, I guess.

that that customer

was experiencing.

and can you repeat, I think

you might have said it, but

what were the triggers again

that, you looked at, in

particular for your customers?

Just, just to give our

listeners some examples of

what that could look like.

Leah: Yeah.

Yeah.

you bet.

so we evaluated a ton of

'em, and I won't go into

all of them, but some of

the ones that I'll just

highlight to give you a

sense of what we did is.

Uh, for example, when they

added a certain number or

above employee threshold,

we know that growth is one

of the key triggers to a

small business considering

offering health insurance.

Maybe for the first time

they're hiring an employee

that doesn't get coverage

through their spouse.

And so for them to be

able to hire that critical

talent, they need to be

able to offer a competitive

benefits package that's gonna

recruit that top talent.

Or maybe they've.

started offering other

benefits, like retirement

benefits, a 401k, but

they have not yet started

offering health insurance.

And we know from our

customer data, uh, that from

an employee perspective,

employees express the

most important benefit

that an employer can offer

them is health benefits.

But even though we know

that at Gusto, 'cause we

have, uh, you know, over

400,000 small business

customers and millions

of, payroll employees that

we're able to serve through

our platform, the average

small business might not

have access to that data.

They might not know that.

And so that's part of the

campaign really surfacing

those key insights that

we're able to extend into

our customer base, uh, to

allow them to make better,

more data-driven decisions

on behalf of their business.

Elle: Ooh, I love that.

So I wanna come back to

that in a minute, but real

quick, let me recap what

I've heard you say so far.

So step one, we have the

customer readiness that

our P-A-P-M-M would try

to identify for their own,

uh, strategy of cross-sell.

And maybe step two

would be trying to

identify those triggers.

within their, ideal

customer profile, I'll say.

so then what would

they do next?

Leah: Yeah, great question.

So next what we do

is we use, uh, a rice

prioritization model.

So reach, impact,

confidence, and effort.

We are looking at reach

the number of customers

that we could reach through

creating this trigger.

How many customers would

qualify for that trigger

on an annual basis?

The impact, if we believe

that this is a particularly

impactful moment of time.

to market this product to

the customer confidence.

Do we have quite a bit of data

to suggest that like, yes,

this is a compelling trigger?

Have we done things like

this in the past that have,

uh, worked out well for,

for the customer and effort?

Is it gonna be a larger

lift for us for some

reason to create this

trigger versus another?

and so based on that, and

we have, like I said, really

fabulous data scientists

that we get to work with.

Uh, and so they sized all

of that out because I'd say

one of the most impactful

things that we could

consider is the overall

reach that we could have

within that customer base.

so based on that, we were able

to narrow those, you know, 20,

25 different ideas we had down

to the five most impactful on

behalf of the customer base.

Elle: Yeah.

And, and is that the reason

why you would want to, like, I

guess like why sizing matters?

Is it to narrow it down?

Is it to try to seek

stakeholder alignment?

Is it to, I guess,

justify the investment?

Like can you talk through

some of the reasons

why using, doing this,

like audience sizing

exercise matters so much?

Leah: Yeah, you nailed so

many of the key things.

we all know that one of the

biggest constraints that we

have, of course, is time.

And so when we invest time,

we wanna make sure that

we're investing it wisely.

And so by being able to

understand the audience sizes.

We make sure that we're

prioritizing the work

that drives the key

metrics that the company

is looking to drive.

and we have great

cross-functional partners

that if we do not properly,

um, prioritize the right

campaigns, they're gonna ask

us very hard questions about

why these aren't being sized

and prioritized properly.

And so we wanna make sure

that we have good answers

for our cross-functional

partners and they feel

really bought into the work.

Because this work, this

project required work from

at least probably seven

or eight different teams.

And so we want everyone

to feel really bought

into this initiative.

And that we're all growing

in the same direction.

We're all in this together.

and then finally, because

by sizing this out, we're,

we're really able to

impact the lives of more

customers and more customers

that have more employees.

It's not easy to navigate

the health benefits landscape

in the United States.

We hear from small

businesses all the time that.

they wish they had a more

guided and opinionated

partner that could

help them through this.

And we believe that Gustos

solution is easy to use

and does provide just so

much value to those small

businesses, taking that

work off of their plates,

simplifying the entire process

and getting health benefits

to the people they love most.

Elle: Yeah, I, I

liked your comment.

or I guess reflection

on being inclusive of.

All the customers that

would benefit from

what you have to offer.

So doing the sizing

exercise can make sure that

you are doing just that.

okay, so we did the

customer readiness.

we identified our,

customer triggers.

We did the audience sizing.

What do I do next as

I am pursuing this,

cross sell strategy?

Leah: Yeah.

So at this point it goes into

a bit of a parallel path, uh,

from a marketing perspective.

We're gonna go off and we're

gonna build the messaging

framework, all the content

for the emails, and we're

gonna send our growth, our

engineering product and design

teams and data scientists.

Off to create the audience

triggers in our CDP, our

customer data platform.

And that is going to then

feed into Marketo, our

email platform to enable us

to send out those emails.

So they're gonna

go off and do that.

Meanwhile, product marketing,

we are developing our

messaging framework and as I

was saying, it's just a such

a huge moment of pride for a

small business when they can

finally afford to offer health

insurance for their teens.

These are lifelong friends

and family members that

they are working with,

and so it makes it quite

meaningful and personal.

When they're able to afford

to do that for the first

time, their cash flow

is in a place where, uh,

they can finally make this

dream that they've had

probably since they started

their business, a reality.

And so we do lots of message

testing and we start with,

all the content that we've put

out over the last year that

we've seen really resonate and

drive really positive results.

And that becomes kind of

the, the base of the content.

We then look at each

individual trigger and what's

the context in which that

email is going to be going

out into, and how do we make

sure that the messaging is

highly relevant to what the

customer is experiencing

at that moment in time.

So we know, for example, that

when an employer is adding

employees and crossing a

certain employee threshold,

that's a strong indicator

that they might be interested

in offering benefits.

They're growing their team

and maybe they're having

recruitment challenges.

and that could be because

they're not offering benefits

and so we can speak to

that pain and how we can

help solve that for them.

and we also know, for

example, that when the average

business hires someone where

the salary is greater than

$60,000 per year, I. Offering

health insurance actually

has a positive return on

investment because it just

reduces that worker attrition.

And so that's something

that we can also highlight

to our, our customers.

They might not know that

offering benefits after 60

k salary is positive ROI.

And so that's just amazing

insight that we can

extend into our customer

Elle: Yeah, you mentioned

that and I wanted to

come back to this.

Offering that those

pieces of insights to

your customers, and that's

something that they crave.

Leo, you're such a

strong advocate for your

customer, I can tell that

you truly empathize with

them and you've taken

time to know who they are.

Really well.

it shows.

That's awesome.

So, getting back to our cross

sell, you know, step-by-step

process, you mentioned

two parallel work streams.

You've got product marketing

hunkering down on the

messaging and message testing

and building out the content.

can you speak a little bit

more about that parallel

work stream, that's happening

going on at the same time?

Leah: Yeah, sure.

we try to get to market as

quickly as possible once

we've decided to invest

in something, and so we're

always looking for efficiency

gains and making sure that

we're not just, having one

step occur after another.

We're trying to make sure that

they happen simultaneously,

and so we have the data

scientists working with the

engineers to figure out how

to instrument these different

audiences within Telium.

Meanwhile.

Marketing is building

out a batch campaign.

'cause what we're gonna do

with that batch campaign

is we validate that this

is a high performing.

Quote, unquote trigger for us,

we're gonna simulate that this

is, um, an automated triggered

email by sending it to the

people that would've qualified

for that trigger during

a particular time period.

And validating that we've

got the content right, that

the open rates are high,

that the click-through rates

are where we wanna see 'em.

and also during this time,

we established that we

wanted to do a 50% holdout.

This was quite critical

because we have, an

incredibly high bar for

performance at Gusto.

And so our KRS for

the year are, always.

Very high.

And there's always a certain

degree of anxiety that

comes with figuring out,

are we gonna hit our cares?

We're gonna damn well

try to make that happen.

that's a big deal when you

have 50% of your audience

that could qualify for

an email that will help

them get this product.

Uh, and we're gonna

hold 'em back.

We're, we're actually not

going to send this campaign.

'cause what's important

for us, as we understand

the incremental impact that

we're able to drive through

these initiatives, there's

huge amounts of time that

teams are investing in this.

Uh, and so it's very important

for us to understand really

what is that incremental

impact that we could drive.

we also established this

time that we are going to do,

uh, a 50% holdout to be able

to establish that baseline.

Elle: Oh, awesome.

Okay.

So talk a little bit more

about, and, and you, you

mentioned some of this, right?

Like why you do

that 50% holdout.

but can you say a little bit

more around why that matters?

Like as a PMM, why should

I incorporate that into

my, you know, cross

sell, program planning?

Leah: Yeah, absolutely.

it matters because that

one debate that we often

have at Augusta was like.

When you do something,

like a marketing

campaign, you can see the

performance results of Yes.

The open rate, yes,

the click through rate.

But how do you know that your

campaign motivated a customer

to do something that they

wouldn't have done otherwise?

And so this is why the

holdout is quite important.

what we did with this holdout

is we only held them out from

the triggered campaign emails.

They were going to get

all the other in-app

messaging that they

otherwise might have gotten.

Everything else about their

experience remained the same.

And so when we look at

the performance, we can

very easily say, oh, hey,

if our holdout group,

performs differently

than our treatment group.

We know that the treatment

actually drove incremental

impact for the business.

And that's things that

can be celebrated in

our performance reviews.

that's, you know, part of

what gets our marketing

funding at the end of the

day, would we be able to say,

Hey, we're driving business

results that really matter.

Elle: I was about to say that

that's something that you

can take with you to strategy

conversations internally,

getting it back to your OKRs.

it's quite clever.

I've never seen that before.

Um, not that I, I, I haven't

worked too closely with,

these type of campaigns

before as a product marketer,

And what I have been

exposed to, I haven't seen

anything like that before.

So it's quite clever.

such a helpful tip

for our listeners.

okay, so let's recap again.

We've got the customer

readiness score, making

sure that we have the,

target market, right?

And then we have the,

triggers, identifying the

triggers for our target

market and our our, customers.

We have sizing the audience.

And then step four,

you kind of have two

parallel work streams.

You got the message testing,

you're creating the content

and validating, assessing

incremental impact.

I guess like, bring us

home, like what happens now?

Like you're launched, like

we're ready to go, we've got

validation, we've got the 50%

holdout that you mentioned.

what happens next?

Leah: Yeah, great question.

Uh, so one of the things I

should also mention when it

comes to creating the content

that Elle, I know that you

are also very passionate

about, is using social proof

and stats in our emails.

Uh, and so we thought that

this was quite central

to the strategy as making

sure that our customers

could see themselves.

In the emails and that when

we were talking about, the

positive changes that this

product can bring in these

people lives, they weren't

hearing it from Gusto.

They were hearing it from

people in their peer group.

They were hearing it from

people who had just figured

out how to offer benefits

for the first time and the

transformational impact that

it made for their business.

and so we made sure to

really incorporate that into

each of the emails, whether

it was a link to a case

study, whether it was a pull

quote or whether it was.

Uh, a third party accolade,

an award that we had won.

We really made sure to embed

that in each of the content.

The other thing that we

know from having talked to

customers and just having

tested it into this over time,

is the importance of providing

customers multiple CTA

options in a nurture series.

Some customers, they're

self-serve, first customers,

they're very comfortable

with the technology.

They are.

you know, this is maybe.

They're not their first time

offering benefits overall.

Maybe they've offered

them at the different

company that they were

a pay payroll admin for.

It's only their first time

offering benefits at this

particular business, and so

they're ready to self-serve.

They're ready to

dive right in.

There might be another

customer who has never

offered benefits before.

They're having trouble

figuring out how to navigate

the very complex employee

benefits landscape, and so

they wanna talk to someone.

They wanna get on the

phone with a licensed

benefit advisor who can

talk to them about the

plans that are available

in their area, how to make

decisions between offering.

A bronze plan or a silver

plan, uh, and what might

be a best fit for their

business, their goals, and the

employee base that they have.

and then we have customers

that are earlier on

in their exploration.

Maybe they don't

wanna self-serve yet.

Maybe they don't wanna

talk to sales, they

just wanna learn more.

They wanna click through,

they wanna read more of a

case study or they wanna

read what's the difference

between, uh, small group

health insurance and a health

reimbursement arrangement.

Uh, and they're just looking

to learn a little bit more.

So throughout, we really

do offer customers the

opportunity to, click into

whatever type of content

is best for where they

are in their journey.

Elle: Yeah, meeting the

customer where they are.

Um.

We've also done that at

Cisco before in so many other

places that I've worked.

we've heard very similar,

not strategies necessarily,

but just philosophy of

how we communicate and

engage with customers.

fantastic.

So, I just wanna call out

that this is so methodical,

this entire process that

you mentioned and, and have

just talked us through,

and I'm sure that was

such a big factor in the

success that you saw.

so two questions.

One, I think you mentioned

it at the start of our

conversation, but it's worth.

Talking about, again,

would love to hear like the

results that you saw through

the cross sell campaign.

Again, I know you mentioned

it already, but let's

bring it back up and then,

because this was such a

methodical process, talk to

us about the stakeholders

who helped you achieve that

amazing result that you saw.

Leah: so we knew that based

on the audience sizing

that we had done, it was

going to take us a few

months to get stat results.

So at launch we started

monitoring the campaign

performance indicators

just to make sure that the

send volumes were accurate.

And what we were anticipating,

these were brand new triggers.

We were pumping data from

one system into another

system that had never

been collected or never

been connected before.

so just making sure that

these systems were operating

as expected was, was a big

part of the QA process.

and then looking at the open

rates, the click-through

rates, making sure that we

were seeing in those automated

campaigns what we were

expecting to see based on the

batch campaign performance.

And then after about four

months, we had enough volume

of data to determine that

the triggered email nurture

program was performing.

you know, above expectation,

when we looked at the holdout

versus the performance of

the treatment group, we were

generating nearly 20% lift

in new sales opportunities

for our health insurance

product among the recipients.

so for those recipients that

got the emails, they were.

We produce 20% more

opportunities and leads for

our sales team to follow up

on, uh, than the folks that,

that didn't get an email.

and this is a pretty

mature product, so to get

a 20% lift on a product

that's been around for

roughly two years, We are

not talking about a product

that was launched, you know,

like yesterday or last week.

We're talking about a

product that's been in market

for, for 10 years, and of

Elle: a decade.

Leah: And the product team

is amazing and you know,

they're always working to

make improvements to that

shopping flow and how it

works on behalf of the

employees that are accessing

their benefits in Gusto.

So it's not at all to say

that product has been stagnant

for 10 years, but still

in the market it's, it's

a fairly mature product.

So to get a 20% lift in that

is, is pretty incredible.

Elle: Awesome.

Awesome.

And real quick, like who

are all the stakeholders

who were involved in

making this happen?

Leah: Yeah, great question.

So we have got, at

Gusto we are organized

into what we call apps.

And you can think of apps

as like mini business units.

And so we have a benefits

application and, There are

cross-functional teams,

horizontal teams that have

a dotted line reporting

structure up through this app.

We really want people

to go deep on the app or

product area they work in.

And so this, uh, dotted line

reporting structure, this

matrix organization really

does allow us to do that.

We get the craft excellence

of reporting up through,

a manager at Gusto.

We call them PEs.

We don't have managers.

We have people

in.

Elle: wow.

Leah: Uh, so that's a fun

fact about Gusto culture.

So you get to report up

through a people in power

who really understands your

craft, and you are still

very accountable to the

head of the business unit.

Um, that you're doing

your work on behalf of.

And so because of that

we have a, a growth team

that sits kinda like out

of the app framework.

That's just a growth

team that helped us.

These are, these are

engineering, product

design and data scientists.

that help us figure out

how to instrument these

triggers, how to get the

data passed, from our CDP

into our marketing platform.

We've got the data

scientists that work within

the benefits app itself

that are working with us

to size these audiences.

Uh, make sure that all

the data is flowing

correctly because they

are really experts on,

on those audiences.

In that data set, we

have got cross-functional

marketing counterparts.

Lifecycle marketers that

we're working with and all the

campaign operations, marketing

ops people that are working

within Marketo to make sure

that everything is set up

and instrumented correctly.

Uh, and there's just a huge

amount of highly technical

work that has to go on there.

And we've got

great very detailed

cross-functional partners

that help us with that.

All the product managers

that work within benefits,

you know, they are very

interested in making

sure that we're getting

customers into the right

applications into the right.

Flows, so that they

can get a really easy to

use benefits experience.

our legal and compliance

counterparts that, uh, are

fabulous.

Making sure Uhhuh, making

sure that we keep our

business on the, the rails.

I think those are the

key, the key people.

Elle: Yeah.

Yeah.

all, all the usual folks,

but I will call out your

access to the, the growth

team, I think you called it.

You know, like the, the

data scientists, those

who are, building or

maintaining that, is that

the team that does like the

customer readiness scoring

and that heavy analysis?

Leah: That actually

all goes through our

benefits data scientists.

Elle: Oh, interesting.

Leah: And there's different

ways that Gusto does it.

So the growth team actually

does it on behalf of other

products that are less mature.

But, the benefits team

is, is so mature that we

are fortunate enough to

have data science that are

kind of dedicated to that.

Elle: That's so helpful.

Yeah.

As a pm m at a big

organization, I. Never

even occurred to me to

look for such a team.

So it's definitely

something that I'm gonna

go check out for myself.

Leah: Yes.

Oh, and the last partner

that I would be so remiss

if I didn't mention, I

mentioned them earlier.

Uh, but our sales team,

of course our sales

team,

we are opportunities

over to our sales team.

Um, and so they are with

us through the whole

journey to make sure that.

We are contextualizing the

customer's experience at the

moment in time, but they are

like excited about the high

quality leads that we're

gonna be putting, into

their hands to help them

navigate the benefits process.

Uh, so sales is a, a

great cross-functional

partner for us too.

Elle: Yeah, great to get

those high quality leads.

okay.

Last question for

you on this topic.

Any tips for pmms who are

pursuing or in the midst

of a cross-sell campaign?

what's one big takeaway

that they should consider?

Leah: I would say the biggest

thing to consider is that

holdout, that holdout is

just so key to being able

to definitively say the

incremental impact and

the power of the campaign.

if I have, one piece of

advice for you, it's going

to be that and then the last.

The second piece, which you,

you didn't ask me to offer

a second piece, but I'm,

I'm gonna offer it anyways.

Uh,

Elle: do it.

Leah: which is a lesson

that every PMM knows.

is just like, bring your

stakeholders in early and

often get everyone rowing

in the same direction.

Get everyone excited about

the work that they're gonna

get to do to together, and

find people, find like low

lift ways to keep people

abreast of the progress

that you're making and the

results that you're driving.

Elle: I like that.

Yeah.

And I bet that 50% holdout

is such a great way to

bring everyone together.

You can tie it back to

group, goals and OKRs.

so that's a really

helpful tip.

okay, so with the close of

the first segment, uh, I'd

love to move on to our next

segment, the message critique.

I love this segment.

So much because it's just

really fun both for us

and for our listeners.

So, for listeners out there,

I've asked Leah to bring a

company who is messaging her

product she really admires

and to give us her take.

But before we get

started, let me just throw

out the ground rules.

So first, Leah, I wanna hear

something that you're loving

about the messaging or the

product, like what's working

and what stands out to you.

Second, what's something you

wish the PMM would have done

differently or considered

to make the messaging

clearer, more impactful?

And then third, what are

some ways that the PMM could

take it to the next level or

iterate to maybe pair it with

a creative campaign or content

or something, something

like that to consider.

So, what company do

you have for us today?

Leah: Yeah, so I'm excited to

talk about Segment by Twilio.

As you can see from my last

answer, CDP customer data

platforms very top of mind.

Uh, and so we've been

looking at a variety of

CDP providers and yeah,

that, that's what Twilio

does or segment by Twilio.

Elle: Yeah.

Yeah.

No.

Uh, so just as the guest,

obviously having worked at

Twilio, I'm familiar with

Segment, but help our audience

better understand Yes.

Their, customer data platform.

Like, who are they for

and what do they do?

And, and I guess like maybe

talking through your own

potential uses as, as a

customer would be helpful.

Leah: Yeah, you bet.

So, segment really does

enable businesses to collect,

unify, and activate their

customer data that comes

in from various sources,

and that allows them to

create comprehensive and

real time customer profiles.

So by consolidating data from

websites, mobile apps, other

touchpoints segment helps

organizations gain valuable

insights into customer

behavior and preferences.

And then facilitating

those personalized and

effective engagement

strategies from there.

Elle: Yeah.

The, the biggest example I

can think of from my time

at Twilio was Domino's,

like the, the pizza company.

So Domino's, I remember,

used a segment and they would

unify customer data from

all these different digital

channels and they, they

brought it together in, in.

You know, through the

platform and their marketers

would be able, would be

able to create these like

hyper personalized marketing

campaigns tailored to super

distinct customer behaviors,

which as a marketer, I think

is so fun and really exciting.

So, Leah, tell us what

about their messaging

or their product?

Like what are you

loving about it?

Leah: Yeah, great question.

Okay, so if you go to

segment.com, you will see

that, The headline and then

what is underneath it says,

the leading customer data

platform powered by ai.

Twilio segment brings together

clean, consented customer data

for real-time insights so that

you know each customer like

they're your only customer.

And that last bit is

what sticks out to me.

So you can know each

individual like they

are your only customer.

It is written just so

plainly and so cleanly,

and that speaks to me.

that is how I think us all

as marketers really wanna be

messaging to our audiences.

Elle: Yes, it's certainly

something to aspire to and,

and this is something that

I even admire about even

managers or leaders, at big

companies with big teams,

people who can make you feel.

Like they're sitting,

they're listening to

you, they're hearing

you, your voice matters.

I almost think, and I don't

wanna get too into our

critique, but I almost feel

like that bit that you pointed

out, that they should bubble

that up to a bigger headline.

cause it does

resonate so much.

And if, if I was scam scanning

this page, I might miss that.

And that's a piece

that as a marketer.

So resonates with me.

but what about you?

What do you think is kind

of like, what are ways that

are something you maybe you

wish the pmms, would've done

differently or, or a different

take on the messaging?

Leah: Yeah, great question.

overall I think the messaging

is, is pretty spot on.

Uh, you know, some of

their key value props

enrich customer profiles.

Activate customer data,

optimize ad spend,

boost, cross sell, and

upsell, which is exactly

what

our episode, uh, um,

so all of that is like

very much speaking to me

when I visit the page.

One thing that I'm kind

of craving and I wish

for is there's lots of

like imagery on the page.

And a lot of the imagery

feels very stuck.

I do not see my customers

and that maybe it's

because I serve a small

business audience, but all

these just, I don't know.

They're, they're very

square, they're very stuck.

They don't feel very emotive.

Um, and so I am very much

wishing that the visuals were

a bit more poppy and creative.

Elle: Yeah.

Yeah, I can see that.

so for listeners, if you go

to the segment.com page and

you scroll down a little

bit, they've, kind of got

these columns across the page

that list out each of the

messaging pillars essentially,

or the values that you'd

get out of the product.

And there's an opportunity,

there's real estate

on the page for.

Impactful, imagery,

and I agree.

I almost wonder.

and I know they do have a

carousel of customers at the

bottom, but I almost wonder

if they could do something

like, put in a customer

example for each one of those.

I'm sure there's endless

opportunities for, for

ways to do that or, or

even like product imagery.

but that's also complex

because you don't wanna

reveal too much before

telling the product story or

telling the, the narrative.

So it's a tricky situation.

it's certainly not

straightforward or easy,

but yeah, I hear you.

It, it does feel

a little stock,

Leah: I think that,

the product oftentimes.

people are interested in what

the product looks like, and

so they have done a really

great job of creating these

abstracted UI images that

start to get at what does

the product look like, but

it's just like you're dipping

your toe in the water.

Um, and so one of the

things that I would love

to see slightly more on

this page is what does

the UI actually look like?

How am I gonna be, um,

using this platform to

drive, you know, the key

value props that you're,

you're marketing at me.

Elle: Yeah, I

completely agree.

And this has come up

in other episodes on

the podcast as well.

I wanna see what the

product looks like.

Anytime I don't see

what the product looks

like on a SaaS website.

It makes me wonder, either,

it's too complicated.

And you don't wanna show

it because it's gonna

scare me off because

it's too complicated

or something about what

you're showing isn't real.

So, either way I realize

sometimes it's, it can

be hard to show, the

product, but, uh, I agree.

I think as, PMM as a marketer

and this being a product

for marketers, or at least

a subset of marketers.

This is something I would

wanna see, so Agreed.

Okay.

So how can they, elevate it,

take it to the next level?

Leah: Yeah, I think making

some iterations on those

visuals would be a great idea.

Maybe it's something that they

could test into, maybe test

the page with what might it

look like with, some different

visuals versus others.

And, uh, because we are

both very passionate about

customer proof points,

uh, making sure the case

studies, uh, and customer

testimonials are part of it,

I would love to see, uh, a

little bit more of that at

the very bottom of the page.

They have one case

study that is linked.

but I would, I would love

to see a little bit more

of that customer voice

represented on the page.

Elle: I totally agree.

I personally am more

interested in how are my peers

using a certain tool and I.

How are they winning with it?

so I couldn't

agree more on that.

okay.

Fantastic.

Okay, that's the

close of that segment.

so.

Leah, before we go, I just

wanna make a note to say

how grateful I am for having

you on the podcast today.

And I, I said it

kind of at the start.

You are so generous with

your time and your skills in

terms of mentoring others.

So thank you so much for, uh,

your willingness to come on

and, be a mentor to the PMM

community in this capacity.

Um, and just as the

gratitude moment, I would

love to let you give a

shout out to a PMM who has

really shaped your career.

Leah: Yeah, absolutely.

Well, first, Elle, thank you

so much to you, uh, for not

only having me on the podcast,

but starting this podcast,

product Marketing Adventures.

You know, um, this is a,

first time podcast that's

really trying to bring

practical advice into.

The community, which I

just, I love and I'm so

passionate about, I am just

so grateful for having had

such an amazing PMM community.

I've had the privilege

of getting to work with

throughout my career and

exposed to, through, you

know, podcasts like this,

or sites like Share Bird.

so I, I just love

stuff like this.

there have been so many.

Pivotal people who have

influenced my career, and

I'm so grateful for a few

people that are top of

mind for me this week.

Emily Ritter, who is the

former head of p and m at

Gusto, she originally hired

me over five years ago,

Gusto, and it's just a place

that I loved getting to work.

Um, so I'm grateful

for everything.

She saw me five years ago

and, Christina Damp, she

is a, a new head of PMM we

hired about six months ago,

and she has just brought

such incredible insights

and leadership to the team

at a moment of time where.

Wow.

Uh, she is really

helping us take the

team to the next level.

And so I am, I'm grateful

for her leadership every day.

And finally, Chen, James

Lee, Calvin Young fellow

pmms that I've had the

privilege of getting to work

alongside Augusto for many

years now that are just great

sounding boards and just

make it fun to come to work.

Elle: I love that.

Yeah, it's really special

when you have a product

marketing leader who.

has been with you for a

long haul and not only has

helped you grow within that

one organization, but then

as you get to be the PMM,

bringing in a new leader

and then having that new

leader, then come on and then.

Pick up right where that

old leader left off and

then be able to shape

the next few years.

that's so amazing.

So, yay.

Thank you.

Old amazing Pmms.

and my last question for

you, Leah, is where can

we access your expertise?

Leah: Yeah, you bet.

Best places to find

me are going to be

LinkedIn and Cher Bird.

Uh, so Leah, that's LEAH and

Bright, that's B-R-I-T-E.

So a fun fact about

my last name, my, uh.

Name, before I was married,

my last name was actually

white and my husband's

last name was Bran.

I like to do things that

are unconventional and, you

know, might rock the boat.

I'm always down for

something a little bit

spicy, and so when we

got married, we actually

combined our last names.

Uh, so we could have

gone with WAN or we could

have gone with Bright.

Uh, bright was the clear

winner for us, so both my

husband and I changed our last

names when we got married.

Elle: That's amazing.

I love that.

So you've created a new

family in so many ways and

everybody got the experience

of changing your name,

which I can also attest is.

Cumbersome to say the least.

Leah: it sure is.

Elle: Awesome.

Well, thank you again so

much and, thank you to the

PMM listeners out there who

have come along, on this

adventure with us today.

And I hope this episode

leaves you with inspiration

to take with you, in the next

steps of your own journey.

Lead cross-selling like a Gusto PMM
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