Hi, you're listening to The Get, the podcast about finding and keeping

great marketing leaders in B2B SaaS.

I'm Erica Seidel, your host.

If you're doing well and scaling, it may feel like your path is set.

Maybe you feel like you have paradoxically less room for experimentation.

After all, shouldn't you double down on what works and focus there?

Today, you'll hear about how to thread that needle.

Today, you'll hear from Cynthia Gumbert.

She's the CMO of SmartBear, the 750-person PE-backed SaaS company

that's on a growth tear, serving more and more software developers every day.

You'll hear about the transition from VP of Marketing to CMO.

And you'll hear about the difference between a marketing-centric

mindset and a 'business first, marketing second' mindset.

Listen for what Cynthia says about putting yourself into the CEO's shoes and thinking

about how to help the whole company grow, not just how to grow marketing's results.

Listen for all the different ways in which Cynthia injects

discomfort into her scale journey.

expect to hit plateaus as you scale.

When you do, you need to ask, 'How do we double doing well here?'

You'll also hear about an important trend for 2022 for product-led growth

CMOs - the need for micro-market research.

Here we go.

So, Cynthia, thank you so much for joining the show.

I'm so happy to have you on, Cynthia Gumpert, CMO of SmartBear.

So thank you for joining!

Thank you, Erica.

Thrilled to be here and appreciate you having me.

So, you have an interesting aspect of scaling in your background.

You worked at a lot of bigger companies and now you're at SmartBear

as part of this kind of great scale up, and you were saying, before we

talked, you're like the PE darling.

I forget how you said it, a PE dream kind of company.

Can you talk about your experience going from VP of marketing to CMO?

Cause, you know, it seems like it's like a different lens and it's a bit

of a leap from leading all of marketing to kind of thinking business first,

marketing second, as I like to say.

I'm curious to hear about that leap that you made, what was hard, how should

other marketers that are new to the CMO role align with others specifically?

Yeah, I feel like I had to tap way back

into my history and background.

I was an engineer before I became a marketer.

And then I worked in sales, sales engineering, and then went to business

school, and then went into marketing.

So, part of it was going back to, okay, I've been in different

parts of the business and had a perspective beyond marketing.

So it didn't just come up through the marketing organization and I've had

to exercise those parts of my brain.

Not so much like understanding everything engineering is doing,

but being empathetic to what the whole business is going through.

Kind of going back to my MBA roots on alright, how do we think about growth

from all levers perspective and really put yourself in the seat of the CEO and

what does he or she need to be worried and concerned about and how am I helping that?

How am I helping the entire company grow and not just managing

my team and my own department?

That's great.

So talk a bit about how that comes out in practice.

Are there different conversations where you're working on that

alignment with the CEO and the CMO?

Like, what are those critical conversations that happen or that have

happened over the course of your time at SmartBear that kind of stick out to you?

You know, I look at just, when I'm thinking with only my

marketing hat, it really comes out largely when we're doing annual planning

and budget planning and looking at it in terms of, alright marketing

needs to do these five things and we really want to start experimenting and

working on new things and doing this.

It's reframing that to, "the company needs this."

And I understand that I'm not going to get every dollar of budget that I'm

asking for in marketing, and I'm not just looking at building more for myself.

It's what do we need to do as a business, here's why.

Oh, product is investing in that, then we should invest in that part of marketing.

I'm okay giving up these other things here and I get it and I will go and translate

that back to the team and say, sorry, you know, we can't invest in these new

tools because they're nice to have, but they're not must-have for the business.

So, it just helps me frame, you know, we don't all have infinite, unlimited

budget and have ability to hire.

We have to make trade-offs.

And it really helps me give the context back to the team on here's

why we're making these trade-offs.

But making sure that you're all working on the most important

things for the business.

That's one.

Another area of just thinking business first is I feel like you can't

over-communicate with your team and, yeah, there's some things in board

meetings that we can't share, numbers and whatnot, but I'm very open.

One of our values of the company at SmartBear is open, our core values.

And I really take that to heart and try to share immediately after any executive

or board meetings what is relevant to the team, say here's the context

that we're having conversations in.

I don't think there's any level too low that we should

avoid sharing strategy with.

I just, I have all-hands meetings with my organization every single week and we have

a standup and I will share as much as I possibly can without crossing a line and,

you know, oversharing anything sensitive.

But I think they really appreciate that because they kind of start to think

that way too and understand what else is going on at the organization, how

they can think about getting creative and doing their jobs better in a

way that's relevant and important.

Yeah, it's so interesting when I talk to candidates lately,

I don't hear people say so much, "I want to work in this industry," or "I

want to work in this size company."

What they say is "I want a transparent culture" and "I

want a culture with integrity."

And so I think it's so important.

Obviously, transparency, it means a lot of things, but I think that's, you know,

step one is sharing what's going on in conversations where you're not necessarily

going to be in the conversation.

Yeah, transparency's important.

And I've found that I'll uncover places where they're opportunities to communicate

more, where I see something happening in a different org and ask a leader of

that team, do you mind coming in to share with marketing what you're working on?

Because I liked what I heard, and it's not relevant to every

single person in my team, but it's going to be interesting to them.

We have guest speakers all the time coming into our marketing all-hands,

and that's the other benefit of looking business first is just

finding opportunities to share more information across different parts of

the business that wouldn't normally talk.

It always sparks some new idea from somebody.

So what's an example of a recent guest that you've had

on the marketing team meeting?

We had the head of channel sales come join us.

And it was really in the context of we give, every other month, we give our team

awards for, we have these spot awards, and they're tied to our core values.

And there's always one given by somebody outside of marketing to someone on our

team or vice versa, or we invite somebody to give an award to outside of our group.

This happened to be head of channel sales was giving a team member an

award, and I asked her, while you're at it, can you just share everything

going on that you're working on?

And what's the plan for our partners and what's going on.

So she ended up speaking for an extra fifteen minutes and it was great.

It was just very interesting hearing that perspective and people

had a lot of questions for her.

So that was fun.

I'm bringing our CEO into my next all-hands.

He's got a few things to say also.

That's great.

I remember talking to a CMO recently, I'm just going to share this idea with

you cause you might get a kick out of it.

But he was doing live personas.

So the idea is like everybody's on zoom these days, so he would get a customer

to just come to a marketing meeting and then he would invite the whole

company and bring the persona to life.

And, you know, anybody could fire questions at the customer and it

was all about learning and stuff.

That's awesome.

I may end up stealing that.

Yeah, exactly, I thought that might be interesting for you.

You guys are doing well and I'm going to ask you this kind of funny question.

You guys are growing, you're profitable, and I've been wondering,

does this give you paradoxically less room for error and experimentation?

I'm wondering if this is something that a lot of companies that are

doing well now are like a little nervous about experimenting.

Any thoughts on that?

Like where does the experimentation come in for you?

Yeah.

I mean, it's very easy to fall into the trap of being very comfortable and saying,

we're doing fine, don't mess with it.

Just don't mess with it because we don't want anything to fall off the rails and

just keep doing more of what we're doing.

There are these, just like when you're training for an athletic

thing or, you know, I do Peloton, you get to these plateaus.

It's like, I'm doing fine, you're doing fine, wait, why can't I PR anymore?

Why can't I just keep getting a little bit better?

And I think there are these plateau points where we need to get to that

next level and we can't get there with just the same exact thinking.

We gotta start adding stuff on top of what we're doing.

We absolutely carve out room for experimentation and just saying we need

to layer in some new things into our mix in order to really find avenues of growth.

And then there's, at the same time, new products coming out of our

product team that we've got to find new ways to get those to market.

There's some new personas.

So we have to, not just experiment, but find a path to success.

Also, people are a little scared when things don't work out well.

So I think building into the culture that part of layering in new things,

you have to be willing to be okay with failure, celebrate it, you know, even

share that, hmm, that's not working.

We've had a few vendors that we've worked with for seven, eight months, and

we're not getting anything out of them.

Our director, VPs come to me and say, eh, we're going to kill it.

Try something new, and I'm totally okay with that.

I think that's part of the evolution.

So, is it harder to experiment when you're - is

it like, okay, great, we have more budget for experimentation

because we're making more money?

Or is it just the same when things are going well?

Yeah, I know what we're doing.

Our budget, it's never as much as we want to do all the experimentation we want.

So it's always a balance.

There's a little bit of baseline of we have to grow by this amount.

This is our absolute floor just to keep the lights on, keep the growth going.

And here's over and above.

And it's that experimentation over and above that always gets shaved,

but I put my foot down and this is me with our chief financial officer and

with my boss saying, we can't go below this because we have zero wiggle room.

So, I always kind of not argue, but just, you know, negotiate for a baseline

level of experimentation, even though it's not as much as we want, but we

need to be able to take some risks and have an envelope to do that.

And there's always room to do some of that.

And at the same time, there's always something that's not working that it

might feel like that was our floor, but a vendor that just has never

produced a single good lead for us.

So the team's always looking for those to say we can cut here and cut

there, and then layer in something brand new that might help us.

So, yeah, it's a balance.

I don't think, you know, there's no perfect answer.

If you're a venture-funded very early stage startup that doesn't

need to look for profitability, you can try a lot of things.

Honestly, if you're not spending more budget than you have at that

stage, you're probably not doing your job, according to the board.

And that's why, at the beginning you said we're kind of the

perfect Goldilocks P firm.

I look at it as we have enough wiggle room to try these things, have some

budget to really play with, and we're super profitable, but we're

not like cutting budget or not like an incredibly tightly squeezed.

So I think it is a perfect balance.

It never feels perfect because there's always more that we can ask

for that we don't always get, but of course there's some trade-offs.

So let's talk about top lessons for a SaaS CMO to

bear in mind while scaling up.

Yeah, I mean, I have three.

Primary one is scaling does not just mean more of everything.

It does mean, you know, what are we going to stop doing so that we can really

put in the things that are growing?

It doesn't feel, we've got some products we're not investing in marketing as much.

We have quite a few products and it's painful to cut something that

someone's put effort into, but I think saying, we're going to focus.

We're going to focus more and we're going to do better as a result, even though it

might not feel like everything's scaling up, a few things are scaling up more than

others, and that is critically important.

Just to focus and constantly, not narrow, but just make sure you're not doing

peanut butter, a little bit of everything.

You've got to say no to a few things.

And that's true with people's time.

People can get completely overloaded and overwhelmed with taking on too much.

So be constantly telling my leaders, you can not go to some of these meetings.

Just look at how your time is spent.

So it's just a constant leveling of how much you do take on and how

much you do take off your plate.

So that is one.

Another area for scaling up is we're growing our team.

There's always people to hire and we've gone through a process of

looking at our personality preferences, using the predictive index.

There's several different versions of looking at the personality of

individuals and of the team as a whole and where we're trying to go.

There's several ways to do that.

We've used predictive index.

And when we're looking at hiring across the team, I think

hiring for pure culture of fit.

Do they think and act and behave just like everyone else on the team?

Or do we actually need somebody or some new people who think and act and behave

very, very differently, who can help push the envelope and bring in new ideas?

So that's another thing that we're looking at filling out a balance of our hiring,

not just based on skills, but based on what approaches they take to work.

And it might be a little different than what we're used to, but we need

to get a little bit uncomfortable sometimes and shake it up a little bit.

Again, it gets back to a little bit of new thinking is important to get

past those plateaus and keep growing.

So that's the second one.

And third lesson for scaling up is, and this one I've alluded to before, but

it feels like just when you get to a comfortable place, you've got to find

ways to make yourself uncomfortable.

You know, once we know we're doing really well in a lot of areas

we have to look at alright, how do we double doing these areas?

There's a lot of incremental ability to say, we can just do a little

more of this, a little more of that.

How do we make ourselves uncomfortable to get past those plateaus?

We have to do that through some experiments, some of them will fail.

Getting new people in the mix who have very, very different backgrounds

and personas than other folks in the team is another way to do it.

But growing, especially once we're several hundred million dollars, if

you think about what we look like when we're double the size we are today,

there's some discomfort along the way.

Not a bad discomfort, but just a little bit of we've got to think in new ways.

It's interesting because you know, often when a company is kind

of earlier, it's all about cultural fit, and then you get to this point where

you realize you need the cultural add.

And that can be really messy and uncomfortable.

I interviewed somebody else on this podcast who said, well, just like my

budget is 20% or 15% or whatever it is for experimental things, I think

of my people budget the same way.

So I make myself uncomfortable with a hire, like, 20% of the time

or whatever, one person in five is a bit of an experimental hire.

I mean, not to make it harder for that person coming in, but like somebody

whose background might be a little bit different and not what you expect.

And I really liked that.

I'm wondering, can you take us into a recent hiring situation and how

you struggled and how you got through the, well, this person doesn't

feel like a fit on paper, but maybe they would help us add and grow

and do that, double the good stuff.

Yeah.

I mean, I'm right in the middle of the process of doing that right now.

So I've had a very stable leadership team for a while.

The team has been fantastic and working very well together.

And we did the whole predictive index and everybody's in the same quadrant,

outgoing and extrovert, and like to think about big picture and creating new ideas.

And I've been interviewing somebody now who's very, very process-oriented

and just, you know, going to hammer things and get it done.

And might be some people are like, I don't know if they'll fit in

the culture, but I do think it's going to work out extremely well.

Can you talk a little bit in more depth about hiring and I'm

wondering if there's an organizational decision that you've made that turned

out well, or that didn't turn out well, to support the business as it scales?

Is there something unique about your org chart that you

haven't had in other places?

So we have a team, we have the typical, traditional marketing

functions within the org chart that most people see in product marketing,

growth marketing that has demand digital inbound, some international teams,

communications and PR, creative team and a marketing program operation leader.

And then I've got a web and digital experience leader and team.

Before I got to SmartBear, it was web developers or our websites.

And I changed the name to web and digital experience.

We took over our communities and our academy for all of our

training, moved it into that team.

I took it out of a different organization altogether.

I like that under marketing.

I think the experience that customers have online with our communities and

with our training is very related to overall digital experience and marketing.

And it's related to our brand and our own web developers can make a

huge impact on the academies and all the experience customers have.

And it was sitting in a different part of the org and doing okay, but

bringing that under marketing has made an unbelievable impact on thinking about

community and training and the sense that we think like treating customers

as, not so much leads, but as you know, it's a journey that we're taking them in.

It's very cross-functional.

We have engineers and product owners and customer support and sales, very

close to those teams, but it's a little bit unusual of an org within marketing.

And then I'm seeing more and more people with this sort of customer journey,

variance being coming under marketing, I'm seeing that trending a little bit more.

Certainly if you look at e-commerce where we are full B2B company, if

you go look at B2C in e-commerce, that is the marketing function.

It's sort of that customer and communities.

But with B2B, it's something a little bit new and different.

So we're still shaping that.

I get so excited when I see, you know, we redesigned the web page based

on best practices and based on our branding and redid all the messaging

and our academy enrollments went up by 400% just because of a redesign.

And I don't think outside of marketing people would think

of doing that sort of thing.

So it's been great.

Our customers are developers themselves.

They're on software development teams.

They either develop or they test software and having that team made

up of people who look like our customers for us works really well

because they're looking at journeys.

If you were technical and you want to get a question answered, you go here,

or they do connect with our social media team, which is under comms.

Because we do have a lot of developers just raise their hand on

Twitter and say, "Hey, SmartBear, I have a question about this."

And you know, we'll have to direct them back like that's a great question.

It's already answered here on our community.

So, come on back over.

So we do look at that holistically.

It's not the cleanest in terms of product marketing gets involved

and so does technical support.

But I feel like the cross-functional aspect works as long as somebody's

looking out for the whole picture.

They just know who to go to.

We're not big enough that we don't know who to work with on

different teams to get some of these answers or get some of this done.

Well, thanks for giving a view into the organization.

I think that's really cool.

Let's talk about hiring.

Do you have a favorite interview question when you are hiring?

Anything that's surprisingly revealing?

Yeah, I usually ask candidates what accomplishment

are they most proud of, and we'll go through different things in the resume.

I don't know if that's the most unique question in an interview, but

to me it's super revealing because I get a sense of, are people going to

share something that they led or they completely did themselves, or they

worked with an entire team to accomplish?

Or are they going to share something that was completely broken that they fixed or

just something that got great results?

So it really gives me insight into how they think in terms of what they value,

their most salient accomplishment.

And sometimes I'll get stories that are outside of work.

Like, I started volunteering at something, you know, sports coach and

it was so valuable because X, Y, and Z.

So it's always a helpful question to ask.

A lot of those tend to be just going through, can you do this job?

And tell me about something that relates to what you're going to face here.

That's the one question I ask everybody.

Yeah, that's great.

I like it.

I have a friend who asks what are you famous for personally and professionally?

But that's like the famous part and not the proud part.

Cause I think you might get the quiet competence that comes

out through your question.

Right, right, right.

Yeah, and sometimes, you know, what's your superpower?

And I've had to answer that a few times in my past life interviewing.

What kind of CMO are you?

What's your superpower?

Are you a demand gen?

Are you a product marketing?

Are you a brand?

What do you say?

I kind of came up through all of those functions, but my

answer to that has always been primarily demand and driving business, but not

without minding the messaging and how it's coming across to customers.

Right.

So like a major and a minor, or maybe it's like a native language and then a fluency?

Like second language that you speak fluently?

You know, cause it's like you spent 51% of your time with one parent and 49% with

the other that spoke a different language.

So what keeps you there at SmartBear?

You know, the market is so tight, I'm sure you get hit up a lot of times for jobs.

What is it that's sticky for you?

Yeah, I have zero desire to move right now.

I'm enjoying it so much at SmartBear.

What's kept me at the company is it feels like a new job every six months.

I don't need to go anywhere to feel like, oh, I've got to exercise new skills.

We're getting to the next level.

The team is growing.

We're adding a whole product focus.

Every growth stage and growth spurt is like being in a new company.

At first, it was managing a team at what felt like a startup, now we're at mid-size

company, we're growing in different regions of the world and we're adding ABM

and outbound, which we haven't had before.

It's all something new all the time.

So it just keeps, you know, it gets back to the idea of you

can't just get too comfortable.

You have to make yourself uncomfortable once in a while and start expanding

and exercising skills and muscles that you haven't in a while.

That's great.

So looking ahead to 2022, the arc of that year for B2B SaaS marketing,

are there any particular trends that you forecast for next year?

Yeah, I think there is a bit of, not a return so much as

just reinforcement of, really knowing your ideal customer profile and talking

directly to who your customers are that I see as more important more than ever.

Why?

People are, if they weren't digital, primarily

digital before they're a hundred percent digital first now.

And I think every, no matter what, you know, I'm getting bombarded fifty times

a day by emails from various vendors.

No matter your role, whether it's me or the new person on my team or the sales

rep or our developer teams, there's so much just vying for their attention

that's just beyond what it's ever been.

If it was bad two years ago, it's crazy.

And I think nobody's listening to inbound messages like that anymore.

They just need to go find what they need online or through reviews

or through peers that they trust.

And we need to be there at every digital touch point that our customers are

self-serving to solve their own problems.

It's not just digital first, it's faster everything, especially our industry, you

know, we're serving software development team, app development teams, which are

serving the whole market as a whole.

And they're running fast to get out the gate faster than competitors

and develop more apps and really faster, just like everyone else is.

So as a supplier vendor, getting people what they need quickly and

answers to their questions and finding what they need and speaking

their language is so important.

So I think that translates back into marketing as we're doing a

lot of work to make sure we know who that ideal customer profile is.

There aren't software developers.

There's fifty different kinds of software developers that each

have their own jobs to be done.

And product management is working on that.

We need to bring that back into marketing.

Do we really know what they're trying to do?

You know, our language on our website, on our materials, in our

product, in trial has to translate well to what they're looking for.

And that's foundation to, marketing's doing a lot more in trial experience.

There's big buzzword in the industry Product-Led Growth,

which you hear about everywhere.

And what does that mean to a marketing organization?

It means that all those touch points, again, they're digital

and they're in your product.

They go from website straight into trial, straight into product, and

there's language everywhere that the customer is reading, even in trial.

What are those little help units?

What messages are they getting along the way to help them get to the next stage?

And marketing's creating a lot of that content.

So we need to really know what our customers are trying to do.

And for marketing to do well, PLG, in Product-Led Growth, we need to really

know what the customers are trying to do and who they are and what their job

is and what pressures they're under.

So I think that's a trend of just market research in a way that's not macro

market, but micro market research.

You know, creativity, the strategic value product marketing is right in there too.

And that is now I think the hardest role to hire in marketing.

Incredibly tough, and having product marketing focused on that, focused on

understanding customers and getting creative beyond just write and create data

sheets and create sales training, there's fundamental set of things they need to do,

but a truly strategic product marketing function is an incredible advantage.

So final question for you, just bonus question.

CEOs hiring CMOs, do you have a piece of advice for a CEO who has not hired

a CMO before in B2B SaaS, and what should that person think of or know

about to make a successful hire?

Yeah, I think, CEO, just thinking first about

what their business needs the most.

What do they really need from a marketer at that stage of the company and what

do they need from a marketing lead?

That stage plus a year or two years ahead of time.

Especially if it's the first hire then there might be some very short-term,

you know, we need to rebrand.

So you look for somebody who can rebrand the company.

And then when that's done, wait a minute, now we need some growth

marketing and demand, and this person doesn't know how to do that.

I need

another CMO.

So, I think

there's some of that going on in the industry.

So really think about what are the next two to three years look like for

how the company's going to evolve, how the needs of the marketing leader are

going to evolve, and frame both the job description and what you're looking for

in terms of somebody who could do all of that, and not just the one thing.

Sometimes it's just pure, oh, leads, our salespeople need more leads.

Can we bring in a CMO who can do that?

And then you're going to have mismatched expectations when

something else becomes important.

So I think really matching the expectations with what stage of

growth you're in and we'll be in for a little bit of foreseeable future.

Right, right.

But not thinking five years ahead necessarily, but thinking

a couple of years ahead.

I like that.

I like that.

I think sometimes companies trying to hire, you know, oh,

we're the $30 million company.

We want somebody who could take us to a hundred million.

It's like, well, maybe if you focus on the 30 to $50 million range, you're

going to find the person that inhabits that really well, and then you bring in

somebody else or somebody in addition to help you do the fifty to one hundred.

Yeah.

And also the one company's journey from fifty to a hundred

doesn't look like the next.

So just because somebody has done it before doesn't mean, you know,

can they do it at your company?

You might have a completely different go-to-market model,

different product model.

So I think looking at what is that track record of that big

hyper-growth phase does not translate from company to company perfectly.

Yeah.

Yeah.

Oh, it's so true.

Yeah.

Well, this was great.

Thank you so much for joining me.

It's been a pleasure chatting with you.

Thank you, Erica.

It's been a pleasure.

That was Cynthia Gumbert, the chief marketing

officer from SmartBear.

Now that you've listened, ask yourself: how can you inject

discomfort into your scale journey...

even when things are going well?

Next time on The Get, you'll hear from the head of marketing and communications

for Stack Overflow, Khalid El Khatib, about how to sidestep a CEO or Board's

expectations of marketing being a dollar in/dollar out proposition.

Thanks for listening to The Get.

I'm your host, Erica Seidel.

Hiring great marketing leaders is not easy.

The Get is designed to inspire smart decisions around recruiting and

leadership in B2B SaaS marketing.

We explore the trends, tribulations, and triumphs of today's top

marketing leaders in B2B SaaS.

This season's theme is Solving for the Scale Journey.

If you liked this episode, please share it.

For other insights on recruiting great marketing leaders, what I

call the 'make money' marketing leaders rather than the 'make it

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