Episode 6

How to Inject Discomfort Into Your Scale Journey

Cynthia Gumbert is the CMO of SmartBear, the ~750-person PE-backed SaaS company that is on a growth tear, serving more and more software developers every day.

Cynthia reflects on her transition from VP of Marketing to CMO. We discuss the difference between a marketing-centric mindset and a 'business first, marketing second' mindset. It's this 'business first' mindset that is key for a CMO in scaling mode. That mindset entails 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. In other words, change your frame from 'what marketing is doing' to 'what the company is doing.'

A big part of scaling is creating discomfort with the status quo. You'll hear these learnings:

  • Expect to hit plateaus as you scale. When you do, ask, “How do we double doing well here?”
  • Hire for 'cultural add' as opposed to 'cultural fit' as you scale… even when that involves overcoming some discomfort.
  • Look for ways to organize to reflect the full arc of the customer experience. In Cynthia's case, she expanded the marketing org to include communities and the training academy, as part of one web and digital experience team. This led to a 400% increase in academy enrollments.

Cynthia also touched on an interesting trend for 2022: the need for micro market research. With product-led growth, customers will follow the journey of website --> trial → product. Marketers must be hyper-aware of micro customer segments and the messages that will help customers accomplish their specific goals.

 

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Key Links

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Hiring great marketing leaders is not easy. The Get is a podcast 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.

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at erica@theconnectivegood.com. You can also follow Erica on LinkedIn, or sign up for her newsletter at TheConnectiveGood.com

The Get is produced by Evo Terra and Simpler Media Productions.

Transcript
Erica Seidel:

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

Erica Seidel:

great marketing leaders in B2B SaaS.

Erica Seidel:

I'm Erica Seidel, your host.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

Today, you'll hear from Cynthia Gumbert.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

Listen for all the different ways in which Cynthia injects

Erica Seidel:

discomfort into her scale journey.

One takeaway:

expect to hit plateaus as you scale.

One takeaway:

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

One takeaway:

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

One takeaway:

CMOs - the need for micro-market research.

One takeaway:

Here we go.

One takeaway:

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

One takeaway:

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

One takeaway:

So thank you for joining!

Cynthia Gumbert:

Thank you, Erica.

Cynthia Gumbert:

Thrilled to be here and appreciate you having me.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

talked, you're like the PE darling.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

marketing second, as I like to say.

Erica Seidel:

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

Erica Seidel:

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

Cynthia Gumbert:

Yeah, I feel like I had to tap way back

Cynthia Gumbert:

into my history and background.

Cynthia Gumbert:

I was an engineer before I became a marketer.

Cynthia Gumbert:

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

Cynthia Gumbert:

school, and then went into marketing.

Cynthia Gumbert:

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

Cynthia Gumbert:

parts of the business and had a perspective beyond marketing.

Cynthia Gumbert:

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

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to exercise those parts of my brain.

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Not so much like understanding everything engineering is doing,

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

my team and my own department?

Erica Seidel:

That's great.

Erica Seidel:

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

Erica Seidel:

Are there different conversations where you're working on that

Erica Seidel:

alignment with the CEO and the CMO?

Erica Seidel:

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

Erica Seidel:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

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working on new things and doing this.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

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budget and have ability to hire.

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We have to make trade-offs.

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

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why we're making these trade-offs.

Cynthia Gumbert:

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

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things for the business.

Cynthia Gumbert:

That's one.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

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

Cynthia Gumbert:

that we're having conversations in.

Cynthia Gumbert:

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

Cynthia Gumbert:

avoid sharing strategy with.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

you know, oversharing anything sensitive.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

way that's relevant and important.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

want to work in this size company."

Erica Seidel:

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

Erica Seidel:

want a culture with integrity."

Erica Seidel:

And so I think it's so important.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

going to be in the conversation.

Cynthia Gumbert:

Yeah, transparency's important.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

finding opportunities to share more information across different parts of

Cynthia Gumbert:

the business that wouldn't normally talk.

Cynthia Gumbert:

It always sparks some new idea from somebody.

Erica Seidel:

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

Erica Seidel:

on the marketing team meeting?

Cynthia Gumbert:

We had the head of channel sales come join us.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

going on that you're working on?

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

It was just very interesting hearing that perspective and people

Cynthia Gumbert:

had a lot of questions for her.

Cynthia Gumbert:

So that was fun.

Cynthia Gumbert:

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

Cynthia Gumbert:

He's got a few things to say also.

Erica Seidel:

That's great.

Erica Seidel:

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

Erica Seidel:

you cause you might get a kick out of it.

Erica Seidel:

But he was doing live personas.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

company and bring the persona to life.

Erica Seidel:

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

Erica Seidel:

was all about learning and stuff.

Cynthia Gumbert:

That's awesome.

Cynthia Gumbert:

I may end up stealing that.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

doing well now are like a little nervous about experimenting.

Erica Seidel:

Any thoughts on that?

Erica Seidel:

Like where does the experimentation come in for you?

Cynthia Gumbert:

Yeah.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

just keep doing more of what we're doing.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

There's some new personas.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

share that, hmm, that's not working.

Cynthia Gumbert:

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

Cynthia Gumbert:

we're not getting anything out of them.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

I think that's part of the evolution.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

because we're making more money?

Erica Seidel:

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

Cynthia Gumbert:

Yeah, I know what we're doing.

Cynthia Gumbert:

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

Cynthia Gumbert:

So it's always a balance.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

And here's over and above.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

produced a single good lead for us.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

So, yeah, it's a balance.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

perfect Goldilocks P firm.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

So I think it is a perfect balance.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Erica Seidel:

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

Erica Seidel:

bear in mind while scaling up.

Cynthia Gumbert:

Yeah, I mean, I have three.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

put in the things that are growing?

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

others, and that is critically important.

Cynthia Gumbert:

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

Cynthia Gumbert:

peanut butter, a little bit of everything.

Cynthia Gumbert:

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

Cynthia Gumbert:

And that's true with people's time.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

Just look at how your time is spent.

Cynthia Gumbert:

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

Cynthia Gumbert:

much you do take off your plate.

Cynthia Gumbert:

So that is one.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

looking at our personality preferences, using the predictive index.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

There's several ways to do that.

Cynthia Gumbert:

We've used predictive index.

Cynthia Gumbert:

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

Cynthia Gumbert:

hiring for pure culture of fit.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

past those plateaus and keep growing.

Cynthia Gumbert:

So that's the second one.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

ways to make yourself uncomfortable.

Cynthia Gumbert:

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

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

Cynthia Gumbert:

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

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more of this, a little more of that.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

there's some discomfort along the way.

Cynthia Gumbert:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

you realize you need the cultural add.

Erica Seidel:

And that can be really messy and uncomfortable.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

of my people budget the same way.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

And I really liked that.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

and do that, double the good stuff.

Cynthia Gumbert:

Yeah.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

The team has been fantastic and working very well together.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

Is there something unique about your org chart that you

Erica Seidel:

haven't had in other places?

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

And I changed the name to web and digital experience.

Cynthia Gumbert:

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

Cynthia Gumbert:

training, moved it into that team.

Cynthia Gumbert:

I took it out of a different organization altogether.

Cynthia Gumbert:

I like that under marketing.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

It's very cross-functional.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

It's sort of that customer and communities.

Cynthia Gumbert:

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

Cynthia Gumbert:

So we're still shaping that.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

of doing that sort of thing.

Cynthia Gumbert:

So it's been great.

Cynthia Gumbert:

Our customers are developers themselves.

Cynthia Gumbert:

They're on software development teams.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

because they're looking at journeys.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

It's already answered here on our community.

Cynthia Gumbert:

So, come on back over.

Cynthia Gumbert:

So we do look at that holistically.

Cynthia Gumbert:

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

Cynthia Gumbert:

and so does technical support.

Cynthia Gumbert:

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

Cynthia Gumbert:

looking out for the whole picture.

Cynthia Gumbert:

They just know who to go to.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Erica Seidel:

Well, thanks for giving a view into the organization.

Erica Seidel:

I think that's really cool.

Erica Seidel:

Let's talk about hiring.

Erica Seidel:

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

Erica Seidel:

Anything that's surprisingly revealing?

Cynthia Gumbert:

Yeah, I usually ask candidates what accomplishment

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

worked with an entire team to accomplish?

Cynthia Gumbert:

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

Cynthia Gumbert:

just something that got great results?

Cynthia Gumbert:

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

Cynthia Gumbert:

their most salient accomplishment.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

So it's always a helpful question to ask.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

That's the one question I ask everybody.

Erica Seidel:

Yeah, that's great.

Erica Seidel:

I like it.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

Cause I think you might get the quiet competence that comes

Erica Seidel:

out through your question.

Cynthia Gumbert:

Right, right, right.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

What kind of CMO are you?

Cynthia Gumbert:

What's your superpower?

Cynthia Gumbert:

Are you a demand gen?

Cynthia Gumbert:

Are you a product marketing?

Cynthia Gumbert:

Are you a brand?

Erica Seidel:

What do you say?

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Erica Seidel:

Right.

Erica Seidel:

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

Erica Seidel:

Like second language that you speak fluently?

Erica Seidel:

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

Erica Seidel:

the other that spoke a different language.

Erica Seidel:

So what keeps you there at SmartBear?

Erica Seidel:

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

Erica Seidel:

What is it that's sticky for you?

Cynthia Gumbert:

Yeah, I have zero desire to move right now.

Cynthia Gumbert:

I'm enjoying it so much at SmartBear.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

We're getting to the next level.

Cynthia Gumbert:

The team is growing.

Cynthia Gumbert:

We're adding a whole product focus.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

and outbound, which we haven't had before.

Cynthia Gumbert:

It's all something new all the time.

Cynthia Gumbert:

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

Cynthia Gumbert:

can't just get too comfortable.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Erica Seidel:

That's great.

Erica Seidel:

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

Erica Seidel:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Erica Seidel:

Why?

Cynthia Gumbert:

People are, if they weren't digital, primarily

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

a day by emails from various vendors.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

or through peers that they trust.

Cynthia Gumbert:

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

Cynthia Gumbert:

self-serving to solve their own problems.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

serving the whole market as a whole.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

answers to their questions and finding what they need and speaking

Cynthia Gumbert:

their language is so important.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

There aren't software developers.

Cynthia Gumbert:

There's fifty different kinds of software developers that each

Cynthia Gumbert:

have their own jobs to be done.

Cynthia Gumbert:

And product management is working on that.

Cynthia Gumbert:

We need to bring that back into marketing.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

which you hear about everywhere.

Cynthia Gumbert:

And what does that mean to a marketing organization?

Cynthia Gumbert:

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

Cynthia Gumbert:

and they're in your product.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

What are those little help units?

Cynthia Gumbert:

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

Cynthia Gumbert:

And marketing's creating a lot of that content.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

is and what pressures they're under.

Cynthia Gumbert:

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

Cynthia Gumbert:

market, but micro market research.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

understanding customers and getting creative beyond just write and create data

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Erica Seidel:

So final question for you, just bonus question.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

about to make a successful hire?

Cynthia Gumbert:

Yeah, I think, CEO, just thinking first about

Cynthia Gumbert:

what their business needs the most.

Cynthia Gumbert:

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

Cynthia Gumbert:

do they need from a marketing lead?

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

you know, we need to rebrand.

Cynthia Gumbert:

So you look for somebody who can rebrand the company.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

I need

Cynthia Gumbert:

another CMO.

Cynthia Gumbert:

So, I think

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Cynthia Gumbert:

Can we bring in a CMO who can do that?

Cynthia Gumbert:

And then you're going to have mismatched expectations when

Cynthia Gumbert:

something else becomes important.

Cynthia Gumbert:

So I think really matching the expectations with what stage of

Cynthia Gumbert:

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

Erica Seidel:

Right, right.

Erica Seidel:

But not thinking five years ahead necessarily, but thinking

Erica Seidel:

a couple of years ahead.

Erica Seidel:

I like that.

Erica Seidel:

I like that.

Erica Seidel:

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

Erica Seidel:

we're the $30 million company.

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Cynthia Gumbert:

Yeah.

Cynthia Gumbert:

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

Cynthia Gumbert:

doesn't look like the next.

Cynthia Gumbert:

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

Cynthia Gumbert:

can they do it at your company?

Cynthia Gumbert:

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

Cynthia Gumbert:

different product model.

Cynthia Gumbert:

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

Cynthia Gumbert:

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

Erica Seidel:

Yeah.

Erica Seidel:

Yeah.

Erica Seidel:

Oh, it's so true.

Erica Seidel:

Yeah.

Erica Seidel:

Well, this was great.

Erica Seidel:

Thank you so much for joining me.

Erica Seidel:

It's been a pleasure chatting with you.

Cynthia Gumbert:

Thank you, Erica.

Cynthia Gumbert:

It's been a pleasure.

Erica Seidel:

That was Cynthia Gumbert, the chief marketing

Erica Seidel:

officer from SmartBear.

Erica Seidel:

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

Erica Seidel:

discomfort into your scale journey...

Erica Seidel:

even when things are going well?

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

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

Erica Seidel:

Thanks for listening to The Get.

Erica Seidel:

I'm your host, Erica Seidel.

Erica Seidel:

Hiring great marketing leaders is not easy.

Erica Seidel:

The Get is designed to inspire smart decisions around recruiting and

Erica Seidel:

leadership in B2B SaaS marketing.

Erica Seidel:

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

Erica Seidel:

marketing leaders in B2B SaaS.

Erica Seidel:

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

Erica Seidel:

If you liked this episode, please share it.

Erica Seidel:

For other insights on recruiting great marketing leaders, what I

Erica Seidel:

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

Erica Seidel:

pretty' ones, follow me on LinkedIn.

Erica Seidel:

You can also sign up for my newsletter at TheConnectiveGood.com.

Erica Seidel:

The Get is produced by Evo Terra and Simpler Media Productions.

About the Podcast

Show artwork for The Get: Finding And Keeping The Best Marketing Leaders in B2B SaaS
The Get: Finding And Keeping The Best Marketing Leaders in B2B SaaS
Your inspiration from the best marketing leaders in B2B SaaS today... from hiring, getting hired, leading, organizing, and more!

About your host

Profile picture for Erica Seidel

Erica Seidel

Erica Seidel recruits the marketing leaders of the 'make money' variety – not the 'make it pretty' variety. As the Founder of The Connective Good, a boutique executive search firm, she is retained to recruit CMOs and VPs in marketing, digital strategy, marketing analytics, and marketing technology. She also hosts The Get podcast. Previously, she led Forrester Research's global peer-to-peer executive education businesses for CMOs and digital marketing executives of Fortune 500 companies. Erica has an MBA in Marketing from Wharton, and a BA in International Relations from Brown. One of her favorite jobs ever was serving as the Brown Bear mascot.

You can find her on LinkedIn at https://www.linkedin.com/in/ericaseidel/, or on her website/blog at www.theconnectivegood.com, or on Twitter at @erica_seidel.