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.

Lately, I've noticed something that all my best CMO candidates do.

When they hear that a company wants to, say, double in revenue, they make sure to

"How exactly do you plan for the growth to come from?"

Our guest today reminds CMOs to take the reins for growth planning.

You'll hear from Jay Gaines, who now runs marketing for the insurance

tech company AgentSync and is the former CMO of SiriusDecisions.

You'll hear about mistakes to avoid when starting to scale.

Spoiler alert - and this was surprising: Don't hire too

heavily in demand generation.

You'll also hear about the importance of hiring fast and hiring for

diversity and equity and inclusion.

And you'll hear about what candidates are looking for today and how

that's different from before.

Jay, welcome to the show.

Let's talk about key things to avoid as a CMO embarks on a scale journey.

I think the main thing, and all of these things are a little bit connected, the

main thing to avoid is letting the scaling of the organization impact negatively

the focus and purpose of marketing.

Now, inevitably as a company scales, you're going to have a lot more

products that are going to be launched.

You're going to add complexity as you expand into new vertical

industries, into new geos, all of those things are going to expand the

scope of marketing's work for sure.

But the other thing that happens along the way is that a lot of

random projects come up and people aren't quite sure where they belong.

The default seems to be marketing can do this, right?

They've got limitless capacity, sure.

Just throw it to marketing and they'll take it on.

So you want to avoid allowing that to happen, and there's

a few ways to avoid that.

The first is to be constantly marketing internally.

Being sure to reinforce with the CEO, the head of sales, other leadership in

the company the role that marketing is playing at the business as it scales.

Like I said, that will expand somewhat, but you always want to make

sure that there's a shared, common understanding of what it is marketing

is here to do for the business.

That's important.

The second thing to do is, and it usually falls to the CMO to do this, and this

might be a surprise for some folks, but to seize control of that strategic

planning process at the corporate level.

Not talking about just marketing strategic planning, but I'm talking about

strategic planning for the business.

And when I say seize control, I don't mean that the CMO

necessarily leads the entire thing.

But it usually falls to the CMO to step up within the business and say, I understand

that we are doing some planning and we are intending to hit this revenue number, for

example, and expand maybe into these geos.

And at a high level I understand what we're trying to accomplish as a business.

Usually, it falls to the CMO to say, okay, but we have to go a click or

two deeper than that in our strategic planning process and really define how

it is we're going to hit those revenue targets and what it means for us as a

business as we expand into new verticals or into new geos or scale in terms

of the number of people we have here.

That's important because if you don't do that, what will inevitably happen

is marketing will be asked to treat everything across the business equally.

For example, at my business, we're scaling very fast right now.

We have very clear revenue targets that we want to hit next year, but I had to

work with the head of sales, head of product, the founders, and really get

at when we think about hitting that number, what products sold to which

audience segments do we expect to contribute what percentage to that growth?

And when I'm armed with that information, which we quickly got to, thankfully, we're

a very operationally mature business.

But when we got to agreement on that, that's the information I need to know

how to focus marketing's investment of resources and efforts so we're

not spread like peanut butter across everything the business does equally.

It also puts me in a position to do the most important work as the CMO,

which is create and protect focus for the marketing organization because,

invariably, every product has a product manager that has a number on their head.

You have sales teams that are oriented around different parts of the business.

And as they observe marketing investing more in one part of the business

than another part of the business, you're gonna have people come to you

and be like, hey, what's going on?

Why aren't you giving the part I care about as much

attention as this other part?

So you want to be in a defensible position to say, look, we've all agreed that this

other part is going to contribute more to our growth than the part you care most

about, so I'm investing more over there.

It really creates an environment where there's shared understanding.

And I, as the leader of the marketing team, can help everybody understand

why we're doing the things we're doing and oh, by the way, not doing all of

those other random things and treating everything equally across the business.

I think that's great because it really puts marketing in the

driver's seat of growth, which is what we're all talking about.

But I think a lot of marketers they decide, like, I'm going to inherit

the strategic plan from the CMO, and then I'm going to do my marketing.

But you're right, there can be this kind of gap between CEO can set the plan and

that plan might be, we're going to double in two years or we're going to increase

our ARR growth rate to blah, blah, blah.

But then it's easy to fall into these random acts of marketing or this, what

I like to call, a vending machine kind of marketing, where it's like, oh, hey,

we're just going to press on the belly of the marketing person and a campaign

is going to come out or a new sales enablement toolkit is going to come out.

So I can totally see that.

You've scaled marketing at several companies now.

How often do you revisit that plan?

Because it would seem that every once in a while, you might want to

go back and say, okay that person has been asking for marketing resources.

Maybe we actually do want to allocate some resources to that.

So, I'm curious about revisiting the plan and also the corollary

of revisiting the budget.

Well, you can't be too rigid.

You have to adapt as you go, especially if you're at a relatively early stage

company, which typically are the companies that are scaling the fastest, right?

Things change over the course of a quarter, not just a year, but

things can change pretty quickly.

So you do have to be flexible and willing to adapt.

You want to be revisiting it almost constantly.

To that end, the idea that we have to revisit the marketing plan, for example,

based on shifts that are happening at a high level in the business and the

business's plan because you're learning as you go, everybody's learning.

To make it easy to revisit that marketing plan, I do this thing that

I call a marketing plan on a page.

My mission is literally to get the marketing plan on a single page that

lays out our primary objectives and how they link to the primary business

goals, how we're executing to achieve those goals, how we're measuring it,

and the risks and dependencies that exist that are going to get us there.

It doesn't get into marketing activity planning, that's separate, but it gets

into the strategic plan for marketing.

If that's in place, and it's nicely, clearly defined business goals, when you

do have to revisit it, it's easy to do and you can have a rational conversation

about how things are going to change.

Again, if you can go back to the corporate strategy and the corporate

goals that are hopefully very clear, then you can say is, say, okay, it

appears we need to change because this other thing has changed, but that means

we're not going to do this other thing.

So you can do a bit of, I don't want to call it horse trading, but it's

trade-offs and make it very clear to people that we have X amount

of resources, X amount of budget.

Are we going to get more budget?

Typically, the answer is no, but you never know.

These days, actually, it's increasingly yes, you can have more budget.

And if you can agree to that, you can say, okay if we're going to do it

then there's a few other things that we're not going to do, or we're not

going to give as much attention to.

And if you have that starting point of agreement on focus and how you're going to

grow, if anything changes the trade-offs become pretty clear, pretty obvious.

Something increases in importance and another thing diminishes, and you can

adjust your resources accordingly.

What's harder to do is adjust people accordingly.

Moving budget around is relatively easy, changing up some programs

and tactic mixes, and that sort of thing is relatively easy.

But as you're scaling, you're also building a marketing organization

that's designed to do certain things.

Hopefully, you're not just building it randomly.

And that gets a little bit harder.

So especially when I'm at earlier stage companies where I know change

can be anticipated, it's going to come, I try to populate my team with

people who are multi-position players.

People who, yes, they have strong skill sets, for example, in

product marketing, but guess what?

They've done a little bit of customer marketing, as well, and maybe they've

got a little demand in their background.

So that as things change, people are able to wear a few hats.

It's really important that people can be flexible.

I also, as I'm bringing people on, I get them ready for that.

I make it very clear that, hey, you're joining a company that's at this stage.

We're scaling quickly.

We're going to be learning as we go.

So we all have to be flexible.

We all have to be willing to wear a bunch of hats.

And guess what?

Our roles might shift a little bit as we go along.

Are you down for that?

Is that something that you're okay with as you join us?

That makes it a bit easier, but people change is the hardest, I think.

Can you talk about an organizational misstep that you made at some point?

Sure, I'd be happy to.

Let me think.

The problem isn't finding one.

The problem is picking one.

I've become successful through a series of mistakes that I've

learned through in my career.

I would say the biggest one that I made, and this was probably my first CMO role,

I was building an organization essentially from scratch and it was in a company

that had been around for about twenty years, but was just releasing some new

products and extending into new markets.

So we were scaling pretty quickly.

When I joined, there were two people and I grew us to about twenty-seven people over

the course of about a year and a half.

My background was very much oriented around digital marketing and demand.

I had some product marketing background and some other things as well, but I was

really focused on demand and I completely over-rotated around demand as I was

building out my marketing organization.

I brought on a lot of people who were really good at demand.

I made that part of the function just really big, kind of too big.

I forgot the fact that demand needs to be fed by all kinds of other stuff

like really great product marketing and really great content and all

sorts of other things, and really good comms and messaging and all that.

So, I kind of failed at creating all the demand I expected to make 'cause

I just had too many demand-focused and experienced people and not

enough of the other people that were going to feed that demand engine.

It was just a lack of foresight and, frankly, being too focused on what

I knew best, if that make sense.

That's so interesting because I think a lot of CEOs, I mean, god bless

them, but they're like overgrown salespeople in many cases and they love

the idea of a marketing organization that's over-rotated on demand.

So it sounds good in theory until you realize you can pour more budget into

it, but there are diminishing returns.

And you're right.

I like to think of it as you need the product marketing and branding

people to help you point and then the demand gen people to help you shoot.

That's a very over simplistic way to think about it, but there is that piece.

It's accurate, though.

To your point, the CEO at that company was cheering me on the whole way,

loved the fact that I was building out this huge demand organization.

Since then, including at the company I'm at now and my last

company, the same is true.

CEOs, especially of early stage SaaS companies, they want that demand and

they're right to want that, but in both cases I've gotten a lot of pressure.

Are you sure that's enough demand people?

Which has offered me the opportunity to get into really how demand is fed.

Effective demand comes from the crews over all the things that marketing does.

I would especially emphasize product marketing 'cause you're right, we

have to have a depth of understanding of not just our products, but our

audiences, and really strong positioning and competitive intelligence and

great content and all of that stuff.

If those are in place, then demand becomes far more effective.

So I've had to do that repeatedly to avoid making the same mistake

that I made in that first CMO role I had because it's easy to go along.

When your CEO is like "Build demand!"

Of course you just want to go along, but that's when you've

got to step up and explain.

It makes me think of a former boss of mine who says, "Today's

brand is tomorrow's demand."

Once I heard that

- I love that.

I know it's great, right?

So I started a list of things to say to a CEO who is thinking more on the

demand side than on the brand side.

It might be over-rotating, to use your word.

Are there others catchphrases that you have seen work to

communicate that to a CEO?

'Cause I feel like that's half of my job, that's half of a CMO's job is

to educate and guide a CEO and not get into so much of the weeds, but

get them to see what's going to help make things work and make things grow.

Yeah.

So I don't know if they're as catchy as the one that you just had, but a

few things that I've said and have said repeatedly that seem to resonate

and seem to work are things like I've talked to quite a bit about the fact

that awareness and trust fuel demand.

That's the context that creates the ability to engage audiences, build

audience, and convert audience because you can have the coolest product in the world,

but if you're just driving people to demos without them understanding who you are,

without them trusting you, any of that being in place, chances are, you're not

going to be very effective at doing that.

Obviously, "content is king."

Content is also "the fuel that drives the demand engine" is another big one.

That's become less of a problem.

But as recently as six, seven years ago, I literally had to sit down with some

people and just explain to them why yes, we have to invest in creating content.

I guess a catchphrase I use around that is "what marketing should be delivering

to our prospects all the time is value."

It's all about value and there is no value in asking people to watch that

demo video or fill out that form.

All of the value is in that content that's created.

Oh, and by the way, brand as well and awareness and trust is built

if you can deliver value over time.

The other thing I've been thinking about lately is, there's always this

brand versus demand kind of thing and I think now there's a growing awareness

of the holistic approach to marketing.

I'm seeing more and more CEOs want the demand and the brand.

There's just this concern that the brand person is going to be a typical B2C

person, or the perception of a typical B2C person, who's just going to go and

find an agency and spend a million dollars and that's going to be so expensive.

What I've been thinking about lately is what you really want is the

tight cycles of test and learn, not just for your performance and your

demand gen, but also for branding.

So I've been asking people how quickly can you test out a message?

How do you test out a message?

How do you swap it out, et cetera, which I think can be a helpful way of thinking.

Testing is difficult when it comes to that stuff, I find.

In the world of demand, obviously, testing a subject line or a call to action is

pretty straightforward, assuming you have a big enough audience to do relevant AB

and multivariate testing and all of that.

But testing messaging can be a lot harder and it takes a little bit longer

to figure out what's actually working and resonating and what's not from a

positioning and messaging standpoint.

The way I like to do it is that it's not just marketing's job.

Obviously, you want to do your work up front.

You want to pass things by actual customers and prospects and talk to

your salespeople and all of that.

I'll give you an example, a tangible one.

We just launched a new product in my company earlier this week

and it's pretty groundbreaking.

It's a pretty new concept.

And we had to be very cautious about how we message around it and position

it because, without getting into too much detail, it could change

the way people perceive our company and it could provide an opportunity

for our competition to misposition us if we didn't get it just right.

And I'm brand new so I spent a lot of time talking to customers and people who have

been at the company longer than myself.

But now that it's launched, one of the things I set up right off the

bat was a feedback cycle from our frontline people, our salespeople,

our customer success people who are going to be talking to the recipients

of this message all the time and ask them to constantly create feedback.

But also to set up a series of regular meetings where we're going to sit in

a room and I'm asking them to tell me, from their point of view, how it's

going because it's not always visible to us in marketing as immediately

as it is to those other folks.

So that helps a lot.

I like that.

That's awesome.

You're right, you're going to get sick of your messaging well before your

customers will and that's probably a good thing for you to be ahead of that.

So we talked about organization stuff.

Is there a really unique organizational decision that you have either seen

or implemented yourself that funnily worked but you didn't expect would

work during a period of rapid scaling?

That's a good question.

I'm trying to think.

Marketing organizational design is something that I've done more of than

I care to even either think about.

Because, as you know, I spent ten years as an analyst as well, working

with CMOs, and one of my areas of expertise was organizational design.

So I've done it across dozens of companies at various scales.

I'm trying to decide there's this demand center thing, but that's more

like companies that are at scale.

I think for companies that are smaller and scaling quickly, probably the

most unique one and the one that I still get pushback on quite a bit.

In fact, I'm hiring this person, my new company right now, is this idea of a

senior leader who is head of campaigns.

It sounds logical and pretty obvious, but when you're a relatively small

company that's scaling pretty rapidly and you're the head of

marketing, oftentimes the pushback you'll get is why is that necessary?

We're pretty narrowly focused.

We're not that complex in how we're going to market.

Oh, and by the way, isn't that your job as the head of marketing to

play that role of head of campaigns?

Because the way I define the head of campaigns is somebody who is helping to

coordinate activity across marketing, make it cohesive and programmatic to

drive the desired optimal outcomes that you're trying to drive.

At a relatively small scale of company, you would say, well, yeah, that's

definitely something that the head of marketing can and should be doing.

But I found bringing somebody in who owns that role completely and all the

time, is critically important and plays, again, this effect of focusing and

aligning within marketing everything that we're doing in a huge way because I, as

the head of marketing, in this rapidly scaling company, have many, many jobs.

I can give that a bit of my attention and if it's only getting

a bit of somebody's attention, it's not getting enough attention.

So it's one of those things that I've found to be very valuable

and that person oftentimes ends up becoming my right-hand person.

I will say that the last person who had that role for me is now CMO of a

really great company in their own right.

The person who had the role before that person is also a CMO.

So it's this path to the CMO role because you're organizing a lot of what

marketing is doing, a lot of coordination across all of what marketing does.

And again, it sounds like something that a big company would have,

but not a smaller company, but I think it's critical very early on.

And how was that role different from a head of demand gen?

Good question.

So for example, the role I'm hiring for right now is Head of Demand and Campaigns.

I oftentimes blend them together and the same is true at Sirius.

It's different in the sense that a head of demand, what I found is if

you're just kind of director of demand or VP of demand or whatever it is,

you are very exclusively focused on designing and executing demand programs

that generate leads, or focused on end-to-end demand management.

You're working with ops to measure it.

Whereas this campaigns person is taking a much more holistic view and saying,

when I think about all the work we're doing across brand and comms and product

marketing and digital and all of those things, how do I make sure that they

are accruing to cohesive programs that drive ideal demand outcomes?

I should mention, without getting too deep into it, this role becomes

necessary when you take a specific approach to your go-to-market strategy.

I take a campaign framework based approach to go-to-market and was something that

was developed at Sirius when I was there.

It's something that I've implemented many times.

I've seen it work over and over again, and it basically aligns

all sub functions within marketing around a set of programs and a mix

of tactics to drive optimal outcomes.

The reason I blend demand into that role is because, at the stage I'm

at, and usually when you're scaling rapidly, the primary arrow comes

through trying to drive our demand.

So that's why I blend them.

Thank you so much for sharing.

That's going to be great for folks to hear about.

So we talked about organization, let's talk about hiring.

One thing that people can struggle with is, should I hire fast, or

should I hire slow and fire fast?

Can you talk about how you've thought about it?

What's a CMO to do?

What's your perspective now?

In my two and a half months in my current role right now, I've probably spent 60%

of my time on hiring, and that's painful because there's so much else to do.

But I also know my greatest risk of not being able to do what I know I

need to do for the business will be not having the right people in place.

So I have to give it time.

That means writing really good job descriptions, reaching out to my

network and engaging them in every way I can, talking to people like yourself.

I think I've reached out to you a couple of times along the way.

It's really critical.

Then, engaging the rest of my business as well.

I get our COO, our head of sales, other people involved in the hiring process

too, and the interviewing process.

So it's not just me making these decisions along the way.

And as my team grows, my team gets involved in it as well.

My current company, AgentSync, we are scaling very, very fast.

I think I was in the low seventies two and a half months ago, and

we've surpassed a hundred people.

And we're just adding more and more and more, very quickly.

And we, as a leadership team, know that our greatest risk to us not

hitting our number is not getting the right people in place fast enough.

That's across everything from engineering to customer success, to sales, to

marketing, and everything in between, program management, you name it.

Yet, we made a deliberate decision as a team, and this was top-down from our

founders, that we're willing to miss our goals to slow down the hiring a little

bit to make sure we hire the right people, but also hit our diversity, equity,

and inclusion goals, which I can tell you is having the effect of actually

helping us bring on talent a lot faster.

A commitment to DEI, for example, and a commitment to work-life balance that

is tangible and very real, is the kind of thing that's a differentiator today.

We find that people care about and want to join companies that are truly

committed to that and see companies taking action, not just speaking to it.

For example, I think I shared this story with you on the work-life

balance thing as we've been on boarding and bringing on a lot of people.

Everybody who's a go-to-market hire in sales and marketing and product,

the CEO still talks to as the final stage in that interviewing process.

We're going to get past that point pretty quickly, but we're still at

the scale where we can handle that.

And the CEO has a new young daughter at home.

So as I was hiring my initial hires, when I first joined and said we've

got to set you up to talk to Niji, our CEO, there were moments where we said,

ooh, well, Niji can't do it after a certain time because that's family time.

He spends that time with his daughter.

And when these people then joined the company, they told me that was the

deciding factor, hearing that your CEO set aside that time for family every evening

was all I needed to hear to know that this is the kind of company I want to be at.

It was unintentional.

It was just a nice side effect.

But also being able to tell the story and demonstrate through our actions

and how we bring people on that we are really dedicated to achieving very

aggressive DEI goals is something that really appeals to a lot of people and

causes them to want to be with us.

So this kind of decision we made that we're going to slow down to get this

right has actually helped us accelerate in a strange way, in terms of our ability

to bring on the people we really want.

I think that's great.

It just speaks to the fact that what people want out of their jobs is changing.

I don't want to say they're looking for a family, there's a little bit of that.

But when a company and an employee come together, it's like you're

hiring the whole person and you're ingesting the whole company.

That is very different from how it used to be.

What I'm seeing on the hiring side is, I always ask people,

what are the top three things that you're looking for from a company?

It used to be upside is key, and I need this industry and I need this growth

rate, and that can still be important, but what I'm hearing more and more

is this pivot towards a really great culture, a really great leadership team,

integrity, transparency, authenticity.

It makes me realize that those things that you think are, not a throwaway

thing, but, okay, the CEO's busy with his kid, but these signals become almost

the most important thing to put forward.

It's not that they're intangible, but they need to come across naturally.

It's not the kind of thing that I think can be forced, so it's gotta be authentic.

It's gotta be just an actual part of the culture and the way that the

business is for it to be effective.

And I think you're right, with COVID and so much that's happened over the past

year and a half plus, people's values have shifted in very tangible and real ways.

People want to be part of successful businesses that are growing, but they

also, for the most part, and I know I'm making generalizations now, aren't

all that interested in being part of growth-at-all-costs kind of companies,

like sacrifice all elements of your personal life to achieve these goals.

I know I personally have no interest in being part of that, and I think

that's pretty common these days.

It's not as cool as it once was to talk about how sleep deprived

you are and how you have no life because all you do is work.

I think that's out right now and I'm glad.

Exactly.

The world has changed and companies need to change along

with it to get the top talent.

My last question for you is can you share your favorite interview question?

What is the question that you find most revealing when you

interview people for your team?

Sure.

It's a tough one 'cause I have a few that I really, really like to ask.

The one I'll talk about, and it sounds like it's a very cliche question, but

I like to think that the way I do it is a little bit different and it actually

links to what we were just talking about because I do think that part of

the shift that I perceived happening in the world is people allowing themselves

to be a little bit more vulnerable than we used to allow ourselves to be.

And just more human than we used to allow ourselves to be.

One of my favorite questions starts with me telling a story about

myself, a very self-effacing story.

I pick from a few where I just failed miserably at something, like

I really got something wrong or something I'm really not good at.

And I tell it in a very tangible way, like I really mean it,

and I make myself vulnerable.

Then I ask the person to tell me a similar story about themselves.

So, it's kind of cliche in the sense that it's like, hey, what's your

greatest weakness kind of question.

But again, I do it in such a way where I make myself vulnerable and I'm seeing if

this person who I'm talking to, who, by the way, is in an interview situation,

which is difficult to begin with, is willing to be honest and vulnerable in

that situation and be very open with me.

Because very often what people will respond with are things like "I care

too much," or "I just work too hard."

And that's not what I'm looking for.

I'm looking for somebody to get pretty honest and be like, you know

what, here's something that I really messed up or that I'm really not good

at, and by the way, I don't think I'm ever going to be good at it.

That's real.

I love hearing that from people because it tells me that they're

human, they're willing to get vulnerable, and they're going to

be transparent, which I care about.

There's a lot of stuff I'm not good at.

And the extent to which I'm honest about that with others and myself is the extent

to which I can augment myself and build really good teams and be effective.

So that's a big one that I like to ask.

The other one, 'cause I have to say two, sorry.

The other one is, usually at the end, I ask them, "Is there anything I didn't

ask you that you wish I had asked you?"

It's just fascinating to see what people come out with.

Some people are totally stumped.

Other people come out with really revealing things.

Because if there is something that they wish I had asked that I hadn't asked,

it's because there was something they really want to tell me about themselves

that they haven't had a chance to.

So it gives them a window to do that.

Do you get more personal and more professional stories from that?

It's fascinating, I get a mix of the two.

I would say it's weighted towards more professional, but

- actually, I wouldn't say that.

It might be weighted towards more personal.

Usually, people tell me something about themselves that they're really proud of.

So I think it's a mix of the two, but I just find it interesting

to see what people say.

It also helps me get better too, because I get great ideas for other

questions to ask when they tell me what I should have asked that I didn't.

Yeah, it's interesting 'cause I think so much of interviewing,

on both sides, is just getting comfortable with the other person.

And while there is a professional benefit to somebody who can admit that they

don't know it all or have some soft spots that they need to augment themselves

around, I think a big piece is it makes the interviewer feel more comfortable.

Oh, I'm actually getting at the real person here and it's not just

some polished interview thing.

Thank you so much for sharing Jay.

This has been great to chat with you and I appreciate all of your insights on scaling

and org design and hiring, and I really appreciate your insights for the show.

So thank you again.

Well, thank you, Erica.

It was really fun to be here.

That was Jay Gaines, who runs marketing for SaaS insuretech scaleup AgentSync, and

earlier was the CMO of SiriusDecisions, sharing some hard-won do's and don'ts on

scaling -- and focus -- for B2B SaaS CMOs.

Next time on The Get, we'll do a deep dive on budgeting for marketing during growth

with CMO scale-up queen Kristin Hambelton.

Don't miss it.

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.

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For other insights and recruiting great marketing leaders, what I

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