Growing SaaS start-ups

The Good Marketers

Leveling the playing field to assess start-up marketers relative to one another

August 8, 2024
2 min read

Last week this tweet from Andrea Bosoni caught my attention.

The tweet speaks to two common themes in the start-up world.

  • There’s a recurring sentiment that developer-founders with large audiences only launch successful products because of the size of their audience. Without the advantage of their audience, we might not think of them in the same way.
  • More generally, it’s difficult to assess how “good” any given marketer actually is relative to other marketers.

In this post I want to address the latter point, because my inbox is literally filled with founders and companies telling me that they are struggling to find good marketers. And it’s very apparent to me that hiring decisions are more often than not being made on the basis of false signals.

Let’s start with a bit of my own experience.

It’s more often the market than the marketer

I was very fortunate to start my career at Buildium, a company that was a smashing $580M success. I was the company’s first full-time marketing hire, and led the marketing team for 5 years.

There’s no other way to put it—on the back of that success, many of tech’s closed doors opened to me. I was offered big salaries and VP positions. One of Sequoia’s partners started emailing me job opportunities. A VC firm slid a piece of paper across a table at me, and told me to “tell them my number.”

Honestly, it all felt wonderful. But with another decade of experience under my belt now, I can also see the folly in it. 

Was I a young person that was something of a high potential hire? 

Sure. 

Was I worth it? 

Maybe?

But was I that good of a marketer that it warranted being offered these opportunities?

Unequivocally, no.

You see, Buildium had found product market fit in a hugely attractive market with very little competition.

Frankly, the company would have been successful whether I was leading marketing or not.

While I don’t want to totally discredit my contributions, that’s the truth. I did a good job, and I didn’t fuck things up. But with someone else at the helm, maybe that $580M acquisition is a $780M acquisition. Or a $380M acquisition. A level playing field would provide a much better measure of how good of a marketer someone is, wouldn’t it?

That’s the point Andrea is making.

But because of Buildium’s success I was suddenly something of a golden child… even though the market was much more responsible for our success than I was.

Lessons from turnarounds and competitive markets

In the years since Buildium, I’ve led marketing at four companies. Two I would classify as turnarounds—they were once high flying start-ups that eventually fell on hard times.

The other two I would classify as good companies that operated in really competitive markets. They had good teams, good products, and they grew—but neither was a rocketship.

The first lesson from these experiences was that turnarounds are hard. I was able to have a pretty significant impact on one of them, but neither “turnaround” was successful. Both companies eventually found soft landings, but were sold for a fraction of what their valuations had once been. Perhaps my biggest learning from these experiences was that a turnaround typically requires a lot more than a change in marketing strategy. There’s a fundamental flaw in some aspect of the business, and it’s a full company effort to redirect the ship. Frankly, neither of these experiences taught me too much about how good of a marketer I was.

The two “good” companies in competitive markets (one of which is Outseta) is where I truly learned something about my mettle and skill as a marketer. Having to create something from nothing and acquire customers for it is something that can’t be faked, but it’s not the only circumstance in which you really learn how good you are. 

Just the experience of marketing a product in a hyper-competitive market—or one where you’re the second or third best product offering—or one where a competitor has a really meaningful point of differentiation that you don’t have—is where the learning happens.

It’s easy to market, it’s easy to sell, and it’s easy enough to earn trust when there are few other alternatives or when your product offering is obviously the best. It’s when you’re not that you learn how good of a marketer you truly are, because you have to make something happen in the face of adversity in order to survive.

The “best” marketers are often untested

With my experience in the back of your mind, let’s now turn our attention to the very “best” marketers out there. The big names that you recognize on your social media feeds. The marketers that bounce from home run company to home run company. 

First of all, make no mistake about it many of these people are in fact great marketers. But I know for a fact that a lot of these people don’t really know how good they are or aren’t, because they haven’t been tested. They jump from rocketship opportunity to rocketship opportunity, based on an initial success and the strength of their network. And you can’t blame them for doing so—why wouldn’t they sign up for the great opportunities?

If you were them, you probably would too.

But when these people do change the trajectory of their careers for one reason or another, I see two common patterns:

  • They join a company that's not a rocketship, realize growth is much harder than they thought, and leave within a year (often with their confidence somewhat shaken).
  • They start their own company and quickly realize how hard bringing a new product to market actually is.
When you can’t hide behind a great market, or great agencies, or boatloads of venture capital—that’s when you learn how good of a marketer you actually are.

This is not a knock on marketers that have consistently put themselves in good positions—again, why wouldn’t you? But it is why marketers with 15 or 20 years of experience learn to recognize marketing talent quite differently from the rest of us. They’re able to look beyond the gloss and find the substance based on the diversity of their own experiences.

Many of the folks you consider to be the “best” marketers really aren’t that formidable when you strip away the advantages of great markets and endless resources—I know because that was me. My own abilities as a marketer were honed and improved significantly faster when I was operating in less than ideal circumstances. Challenges became a forcing function. With nowhere to hide my options were simple:

Grow or die.

Avoiding false signals when hiring marketers 

I can’t tell you how many start-ups I’ve met with where the technical founders say something to me like, “Yeah, it’s a super exciting time for us. We just hired a new Head of Growth from Hubspot.”

Fast forward a year, and it turns out Jonny from Hubspot can’t market his way out of a shoebox. 

What went wrong?

(Sidenote: I think highly of Hubspot—I’m just using them as an example because they are a household name and employ lots of good marketers.) 

Well, it turns out the company associated Hubspot’s success with Jonny. Maybe he even had a sizable social media audience. And maybe Jonny wasn’t just a cog in a wheel—maybe Jonny did contribute meaningfully to Hubspot’s growth! There’s no doubt about it—if you work at a company like Hubspot, you’ll pick up some good habits simply by being in that environment.

But just as people wrongfully assumed that I was some magical marketer when I left Buildium, the company was looking at false signals when they hired Jonny.  A great company hides a lot when it comes to hiring marketers.

I also want to be clear that you shouldn’t discount experiences at great companies—I am firmly of the belief that in most instances you learn more from your successes than your failures. I certainly learned more from my experience at Buildium than I did anywhere else, but what I learned is equally important to this discussion. 

Buildium gave me a PhD in how SaaS businesses operate, in hiring, in working with agencies, in motivating people and in managing a team. But frankly I didn’t need to sharpen my marketing skills all that much, because our product was already flying off the shelves. The skills that I did develop were very different from an individual’s ability to move the needle in terms of growth at your business.

What Andrea’s tweet is getting at is that if you strip away our pre-existing audiences and networks and market advantages, the story changes. Put everyone on a level playing field, and there is this notion of how effective you can be. How good of a marketer are you

And that’s often what early stage start-ups need to hire for. 

Positive signals in identifying overlooked marketing talent

If you’re a rocketship company that just raised your series A, you probably do want to hire that rocketship jumping marketer—because their experience in hiring and managing teams is actually what you need. In many instances, the VP of Marketing or CMO might not even need to be that skilled of a marketer themselves! I know that sounds crazy, but it’s no different than saying your CTO doesn’t need to be the best person at writing code on your team.

But if you need an individual who can influence the growth of your company—without a home-run market opportunity or every resource under the sun—then you’re looking for something very different.  

Big company names or the large social media followings aren’t necessarily it.

  • Ask marketers about their experience in competitive markets, and what they did to compete.
  • Look for evidence that they’ve built something from the ground up—anything from a start-up to a personal blog or YouTube channel.
  • Probe into the diversity of their experiences for evidence that they’ve delivered net-improvement in the different scenarios in which they’ve operated.
  • Assess the extent to which an individual has continued to invest in their own professional development.
  • Ask them directly what factors outside of their own skills impacted their successes!

Learning to identify these signals of grit, creativity, diversity of experience, and self awareness will go much further in helping you hire great marketers than anything else. It’s something that very few outside of experienced marketers themselves are good at.

Back to Andrea’s tweet—I think you would be quite surprised who would win the “Marketing Olympics.” The leaderboard would be filled with a lot of names that you don’t immediately recognize… and that’s a major opportunity for you.

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