Hiring Your B2B Startup's First Marketer

Kind of like hiring an NFL head coach. But not really.

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This week’s episode of Lenny’s Podcast featured Jason Lemkin of SaaStr.¹ They spent a long time digging into the do’s and don’ts of hiring your first Sales roles and first Sales leader. And their chat got me thinking, “What advice would I give to founders for their first Marketing hire?” 

Listed below are factors I would consider in a probabilistic analysis. None are requirements, as may be obvious. There are lots of exceptions to every rule. If someone checks every box but one, hire that person. If they only check one, I probably wouldn’t.

Career phase

In the podcast, Jason’s advice is to make your first Sales hires a couple of AEs rather than a VP of Sales. His rationale is solid. Your first hire needs to focus on selling. Sales executives and even sales managers are often no longer carrying quotas or even interested in selling. I don’t think the same logic applies in Marketing.

Most Sales orgs have three functions - pipeline sourcing (SDRs), deal closing (AEs), and operations. Within their first handful of hires, a Sales leader can have all functions covered by an IC. It may have been a decade since they opened a demo with a prospect. Marketing has 3-4X as many speciality functions as Sales. At a startup, even Directors almost have to be player coaches for everything to get done. . 

First, if you can find someone who was recently successful as marketing hire #1, hire them. You probably won’t be so lucky. Hiring a first timer, I would give bonus points to Directors over VPs because they have the ability and willingness to do the work themselves. Ideally, you’d find a Director with a team of five or so people. Directors overseeing a 15-person org may have less dirt under their fingernails than early-stage startup VPs.

I prefer hiring a Director to start the department to someone lower on the org chart. The Director will give you:

• more experience in more marketing functions (more on that later),

• more experience with higher level thinking/decision making,

• more experience building teams,

• the ability for your presumptive marketing exec to hire all of their own people.

Employer Size

Back to my point about the size of the Director’s team. Smaller employers are better. Larger and more mature orgs have lots of resources to hire headcount or outsource less glamorous work to agencies. They have fleshed out roles and responsibilities. They have standardized processes and well organized knowledge bases with all the answers.

Most early stage companies have none of that. Maybe there’s value in hiring someone with experience in an org where those things were done well. But there’s a risk they’ve forgotten how to create everything from scratch using only their time and curiosity. Or that they never learned how to in the first place.

Marketing Function

Earlier in my career an advisor told me that if I wanted to eventually become a CEO, I should get experience in another discipline (Finance, Operations, etc..). He knew I was a football fan, and pointed out that an unusual percentage of NFL head coaches get the job because they have experience in at least two of the three phases of the game.²

The same logic applies to your first marketing hire. The right person will be intellectually curious and pick up new skills quickly. But, there’s a big advantage to starting day one with experience in product marketing and demand generation. Or in demand gen and marketing ops. Or in product marketing and marketing communications, and so on. Of these, the gold standard combo would be product marketing and demand generation. In almost every startup, the most critical jobs for the first marketer are to (a) define how they talk about the product and (b) test different ways of taking that message to market with the ultimate goal of handing higher intent leads to Sales.

Customer Size and Vertical 

Maybe you can find a unicorn who has marketed a product in your vertical to customers who are the same size as yours. But if forced to pick one, I would favor customer size over product vertical. In many ways, marketing an SMB accounting product has more in common with marketing an SMB email marketing tool than with marketing an enterprise accounting system. 

An enterprise marketer has spent their career producing white papers, events, and handwritten direct mail pieces to persuade a short list of accounts to sign six- or seven-figure deals. It’s difficult for them to flip the switch to running million dollar direct response ad budgets, high velocity A/B testing programs, and airtight ops machines delivering thousands of MQLs per month to the right person at the right time. And visa versa. More difficult, I think, than learning a new industry and where your new company’s product fits in it. Which is a good segue to…

Filtering Questions

One of my favorite bits of Lenny’s interview with Jason is Jason’s biggest filtering question for Heads of Product and Sales roles - what do they plan to do in their first two weeks? “And if I don’t hear…that I’m going to meet customers,” he says, “I’m out.”

For Marketing, the same applies. Though I might be OK with focusing on listening to lots of sales calls and interviewing AEs. If they want to spend their first two weeks setting up/tweaking ad accounts? Run. Getting the tech stack right? Run. A/B testing emails or landing pages? Run. Pretty much anything that's not learning what problems your product solves, who it solves them for, and the language that helps customers understand your value? Run. Effective messaging is a prerequisite for effective marketing.

Another great question which I’ve been asked for first marketer roles is, “Here are the company’s

• Revenue goal, customer goal, whatever, for the coming year

• Where we’re at right now for that metric, and

• This year’s marketing budget

What’s the best plan to hit our number?”

That kind of question will help you understand a few key things pretty quickly

• How does the candidate handle ambiguity? There’s tons of it when you’re building marketing from scratch.

• Are they able to reverse engineer goals into logical steps to reach them? This applies not only to budgets and KPIs but to everyday tactical problem solving. For example, "Why are MQLs down this week? Why did ROAS spike last month?"

• How curious are they? Do they ask lots of good questions before they form answers?

• How fast do they learn? Do they “get” your space/customers/product as well as they should given the phase of the process?

That’s a wrap for this week. But if any of you making early marketing hires want to chat through your questions, just reach out directly for a chat. I’m here for it.

Until next time,

TB

1. On the off chance you aren’t already listening to Lenny’s Podcast, start now. The quality of hosting, guests, and production are the best I’ve encountered in the business podcast field. This is not a podcast of blowhards who like to hear themselves argue. The amount of practical takeaways for operators in the tech space and business more broadly is unmatched. The vibe and pacing are great. There’s very little wasted time.

2. Understanding the predictive value of NFL coaches having experience in multiple phases on their chances to become head coaches is an analysis I am not up for. We’d need to understand what % of NFL coaches who have not become head coaches have such experience. But just looking at the current 32 NFL head coaches, the case doesn’t appear strong. At most, I count 8 who can make the claim to focusing on 2 phases before their first NFL HC job (Raheem Morris’s stint as a WR Coach for the Falcons in 2016-18 comes after being Tampa Bay’s HC in 2009-2011). But 5 of those hang their claims on brief spells coaching college teams outside their normal phase (Dave Canales, Shane Steichen, Robert Sales, Nick Sirianni, and Mike Tomlin) or even high school teams (Mike Macdonald). Only John Harbaugh and Brian Daboll have airtight claims to having coached multiple phases in the NFL prior to becoming HCs. Famously, so did Bill Belicheck, and I imagine it’s the perennial success of Belicheck’s Patriots and Harbaugh’s Ravens around the time of my advisor’s comment that colored his view of the situation.