TL;DR - Your first marketing hire should probably be a director-level person who can be made accountable for generating a sales pipelines, with experience at a company 2-5x your size.


In this article you’ll learn to hire a great first marketer for your startup. It’s based on all the good and bad first marketing hires I’ve witnessed at over a dozen enterprise software startups. (Surrounded by some of my cartoons, for added flavor.)

Cartoon about a high-energy employee

I wrote this guide because I often get asked by founders of B2B software startups for advice on hiring their first marketer. It’s not an easy task, because all marketers look the same to a technical founder, and the stakes are high, with pressure to get customers, increase revenue, and demonstrate an ability to grow both of those at a predictable and nonlinear rate.

What’s covered:

  1. Goals
  2. Key Criteria
  3. Seniority and the Strategy-Tactics Spectrum
  4. De-risking

Goals

Let’s start with the goals of a first marketing hire:

  • Pipeline - Assuming you’re past product-market-fit by the time you set out to hire your first marketer (recommended), the next most important thing becomes acquiring customers and gaining a foothold in the market.
  • Explore - Learn what strategies and tactics are effective for acquiring customers, and which ones aren’t. This will help allocate future resources with greater confidence and higher return, and is the first step to building a scalable process (flywheel).
  • Lay the foundation - Ensure the basics are in place: Messaging, a website that attracts and converts visitors into sales leads, basic funnel and attribution analytics, building a contact list, and so on. This will accelerate ramp-up and multiply the effect of future marketing projects and hires.
  • Free your time - Marketing is just another thing that takes up time you’d rather spend on the product, closing deals, supporting customers, and growing the company. A successful first marketing hire would free you to focus on those things.

Those goals help shape the criteria and seniority of your ideal first marketing hire.

Key Criteria

Unless you have another reason to believe the person will be successful in their role—such as a trusted recommendation, or you know the person well—then your first marketing hire must meet the following three criteria:

1. Growth Ownership

The person must be capable and willing to be held accountable for growth of the company, as measured by concrete metrics such as growth rate and revenue (CMO/VP), or sales pipeline quality and volume (manager/director).

I’m not suggesting you tie compensation to these metrics; only that you make them a key responsibility and screening criteria for the role.

Cartoon about talent

Reporting on these metrics is not the same as affecting them. Anyone can plug in Google Analytics or generate a Salesforce report to see lead quantities and ARR, but not everyone is capable of doubling those metrics or willing to be held accountable for it. Here’s why:

Marketers from large companies are insulated from growth metrics by the management layers above them. Their performance was measured by the amount of work completed, by their department’s performance, by distant downstream metrics (such as site traffic, blog readership, or search keyword rankings), or even by how their boss thinks they’re doing. To early stage startups these are vanity metrics; they look great but don’t make a meaningful difference.

Marketers from sales-centric companies might see their primary role as supporting the sales team and accelerating the sales cycle. They measure their performance by metrics such as the number of collateral materials they produce (eg, whitepapers, case studies) and consider it the sales department’s responsibility to close deals and grow revenue. This won’t fly at a startup where the length of sales cycles is a second-order concern.

Cartoon about social media marketing

Marketers with a more traditional background view their mission as increasing awareness in the market and conveying the “right” message. They prioritize activities such as branding, communication, tradeshows, website designs, and social media. The value traditional marketers can add to an early stage software startup as a first hire is close to zero, regardless of their seniority. Communications and branding will help scale reach, but only after you have a decent customer base.


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Lastly, some marketers want to join a startup for reasons other than taking on growth responsibility. For example, they might just want to get in on the ground floor, to experience the startup life, to have more freedom, or to work on a greater variety of projects. These people are neither prepared not expecting to take accountability for growth of the company.

Marketers with demand-generation experience (ie, demand-gen marketers) are good candidates because they’re used to having responsibility for pipeline metrics and they know some strategies and tactics to try.

Qualifications

  • Ability to tie marketing projects to business objectives.
  • Ownership of growth-related metrics.

Interview Questions

  • What metrics are you responsible for at your current position?
  • Tell me about one of your projects that made a big impact on growth?

2. Ability to Execute

At this stage of the startup there isn’t much value in making long-term marketing plans, nor is there enough data to make good plans. Therefore, the first marketing hire must be able to create rough plans, execute them, and then iterate. That requires:

  • Bias for action over meticulous planning.
  • Skills (or interest in learning) to run many different types of marketing campaigns.
  • Experimental and analytical approach to marketing campaigns.

One of my clients hired a head of marketing who spent their first three months crafting a 12-month marketing plan instead of actually doing anything. That’s three months of missed experiments, learning, and iterating. It also suggests they didn’t plan on learning anything then or in the next year that might alter the course. Months later the CEO saw behind the smokescreen, but it was a costly mistake that could have been avoided if the candidate was screened for ability to execute.

Cartoon about poor performance

One indicator that a person can execute is if their current/previous company is 2-5x the size of yours, either in headcount or revenue. You want somebody who’s been where you’re headed. They remember what the journey looks like and have an idea of how to repeat it, they’re accustomed to wearing multiple hats, and they can make do with slightly smaller budgets. If the gap is any larger than that—for example, if you’re considering a marketer from a post-IPO company for your $2m ARR startup—then they might turn out powerless without the resources and management structures they’re used to.

Some marketers, unfortunately, tout their experience running different campaigns when they really mean they have experience being an intermediary between their company and a marketing agency that ran those campaigns. You don’t want to realize too late that the marketing hire thought they’d have help from an agency when you didn’t plan or budget for that.

If you’re looking to hire a CMO or VP (more on that below) for their vision and direction and not for their hands-on abilities, they must still be able to execute in terms of building out an exceptional marketing team with the resources and runway available.

Qualifications

  • Experience executing marketing campaigns at a company with X-Y employees/revenue.
  • Ability to plan, execute, and iterate marketing campaigns at a rapid pace.
  • Experimental and analytical approach to marketing campaigns.

Interview Questions

  • What would you want to accomplish in the first 90 days, and how?
  • Tell me about a campaign you took from idea to completion?
  • Tell me about a campaign that failed, and what did you do?
  • What resources would you need to be successful?

3. Domain Knowledge

It’s important to have a marketer experienced with the domain you’re in, such as B2B, B2C, enterprise software, SaaS for SMB, consumer app, online media, etc. Enterprise buyers, mid-size companies, startups, SMBs, professionals, and consumers all make purchase decisions in different ways, so marketing tactics and strategies don’t always translate well between these markets. What works for a consumer-app startup might not work for an enterprise-software startup that has six-month sales cycles; what works for that enterprise software startup won’t work for an SMB SaaS that has lower customer lifetime values and therefore can’t survive with high acquisition costs.

You should also choose a marketer who can grok or demonstrates the ability to grok your product and target audience. They don’t need to know the product and audience inside-out on day one, but they should have a basic understanding right away and be able to gain a deep understanding within three months. Finding such a person is tough if your product is complex (eg, enterprise software) and your audience is marketing-averse (eg, engineers), but it’s critical if you want (and you do) to choose a first marketer who adds value instead of just being a coordinator or a people-person.

First marketing hire shouldn't just be a people-person.

Qualifications

  • Experience driving growth in [B2B/B2C/SMB/…] markets.
  • Domain knowledge of [industry/product/audience] space.

Interview Questions

  • What’s your interest in the [industry] space?
  • What company in the [industry] space do you think is doing marketing well, and why?

Seniority and the Strategy-Tactics Spectrum

Everyone says they can roll up their sleeves and do work. Not everyone can figure out the right work to do.

How do you ensure your first marketing hire does the right work to maximize growth? Do you start with a CMO, VP, director, manager, or specialist? The answer to both is finding someone balanced in strategic and tactical thinking.

Tactics are short-term plans and their execution, such as answering Quora questions to attract people to the site. Strategies are long-term plans and their execution, such as finding ways to partner with friendly companies to leverage their larger audiences. The difference between the two is in magnitude and timescale, not in how much gets done.

Cartoon about a temporary employee

The more senior the marketer the more they’re able to think strategically but may have trouble figuring out the right way to act on it. Inversely, junior marketers might be more able to think of work to do but have trouble converting it into long-term growth.

As the marketing team grows it becomes more balanced, but there is nobody to balance out the first hire. The first hire must be able to think both strategically (long-term) and tactically (short-term).

Without balance there is no growth: Too many tactics without strategy results in growth stagnation after the obvious and known tactics are exhausted. Too much strategy without tactics results in slow growth as ideas don’t get executed well or fast enough.

Typically, marketers become more strategic as they gain experience and become better at seeing the big picture, so if we graph strategy-tactics and experience, the target first marketing hire should be somewhere in the middle.

Graph of the strategy-tactics spectrum and experience.

A person from the middle of the chart would have the right balance of strategy and tactics to make near-term plans and execute them well enough. They would also have enough experience to work autonomously and get things done.

Since experience also correlates with seniority, we can plot seniority levels on the same chart:

Graph of the strategy-tactics spectrum and experience, and seniority.

This is highly simplified but it’s directionally correct: Executive-level marketers (CMOs and VPs) are likely to be strong strategists, and those with less experience (specialists and managers) tend to be more tactical.

The ideal first marketing hire for startups is therefore a director-level position, though it could also be a veteran manager or rising VP.

Hiring “from the center” also lowers risk as you grow the team: You’ll learn what tactics are worthwhile and will become better informed to hire the right managers and specialists. You’ll also get a better understanding of which strategies show the most promise and therefore what kind of marketing leader(s) you need. It’s likely to take less time to find a marketing director (1-3 months) than a VP (3-6 months) or CMO (6+ months), with less overhead commitment.

Don’t fall into the trap of hiring the most senior person you can (VP or CMO) as your first marketing hire. Even if they have the right vision, they might struggle to convert it into the right actions to make progress.

Recently I interviewed a VP candidate for one of my clients. The person showed fluency in VP-speak (“connect with buyers,” “value proposition,” …) and also boasted of their ability to get things done. Some questions later I learned “things” meant writing lots of short, non-technical blog posts. Sensible strategy, ineffective tactics.

I’ve had many founders come to me for help because they learned too late that first-hire CMOs and VPs are not effective, and now they need to make up for the bad executive hire. This is true even (or especially) for marketing executives who come from very large companies.

Cartoon about firing an emloyee

The other version of this error is starting with an individual contributor or rising manager. They will get various things done but might struggle to ensure or demonstrate that their work results in meaningful outcomes (qualified leads and revenue). Once their tactics dry up (or fail to show results) they struggle to think of a way forward.

I once took a meeting with the CEO of a startup about a large project to help them accelerate revenue growth. They had over $100 million in funding, a CMO, and a marketing team. “Then why do you need me,” I asked him. It turned out their marketing team was made up of specialists and managers—demand gen, operations, events, etc—with nobody between them and the CMO. The team exhausted their tactics and didn’t know what to try next, and the CMO couldn’t translate the strategy into tactics the team could act on. Even with a world-class CMO and all the money in the world the marketing team was completely stuck because it was lopsidedly tactical.

I’ll write about building the perfect marketing team later, but for now that story should illustrate the importance of thinking about the strategy-tactics balance early, starting with the first marketing hire. You’re most likely to find this balance with a director-level individual.

De-risking

Cartoon about hourly contractors

One way to lower the risks associated with choosing the first marketing hire is to work with a consultant. You can achieve the same goals—generate pipeline, explore strategies and tactics, lay the marketing foundation, and free your time—without long search periods, overhead costs, ramp-up times, and long-term commitments. When the time is right to bring the experience in-house, a great consultant can also help you choose and onboard the perfect first marketing hire.

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