Your First Go-to-Market Recruiting: Who to choose and what to look out for

Tiho Bajić

At some point in your startup journey, you’re going to need to hire your first go-to-market (or commercial) leader. This individual will be responsible for generating customer revenue. 

The first go-to-market hire is not necessarily a marketer, as sometimes the first marketer may be more invested in generating brand awareness and overall reach than growing revenue. They may be a marketer, sales leader, or product-led growth expert. No matter who they are, generating revenue and scaling growth is the top priority.

A lot of founders look for a hire that can own global expansion or the launch of a new product. But this is not the right approach. In order for a go-to-market hire to be successful, you need to have generated proof of concept. Basically, the first commercial leader is tasked with scaling your existing success.

I hired the first GTM hires at three different startups I ran and served on the interview committee in over a dozen startups that successfully hired these roles. Over the years, I’ve seen startup founders make powerful choices on their first commercial hires. Today, I’m sharing who to choose and what to consider as you make this move for your company.

Get proof before the person

I see many startups looking to make a commercial hire with the idea that the individual will lead and own an expansion into another market or start making sales. But if you're an early stage startup and you're asking for a person to sign on to grow a product that is relatively unproven and unknown, you’re throwing them into a situation that is very uncertain.

Hiring for this reason doesn’t attract the right individuals, either. You're likely to get people who are okay with a large amount of risk and executional choppiness– which may or may not be what you’re looking for– or people who don’t have the experience and don’t realize how hard it is. You’ll also have a hard time closing top candidates and onboarding them as you won’t be able to clearly point to what it takes to be successful.

Hiring is much better timed when you’ve already had some level of commercial success. For example, if you’ve had proven success in a particular market, then want to grow into an adjacent market, the go-to-market hire will have a playbook to go by. They’ll have enough ingredients to execute, believe your ask is do-able, and ultimately be much better positioned for success.

If you’re curious what this looks like in practice, I’ll share how this usually plays out for startups selling enterprise software. Usually, the founder will sell the first five or so deals and will prove that economics are attractive to a seasoned sales leader, then bring in an executive or enterprise expert who will be tasked with selling the next 50 deals. By selling those five deals before making the key hire, the founder has not only gained proof that the product is salable - and so everyone on the team and on the investor distro list can breathe a sigh of relief - but understands the key aspects of the sales process that help model the opportunity and the appropriate compensation structure to attract the right person.

Align compensation with success

When making a new hire, it’s important to align compensation with success. This goes for every hire, but especially for the first GTM hire it’s prudent to pay close attention. 

This is especially true early in your journey because you won’t have a lot of cash, meaning you should pay more in equity. You don’t want to make a key hire who demands cash that you’re not generating.

But when you do begin generating cash, you need to align compensation with that success. If your go-to-market hire is responsible for generating cash and rises to the challenge, then they should be rewarded. Of course, they should retain equity, but once you begin generating substantial revenue, it’s time to look at the comp plan again and reassess. While it’s sometimes hard to compare equity in one company to another, cash OTE (on-target earnings) are easily comparable and this is where you should look to benchmark against the market. 

Choose those who are already converts

The best go-to-market commercial hires are already converts. They know the product, understand its value, and are ready to go to bat to make it a success. They see the opportunity and are ready to help make it a reality. 

When you start thinking about hiring for this role, start scanning for these converts. Usually, they’ll have some amount of experience with you or your customers already. They might be an early customer, a community leader, or another stakeholder heavily invested in the mission.

The ideal hire is someone who is willing to be a missionary, but is also highly motivated by up-leveling their comp based on performance.

Hire for the role you need and start planning

No business is the same. One startup might be ready to hire a head of sales, while another will be better suited by a performance marketer. 

What's really important is going to market and benchmarking your particular hire’s compensation, as well as what responsibilities they should be expected to have. This is essential because it allows you to plan. If your hire is successful, they’re going to need to grow their team.

You must ask yourself what these growth plans are going to cost in terms of equity and salary vs. what the hire will contribute. When founders do this for the first time, they risk not planning with rigor and not building checkpoints in their plan to re-adjust based on evidence. Many wind up having unrealistic plans or those that haven’t been carefully thought through. The right GTM hire will help you with this planning process and they will grow into owning it over time. 

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