How to Hire a Head of Sales - Mainsail Partners

How to Hire a Head of Sales

This is Part 1 of Mainsail’s How-to-Hire Series: A SaaS Founder’s Guide to Building Out Your Leadership Team. Read why we put together this resource for growing SaaS business and how to navigate it here.

As you scale, it becomes increasingly difficult for a founder or CEO to cover all the aspects of the business that you could wrap your arms around when you were small. At the same time, the early-stage tactics you used for finding and winning new customers now need to be supplemented with larger-scale go-to-market strategies and channels.

In other words, you need to make the transition from founder-led sales to professional B2B software sales.

This is a key moment for your business, and we believe bringing on the right Head of Sales, with the right skillset, at the right time, can increase your likelihood of successfully achieving your next revenue growth milestone. Whoever you hire should have a well-rounded set of experiences, including expertise in go-to-market strategy, people and team development, process excellence, and data and systems thinking.

Having seen this transition play out many times, here are our suggestions for how CEOs can effectively hire their first Head of Sales as their business continues to scale.

Define the leadership profile that will best fit this role

Are you looking for someone to come in, take the reins and completely run your sales team with little to no oversight? If so, you’ll want to hire an experienced leader as a Vice President of Sales.

Are you looking for someone to come in with most of the raw ingredients to lead your sales team but also knowing they will need to develop a few key skills with your help over time? If so, you might want to look for more of an up-and-comer – likely a Director of Sales or a first-time VP.

There are benefits and watch-outs to both leadership profiles.

Experienced sales leaders have likely made many of the mistakes – and learned many of the lessons — executives make when scaling teams. They’ve most likely been the senior-most leader in a business like yours before. They know how to be a part of an executive team, how to present to the board, how to hire and when to fire. They probably have playbooks they can bring to the table that will help launch new functions within your GTM org.

And — they can come with baggage. In some cases, experienced sales leaders may not be as willing to jump back into the action, especially if it means wearing numerous hats. Or, they may not be as open to feedback, coaching or adjusting their strategy/direction. They may also command higher salaries and more equity.

Up-and-coming sales leaders might view joining your team as the biggest opportunity of their career: a chance to prove themselves and succeed at the next level. This can mean they come with extra energy and additional fire to succeed. Their lack of prior experience as the senior-most leader can also mean they come with fresh perspective, new ideas and a willingness to test and learn.

Likely, they will also require more coaching and mentorship. They may not have presented to a board or worked with investors before. They may not have had to complete an annual budget for their department in the past. They may not have been a part of an executive team and will need help adjusting to their new role.

The key here is to be honest with yourself regarding what you’re looking for and what your business needs. Once you identify the sales leadership profile that is most likely to make your business and team successful, and once you’re clear on how much time and energy you have to onboard, coach and mentor your new Head of Sales, the best-fit candidates will become clear.

Characteristics to look for in this role and how to evaluate them

In his book, The Ideal Team Player, Patrick Lencioni describes ideal team members as being humble, hungry and smart. Our experience at Mainsail leads us to agree that these three characteristics should be top of mind when evaluating any candidates to lead your sales organization.

Humble means they will listen and collaborate, be coachable, be great partners to their peers, and seek to give credit to their team. You can test for this characteristic in your interview by asking questions about mistakes they’ve made, times they’ve missed deadlines, deals they’ve lost, or personnel decisions that didn’t go well. Leaders who openly share these stories, take ownership of their mistakes, and identify what they learned from these experiences, are most likely humble.

Hungry means they will proactively seek to exceed targets every month, quarter, and year. You will never need to worry about their drive, their accountability or their creativity. If they don’t have enough pipeline coming in from Marketing, you won’t hear excuses — they will just go out and work with their team to create their own pipeline. If Product is delayed on a release that is reducing the team’s ability to win competitive deals, you won’t hear them complain about it. They will simply train their teams to overcome product-related objections. Test for this in the interview by asking them to share stories from prior experiences. If you hear excuses, you may be hearing a lack of hunger.

Smart means they have a high EQ and can think critically and analytically about your business. They are curious, ask great questions, want to know about the product and the industry, and want to know what makes others on your team tick. Much of this will become clear organically as you spend time with the candidate. In addition, have cross-functional team members interview each person to compare notes on this perceived trait.

Clarify the expectations of the role

Early-stage sales leaders are responsible for a lot. In many businesses below $10M of ARR, this means they can be serving up to five different roles each day:

Selling your product
Directly managing the sellers on your team
Leading sales or revenue operations
Leading sales enablement
Serving as your strategic Head of Sales

Each of these roles is critical as you scale from early stage to a mature business, and not every candidate will be able to perform all five roles. Our suggestion is that you clearly outline each of these for the candidates and describe how much of each role they will be expected to fulfill. The candidate should not only show excitement but should also be able to share stories from previous roles where this was part of their responsibilities.

In addition, let them know your expectations for what you what them to achieve in the first 12-18 months. For example:

Within the first 12-18 months, your Head of Sales should:

Build and integrate into the team. Up-level existing talent, bring on strong new sellers and launch a new function within sales, such as a BDR team, while also fully integrating into the executive team.
Exceed bookings targets across new and expansion sales.
Become an expert in the product and industry of your business

At the same time, we caution CEOs against overloading expectations in this hire. We have seen several CEOs look to hire a Head of Sales and Marketing, or pile on additional functions to fall under the sales umbrella. For an efficient hire and effective org chart, we recommend preserving sales as a unique function.

Making your selection

Creating a successful team starts from the top, which is why hiring the right Head of Sales is critical to the future success of your company. Above all, this hire needs to come with a track record of success, meaning they have exceeded targets as an individual contributor, they have led successful teams as a Manager and Director, and ideally, they have helped a company of a similar stage achieve targets on the way to a successful exit.

Finally, take your time on this search. The goal is to hire an executive leader who will stay with you for the long-term, add to your company culture and help you achieve big things. No need to rush the search process when those are your ultimate goals.

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