Hiring a Kickass Head of Sales
For anyone actively running a VP Sales or CRO search, I’ve included a printable interview cheat sheet with my full framework. Download by clicking here.
Hiring a Kick-Ass Head of Sales
Hiring a sales leader is hard—and it’s not uncommon to get it wrong the first time. I’ve helped several of our portfolio companies with VP Sales and CRO searches, and I thought I would resurface some of what I look for in interviews. Sales leaders come in many flavors, and success in one context doesn’t guarantee success in another. You’ve got to dig deep to understand how their past experience lines up with your product, your team, and your next phase of growth.
While some fundamentals haven’t changed, AI and the modern tech stack are reshaping what great sales leadership looks like. Today’s sales leader needs to drive performance and navigate a buyer journey that’s more digital, more distributed, and increasingly shaped by automation and insights. So, beware the ‘been-there-done-that’ type that just wants one more lap around the track running the old playbook. Index high on leaders that demonstrate strong curiosity and are staying current on technology. Also beware of ‘over-titling’ this individual if it’s your first sales leader. If you are hiring someone to manage 2-10 sellers, this isn’t a CRO level position, and you shouldn’t hand out this title so early in your growth.
One quick caveat: this post is focused on sales-specific questions. Culture fit, values alignment, and leadership philosophy are also critical—but that’s a separate (and equally worthy) post.
When getting to know a candidate, I typically cover the following sales topics:
Tell me about the products you’ve sold in the past.
What was the price of these products?
Describe the typical buyer journey in purchasing your product(s).
Based on what you know about our product, how were your prior products similar or different in type/price/buyer journey?
Have you ever worked in our industry before?
Commentary – experience in your industry is a significant plus but a rock star manager is better than a B player from your industry who claims to have a rolodex. Even if the rolodex is real, it will run out and then you are left with a mediocre manager. That said, experience with similar product types/price points/buying experiences is important. If your product is a six to seven figure price point, complex enterprise sale with a 12 month sales cycle, then a manager who has worked only in low five figure, two call, 15 day sales cycles is not likely to bring the experience you need.
Tell me about the roles you have held in the past.
How big was the team?
Describe the organization and reporting structure – who did you report to and how many reported to you?
What were you personally accountable for in the marketing and sales process?
Commentary – job titles are often inflated in sales, so you need to really understand what the prior team structure was like and her role within it. Get past the ‘we’ answers and get to the ‘I’ answers – what did she specifically lead and manage and how does this compare to the role you would be hiring her for? The Big Co. manager that had several layers beneath her is often not be a good fit if you are hiring the first VP of Sales to manage a small team.
What were the company’s overall sales and marketing goals during your tenure at [prior company]?
What were your team’s specific goals/quotas during each year of your tenure?
How much of the goal was new logo vs. expansion with existing customers?
How did your team perform relative to these goals each year of your tenure?
How did this performance compare to other teams in the company (if you worked in a large organization)?
How did quota attainment breakout within your team - did you have a couple rock star sellers or were you able to scale the majority of your team?
Commentary – sales is probably the most quantifiable job to hire for. If his numbers were not great, pass and move on to other candidates. Make sure to drill down into each year of his tenure. Don’t stop at just team attainment. Drill down to individual seller attainment to see if he has a track record of hiring, on-boarding, and fully scaling individual sellers. If he didn’t scale a majority of his team to at least budget attainment (if not quota attainment), pass and move on.
How much of your team was recruited by you?
How did you manage this team to the desired outcome?
Describe your approach to coaching and developing sellers and sales operations.
Would any of your past team be likely to follow you and join our company? If so, how many and how quickly would you be able to hire them?
How would you identify and evaluate candidates you don’t already know?
Commentary – There is a lot to unpack in these questions. To better understand the candidate’s track record, it’s important to know how successful he has been in hiring talent in the past and also to dig into how he coached his team. Assess whether he is just a ‘co-seller’ who jumps into his AEs deals to try to save them or whether he knows how to analyze the full sales cycle performance of multiple individuals and use analytics to uncover individual weaknesses and implement coaching plans to improve on them. Also, great leaders typically have strong performers who will follow them to their next job. If the candidate can’t name people that would join him, that can be a red flag.
How was your prior team(s) compensated?
What worked well with this approach and what didn’t?
What compensation structure would you advocate in the future?
Commentary – I try to use every interview as an opportunity to learn about successful approaches to sales process and sales compensation. If the candidate has experienced prior success, dive into the details and seek to understand how compensation was aligned to motivate the team. Would these structure(s) work at our company – why or why not?
Describe your prior sales processes.
What were the stages involved and how did these evolve over time?
What AI or automation tools were in place—e.g. lead scoring, pipeline forecasting, SDR automation, conversational intelligence, intent data?.
What KPIs were tracked and how did you generate insights on the process?
Give examples of how these tools and KPIs led to insights and how you applied changes as a result.
Commentary – Influencing people can be an art, but sales process is very much a science. Weak candidates will answer these questions at a high level and will likely just quote their favorite sales methodology framework (Challenger Selling, Spin Selling, Sandler, Target Account Selling, etc). Stronger candidates will be able to share their metrics in detail, discuss the pros/cons of tools they used, how they analyzed results, and be able to give specific examples of where their team’s analysis led to actionable insights. Beyond evaluating the candidate, this can also be an opportunity to collect relevant best practices. Look for candidates that had a strong handle on conversion rates and the velocity within their funnel – the ability to move deals forward and close is what’s key.
What was your target market?
How and why was this selected as the focus?
How did it evolve over time and why?
Was this focus already defined when you stepped in or did you help to define it?
If you played a role, how and why did you select this target? What analysis was done to justify going this direction?
Commentary – Focus is key in the early stages of a company. The first VP Sales you hire will likely have a significant role in determining where you concentrate your time and resources. This is a good opportunity to learn more about her ability to be analytical, see the bigger picture of the go-to-market strategy, and to contribute to your marketing and sales strategy.
How did your prior company build the top of funnel?
How did you build/acquire/maintain prospect data?
Were leads generated by marketing, partnerships, or self-generated by the sellers?
If you had sales partners, who put those deals together and how were they structured?
What worked well with partners and what didn’t?
Commentary – Sales leaders in later stage companies may not have had much involvement with data acquisition and the very top of the funnel. If you are just evolving out of founder-led sales and your marketing team is junior or non-existent, it can be critical for your sales leader to have experience in this area. Many sales leaders covet owning both sales and marketing, but lack the knowledge to be effective. Unfortunately, I’ve seen too many sales leaders with little understanding of the top of funnel stumble around in the dark or outsource to agencies and waste a ton of money.
What will you need to be successful at my company?
How many people should we hire now?
How will you spend your first 90 days?
What type of impact can you make on our sales in the first 180 days?
Commentary – you need to make sure your expectations and available budget align with the candidates expectations, and make sure she can make a logical, cohesive argument for the team and resources needed and near term outcomes that can be achieved.
Hiring a head of sales is one of the most important decisions an early-stage company will make. The right hire can accelerate growth, clarify your go-to-market strategy, and scale repeatable revenue. The wrong one can set you back a year or more.
Ask the hard questions. Look for depth over polish. And don’t overlook how today’s best sales leaders are blending timeless fundamentals with modern, AI-augmented execution. AI won't replace great sellers, but it will amplify the ones who know how to use it.
If you like some additional reading on the VP Sales topic, Jason Lemkin from SaaStr has also done some great posts over the years, including his favorite questions to ask, types of sales leaders, what a great VP Sales does and when to hire. For a more SaaS-specific perspective, this piece from Mainsail Partners is also excellent