7 Mistakes to Avoid When Hiring a Sales Leader for Your Start-up

Welcome to Dear Artemis: Where you ask us tough questions and we use our collective 45+ years of knowledge in the recruiting space to answer them. We normally post this our on website but we've been getting this particular question a lot in recent months... so we thought we'd share it on LinkedIn, as well.

Dear Artemis,

I’m the founder of an early-stage startup and am ready to hire for my VP of Sales. What are some mistakes you’ve seen other founders make when hiring for their sales leader, and what can I do during the interview process to avoid that?

CEO and Co-Founder, Series A startup

Amazing question. Your VP Sales is an uber-critical hire for growth, future funding rounds, and sales culture moving forward. Here are our top 7 Mistakes to Avoid When Hiring a Sales Leader for Your Start-up.

Mistake #1 - Not placing enough importance on the operational/systems side of this role.

There is no universally correct go-to-market playbook that this sales leader will bring in. However, look for a sales leader who has very strong GTM foundations and can adjust/adapt what has worked for them in the past to optimize for your specific revenue model. A recent sales leader we placed quoted Deming’s rule (85% of an employee’s effectiveness is determined by the system they work within and 15% by their own skill).

How to address this in the interview process:

• Have they successfully built out a predictable revenue system? Do they light up when they talk about the processes they put into place?
• Can they share examples of what they’ve tried that hasn’t worked, and how they’ve made improvements along the way?
• What tools are they currently using?
• What questions do they ask us that indicate they have this mindset?

Mistake #2 - Not putting enough weight on a sales leader who values marketing.

The relationship between sales and marketing can have friction, especially when one leader doesn’t understand the value of the other. Having a sales leader who values & respects the marketing leader and team will have a tremendous impact on your GTM-culture and teams moving forward.

How to address this in the interview process:

• Ask pointed questions about how they have worked with marketing in the past - how is their current team working with marketing? What kind of marketing leader have they found best compliments their methodology?

Mistake #3 - Focusing too much on a great salesperson and not a great sales leader.

Good leadership is important all the time, but especially in sales organizations. Typical sales organizations have 1) Very entry-level talent for SDRs/BDRs who would benefit from strong leadership, career development planning and structure and 2) Senior AEs who are used to managing their own “line” of business and prefer hands-off but supportive-when-needed leaders. Not to mention, sales is a rollercoaster experience so having a leader who can guide the team through the highs and lows of sales will reduce turnover. You need a strong focus on people & process leadership, not just “can you personally jump in and close the deal?”

How to address this in the interview process:

• Ask how they have coached underperforming sales reps.

Note: what we look for here is whether they were able to get to the root of the issue where someone might need additional support/coaching.

• Who was their best hire? Who was their biggest mis-hire?
• Ask about the retention rate of teams they’ve led.
• Listen for examples of their teams following them - one of the best leadership indicators.
• Ask about how well the sales team collaborates with other teams like product, marketing, customer success, etc.

Mistake # 4 - Focusing solely on finding a sales leader who has seen your specific stage of growth (ie. seed to Series A, Series A to Series C, etc)

While experience leading through the range of growth you’re expecting is important, it is most important that they’ve seen where you’re heading next and know how to build to get you there. While some leaders whose only experience is in businesses that have evolved beyond your current stage may struggle in a more operational role, it is worth exploring this as a potential fit.

How to address this in the interview process:

• Ideally, they’ve seen your next stage of growth, but they might not have seen where you will be in the next 2-3 years, and this will be compelling to them.
• In many cases, we actually see that a more important success metric is that they’ve had experience selling at your average ACV. Have they also sold in your specific industry? That would be an added bonus as well.

Mistake # 5 - Being wowed by a leader who has great pedigree or experience in your domain.

It can be really tempting to imagine the press release and the impressed looks on the faces of your board members when you announce you’ve landed a sales exec from a hugely successful big tech company, or your big competitor. But we’ve seen it play out time and again, where these leaders land and then fail, as they don’t have any experience building without a big support team, or enabling the sale of a product that doesn’t have a big brand behind it. The customers who buy from Microsoft and Salesforce, may not be the ideal targets for your young company, and the process you need in place to win these deals will be very different. Look for leaders who have scaled a business from obscurity to success, or if considering someone from big tech be sure to test that they can thrive without the big brand and budget.

How to address this in the interview process:

• Dig into the specifics of how deals were brought through the funnel to close, and ensure that your candidate understands where things will be different in your reality. Provide a realistic preview of what they will and will not have as support. If they are scared off by how hands-on they need to be, better do that before they start!
• If they come with a big network, what will they do to grow that? Can they shift and build a new network as your business evolves?

Mistake #6 - Too many decision-makers in the hiring process, which can lead to indecisiveness.

The board/investors and the executive team represent important opinions, and it’s critical to have clarity upfront of a) who are the key decision-makers? and b) who should be involved in the interview process to offer additional insights? Define everyone’s role in the process upfront so that your hiring process is efficient.

How to address this in the interview process:

• Ensure you have the input/alignment from their board/investors and key team members/leaders before you start interviews to ensure there is early buy-in on the ideal profile & process. You need to move quickly, but not at the expense of getting the right outcome.

Mistake #7 - Making decisions purely based on timeline pressures.

The key here - don’t skip steps or compromise on this hire for the sake of meeting a timeline goal. Yes, you probably want a sales leader ASAP… but having a phenomenal leader in 2-3 months is exponentially better than having a “good enough” leader this month.

How to address this in the interview process:

• Assume that many sales leaders will have bonus payouts that may keep them in a role for an extra month or 2 beyond your ideal start-date. If you can’t close the gap with a starting bonus, be prepared to wait
• But - if you have an engaged candidate but they want an extended start date, there are ways to get creative to make it feel more reasonable - ie. having the candidate have a clear ‘ramp up’ plan and have them participate in any key strategic meetings ahead of their start date.
• If you’re planning to engage an agency - do so sooner rather than later.
• Fractional leaders can be a great interim solution while you look for your dedicated, full-time leader.

This just scratches the surface of things to think through when hiring a great sales leader. Every company situation is unique and there are as many exceptions to the rules as there are rules. Remember - any leadership hire should also take into account the existing strengths, expertise, and areas of improvement of the whole leadership team. The ideal candidate for your organization depends on what would round out your leadership team and your strengths as a founder.

We hope this helps. As always - if you have any questions, thoughts, or suggestions… we’re an email away.

Until next time,

Negin & the Artemis Team