sales hiring mistakes

Don’t Make These 5 Mistakes When Hiring Your First Startup Head of Sales

Hiring your first senior salesperson is daunting when your business is new—you don’t know much yet about what has worked so far. And even if you do manage to find the perfect hire, you may find yourself needing someone with different strengths as your business grows and changes over time.

Here are the common mistakes we’ve seen founders make when pursuing their first startup head of sales.

Mistake 1: You don’t try doing the job yourself first.

We often meet founders who hope their new head of sales will bring a playbook of the best sales tools, recruiting tactics, and sales scripts. Some candidates have built a career doing this, but it’s risky to rely on a new hire to import critical pieces of your sales infrastructure. You need to tackle some of these challenges yourself before starting your search. That way, you’ll gain a much deeper understanding of what your business really needs in your new head of sales.

Mistake 2: You only look at candidates from big companies.

Previous success at a public company, or even just a larger startup, does not always translate well to a first head of sales hire. You need someone who’s going to bring in a lot of value from Day One, and it’s hard to measure the value in a candidate from a big company where the resources and support system is much deeper.

Corporate sales leaders also tend to focus more on building processes and operational efficiency, whereas startups sales is more about trial-and-error. So don’t be entranced by resumes full of prestigious company names—look for someone who has proven success at early stages and shows lots of adaptability and problem solving skills.

Mistake 3: You agree to pay a large, corporate salary.

This doesn’t mean you should be cheap. Just don’t try to compete with big company compensation packages and be wary of candidates who try to put you in that position. Be frugal with salary and generous with your commission and equity incentives. Candidates who believe in the potential of the company will put a larger value on future earnings than immediate cash.

Mistake 4: You skip the reference check.

Beyond closing deals and building a sales team, your head of sales is also going to be the face of your brand. Make sure you spend plenty of time making reference calls and background checks to make sure you know the character of the person you are hiring. Ask your own network of people who may have crossed paths with your candidate. And if you have specific concerns about a contender, don’t be afraid to ask his or her references direct questions about what’s worrying you.

Mistake 5: You hire someone with “forever” in mind.

Set modest expectations for how far your first head of sales will lead your company. Even the most successful hires end up having their roles narrow as their breadth of responsibilities widens. Instead, focus your first hire to achieve a few, concrete milestones six months to a year out. Setting these goals will also help you prioritize the relative importance of traits you are looking for in your search.

Still have questions about your head of sales hiring? Give us a shout at

Jordan Wan

Founder & CEO of CloserIQ. Previously Sales Strategy & Management @ZocDoc, Head of Analytics @PayPerks and Trading Strategist @Bridgewater Associates. MIT Bachelor’s & Master’s in Computer Science. CFA Charterholder.