What Software CEOs Often Get Wrong About Hiring For Sales

Hiring the right head of sales is hard even for veteran CEOs. What’s more, CEOs are busy and often can’t dedicate a lot of time to the hiring process, which increases the probability of a mis-hire. Here are eight problems that CEOs face when hiring for sales—and ways to solve them.

Problems of Preparation

1. Hiring before understanding your sales model

You need to understand your sales model before you can effectively hire for it. Start by figuring out the ‘jobs to be done’ in your sales engine, and what you need in your head of sales. If you hire too soon, you risk hiring someone who will implement the sales model they are familiar with, rather than one that will work best for the company.

2. Hiring ‘good resumes’ but cultural misfits

Resumes are important, but they don’t capture everything, like cultural fit--both internally within the company and externally with clients. If your head of sales is not a team player or is difficult to work with, then that person is unlikely to succeed. Your customers also won’t want to buy from someone they can’t work with or don’t find credible. Sales people are remarkable at selling themselves. Make sure to have a tight process and a set of clear needs to help you separate the ‘solids’ from the pretenders.

3. Hiring a head of sales unwilling or unable to follow processes

Having a process-oriented sales engine is important to drive sales growth. If your head of sales doesn’t believe in process, then they not only won’t help build or implement necessary processes but also won’t follow them. Even if they have built processes in the past, don't assume they will want to do it again. There’s certain questions you can ask during your interview process that will help assess this including: how did you prepare for this meeting? What made you successful as a sales rep in your post? [KK1]

4. Hiring too senior or too junior

It’s important to hire someone at the right level for the job. If you hire someone too senior for the position, there’s a chance that they won’t do the job, as they consider it beneath them. Conversely, if you hire someone too junior for the position, they can’t do the job, as they don't have the right knowledge, skills, or experience. Ensure your hire is willing to get in the ‘engine room,’ not just expecting to stay in the observation deck.

Problems of Execution

5. Not providing proper guidance to search firms

Search firms can only provide candidates based on guidance from the company. If you don’t know what you need out of your head of sales, then you can’t tell the search firms who to look for, leading to wasted time and money. Before you involve a search firm, figure out what you need in your head of sales, which starts with mapping out your ‘jobs to be done.’

6. Looking for hard to find ‘unicorn’ unlikely to join

It’s natural to want a head of sales that can do it all—someone who can build a great sales engine, run everything, and solve all your problems. However, these unicorns are extremely difficult to find. Even if you do find them, they undoubtedly have numerous offers to choose from. You have limited time and resources; don’t waste them chasing unicorns.

7. Mistaking style for substance during interviews

Salespeople are naturally good at selling, including themselves. Don’t be misled by smooth talk during interviews. Focus on the qualities you need from your head of sales, and make sure their actions and track record back up their words and promises.

8. Failing to have right hiring process in place

Head-of-sales hires are most successful when the organization accepts them. That’s why it’s important to involve the broader team in the interview and hiring process. Implement a robust hiring process so that different teams, functions, and tenures are all involved in interviewing candidates.

To learn more about how to hire a head of sales, including access to our library of interview questions, and example scorecards and job-descriptions, please reach out.