Dear SaaStr: What Are Some Top Tips for Hiring and Retaining Top Leaders?

Dear SaaStr: What Are Some Top Tips for Hiring and Retaining Top Leaders?

Hiring and retaining top leaders is one of the most critical things you’ll do as a founder or CEO. Great leaders don’t just execute—they elevate your entire organization. Here’s how to get it right:

Hiring Top Leaders

1. Hire Fast, But Hire Right:
   Don’t drag your feet when you find a great candidate, but don’t rush into hiring someone who isn’t a perfect fit. The best leaders will transform your company, but the wrong hire can set you back months—or even years. Look for candidates who have a proven track record of success in roles similar to what you need, and don’t settle for mediocrity.  And don’t be too swayed by that amazing logo:

   • Make 100% sure you’d hire them if they hadn’t worked at that well know / hot tech company before.

   • And make 100% sure they can sell / market / etc at your stage.

2. Look for Leaders Who Bring Their Own Team:
   The best VPs of Sales and VP of Eng especially don’t come alone—they bring a few “ringers” with them. These are top performers they’ve worked with before and trust to execute. If a candidate can bring two or three amazing team members with them, that’s a huge signal they’re the real deal .

3. Focus on Cultural Fit and Alignment:
   Skills and experience are critical, but cultural fit is just as important. Leaders who align with your company’s values and vision will stick around longer and be more effective. Spend time with candidates to make sure they truly understand and buy into your mission.  Especially, folks that understand it.

4. Don’t Outsource the Hiring Process:
   For key leadership roles, you need to be deeply involved in the hiring process. Don’t rely on HR or recruiters to make the final call. Interview candidates yourself, and involve your top performers in the process. This ensures you’re hiring someone who not only has the skills but also fits with your team.

5. Hire Leaders Who Can Scale, But Avoid Leaders Who Only Want to Work on “Process”:
   Early-stage startups need leaders who can roll up their sleeves and execute, but as you grow, you’ll need leaders who can manage teams and more complex operations. Look for candidates who’ve successfully scaled a team before, at least a small one.  But … make 100% sure they are still willing to do the work themselves.  Too many just want to be strategists today, and only work on “process”.  Process sounds like what you need, and to some extent it is.  But mediocre VPs only talk about process.  Not how they’ll actually tilt the curve.

6. Pick One Key VP Hire at a Time — And Go All In:
   We all need to get better as serial recruiters, but for senior roles, most of us can really only do 1 right at a time.  Pick the most critical VP role and just go interview 30 top candidates for the role.  And spend 10 hours a week on that role.  Force yourself to.

Retaining Top Leaders

1. Promote Them Quickly:
   Your best leaders want to grow. If you don’t give them opportunities to advance, they’ll look elsewhere. Promote them as soon as they’re ready—even if it feels a little early. It’s better to stretch them than to lose them.

2. Pay Them Well:
   Compensation matters, especially for top talent. Make sure your leaders are paid at or above market rates, and don’t let salary issues fester. If they feel underpaid or undervalued, they’ll start looking for other opportunities.

3. Make Them Feel Secure:
   Leaders need to know they have a real role and stake in the company’s success. Be transparent about their importance to the organization, and involve them in big decisions. If they feel like they’re just another cog in the machine, they’ll leave.

4. Invest in Their Success:
   Help your leaders achieve their personal and professional goals. Ask them what they want to accomplish and work with them to make it happen. Whether it’s closing a big deal, launching a new product, or developing new skills, show them you’re invested in their growth.

5. Engage Them in Change:
   High-performing leaders hate surprises. If you’re making changes to their role, team, or responsibilities, involve them early in the process. Let them be part of the solution rather than learning about it in an email.

6. Build a Culture of Trust:
   Retaining top leaders is about more than just money and titles—it’s about trust. Be honest, transparent, and supportive. If they know you have their back, they’ll stick around longer.

7. Ask Them to Stay:
   If you sense a top leader is thinking about leaving, don’t ignore it. Have an honest conversation and ask them what it would take for them to stay. Sometimes, just knowing they’re valued can make all the difference.

Final Thoughts

Hiring and retaining top leaders isn’t easy, but it’s worth the effort. These are the people who will drive your company’s growth and help you navigate the toughest challenges. Invest the time to find the right leaders, and once you have them, do everything you can to keep them.