Dear SaaStr: How Should I Approach Hiring My First Executives?

Dear SaaStr: How Should I Approach Hiring My First Executives?

Early-stage hiring is one of the most critical things you’ll do as a founder, and it’s also one of the hardest. Most founders aren’t naturally great at recruiting—it’s a skill you have to force yourself to develop.

Here’s how I’d approach it:

1. Spend 20% of Your Time Recruiting
   You’re probably not spending enough time on this. Almost no one is.  Be honest.  Recruiting isn’t something you can delegate early on. You need to be in the trenches, meeting candidates, selling the vision, and making the call. If you’re not spending at least 20% of your time on recruiting, you’re not doing enough .

2. Hire for the Stage You’re At
   Early on, you don’t need someone who’s scaled a company from $100M to $1B. You need someone scrappy who can roll up their sleeves and figure things out. But—and this is key—don’t fool yourself into thinking that person will grow into a senior leader if they’ve never done it before. Be honest about what you need now and in 6, 12, and 18 months .  You can hire someone from one stage above, but don’t hire anyone that hasn’t at least had a senior role at a start-up no more than 12 months ahead of where you are now.

3. Force Yourself to Interview 30 Candidates for VP Roles
   Yes, 30. It sounds like overkill, but magic happens when you commit to this. You’ll stop settling for mediocre hires, and you’ll build a real pipeline. If you find the perfect candidate at #12, great—but plan for 30.

4. Use Screening Filters
   Create simple tests to weed out unqualified candidates before the first interview. For example, ask engineers to complete a quick coding challenge or have marketing candidates critique your product. The best candidates will find these tasks engaging, and it’ll save you hours of wasted meetings.

5. Beware of Mis-hires
   A bad hire at the VP level can set you back 6-9 months. That’s time you can’t afford to lose. If you’re unsure about a candidate, just don’t hire them. Get help from advisors or mentors to review your picks. Whatever it takes, avoid making a bad senior hire.  If you are sure, but they have holes, or are a smidge too junior, take that risk instead.  Don’t make any VP hire you don’t 100% believe in.

6. Don’t Get Blinded by Resumes
   We all do.  But don’t.  A candidate with a flashy resume from Datadog or Wiz or even Cursor or Codeium or your competitor might look perfect on paper, but that doesn’t mean they’re the right fit for your startup. Focus on what they can actually do for you, not where they’ve been.

7. Close Like Your Life Depends on It
   Don’t assume your charisma alone will close candidates. Bring in your co-founders, investors, and anyone else who can help sell the vision. And don’t underestimate the power of PR—podcasts, blog posts, and events can make a big difference in attracting talent.

8. Hire an Internal Recruiter Early
   Once you’re hiring more than one person a month, it’s time to bring in an internal recruiter. They’ll help manage the process, coordinate with external recruiters, and keep things moving. Don’t wait too long to make this hire—it’s worth the investment.

Early-stage hiring is about building the foundation for your company. Get it right, and you’ll set yourself up for success. Get it wrong, and you’ll spend months cleaning up the mess. Be deliberate, be patient, and don’t settle.

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