Executive Job Search Is Different

"The tactics that got you to senior level won't get you to the next one. Executive job search follows different rules—and most people learn them the hard way."

Why It's Different

If you're a VP, Director, or C-level executive looking for your next role, you're playing a different game than you did earlier in your career. Here's what's changed:

The hidden market is bigger. At senior levels, most roles never get posted publicly. They're filled through networks, search firms, and internal promotions. If you're only applying to job postings, you're seeing maybe 30% of the opportunities.

The timeline is longer. Entry-level roles can close in weeks. Executive searches take 3-6 months or more. There are more stakeholders, more interviews, more deliberation.

Relationships matter more. Your resume gets you in the door at junior levels. At senior levels, relationships get you in the door. The resume closes the deal.

Fit is evaluated differently. Companies aren't just looking for skills. They're looking for leadership style, cultural fit, strategic thinking, and presence. These are harder to assess and take longer to evaluate.

Compensation is more complex. Base salary, bonus, equity, sign-on bonuses, benefits, severance—there are more variables, more negotiation, and more room for creative structuring.

The Executive Search Playbook

1. Define Your Target Before You Start

Don't spray and pray. At the executive level, you need a clear thesis about what you want and why you're right for it.

• Industry: Where do you want to be? Where will your experience translate?
• Company stage: Startup? Growth? Enterprise? Turnaround?
• Scope: Build from scratch? Optimize? Scale? Fix?
• Role: What title and responsibilities are you targeting?
• Geography: Remote? Hybrid? Relocation possible?

The clearer you are, the easier it is for people to help you. "I'm looking for VP Product roles at Series B-C enterprise software companies in the Bay Area" is referrable. "I'm open to anything" is not.

2. Lead with Relationships, Not Applications

At senior levels, your network is your job board.

1. First-degree connections — People who know your work and can refer you directly
2. Second-degree connections — Intros through your first-degree network
3. Executive recruiters — Search firms working on relevant roles
4. Inbound applications — Job postings (lowest hit rate at this level)

• Make a list of 50 people who could help (former colleagues, bosses, peers, board members)
• Reach out personally (not a mass email)
• Be specific about what you're looking for
• Ask for introductions, not jobs

The script: "I'm exploring my next move and would love to catch up. I'm focused on [specific target]. If you know anyone who might be interesting to talk to, I'd really appreciate an introduction."

3. Get Positioned with Executive Recruiters

Search firms matter more at senior levels. Many companies hire exclusively through retained search for VP+ roles.

• They're hired by companies to fill specific roles
• They get paid when they place someone
• They work for the company, not for you
• But they need good candidates, so building relationships helps

• Identify firms that specialize in your function and industry
• Connect on LinkedIn with partners and principals
• Have a clear, concise positioning statement
• Be responsive and professional
• Be a source of referrals (even if you're not right for a role, recommend others)

Reality check: Recruiters are useful, but they're not your job search strategy. They're one channel among several.

4. Craft Your Positioning

At senior levels, you need a clear narrative about who you are and what you do.

• Your superpower — What are you distinctively good at?
• Your trajectory — What's the through-line in your career?
• Your proof points — What results can you point to?
• Your thesis — What do you believe about your function/industry that others don't?

The format: "I'm a [role] who specializes in [specific thing]. I've spent my career [trajectory]. At [company], I [specific accomplishment]. I'm now looking for [specific next thing] because [reason]."

Example: "I'm a VP of Engineering who specializes in scaling teams through hyper-growth. I've spent my career at companies that grew from 50 to 500+ engineers. At [Company], I built the platform team from scratch and reduced deployment time by 80%. I'm looking for another scale-up that's hitting that 50-to-500 inflection point."

5. Prepare for a Different Interview Process

Executive interviews are less about technical skills and more about leadership, fit, and thinking.

• Multiple rounds with senior stakeholders
• Board member or investor interviews
• Case studies or strategic presentations
• Reference checks (real ones, not just the ones you provide)
• Sometimes, a "trial project" or consulting engagement before an offer

• Have stories ready for leadership situations (conflict, failure, building teams, making hard calls)
• Research the company deeply (product, competitors, challenges, culture)
• Prepare thoughtful questions (show you understand their problems)
• Practice talking about your failures (they will ask)
• Know your numbers (revenue, headcount, metrics you influenced)

6. Accept the Timeline

Executive job searches typically take 3-6 months. Sometimes longer.

• Fewer roles at this level
• Longer interview processes
• More stakeholders involved in decisions
• Companies take longer to make senior hires
• Timing has to align (budget, org changes, etc.)

• Start before you need to (3-6 months before you want to start)
• Have financial runway (don't accept a bad offer out of desperation)
• Stay active (keep taking meetings even when things are "in process")
• Don't count on any single opportunity (have multiple conversations going)

Common Mistakes

Mistake 1: Leading with Your Resume

Mistake 2: Being Too Open

Mistake 3: Underinvesting in LinkedIn

Mistake 4: Waiting Until You're Desperate

Mistake 5: Not Asking for Help

What You'll Walk Away With

When you approach your executive job search strategically, you get:

• A clear target — Specific criteria for your next role
• A positioning statement — A concise narrative about who you are and what you offer
• A networking plan — Who to reach out to and how
• Interview preparation — Stories, questions, and presentation skills
• Realistic expectations — A timeline and approach that works at your level

The goal isn't to find any job. It's to find the right job—and to do it in a way that sets you up for success.