The Executive Job Search Framework
Senior job searches operate by different rules. Here's the framework that actually works at the executive level.
The Hidden Market Reality
At the executive level, 70%+ of roles are filled through relationships, not applications. Your job search strategy must reflect this:- Tier 1: Direct outreach to your network
- Tier 2: Recruiters who specialize in your function and level
- Tier 3: Public postings (least effective, but still worth pursuing)
The Positioning Question
Before reaching out to anyone, clarify:- What's your unique value proposition in one sentence?
- What problems do you solve that others can't?
- What size/stage of company is right for you?
The Outreach Cadence
Effective executive job search requires consistent activity:- 5-10 meaningful conversations per week
- Regular check-ins with active recruiters
- Targeted applications where you have an inside connection
The Timeline Reality
Executive searches take longer—typically 4-9 months. Plan financially for this. The rush to take the first offer often leads to repeating the same problems in a new location.
What This Looks Like in Practice
The Scenario: Marcus, a Director of Product at a mid-size SaaS company, was passed over for VP despite delivering strong results. His manager's feedback was vague: "You're not quite ready." He was torn between pushing harder, looking elsewhere, or accepting that maybe he wasn't VP material.
What He Did: Instead of spiraling, Marcus got specific:
- He asked for concrete examples of what "VP-ready" looked like at his company
- He talked to three people who had been promoted to VP recently—inside and outside his company
- He assessed honestly whether the gap was real or political
The Outcome: The diagnosis revealed two things. First, his company had a pattern of promoting people who were highly visible to the CEO—which Marcus wasn't. Second, the specific feedback about "strategic thinking" was valid but actionable.
Marcus decided to address the skill gap while also broadening his external options. He found a VP role at a smaller company within six months, where his operational strengths were valued more than political visibility.
The Lesson: "You're not ready" is rarely the full story. Dig deeper to find out what's actually being said—and whether it's worth addressing there or somewhere else.
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What You'll Walk Away With
Our structured session produces concrete artifacts, not just conversation.
Decision Snapshot A clear-eyed assessment of your current situation—what's true, what's not, and what actually matters for your decision.
Fork Recommendation A specific direction (stay, go, or pivot) with the reasoning behind it, so you understand not just what to do but why.
Risk Map Everything that could go wrong with your chosen path, and how to mitigate each risk before it materializes.
Conversation Scripts Exact language for the hard conversations you need to have—with your boss, your partner, recruiters, or anyone else.
14-Day Action Plan The specific steps to take immediately after our session, so momentum doesn't stall.
30-Day Roadmap The longer-term plan for executing your decision, with milestones and check-in points.
These aren't templates—they're customized to your specific situation, role, and constraints.
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Ready for Personalized Guidance?
Every situation is different. If you want help thinking through yours—with someone who's seen hundreds of similar cases—consider working with a coach.
What you get:- A structured conversation to clarify your situation
- Frameworks tailored to your specific circumstances
- Scripts you can actually use
- A clear action plan