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: Sarah, a VP of Product at a Series D fintech company, had been struggling for months. The CEO kept changing priorities, her engineering counterpart was difficult to work with, and she hadn't shipped a major feature in two quarters. She wasn't sure if the problem was her, the company, or something else entirely.
What She Did: Instead of resigning in frustration or suffering in silence, Sarah got clarity on what was actually happening:
- She documented the pattern of changing priorities—not to assign blame, but to understand if it was solvable
- She had a direct conversation with her CEO about decision-making processes
- She updated her network and had exploratory conversations, not to job hunt, but to calibrate her perspective
The Outcome: The conversations revealed that the CEO's behavior wasn't going to change—it was how he operated. Armed with this clarity, Sarah negotiated a transition timeline that worked for both parties. She landed at a company with a more structured leadership team within four months. Looking back, she wishes she'd started the clarity process six months earlier.
The Lesson: Clarity first, action second. Most people skip the diagnosis and jump straight to reactive moves.
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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