The F500 Hiring Secret Most Leaders Never Learn
Why brilliant leaders fail at job searches—and the product-market strategy that landed a VP $2.4M a year.
I've watched countless leaders spin their wheels spending months—and often over $5,000—perfecting their resumes. Too many agonize over practice interview answers, turning their offices into Dateline war rooms with sticky notes and preparation scripts plastered across the walls.
Hell, I've reviewed resumes and “tell me about yourself” scripts (yes more than one) that were over 30 pages long, as if more bullet points somehow equal more value.
These are people who regularly close eight-figure deals, who can read a boardroom and shift strategy mid-presentation, who build teams that deliver results quarter after quarter.
Yet here we are.
Too many agonize over formatting choices and wonder whether to mention that “cross-functional” initiative from eight years ago. Meanwhile, their inboxes fill with rejection emails from companies that would be lucky to have them.
Sound familiar?
Look, there's no judgment here. We're in the most competitive white-collar market of the last 25 years.
Brilliant leaders often struggle, buried in seemingly trivial job search tactics instead of the right career-forward strategies when moving to another senior leadership role.
They diminish their expertise into what's equivalent to entry-level sales work.
The tactical job search work that you do isn’t necessarily difficult or even thought-provoking—which only adds to your frustration when rejection emails pile up and success feels further out of reach.
"I led a global team of 400 across 12 countries—and I can't even get a junior recruiter to email me back? What's wrong with me?"
I call this period chewing glass.
It shouldn't be discouraging—after all, I'd be more concerned if you were an expert at changing jobs. Ideally, you’re better at keeping them.
But there's a deeper psychological component at play—what researchers call the "rigidity reflex." When the brain experiences the stress and uncertainty of a career transition, it automatically shifts from flexible, strategic thinking to rigid, habitual responses.
Studies from psychology reveal that under pressure, our cognitive resources become overloaded, forcing the brain to revert to familiar, well-learned behaviors that require less mental energy.
For executives, this creates a dangerous paradox.
The very pressure to find your next role triggers a psychological state that makes you less likely to use the strategic, adaptive thinking that made you successful in the first place.
Instead, you are more likely default to tactics that worked when you were a mid-career manager or individual contributor—polished resumes, rehearsed answers, playing it safe.
Research shows this isn't weakness; it's neuroscience.
Stress biases us toward "exploitation" over "exploration"—we stick with what we know rather than investigating potentially better alternatives.
But what got you here will no longer get you there.
Instead of following advice designed for entry-level candidates—which is what most publicly available career strategy focuses on—you must use the thinking that made you successful in the first place.
Instead of signaling desperation, you must operate from a position of strength.
Instead of playing someone else’s rules, you must write and lead your own.
Instead of finding a job—you must create it.
When my former clients have a friend going through this, that’s when my phone lights up with group texts.
If all of this sounds like the hell you’re navigating, then it’s time we reframe the slog for you. Toss the old playbook—let’s focus on your innate talents so you can show them off naturally.
The moment everything changes is when you stop thinking like someone looking for work and start operating like you're bringing a product to market with your expertise.
Because that's exactly what you must do.
You're not a job seeker begging for opportunity. You're the CEO of you.
Which means you must:
Define your mission (personal clarity)
Research the market (find what interests you)
Align with strategic partners (network)
Market your product (resume, LinkedIn, portfolio, thought leadership, etc)
Build awareness for your product (community, networking, thought leadership)
Nurture interest in your product (pipeline, backchanneling)
Navigate sales conversations (interviewing)
Secure financial outcomes that keep you in business (negotiation)
Please the customer (keep your job)
The company isn't doing you a favor by considering you—they're evaluating whether they can afford to miss out on the enterprise-grade professional services solution you represent.
In less buzzy words, what I mean is: You’re expensive. Expensive stuff takes longer to sell. There’s a smaller market of people who can afford to buy expensive stuff. You need to batten down the hatches.
For revenue leaders, I reframe the job search process into what it takes to close an enterprise sales deal.
Think about it—a million-dollar annual contract that takes 6-18 months to close requires turning an average of 6.5 decision makers into champions and navigating the cascading internal politics to win.
See the Challenger Sale for more on this concept.
You need multiple deals in your pipeline to maximize leverage and ensure timing aligns with quarterly budgets. Meanwhile, smaller deals like fractional consulting keep the team profitable during longer sales cycles.
Great senior revenue leaders already know this process inside and out. So we reframe their job search on terms they understand second nature so they can lean into their strengths.
Your executive job search follows the exact same methodology.
You're managing a complex sales cycle with multiple stakeholders (hiring managers, HR, team members, C-suite), building champions who advocate for you internally, maintaining deal flow to maximize your negotiating position, and potentially taking interim or consulting work to maintain cash flow while pursuing the right opportunity.
The same strategic thinking that makes you successful in enterprise sales is precisely what you need for your career transition.
This principle applies across every executive function.
For marketing leaders, it's building a conversion funnel—awareness, interest, consideration, decision.
For consulting leaders, it's treating job descriptions like RFPs that you challenge and improve with your recommendations.
For product leaders, it's creating a PRD for your career where you identify market needs, define success metrics, and build toward product-market fit.
For operations leaders, it's optimizing a workflow where you identify bottlenecks and measure KPIs (such as # of weekly conversations) to improve efficiency.
For communications leaders, it's crafting a narrative strategy that positions you as the solution to their story problem.
For technology leaders, it's leading a system where you build your personal tech stack, iterate based on feedback, and deploy solutions to their technical challenges.
This works for finance, engineering, legal, HR, the list goes on.
Every executive function has a reframe that helps leaders lean into their natural strengths instead of working against them.
The key is recognizing that your expertise isn't irrelevant to your job search process—it's the foundation of your advantage.
This isn't positive thinking or motivational fluff.
This is a fundamental reframe that transforms everything about how you approach, negotiate, and command your next executive opportunity. When you understand the psychology behind why this works, you'll never go back to thinking like a job seeker again.
The $2.4 Million Realization
My lightbulb moment came during a conversation with a VP of Product who had helped grow three unicorns from startup to over a billion in revenue each. Brilliant doesn't begin to describe her track record. Let’s call her Jenny.
Yet there Jenny was, stuck sending the same generic resume and portfolio to hundreds of companies, getting crickets in return.
When I asked her how she'd approach launching a new product in a crowded market, Jenny lit up.
Immediately she outlined a sophisticated go-to-market strategy—market research, competitive positioning, identifying key decision makers, building champion networks, creating compelling value propositions for different buyer personas.
I asked:
"So why aren't you using that same thinking for your career transition?"
Jenny’s silence said everything.
Four months later, she landed a $2.4 million package at a Fortune 500 company. Not because she suddenly became more qualified, but because we started treating her job search like a business challenge she could recognize.
When you understand the psychology behind why this works, you'll never go back to thinking like a job seeker again.
Why A Strategic Reframe Changes Everything
The difference between a successful executive transition and months of rejection emails isn't your qualifications—it's your psychological positioning.
Or yes, this wild market we’re all navigating right now—but I digress.
When you operate from a "job seeker" mindset, you're unconsciously signaling scarcity. You're positioning yourself as someone who needs something from them.
Your brain interprets this as a low-status position, which triggers what researchers call "supplicant behavior"—deferential body language, tentative speech patterns, and a tendency to accept whatever terms are offered.
Research from Joe C. Magee, Adam Galinsky, and Deborah H. Gruenfeld shows that a negotiator's power fundamentally changes their behavior at the bargaining table; those with strong alternatives are more than three times as likely to make the first offer, a proactive move that consistently produces a bargaining advantage.
The difference isn't in their actual leverage—it's in their internal psychology. When you think of yourself as a job seeker, you're priming your brain for powerless behavior. You are perceived to have less leverage, whether that’s a fact or a self-imposed hallucination.
It’s sort of like your very own hellish self-fulfilling prophecy—which only extends the agony of your job search. It’s a mental game above all else.
But when you reframe yourself as the CEO of your own career, everything shifts.
This is fundamentally about taking complete agency over your professional life and leaning into your strengths—not playing someone else’s game.
The alternative—waiting for someone else to recognize your value or fix your situation—leads to a losing mentality that creates a negative spiral of helplessness and a draining bank account.
Breaking the Rigidity Reflex
Psychology research reveals that under pressure, we experience what's called the "rigidity reflex"—our cognitive resources become overloaded, forcing the brain to revert to familiar, well-learned behaviors that require less mental energy.
The very pressure to find your next role triggers a psychological state that makes you less likely to use the strategic, adaptive thinking that made you successful in the first place.
Instead, you default to tactics that worked when you were a mid-career manager—polished resumes, rehearsed answers, playing it safe.
The neuroscience is clear.
Stress impairs the prefrontal cortex (responsible for strategic thinking) while strengthening habit-based systems in the brain. Under pressure, we stick with what we know rather than exploring potentially better alternatives—what researchers call "exploitation over exploration."
The strategic reframe directly counters this by giving your brain a familiar framework to operate within.
You already know how to launch products, manage complex sales cycles, and navigate organizational politics. When you apply this existing expertise to your career transition, you're working with your cognitive strengths rather than against them.
The Confidence-Performance Loop
Confidence creates what psychologists call an "upward spiral effect." Research from Stanford shows that people who approach challenges with a growth mindset—believing their abilities can be developed—perform significantly better than those with fixed mindsets who see abilities as static traits.
When you reframe your job search to leverage your core strengths, you activate growth mindset thinking.
Instead of "Do they want me?" you're asking "How can I solve their business challenge?" This shift moves you from defensive to offensive positioning, from reactive to proactive strategy.
Everything spirals upward from there.
The neuroscience backing is compelling.
Confidence activates the prefrontal cortex. Fear and desperation trigger the amygdala, which narrows your thinking and pushes you toward rigid, habitual responses.
The Authority Principle in Action
Dr. Robert Cialdini's research on influence reveals that authority is one of the most powerful drivers of human behavior. When you present yourself as an expert consultant rather than a job candidate, you're leveraging this principle automatically.
Consider two interview scenarios:
Job Seeker Approach: "I'm really interested in this role and would love the opportunity to contribute to your team."
Versus.
Authoritative Advisor Approach: "There are three challenges that you absolutely must get right to scale your enterprise strategy. Let’s walk through how we should approach each one."
The first signals need. The second signals value.
Companies don't hire executives because they feel sorry for them.
They hire executives because they believe those leaders will solve expensive problems and create valuable outcomes.
When you position yourself as the solution rather than someone seeking help, you align with their decision-making psychology.
Why This Works for Every Executive Function
This reframe works powerfully because it leverages your existing cognitive strengths.
A revenue leader naturally understands pipeline management and champion building. A marketer instinctively thinks in terms of funnels and conversion optimization. A product leader knows how to identify market needs and build toward product-market fit.
You're not learning new skills—you're applying proven skills to a new domain.
This is the psychological antidote to the rigidity reflex that keeps so many executives stuck in ineffective job search patterns.
A Note on Navigating Reality
Let me be clear.
This isn't a strategy for a perfect world—it's a playbook for the messy one we lead in.
It’s designed to overcome the very obstacles that cause the most frustration.
This framework helps you bypass the HR black hole through strategic relationships, navigate internal politics as part of the "sale," and thrive in a downturn by positioning you as the essential solution to a company's biggest problems.
It’s not about ignoring reality; it’s about giving you the agency to master it.
Making Your Strategic Shift
Understanding psychology is one thing. Actually making the shift is another. Here's how to operationalize this reframe into immediate action.
Step 1: Establish The Only KPI That Matters
Forget tracking applications sent, resumes updated, or job boards checked. Your only meaningful KPI is the number of strategic conversations you have each week.
Set a weekly target of 3-5 meaningful conversations with people in your target market. Not networking events or coffee chats—actual conversations with decision makers, industry insiders, or strategic contacts who understand the problems you solve.
Track these religiously.
Create a simple spreadsheet with the person's name, company, conversation date, key insights, and follow-up actions. Your own basic CRM—it's pipeline management for your career.
Everything cascades from this single metric—your number of conversations per week.
More conversations lead to better market intelligence, stronger relationships, clearer positioning, and ultimately, better opportunities. It's the executive equivalent of sales activity metrics—a leading indicator that predicts success.
Start with volume to build the muscle memory.
As you get really good at booking networking conversation, you'll naturally become more selective because your time becomes more scarce. This scarcity forces better thinking: "Is this conversation really worth my time? Why or why not?"
That's when quality improves and real clarity emerges.
Volume → Skill → Scarcity → Quality → Clarity
And it must become a habit for the rest of your career. You scale your target conversation # up and down based on how busy you are, but it must never stop. Even when you land.
You must keep building relationships that pay off at different times—or put differently, you must plant seeds that bloom in different seasons—or risk starving.
Think about it.
If you were leading a sales team and they were confident that one deal was going to close the entire quarter—would they still have a job if they stopped prospecting for new opportunities?
Furthermore, it means that you will have more opportunities to have several irons in the fire, increasing the likelihood that we can navigate bidding war opportunities, better control timing, and better negotiate on the terms that will help you land the most fulfilling—and lucrative—senior leadership opportunities.
Step 2: Conduct Your Market Analysis
Just like launching any new product, you need to understand your market before you go to market. But instead of researching customer segments, you're researching companies and roles where your expertise creates maximum impact.
I call this going to market for your career.
Start with this question: "What expensive problems do I solve?"
Not what you've done—what problems you solve.
A VP of Sales doesn't just "manage sales teams." They solve the expensive problem of unpredictable revenue growth.
A Chief Marketing Officer doesn't just "run marketing campaigns." They solve the expensive problem of inefficient customer acquisition costs and rally the entire company around their vision.
An EVP of Design doesn't make pixels look pretty—they solve the expensive problem of leading product experience and design thinking transformation across the entire organization, ensuring design drives customer experience rather than being an afterthought.
Create a list of 3-5 expensive problems you solve, then research which companies are actively struggling with these challenges.
Look for recent funding rounds, leadership changes, market expansions, or competitive pressures that signal they need your expertise now.
This is where LinkedIn Premium provides the most value.
You can review advanced company insights, recent executive turnover, headcount trends, and compare with their closest competitors, and so on.
If you’re armed with this intel and you're a competent senior leader, you should be able to reasonably predict what the company is experiencing right now, and what hurdles they are about to face.
Now it’s easier to make your value proposition clear—and adapt it depending on what companies you’re speaking with.
This isn't job board scrolling. This is strategic market intelligence.
Step 3: Master Strategic Servitude (Not Networking)
Traditional networking is dead. Strategic servitude is the future.
Instead of asking "How can you help me?" start every interaction with "How can I best serve you?" This isn't soft-hearted idealism—it's hard-nosed psychology based on Robert Cialdini's reciprocity research.
Here’s my decision tree:
If you have something valuable to give—give it.
If you don't have something valuable to give—do more research.
If you don’t know what drives the leaders at the companies that you want to partner with, you haven’t asked the right questions, yet.
Try the following approach.
Identify your top target companies and find the leaders who are most socially active. Follow their accounts (on LinkedIn, ring the bell so you see all their content) then comment meaningfully on their posts for at least 4-6 weeks.
Add a resource when appropriate or tag a colleague for their perspective—especially if that colleague has industry clout—and lead the dialogue. You don't need to know all the answers; you need to be visible and always provide value.
This builds crucial recognition between your headshot and value.
When you eventually move to direct outreach, they're more likely to respond because you've primed them to associate your face with helpful insights.
Before reaching out to anyone, spend an additional 30-45 minutes studying their world.
Read their company's recent moves, their LinkedIn activity, their industry's pressure points.
Run a deep research report on them using Perplexity or Gemini Ultra.
Look for connection points where you can add immediate value.
Your outreach should answer three questions as concisely as possible and create intrigue to speak with you: Who are you? Why should they care? What's in it for them?
Template: "[Name], I saw that you're expanding into [Specific Challenge]. When I went through this, I found this [Specific Resource] useful. Hope it helps."
Followed by a “Happy to chat through it” a few days later if they haven’t replied.
Deliver the value and disappear.
No follow-up asking if it was helpful. No gentle reminders that you exist. You serve and surrender the outcome.
Step 4: Activate Your Network as Your Sales Force
It's much easier to find a needle in the haystack if you have a dozen people sifting through it with you—and three of them also toss a needle into the pile.
The goal isn't to simply ask your network for help. It's to arm them with your narrative so they can go to battle on your behalf.
Organize your existing network into three tiers:
5-10 close contacts who would "pick you up at the airport"
15-20 secondary contacts (colleagues, former teammates, etc.)
3-5 industry leaders or potential mentors you'd like to connect with
These are opportunities to practice your narrative from low-risk to higher-risk contacts. Use language that makes solutions their idea.
Try this approach: "I've been considering the following angles—[specific markets/industries/types of leaders]—what would you do if you were in my shoes?"
Let them naturally come up with people you should speak with. If they don't immediately suggest contacts, follow up with: "Who are your three go-to people for this type of challenge?"
Then you can either follow those people using your strategic servitude approach, or ask if your contact can make an introduction to speed things up.
Research shows warm introductions convert at 10x the rate of cold outreach.
This approach transforms your network from passive contacts into active advocates who feel invested in your success because they helped craft the strategy.
Step 5: Transform Interviews Into Consulting Sessions
Stop going to interviews. Start consulting instead.
Come prepared for all interviews with a strong stance on what the company should do.
The problem with standard interview advice like STAR (Situation, Task, Action, Result) is that it's backward-looking and places you in a reactive position.
You're at the mercy of whatever question comes next, constantly remembering how something happened rather than demonstrating how you think strategically.
Years back, I built the ICARQ framework as a counter to why STAR isn't as effective at the executive level. ICARQ transforms interviews from interrogations into strategic conversations between peers.
I - IMPRESSION: What specific impression must you create to win this role? Strategic but scrappy? Cross-functional leader? Crisis navigator? This is your guiding star—not something you say, but something that shapes how every story comes across.
C - CONTEXT: Set up the business challenge. What problems needed solving? What resources did you have—or not have? Make it relevant to their current situation.
A - ACTION: Describe your approach. Use active language ("we implemented," "we restructured") that centers your leadership while acknowledging team contributions.
R - RESULT: Quantify the business impact. Include a clincher—dollars saved, revenue generated, efficiency gained. Make it meaningful to their context.
Q - QUESTION: This is where the magic happens. Connect your experience directly to their challenges with an open-ended question that shifts focus from your past to their future.
Example in Action:
Instead of waiting for their questions, open with your analysis:
"I looked at your Series B and what you're planning for expansion. It sounds like you're going to hit three big problems that I've dealt with before. Here are a few top-of-mind thoughts: X, Y, Z. Is there anything I missed?"
Then use ICARQ to frame your example, ending with:
"We’re aligned on what we need to do together, what do you think is stopping you from doing this faster? What happens if we do nothing? And are you leaning toward hiring more people or making the team you have more efficient?"
This approach positions you as the expert consultant they're evaluating for a strategic engagement, not a candidate hoping to be chosen.
For a deeper dive on exactly how to do this, read how to Assert Your Future, Don’t Appease Others.
Your 90-Day Implementation Plan
Don't try to transform your entire approach overnight. The rigidity reflex fights against sudden changes. This is why focusing on one metric—conversations per week—changes everything else naturally.
When you commit to hitting 3-5 strategic conversations weekly, you're forced to get creative.
You ask better questions during outreach.
You pay close attention to what people actually say.
You notice patterns across industries and connect people who should know each other.
You provide more value and others recognize this.
If you don’t, you’ll fail your metric. And people like you never miss your marks, let’s be honest.
This creates a virtuous cycle.
The more value you provide by making strategic introductions, the more people want to help you. When someone recommends you, they look good because they know you'll deliver value to their contact. If you want someone to take care of your needs, make sure you understand their drivers and support them without being asked.
Over time, opportunities start coming to you instead of you chasing them.
The Long Game
Most senior leaders miss that this isn't a job search strategy. It's a comprehensive career strategy.
Compound this approach for 10-25 years and you become untouchable. While your peers network only when they need something, you've spent decades building real relationships and creating value for others.
When the next opportunity comes—whether you're looking or not—you don't compete for it.
People bring it to you.
I’m a broken record, “It’s not what you know, it’s who you know.”
The Implementation Timeline:
Days 1-30: Establish your conversation rhythm and basic market intelligence.
Days 31-60: Refine your approach and begin connecting others.
Days 61-90: Start seeing compound effects as your reputation grows.
Repeat for the rest of your career.
The beauty of this system is that it works whether you're actively job searching or happily employed. It's relationship capital that pays dividends for decades.
Beyond Your Reframe
You now have the psychological framework and tactical playbook that the top 1% of executives use to command premium opportunities. But knowing and doing are different games entirely.
The executives who transform their careers aren't the ones who read this once and file it away. They're the ones who start having their first strategic conversation this week.
Your rigidity reflex will fight you.
It will whisper that the old ways are safer, that updating your resume one more time is productive, that waiting for the "perfect" opportunity makes sense. Untrained GPTs will perpetuate this mistake as well.
Ignore it.
Your competitive advantage isn't in perfecting your approach—it's in starting before you feel ready.
While your peers spend months crafting the perfect LinkedIn headline, you're building relationships with decision makers. While they're waiting for recruiters to discover them, opportunities are flowing directly to you through your network.
This reframe doesn't just change how you find your next role. It changes how you think about your entire career.
You stop being someone who hopes to be discovered and become someone who creates value wherever you go. You stop competing for opportunities and start having them delivered to you. You stop playing other people's games and start writing the rules.
The VP of Product who landed the $2.4 million package didn't just get a better job. She got a completely different relationship with her professional future. She now operates from a position of strength in everything she does.
The choice—and the future it creates—is entirely yours.
Need help applying this? Upgrade to paid for monthly live sessions with Jacob.
Stay fearless, friends.