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Description
Most job searches don't fail because of one big problem. They fail because of one or two small ones, and nobody ever points them out. Maybe it's a resume that buries the achievements that actually matter. Maybe it's a networking approach that gets you conversations but never referrals. Maybe it's how you're answering the first interview question. Whatever it is, it's usually fixable, and it's usually invisible to you because you're the one doing it. That's what the Job Search Diagnosis is for. In this 30-minute, one-on-one live session, you'll walk a coach through your entire job search so far: what you've applied to, how you've been networking, what your interviews have looked like, where things have stalled. The coach isn't there to give you generic advice. They're there to find the specific one or two things that are quietly working against you and tell you exactly what they are. You'll leave the session knowing precisely what's been holding your search back, why it's been happening, and what to do differently starting now.
What you'll get from this package
A clear, specific diagnosis of what's actually blocking your job search (not generic feedback)
A concrete plan for what to fix and how to fix it
A clearer path to more interviews and, eventually, more offers
Additional details
Coaching delivered via live sessions.
Services included:
Career Planning
Cover Letters
Resume Review
Networking Strategy
Job Search Strategies
Interview Prep
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
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Custom hourly · $275/hr
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Benjamin also coaches for MBA, College, Master’s Programs, and Executive Coaching. View all.
Offered by Benjamin P.
Joined February 2026
5.0
Analyst → Operator → C-Suite → Boardroom | Elite Career Strategy
I coach ambitious professionals navigating high-stakes career transitions—particularly into investment banking, private equity, venture capital, startups, and global leadership roles. Over 25+ years, I have built and led companies across private equity, venture capital, family offices, and digital health. I have raised and deployed capital, executed cross-border acquisitions and joint ventures across multiple continents, and served as both a C-suite executive and board member. I understand how talent is evaluated at the highest levels—not only by hiring managers, but by investors and boards accountable for performance. My coaching focuses on strategic positioning: clarifying your narrative, sharpening your differentiation, and ensuring you compete effectively in highly selective environments. Whether you are pursuing PE/VC recruiting, transitioning through an MBA, pivoting industries, or stepping into broader leadership responsibility, I help you think like a decision-maker—not just a candidate. I bring both operator and investor perspective so you position yourself not just for your next role, but for long-term leverage.
$49
30m of coaching