Ottavio Maria Campigli (Senior Equity Partner & Founder at W Executive)
Welcome back to Endeavor Talks with…!
Today we chat with Ottavio Maria Campigli, Founder of W Executive and trusted HR advisor to VC funds and scaleups. He’s also an Endeavor Mentor and was recently named among Europe’s Top 40 Under 40 Leaders.
Happy reading!
1. From your early steps at Bocconi to becoming Partner in a multinational executive search firm and then Founder of W Executive when did you realize that executive search – and entrepreneurship – would become your path?
More than a turning point, it was a continuous pull. Even during my time at Bocconi, I was fascinated by the invisible architecture of leadership—how the right person in the right role can shift an entire trajectory.
Before founding W Executive, I served as Partner in a major international executive search firm. That gave me breadth. But launching W Executive gave me depth and skin in the game. Today, we operate in 5 countries with over 400 professionals, and I’ve personally coordinated more than 7,000 projects for VCs, scaleups, and startups across Europe in the past 15 years. At its core, this work is about trust. Supporting founders, investors, and leaders at pivotal moments is both a responsibility and a privilege I take very seriously.
2. You’ve often said that a successful career is about long-term vision, not short-term wins. What’s the most common mistake you see talented professionals make when managing their own path?
Too many talented professionals confuse movement with progress. They chase titles, brands, or short- term pay bumps—without asking if those steps actually serve their long term trajectory.
The truth is that careers compound like investments. The professionals who grow fastest over time aren’t the ones who collect quick wins, but those who deliberately seek learning curves—even when it means discomfort or delayed recognition.
McKinsey’s research on “experience seekers” confirms it: professionals who prioritize growth over status see significantly higher long-term wage progression. The same applies to companies. A 2024 McKinsey study showed that long-term-oriented firms outperform short term players by nearly five percentage points annually—because they invest in leadership, trust, and culture.
The same rule applies to people: when you optimize for learning, not optics, you build resilience, depth, and credibility. Short-term sacrifice isn’t a detour. It’s the fastest way to long-term leverage.
3. As a headhunter, you’ve had a front-row seat to how leadership is evolving. What qualities are truly non-negotiable in today’s C-level roles, especially in fast-scaling companies?
In high-growth contexts, leadership is no longer about control—it’s about clarity, adaptability, and human depth. Three qualities are non-negotiable:
1) Executional clarity: Vision means nothing without execution. Leaders must translate ambition into clear, operational roadmaps.
2) Learning agility: The best C-levels today know how to unlearn. They challenge assumptions, stay curious, and ask more than they answer in their first 100 days. In scaleups, ego-free adaptability is a superpower.
3) People-centricity: Leadership is now relational. Emotional intelligence, psychological safety, and the ability to engage hybrid, diverse teams are not “nice to have”—they’re business-critical. Culture scales through behavior, not slides.
4. How do you balance data and instinct when selecting a candidate? Has technology changed the way you assess people?
At W Executive, we use proprietary tools like the W Leadership Index and W Digital Index to assess leadership capabilities, digital readiness, and organizational fit with precision. But data without method is just noise. And method without experience is theory.
Having personally conducted over 11,000 interviews in the past 15 years, I’ve developed what I call “evidence-based intuition”: not gut feeling, but a trained ability to detect signals, ask the right questions, and anticipate outcomes, because I’ve seen, studied, and solved similar dynamics at scale.
What drives successful outcomes is still professional judgment, shaped by experience, not instinct. We don’t guess. We diagnose.
5. What’s the biggest blind spot founders tend to have when hiring their first leadership roles?
Three common blind spots:
1) Hiring for pedigree, not context fit. Big-name resumes are tempting, but success in a structured, resource-rich environment doesn’t always translate to scaleup chaos.
2) Underestimating onboarding. Even the best hires can fail without a structured, intentional integration. According to Gartner, 40% of executives fail within 18 months, often due to poor onboarding, not poor skills.
3) Undervaluing the complexity of HR. Relying on real professionals, internally or externally, is not a luxury, it’s a growth enabler. Too often, we’re overconfident in assessing people even though choosing the right candidate is hard, and doing it without solid recruitment experience is risky.
6. AND HOW TO AVOID THESE blind spotS?
1) Hire for adaptability, not just past success.
2) Design onboarding like you design product.
3) Treat HR as a core strategic function.
4) Bring in experts when the cost of failure is high
7. Looking back at your own path, is there a piece of advice you wish someone had given you earlier? Or a lesson that still shapes the way you work today?
Early on, I was happy when I received visible wins—titles, applause, momentum. But the experiences that truly changed me were the hardest ones: complex projects, no spotlight, no certainty. That’s where you build judgment, resilience, and real leadership.
Over time, I’ve learned to value depth over speed and above all, to invest energy not just in personal growth, but in helping the people around me grow too. The best leaders I’ve met are those who are willing to step back so others can step forward, who lift others without needing the credit. Because in the end, the big trophies are lifted together.
8. You’ve been close to Endeavor for some time now through a strong and ongoing partnership. What makes the Endeavor community stand out, and why is it important to support entrepreneurs at scale?
Endeavor isn’t just a network—it’s a catalyst. What sets it apart is the quality of the entrepreneurs, the generosity of the community, and the shared belief that scaling a company also means scaling yourself.
The multiplier effect is real: founders support founders, across 40+ markets, with radical honesty and zero ego. Capital and mentorship are curated—not transactional—but tailored to each phase of growth. What I value most is the alignment of values: long-term vision, high ambition, and the drive to build something meaningful. As a founder myself, I know how lonely and complex scaling can be. That’s why I see my partnership with Endeavor not just as a professional role, but as a way to give back to the same ecosystem that I believe in.