Your company is scaling fast. Are you?
I coach leaders to evolve faster than companies scale.
Nobody tells you this part
Every leap forward in the business demands an even bigger leap in you.
You think these are tactical problems. But they’re identity crises.
And if you can’t evolve as fast as your reality changes, you become the bottleneck.
Hi, I'm Dileepan
I’ve walked this path as a leader and coach
Why I coach instead of build?
After 20 years operating, I discovered something unexpected: coaching IS my startup. This is where I'm world-class—not just good, but operating at a different level. Every colleague told me: "You've always been a coach." When I build again, it'll be in this space. Because I've learned that building leaders who scale companies creates 100x the impact of any single venture.
My approach
Experiments, not theory. Practice, not scripts
Coaching with me is not "What would you like to talk about today?" We build on our progress because I'm tracking your evolution between sessions, not just showing up to chat.
I step into the role you need in the moment. Strategic advisor when you're navigating stakeholder dynamics. Performance coach when patterns hold you back. Mentor when you need someone who's been there. Sometimes even champion when you need motivation.
We don't theorize about leadership — we run experiments. Test. Learn. Iterate. The same way you grow companies is how we grow you.
No generic frameworks. No scripted sessions. Just applied practice that works.
How we work together
Scale yourself, fix your partnership, align your team
What clients say
Real transformations from real leaders
Helson Taveras
Co-founder & CTO at Keep Technologies, Series B startup
“Before working with Dileepan, I was still thinking and operating like a founder: reactive, spread thin, and uncertain in high-stakes moments. Through his coaching, I stepped into the operational CEO role and have grown into the kind of leader I once looked up to. I was avoiding the exact conversations that would unlock our growth – tough feedback with executives, strategic planning, even celebrating wins. Dileepan showed me these avoidance patterns were my biggest bottleneck. He helped me restructure our leadership team, navigate major organizational changes, and finally stop waiting for permission to lead strategically.”
Kian Raiszadeh
CEO @ SpineZone, Series A startup
"I was drowning trying to manage every aspect of my company—board dynamics, team building, and my own emotional rollercoaster. Dileepan became my strategic partner, helping me transform from overwhelmed founder to confident CEO. He taught me to distinguish what only I could do versus what to delegate, showed me how to prepare for board meetings with authority instead of anxiety, and helped me build systems that let the business run without me micromanaging. Now I lead with clarity instead of chaos, and my team finally has the space to excel."
Alice Bisgrove
SVP @ Procore (NYSE, 4000+ employees)
“When my strategic initiatives weren't gaining traction with leadership, Dileepan helped me change my approach. He taught me to identify stakeholder dynamics, own my wins, and advocate strategically. I applied his frameworks immediately – turning a potential million-dollar loss into a company-wide victory that got CEO attention. Six months later: promoted to SVP. But the real transformation? I stopped waiting for permission to be strategic. Now I shape company direction beyond just legal. His coaching was the catalyst for the biggest impact of my career."