
Executive coach for scaling founders and executives | 3 startup exits | 2 Fortune 500 exec roles | Harvard MBA
Your company is scaling fast. Are you? I've sat where you're sitting. Fundraise closed. Team doubles overnight. Board expectations shift from patient to pressing. And suddenly, the playbook that got you here stops working. After three startup exits and two Fortune 500 executive roles, I learned something counterintuitive: The moments that make or break leaders aren't operational—they're personal. They're identity shifts disguised as business problems. Nobody tells you this part: You close a deal or round—and suddenly you're managing egos, not just metrics. Your team doubles—and your hands-on approach starts choking growth. You become CEO—and execution stops being your job; influence does. These aren't tactical adjustments. They're identity crises. And if you can't evolve as fast as your reality changes, you become the bottleneck. I coach leaders through these exact transitions. Not with "how was your week?" check-ins, but with frameworks forged from 20+ years building and scaling companies. We work on real situations—that board presentation, the co-founder tension, the strategic pivot you've been avoiding. My approach is different: When you need tactical tools, I'm your advisor. When patterns hold you back, I'm your coach. When you need someone who's walked this path, I'm your mentor. The role shifts based on what the moment demands. How we work together: - 1:1 Coaching: 2x month sessions plus support for high-stakes moments - Co-founder Alignment: transform tensions into competitive advantage - Executive Team Sessions: move from endless debate to clear decisions If you're navigating the gap between who you are and who your role demands, let's talk. hello@dileepansiva.com
ebayinc.com
nuorder.com
twitter.com
synergos.org
symphonycommerce.com
ndi.org
unsure.com
Los Angeles, California, United States
Dileepan Siva
Executive Coach
Jan 2022 - Present
Los Angeles Metropolitan Area
Founder + CEO
Upscribe
• www.linkedin.com/company/upscribesubs
Jan 2020 - Dec 2024
Los Angeles Metropolitan Area
Senior Advisor (acquired by Lightspeed)
NuORDER
• www.linkedin.com/company/nuorder-inc
Jul 2018 - Dec 2018
Los Angeles Metropolitan Area
Chief Revenue Officer (acquired by Limelight)
Moovweb
• www.linkedin.com/company/moov-corporation
May 2016 - Dec 2018
San Francisco Bay Area
Strategic Partnerships
• www.linkedin.com/company/twitter
May 2015 - Apr 2016
San Francisco Bay Area
Head of Sales (acquired by Quantum Retail)
Symphony Commerce
• www.linkedin.com/company/symphony-commerce
Jun 2013 - May 2015
San Francisco Bay Area
edg.io