Olga Skipper

Executive coach for founders, CEOs & business owners

Lead with clarity, courage & empathy.

I partner with founders and innovation leaders who are called to find fresh ways of thinking and step into new roles — in business and in life. My work is primarily individual coaching, tailored to you.

Portrait of Olga Skipper

The path to coaching

From restless achiever to executive coach.

I was a startup founder, then an executive at every stage of company growth — from pre-seed to acquisition and IPO, across three continents. I knew how each stage felt. I didn't yet know how I felt.

Read my full storySpeaking & interviews

8+ years
coaching founders and senior leaders
15+ years
in executive roles — CEO, VP, MD
6
coaching certifications, led by Columbia University
3 languages
English, German and Russian

More than theory. Venture-building experience across Europe, the U.S. and Asia as well as a deep coaching training give me both lived and professional insight.

1:1 executive coaching

For founders, executives and innovation leaders in a new chapter.

When to work with me

How I work depends on what you need — sometimes as a coach, sometimes combining the roles of coach, mentor or consultant in one partnership. If you recognise yourself in any of the situations below, that's where I can support you.

  • Launching a new venture or seeking deeper purpose
  • Transitioning into a new executive role with purpose and meaning
  • Feeling burnt out, misaligned, or stuck
  • Conflict with co-founders, board, or leadership team
  • Navigating a major business or life transition
  • Realigning strategy and team dynamics
  • Scaling the leadership team as the company grows
  • Planning and executing succession and M&A
  • Realigning executive team culture and efforts after a key person's departure
  • Investor pressure around people and culture decisions

Selected clients

  • Supercell
  • Praktika
  • Dwelly
  • Rasa
  • Mister Spex
  • Inkitt
  • SpeedInvest
  • Accenture
  • S16VC
  • Inficon
  • Tenjin
  • dltHub
“Olga is extremely professional and just really good at what she does. She keeps her own ego low and never judges, but guides you to the best path.”
Beatrice AliprandiChief Revenue Officer at Praktika
“Olga is an outstanding professional and very warm and caring human being! Olga helped me a lot to achieve our coaching objectives while creating a safe environment to just enjoy the process!”
Ilya DrozdovDwelly co-founder & CEO
“What I valued most was the journey itself - the conversations, reflections, and discoveries along the way. I warmly recommend her to anyone looking for a thoughtful partner on their own journey.”
Mika TammenkoskiSenior Advisor at Supercell

The newsletter

A monthly letter on the human side of building things together.

Leadership, relationships, new podcast episodes and the occasional open seat for 1:1 coaching — straight to your inbox.

The Emotional Business podcast

The human side of scaling a business.

Raw, honest conversations with founders and CEOs about leadership, relationships and the emotions nobody puts in the pitch deck.

Featured episode

Trailer Season 3 - Why Most Business Problems Are Relationship Problems

31 Aug 2026 · 02:59

Interviews & podcast appearances

In conversation.

A few conversations I especially enjoyed — as a guest on other people's shows. More interviews and talks live on the speaking page.

See more or listen to more interviews

На русском языке

Let's meet

Your next chapter starts with a conversation.

A free 25-minute chemistry call to see if we're a good match. If I'm not the right coach for you, I'll happily recommend someone who is.