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. This is the story of how I got here.

Portrait of Olga Skipper
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.

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 story

Work with me

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

Getting unstuck, transitioning into a new role, crafting a strategic approach to leadership, or resolving leadership, ownership and investor conflicts. I may combine the roles of coach, mentor or consultant depending on what you need.

Olga Skipper in a coaching session chair

Core offer

1:1 executive coaching

A six-month partnership for founders, business owners, C-suite leaders and investors. Most of my work happens here — deep, confidential and fully tailored to you.

Single sessions

One focused conversation for a decision that can't wait

Teams & groups

Founder & executive teams · Mastermind circles · Mediation, workshops

Advisory

People due diligence · Innovation strategy · Internationalisation & people strategy

Certified Organisational & Executive Coach, Columbia University · MBSR, UMass Chan Medical School · Coaching in English, German & Russian · Techstars mentor

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.

  • 01Why most business problems are relationship problems — Season 3 trailer
  • 02Human-first in an AI world, with Alina Verbenchuk
  • 03Leading into the unknown, with Lana Khimka
  • 04Anchoring with intention, with Julia Derndinger

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

Writing

Notes from the coaching room.

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.