Anna Skrypka
Anna Skrypka

Former Autodesk Japan GTM Leader ($40M ARR) | Ex-Toyota Brand Strategist | Cultural Intelligence for AI & Tech Expansion

About me
LinkedIn

I fix go-to-market where Western playbooks break — in Japan and across cultures. I spent 15 years building and rebuilding GTM in Japan and APAC, often at the moments where strong products fail due to cultural misalignment rather than execution. At Autodesk Japan, I rebuilt the GTM motion and helped to scale SaaS business revenue from $0.5M to $40M ARR, then extended the model to Korea ($7M ARR) and APAC cloud products ($11M ARR) by adapting for local buyer behavior. At Woven by Toyota, I led growth and customer success during early product-market fit exploration for an AI-powered HR SaaS with Toyota’s corporate venture team. Earlier, I worked as a Brand Strategist at Toyota Motor Corporation on global brand and digital transformation initiatives. Today, I advise founders and enterprise leaders on Japan market entry, cultural positioning for AI and tech products, and cross-border GTM strategy. I also built SignalGTM, a cultural intelligence diagnostic for market readiness, and mentor Techstars portfolio companies on international GTM, hiring, AI adoption. Who I Help - Global founders entering Japan who have strong products but stalled traction - Japanese founders going global whose messaging works in Japan but fails in US/EU markets - Enterprise leaders in Japan whose GTM works elsewhere but breaks locally - Corporate operators transitioning to enterprisers (founders, advisors, product builders who struggle with own positioning, industry credibility, or investor narrative) My Approach - I don’t give generic startup advice. I diagnose why your GTM is breaking, then give you specific, actionable frameworks to fix it. - Most consultants say “localize.” I show you how: narrative positioning, decision-making flows, trust architecture, and GTM design that actually work across cultures. I’m especially useful when you’re stuck between “we have a great product” and “why isn’t this working in this market?” Also “I don’t know how to go from A to Z, but here’s my vision”

What to expect

15 minute session

  • - gtm and positioning
  • - market expansion reality check
  • - clear “go / not go / fix this first tip
  • - first-time japan or global expansion tip

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