Josh Lillie

Josh Lillie

Verified

Startup & GTM Leader | Director at Databricks | AI Advisor & Early-Stage Investor

I specialize in

Marketing & GTM
Building with AI
Career Advancement
AI strategy
GTM Strategy
Founder Coaching
Hiring

Databricks startup director helping founders turn data to edge

Background & Highlights

Director, Startups

Databricks

2022 – 2024

Databricks

Resident Expert

AI2 incubator

2026 – Present

Limited Partner, Stage 2 Capital Catalyst

Stage 2 Capital

2023 – Present

Stage 2 Capital

Global Business Program Manager, Digital Sales

Microsoft

2017 – 2022

Microsoft

About me

Startup & GTM Leader | Director at Databricks | AI Advisor & Early-Stage Investor I’ve spent my career helping startups scale—first as a top-performing seller, then as a go-to-market leader at Microsoft, and now as Director of Startups at Databricks, where I help founders turn data into a competitive edge. I’ve worked with everyone from early-stage scrappy builders to scaling unicorns—and I know firsthand how messy and ambiguous growth can feel. My goal is to help you cut through the noise, make smart, confident decisions, and build something that lasts. What I Can Help With: ✅ Early GTM strategy ✅ AI product positioning ✅ Founder sales coaching ✅ Scaling startup teams ✅ GTM career growth Whether you're figuring out your wedge, pitching your first few customers, or trying to scale something that’s finally working—I’ve been there, and I’m happy to help.

You'll get advice on

  • Early GTM strategy
  • AI product positioning
  • Founder sales coaching
  • Scaling startup teams
  • GTM career growth

Real feedback from real sessions

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