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Oliver Grant

Oliver Grant

VP of Engineering · Datadog
4.9 (52 reviews) Accepting mentees
18 yrs experience 210 sessions held Replies within 12 hours English

About

I've grown engineering orgs from 5 to 200. I coach senior leaders on scaling teams, org design, and navigating the path to VP and beyond.

I focus on long-term mentorship rather than one-off advice. We'll set clear goals, work through real problems from your day-to-day, and check in consistently so you actually build momentum. Expect candid feedback, frameworks you can reuse, and someone genuinely invested in you reaching the next level.

What I can help with

Executive Coaching Org Design Scaling Teams Strategy Career strategy Mock interviews

Experience

VP of Engineering

Datadog
2021 — Present

Senior Engineering

Amazon
2017 — 2021

Mid-level Engineer

GitHub
2013 — 2017

Reviews 4.9 · 52

Elena Vasquez
Elena Vasquez
2 weeks ago · ★★★★★

Working with Oliver completely changed how I approach my work. Every session was packed with practical, actionable advice — no fluff.

Raj Patel
Raj Patel
1 month ago · ★★★★★

Incredibly generous with time and knowledge. Oliver pushed me to think bigger and held me accountable to my goals. Highly recommend.

Chloe Adams
Chloe Adams
2 months ago · ★★★★★

The best investment I've made in my career this year. Clear feedback, real industry insight, and genuinely cares about your progress.

Kenji Watanabe
Kenji Watanabe
3 months ago · ★★★★★

Oliver helped me turn a vague ambition into a concrete plan — and I actually hit it. Worth every penny.