David Hollestelle
Executive and career coach for tech, VC and PE professionals
| Hourly rate range | $95 to $175 an hour |
|---|---|
| Focus areas | Job searchInterview coachingTech careersMilitary transitionExecutive presence and communicationTransitions and new roles |
| Works with | Professionals and Executives |
| Also coaches | Executive coach and Business coach |
| Sessions | Online |
| Credentials | Master's in Coaching in progress, University of Texas at Dallas (ICF accredited, expected 2026); Working toward ICF Associate Certified Coach (ACC) |
| Practice | Hollestelle Holdings |
David Hollestelle is a career and executive coach for people in tech, venture capital and private equity. He has over 15 years of experience recruiting and leading teams at companies like a16z, Meta, Intuit and Zoom. He knows how hiring works from the inside. He left the military earlier in his career and now coaches others through career moves. He is finishing a coaching master's degree that is accredited by the ICF.
What David helps with
David helps professionals move through career changes and hiring processes in tech, venture capital and private equity. He also covers AI careers and cybersecurity.
- Landing a job in AI and machine learning
- Breaking into top AI and Web3 companies
- Understanding what happens during the hiring process
- Building a career in venture capital or private equity
- Setting career goals and finding strengths
- Moving from the military into a new career
- Product development with AI
Who David works with
David works with individuals building careers in tech, venture capital and private equity. His offerings also cover people who want to break into AI careers, and those exploring cybersecurity or executive coaching.
Background and qualifications
David has over 15 years of experience recruiting and leading teams for companies like a16z, Meta, Intuit and Zoom. He was a recruiting leader at Andreessen Horowitz from April 2022 to February 2024. In 2024 he worked as a Talent Acquisition Consultant at Intuit, and later hired AI and ML talent. He is Principal at Hollestelle Holdings, a professional services firm for talent acquisition and marketing communications. He is studying for a Master's in Coaching at the University of Texas at Dallas, and is working toward ICF ACC certification.
David Hollestelle pricing
Programs and services
- One-on-one coaching sessions
- Executive coaching
- Venture capital coaching
- AI career coaching
- Cybersecurity coaching
David Hollestelle reviews
David Hollestelle has a 4.9 out of 5 rating from 73 reviews on Leland, as of September 2026.
The CoachVouch take
A former a16z recruiting leader who coaches tech, VC and PE professionals on how hiring really works.
Best for tech, VC and PE professionals who want to land a job or move up, and want advice from a longtime recruiter.
Common questions
How much does David Hollestelle charge?
Coaching with David runs $95 to $175 an hour. Request an intro for an exact quote.
What does David Hollestelle help with?
David Hollestelle helps with landing a job in AI and machine learning, breaking into top AI and Web3 companies, understanding what happens during the hiring process and building a career in venture capital or private equity.
Does David Hollestelle coach online?
Sessions are online.
Does David Hollestelle have reviews?
David Hollestelle has a 4.9 out of 5 rating from 73 reviews on Leland, as of September 2026.
Is David Hollestelle certified?
David Hollestelle lists: Master's in Coaching in progress, University of Texas at Dallas (ICF accredited, expected 2026); Working toward ICF Associate Certified Coach (ACC).
Does David Hollestelle help people get AI jobs?
Yes. He offers coaching on breaking into AI careers and landing roles as an AI or ML engineer. He has also recruited AI and ML talent.
Has David Hollestelle worked with people leaving the military?
He left the military himself and was helped by coaches and mentors during that move. That experience is why he coaches.
How do I contact David Hollestelle?
Request an intro on this page. It's free, and we'll connect you with David and, if you want, 2 or 3 similar coaches to compare.
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Last updated September 2026. Request a correction.