Kevin O'Brien
Executive and entrepreneurship coach for founders in Boston
| Rate | $250 to $500 per hour |
|---|---|
| Focus areas | CEO and founder coachingLeadership developmentTeam performanceConflict and difficult conversationsTransitions and new rolesStartups and foundersScaling and growthLeadership and team building |
| Works with | Founders and business owners and Executives |
| Also coaches | Business coach |
| Based in | Boston, Massachusetts, United States |
| Credentials | BA in Philosophy, University of Massachusetts Amherst |
Kevin O'Brien is an executive and entrepreneurship coach in Boston, Massachusetts. He helps founders and senior executives lead through uncertainty. Kevin is a former technology CEO and founder with 25 years of experience building, leading and selling startups. He has raised over $30m USD and managed complex exits. He has also served as a mentor, advisor and board director for multiple companies.
What Kevin helps with
Kevin works with leaders who face change, conflict and uncertainty. He helps them grow as authentic and effective leaders.
- Navigating complex dynamics and major change
- Managing and resolving conflict
- Handling market changes, downturns and pivots
- Scaling teams up or down while keeping trust and results
- Leadership development
- Fundraising
- Product market fit
- Early stage go-to-market issues
Who Kevin works with
Kevin works with founders and senior executives. His clients are leaders who deal with uncertainty, team growth, market shifts and conflict. He also supports early stage companies working on fundraising, product market fit and go-to-market plans.
Background and qualifications
Kevin is a former technology CEO and founder. He has 25 years of experience working in, building, founding, leading and selling startups. He knows the venture-backed world well. He has raised over $30m USD, led multiple companies and managed complex exits. He has served as a mentor, advisor and board director for multiple companies. He holds a BA in Philosophy from the University of Massachusetts Amherst.
Kevin O'Brien pricing
Programs and services
- Free consultation
Kevin O'Brien reviews
The CoachVouch take
A former technology CEO and founder who has raised over $30m USD and managed complex exits.
Best for founders and senior executives who face change, conflict or pivots in a startup.
Kevin's rate sits above the range most executive coaches charge ($102 to $238 an hour).
Common questions
How much does Kevin O'Brien charge?
Kevin O'Brien's rate is $250 to $500 per hour.
What does Kevin O'Brien help with?
Kevin O'Brien helps with navigating complex dynamics and major change, managing and resolving conflict, handling market changes, downturns and pivots and scaling teams up or down while keeping trust and results.
Is Kevin O'Brien certified?
Kevin O'Brien lists: BA in Philosophy, University of Massachusetts Amherst.
Has Kevin O'Brien worked in venture-backed companies?
Yes. He has 25 years of experience with startups and has raised over $30m USD. He has also led multiple companies and managed complex exits.
How do I contact Kevin O'Brien?
Request an intro on this page. It's free, and we'll connect you with Kevin and, if you want, 2 or 3 similar coaches to compare.
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Last updated September 2026. Request a correction.