Kevin O'Brien
Executive and founder leadership coach, former cybersecurity CEO
| Hourly rate range | $130 to $255 an hour |
|---|---|
| Focus areas | CEO and founder coachingLeadership developmentEmotional intelligenceConflict and difficult conversationsStrategy and decision makingStartups and foundersLeadership and team building |
| Works with | Executives and Founders and business owners |
| Also coaches | Business coach |
| Credentials | University of Massachusetts Amherst |
Kevin O'Brien is a leadership coach who helps senior executives, founders, and entrepreneurs lead with more skill and authenticity. He co-founded GreatHorn, an email security company, and served as its CEO until it was sold to private equity in 2022. He then formalized his coaching practice and has worked with more than 60 leadership coaching clients. He focuses on authenticity, C-level conflict, board dynamics, and strategic change management.
What Kevin helps with
Kevin works with leaders on the human and strategic sides of running a company. He focuses on conflict at the top and on leading through change.
- Building authenticity as a leader
- Resolving conflict at the C-level
- Handling complex boards
- Strategic change management
- AI strategy
- Emotional intelligence
- Ethical leadership
Who Kevin works with
Kevin works with senior executives, founders, and entrepreneurs. He is also interested in working with entrepreneurs and executives who are earlier in their careers.
Background and qualifications
Kevin spent over a decade as a working CEO in the cybersecurity space. He co-founded GreatHorn in 2015 and led it from start to exit, raising venture capital along the way. The company was sold to private equity in 2022. He has a background in venture capital, board management, and entrepreneurship. He has mentored for Techstars for 10 years and served on state advisory boards focused on leadership and talent. Since October 2022 he has been an independent board director at a B2B SaaS platform for registered apprenticeships. He studied at the University of Massachusetts Amherst.
Kevin O'Brien pricing
Programs and services
- Leadership development program of 10+ hours of coaching
- Custom hourly coaching
Kevin O'Brien reviews
The CoachVouch take
He is a founder who ran a company through a private equity exit and now coaches leaders on boards, conflict, and change.
Best for founders and senior executives who face board issues, C-level conflict, or major change.
Common questions
How much does Kevin O'Brien charge?
Coaching with Kevin runs $130 to $255 an hour. Message Kevin from this page for an exact quote.
What does Kevin O'Brien help with?
Kevin O'Brien helps with building authenticity as a leader, resolving conflict at the C-level, handling complex boards and strategic change management.
Is Kevin O'Brien certified?
Kevin O'Brien lists: University of Massachusetts Amherst.
Has Kevin O'Brien run a company himself?
Yes. He co-founded GreatHorn and served as its CEO from 2015 until the company was sold to private equity in 2022.
Does Kevin O'Brien coach on AI strategy?
Yes. AI strategy is one of the topics he lists, along with change management and conflict resolution.
How do I contact Kevin O'Brien?
Send Kevin a message from this page. It's free and takes a minute.
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Last updated September 2026. Request a correction.