Jonathan Raymond
Executive advisor to CEOs and leaders in Portland, Oregon
| Hourly rate range | $175 to $325 an hour |
|---|---|
| Focus areas | CEO and founder coachingLeadership developmentTeam performanceConflict and difficult conversationsLeadership and team building |
| Works with | Executives, Founders and business owners and Managers |
| Also coaches | Business coach and Life coach |
| Based in | Portland, Oregon, United States |
| Sessions | Online and in person |
Jonathan Raymond works with CEOs and their leaders to build a culture of high accountability through direct and kind conversations. He ran someone else's company for five years and has run his own for ten. He is the author of Good Authority, which has sold more than 500,000 copies. He takes on only eight companies a year and works with each one for a full year.
What Jonathan helps with
Jonathan helps CEOs who feel the culture slipping as the company grows. He also works on the hard conversations leaders have been putting off.
- Feeling like the company culture is being lost
- Disagreement moving to back channels
- Leaders avoiding hard conversations
- Balancing high standards with care for people
- Building accountability across a leadership team
- Keeping culture strong as headcount grows
- Bringing AI into the company on purpose
Who Jonathan works with
Jonathan works with a CEO and their leadership team inside one company for a year. He sees the most value when a company is past a hundred people and the culture can still be shaped. He takes on eight companies a year.
How Jonathan works
The work is built on the Good Authority method. It teaches leaders to use enough authority to be useful, and not so much that people disappear. The year starts with a talk to the whole company. Jonathan spends two days on site with leaders at the start, and one more day mid-year. He adds video time when it helps. The CEO can reach him and hear back the same day. Ren, a tool shaped to the company, carries the approach to everyone.
Background and qualifications
Jonathan ran someone else's company for five years. He has run his own company for the last ten. He is a former CEO of EMyth and has been published in Harvard Business Review. He wrote Good Authority, which has sold more than 500,000 copies. Leaders at Apple, Amazon, TikTok, Strava and Fidelity read it. Clients include people at Amazon, TikTok, Okta and Panasonic.
Jonathan Raymond pricing
Programs and services
- Year-long CEO and leadership engagement
- Two days on site to start the year
- One mid-year on-site visit
- Talk to the whole company
- Same-day access for the CEO
- Video sessions with leaders
Jonathan Raymond reviews
The CoachVouch take
He wrote the 500,000-copy book Good Authority and works with only eight companies a year.
Best for CEOs of growing companies who want to keep standards high and keep the culture caring.
Common questions
How much does Jonathan Raymond charge?
Coaching with Jonathan runs $175 to $325 an hour. Request an intro for an exact quote.
What does Jonathan Raymond help with?
Jonathan Raymond helps with feeling like the company culture is being lost, disagreement moving to back channels, leaders avoiding hard conversations and balancing high standards with care for people.
Does Jonathan Raymond coach online?
Jonathan is based in Portland, Oregon, United States. Sessions are online and in person.
How many companies does Jonathan Raymond work with?
He works with eight companies a year. Each engagement lasts a full year.
Does Jonathan Raymond work with the whole leadership team?
Yes. He works with the CEO, the leaders, and gives a talk to the whole company.
How do I contact Jonathan Raymond?
Request an intro on this page. It's free, and we'll connect you with Jonathan and, if you want, 2 or 3 similar coaches to compare.
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Last updated September 2026. Request a correction.