ADVICE | STRATEGY | MENTORSHIP

Leading can be heavy.
Let’s share the load.

Empathetic support and experience-based strategy. For emerging and experienced organizational leaders who want to rise to every occasion.

Hi, I’m Jonathan Bennett, a founder, entrepreneur, longtime board director, and business generalist turned trusted advisor and strategist. 

After joining the C-Suite of a large hospital, I spent a decade building a management consulting company. We served over 200 organizations nationwide and became a proud B Corp.

Then, in 2021, I sold up and moved on to my next adventure: serving not just organizations but the leaders who run them through trusted advisory, professional mentorship, and strategy services.

“Jonathan is a one-stop shop. Whether it's government relations, governance, communications, issues management, crisis communications, HR, business, politics, or the social stuff. Who knows you, knows your career, and believes in you, but who also understands all those things? Once he is invested in your success, he’s all in. I don’t know how I would have navigated my path without him.”

Hon. Maryam Monsef, CEO, Onward | Former Minister of Women and Gender Equality, Govt. of Canada

Lead with confidence and compassion.

My goal is clear: stand in your corner and share the calm confidence and optimistic perspective I’ve gained from having been through it before—and knowing there is always a way through.

I CAN HELP YOU GET THERE WITH:

Professional Mentorship

FOR NEW LEADERS

For emerging and mid-career leaders who are confident in their fields but new to leadership. And experiencing self-doubt, imposter syndrome, and overwhelm.

Trusted
Counsel 

FOR EXPERIENCED EXECS

For senior leaders navigating complex issues with lots of ambiguity, high-stakes decisions, and potential paths forward—but no easy playbook to follow.

Strategy
& Planning

FOR TEAMS & BOARDS

For organizations and leaders
who are planning for, rolling out, and navigating change. And want support to make it impactful—
and make sure it sticks.

Team Training
& Workshops

Virtual and in-person sessions are the quickest and most effective way to introduce new perspectives, bring everyone together, and move forward with meaning. I’m available for workshops, retreats, and team training sessions.

BUT WHAT’S IT REALLY LIKE?

Hear Jonathan In Action

Experience the essence of the advisory, mentorship and strategy work I do while gaining practical insight you can apply to your leadership journey by listening in on six actual conversations I’ve had with real (and fully consenting) leaders. Listen anywhere!