I'm Jenn. An entrepreneur, speaker, writer, and former Fortune 100 executive dedicated to helping you lead from within to drive real outcomes.
"Some things are in our control and others not... The things in our control are by nature free, unrestricted, unhindered..."
- Epictetus
Hey!
About jenn
Two decades inside Fortune 100 organizations. A philosophy professor who changed everything. A deer behind a corporate fence. And a framework built to keep leaders free — including myself.
I learned leadership the hard way.
In my early 20s, my life was a mess. Toxic relationships. Failing out of college. Feeling unseen and stuck in a story I hadn't chosen. One afternoon, a dean looked at my transcript, looked at me, and asked a single question: "What happened to you?"
It cracked something open. A philosophy professor finished the job by handing me a worn copy of Epictetus. Focus only on what you can control. That one idea became my anchor. I rebuilt from it — finished my degree while working full time, found my footing, and eventually climbed to an executive seat at a Fortune 100 company.
the story
It started in the wreckage.
Then one afternoon, standing at the top of what I thought I'd wanted, I looked out a corporate window and saw a deer standing behind a fence. She was trapped. And I realized — so was I.
Toxic leadership. Stalled progress. A culture that drained rather than developed. I began to question the very strengths that had gotten me there. So I left. I took with me a draft manuscript I'd started years earlier and a clarity about what leadership could and should look like.
That work became The LEAD Framework™ and the LEAD By Choice™ programs — designed to transform leaders from the inside out so they drive better outcomes at work and build a life they actually want.
"Some things are in our control and others not. The things in our control are free, unrestricted, unhindered."
— Epictetus
the work
For more than two decades, I led transformation inside Fortune 100 organizations — working at the intersection of leadership, communications, and human capital before I ever called myself a coach.
I developed leaders across technology, financial services, and corporate transformation. I launched products, drove $300M+ initiatives, and sat in rooms where the stakes were real and the pressure was constant.
Now I bring that lived experience to executives, business owners, and high-achievers ready to close the gap between where they are and what they know they're capable of.
Every engagement is built on The LEAD Framework™ — the same methodology I use daily to stay steady, strategic, and clear under pressure.
Twenty years in the room.
Now I help others lead it.
$300M+
In initiatives led across enterprise transformation and strategic planning
200+
Senior leaders developed across technology and financial services
25+
Years inside complex organizations, Fortune 100 executive roles spanning communications, strategic planning, and transformation
credentials
The experience behind the work.
Founder, Jenn Cloutier International · SVP, MDL Executive Network · ICF New England Board, VP, Marketing & Communications
current
Communications · Marketing · Business Transformation · Strategic Planning · Leadership Development · Human Capital
functional expertise
Financial Services · Insurance · Technology · Healthcare · Coaching · Consulting
industry experience
chocolate & rose, the perfect combo
my beagle, Always with me
a few more things
The person behind the work.
happiest by the beach, dressed in all linen
Getaways, golden lattes, coco chanel parfum, self care, and chapstick, are my go-to classics
- jennifer L., senior leader
what people say
She creates space for the kind of honest conversation most people avoid. Working with Jenn means being seen — really seen — and leaving with more clarity than you walked in with.
"Jenn is genuine, relatable, and has had significant positive impacts on my personal and professional life."
- cori s., service leader
what people say
She met and exceeded my expectations!
Jenn offered a safe space so I could process my self-limiting beliefs.
ready to work together?
Whether you're ready to start or just want to explore what's possible — all of it begins with a conversation. Let's talk.
