The Fractional Founder: Jamie Henning’s Blueprint for Entrepreneurial Freedom

Jamie Henning's journey from Executive Assistant to entrepreneur is a testament to the power of perspective and perseverance. Initially an 'accidental entrepreneur,' Jamie's leap of faith led to the creation of J Force, a transformative service for founder-led businesses. In this Wantrepreneur to Entrepreneur Spotlight, discover how Jamie's unique insights into the "Founder-as-Executor Trap" inspired the development of the CEO Operating System and The Fractional Founder. Her story highlights the importance of surrounding yourself with believers and embracing the evolution from support role to strategic partner, all while redefining the path to sustainable business success.

Hi, Jamie Hennning! Thanks for joining us today. Tell us about your business. Who do you serve, how do you serve them, and what's the impact that your business and work makes?

I’ve spent my career orbiting founders, and it’s given me a view of their struggles that most people never get, and a perspective that you only get from having sat on both sides of the table.  I’ve been the business partner, the business observer, and now the business owner.

I started as an Executive Assistant, where I had a front-row seat to how CEOs actually operate: where their time goes, where the bottlenecks hide, and what quietly falls apart when no one’s watching. Then something unexpected happened. I started managing a chapter of YPO as a side hustle - and word spread. Three more chapters came to me. What began as extra income and a passion for helping and being around high-performing executives became the launchpad for my business. Today my business manages four YPO chapters, working alongside founders through their strategy sessions, their hardest decisions, and their most vulnerable moments. I’ve seen what makes founder-led businesses thrive, and I’ve seen the patterns, lack of processes, and personal fears and insecurities that make them stall.

I call it the “Founder-as-Executor Trap.” The CEO builds the business around themselves, becomes the bottleneck, and can’t see the structural problem because they are the structural problem. I know it intimately because I was living in it too, when I first started my business; all founders bootstrap and do it alone initially until the revenue starts coming in.  By then, they’ve already created a habit and pattern of doing it all themselves that’s hard to break.
That realization, sharpened by completing Harvard Business School’s Program for Leadership Development, is what J Force is built around. I’m creating the CEO Operating System, a diagnostic assessment that helps founders finally see the invisible barriers keeping them stuck, and The Fractional Founder, an ongoing strategic advisory service that gives them a real partner in rewiring how their business runs - without the full-time executive price tag.

There are millions of founder-led businesses where the CEO is the single point of failure and doesn’t know it. I’ve sat beside these leaders for years. Now I’m building the tools I wish someone had handed us sooner.

Tell us about the moment you finally felt like you went from wantrepreneur to entrepreneur.

Finishing the Harvard Business School Program for Leadership Development was a turning point in my journey. I came out of the program with a plan and roadmap for what the next phase of my business looked like and how to scale it, and I felt the momentum that you feel from putting in the work and knowing it's coming to fruition. 

Describe the moment or period in your life/career that motivated you to make the entrepreneurial leap.

I consider myself an 'accidental entrepreneur' who gained momentum once I became one.  I took a huge leap of faith when I quit my W2 job and I didn't have the confidence or that entrepreneurial drive that a lot of entrepreneurs talk about.  I borrowed a lot of faith, confidence, and conviction that OTHER people had in me and I listened to them, and faked it until a I made it, and now I can't imagine doing anything else, but my moment was less of a lightning strike than a lot of other stories, and I think being honest about that is valuable.

Describe a tool, service, or software that has been a game-changer for your business. How does it contribute to your success?

Claude.ai has been a game change for me and my team.  It's a really powerful AI tool that works as a great thought partner and has helped me refine many of my business SOPs, pricing models, etc.  It's also helped organize my calendar, schedule, and daily operating rhythm. 

We know that success is very often a non-linear path. Tell us about a failure, pivot point, or lesson that changed your course or direction and helped to get you where you are today.

The first client that I lost, was because I had to walk away from them.  It was a with a client that did not value the level of partnership that my company brought to servicing their organization; they wanted an admin to do what they said, they were not looking for a collaborative business partner that brought strategy and subject-matter expertise and it caused a lot of strife and misalignment.  The lesson I learned is that while we may have to service and cater to clients, there are also choices and it's why we start our own companies, and not every client will align with our values, vision, and capabilities and that's OK.  I learned it's OK to be selective in the clients I take on and that to let go of the ones that no longer serve the business and its mission and values. 

What unconventional strategy did you employ that significantly impacted your business?

I brought a fractional and professional services level of service to the YPO chapters I serve. Chapters have historically brought on a single Chapter Director to run their back end operations and serve as the community manager for the membership, and I implemented a model that leverages a team of people to provide the same level of service members get from a single, dedicated resource, and I get to focus on the parts of the role that only I can do, which is helping the boards build strong, engaged chapters, bring years of YPO historical knowledge and expertise, and focus on building relationships with the members, instead of admin.

What’s something you wish you knew sooner that you’d give as advice for aspiring or newer entrepreneurs?

There are so many people rooting for you and who believe in you!  We tend to be hardest on ourselves, but if you let people in on our goals and your vision, you'll find they want to support you morally, and they'll help you tangibly - by giving you resources, advice, and an ear to bend when you're having your worst days.  You don't have to do it alone!

Want to dive deeper into Jamie's work? Check out the links below!

• Connect with Jamie Henning on LinkedIn: Jamie Henning
• Follow  J Force on LinkedIn:  J Force
• Follow J Force LLC on Instagram: @jforcellc
• Find J Force LLC on Facebook: J Force