E113: Work Less, Grow More: Jill James' Blueprint for a Self-Sustaining Business

Scaling Expertise

What if the biggest thing holding your business back… is you?

In this episode of Scaling Expertise, I sit down with Jill James, founder of The Jill James, a fractional COO firm that helps expert founders scale without burning out or staying stuck in operator mode. Jill built her firm by asking one powerful question: “How can I help people do the work they love without being buried in admin?”

We dig deep into the invisible costs of overwork, the identity shift from doer to leader, and the moment Jill realized she needed to break her own rules to scale. If you’re feeling like your business can’t run without you, this episode is your wake-up call.

Jill shares hard-earned wisdom from scaling businesses to $10M+ and offers actionable ways to reclaim your time, build operational clarity, and let go of control—without compromising your vision.

Key Takeaways:

• Founders can be the bottleneck. If your business can’t function without you, it’s not scalable.
• Don’t sell your time—sell your thinking. Experts grow when they stop doing and start designing systems.
• Scaling isn’t about doing more—it’s about doing less, better. Create space so the business can operate without you.
• You don’t need to be a “visionary.” You just need to be clear about where you want to go.
• Resist the "fixer" urge. Let your team solve problems so they can grow into their roles.
• Fractional leadership. This can help expert founders transition out of operator mode with structure and sanity.

Jill is a featured author in The Wisdom Collection: Stories That Transform How We Live, Connect, and Lead—an anthology of powerful insights from business leaders who’ve built, failed, and figured things out the hard way so you don’t have to. Each chapter is practical, quick to read, and full of hard-won wisdom.

The book launches June 24 and will be available for just $1.99 during its first 24–48 hours.

Want the launch link or more details? Check out Jill’s announcement post on LinkedIn.

Resources Mentioned in the Episode:

🔗 Check out Jill’s firm: The Jill James

📬 Get her insights: Subscribe to the newsletter

🤝 Connect via Beehiiv

More About Our Guest:

Jill James is CEO & Founder of The Jill James. As a recent client summed up, she is what would happen “if you could hire Sallie Krawchek, Dany Garcia, and Mackenzie Scott to run your company.” Jill started her career in New York City as an investment banking analyst with J. P. Morgan and personal wealth planner with AXA Financial (now Equitable). She moved to tech start-ups and held nearly every non-programming job in early stage companies, including product, marketing, sales, and C-level leadership. She used these experiences to found The Jill James in 2015, and now partners with self-funded founders to grow and run purpose-aligned companies.

At the University of Chicago, she earned a BA with honors in Political Science from The College and an MBA in entrepreneurship, strategy, and marketing from Booth School of Business. Originally from Greenwood, Wisconsin, Jill lives in Los Angeles with her kiddo and their very squeaky guinea pigs. She writes a weekly Beehiiv newsletter for owner/operators of small businesses. Learn more at thejilljames.com, including a video introduction and our most recent newsletters and blog posts.

Connect with Jill James:

• Website
• LinkedIn
• Instagram
• Bluesky

Charity: https://www.wearebgc.org/

Connect with Erin to learn how to Turn Your Expertise into Scalable Recurring Revenue.

LinkedIn: www.linkedin.com/in/erinaustin/

Think Beyond IP YouTube Page: https://www.youtube.com/channel/UCVztXnDYnZ83oIb-EGX9IGA/videos

Music credit: Paphos by Mountaineer

A Team Dklutr production