The Power of Bold: Jess Lane’s Strategy for Redefining Executive Success

After two decades as a high-impact executive, Jess Lane found herself laid off from a unicorn tech company she helped build—a moment that catalyzed her entrepreneurial awakening. Rather than return to the grind, she chose to rewrite the script entirely. Through The Full Cup Co. and her signature product, The Strategic Executive Exit™, Jess empowers leaders to design work that aligns with their purpose. As part of our Wantrepreneur to Entrepreneur Spotlight series, Jess shares how she defied burnout culture, created a new category of transformation, and boldly stepped into the work she was always meant to do.

Hi, Jess! 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?

The Full Cup Co. is a Human Sustainability Design™ company and we help executives transition out of corporate or tech and design their next chapters with The Strategic Executive Exit™. We also help companies improve employee well-being and productivity with leadership and management trainings.

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

When I "launched" my first product - The Strategic Executive Exit. It was like putting out into the world the best I could offer of my own unique magic so I could help everyone else do the same for themselves, in their own way. It was like putting on a shoe that fit perfectly - what I knew I was meant to be doing.

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

I was laid off late 2022 by the same company I'd helped reach unicorn status earlier that year. I decided I was finally going to create what I wished to see in the world instead of waiting for another company to choose me. And that was a way to purposefully design a career that creates the most impact, abundance and purpose instead of continuing to grind on the corporate and tech hamster wheel.

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

My coach has been a game-changer for me because he's given me proven frameworks, a sense of accountability and great advice along the way. AI is also a great executional tool.

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.

As an award-winning executive of 20+ years, I never thought I'd be laid off especially from a company that I'd helped reach unicorn status (worth a billion+ dollars). That was a turning point for me to say, ok now what? 

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

I was bold. I took the opposite approach to the market than my competitors who are "burnout coaches." Instead - I created a "product" that was an offering to the problem I saw in the world. Instead of just telling people that this is what I do and offering a service, I created an actual product offering based off of the problem I saw. I worked on creating new demand and a new category vs. trying to fight for space in a crowded "executive burnout" category, when we know based on research that it's the systemic environment that matters. So I'd rather help executives exit out and create their own work based on their unique magic and help companies improve employee well-being and productivity at the org level vs. coach executives back into the same environment that's been burning them out. Because they won't fix it and that won't fix their burnout. New, purposeful work design will. 

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

It can be lonely, so you really have to believe in what you are doing for whatever reason you believe in it. Intrinsic motivation is the key to sustainable change. This way, you will be able to keep going when no one else is cheering you on. For this reason, I also recommend community. Anytime you go through change or growth, surround yourself with like-minded, aspirational people that will help you get there.

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

• Visit The Full Cup Co.'s website: fullcupco.com
• Connect with Jess Lane on LinkedIn: Jess Lane
• Follow The Full Cup Co. on LinkedIn
• Follow The Full Cup Co. on Instagram: @thefullcup