Entrepreneur Spotlight: Chapelle Ryon of WorkBright
As CEO of WorkBright, Chapelle Ryon is leading the company through an exciting new stage of growth and transformation. WorkBright’s onboarding platform streamlines hiring for remote and distributed teams, helping organizations complete paperwork faster, stay compliant, and get new hires to work sooner.
This month, Chapelle began her second round of the BEN Signature Program, a highly personalized 12-month advisory experience that connects scale-up founders and CEOs with experienced advisors who’ve built and led companies themselves. The program is designed to help leaders navigate critical inflection points, challenge assumptions, and accelerate growth with clarity and confidence.
In our latest conversation, Chapelle reflects on what’s changed since her first Signature round, the impact it had on WorkBright’s evolution, and how she’s continuing to grow as a leader.
Q&A with Chapelle Ryon
1. Why go through Signature 2?
It was really about timing and alignment. We’re at a critical inflection point with WorkBright - the challenges we face today are different than they were in my first year as CEO. We need to prove repeatable enterprise go-to-market, tighten our GRR metrics, and embed AI into product and operations.
The first Signature program helped us get unstuck, and I see this round as a way to pressure-test where we’re headed, sharpen our outside perspective, and accelerate on those fronts.
2. Biggest win from the first round?
Clarity on what was holding us back and personal coaching for stepping into my leadership role. The advisor feedback around my role as a bottleneck was a wake-up call - delegating more, building the leadership bench, and stepping back to focus on strategy.
We saw direct impact: churn reduction, improved NRR, and the ability to expand the platform beyond just I-9. There are things I remember like “Reducing churn needs to be your rallying cry,” which I didn’t even understand to be as true as they turned out to be. They saw things before I did.
3. Biggest change as a founder?
Getting comfortable not being in every detail - trusting the team, and focusing on leverage rather than control. The outside perspective from BEN advisors forced a level of self-reflection and honesty I wouldn’t have gotten elsewhere.
4. Advice for other founders considering the Signature Program:
You get out of it what you put in. Be totally transparent about where you’re stuck - the advisors can only help if they see the real picture. And don’t go in expecting easy answers; the value is in the pushback and the questions you haven’t thought to ask.
5. What I’d tell my 10-year-old self:
What matters most later in life is building resilience. The highs and lows never stop, but how you respond is what defines you.
Chapelle’s journey with WorkBright captures the kind of growth-minded leadership that defines the BEN community: honest, reflective, and always evolving. As she enters her second round of the Signature Program, BEN is proud to support her continued success, helping her sharpen strategy, challenge assumptions, and lead with clarity through WorkBright’s next stage of growth.
