CEOs who treat employee well-being as a perk instead of a business strategy are losing ROI, talent, and product intelligence — often without realizing it. Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sat down with Lindsay Johnson, founder and CEO of Fitprose, to unpack how that blind spot compounds as companies scale. Fitprose is a global workplace wellness company serving Fortune 500 corporations down to small and midsize businesses. Johnson built it from scratch in 2016 with no investors, reached profitability in six months, and now works with hundreds of thousands of employees worldwide through a platform powered by over 1,000 certified instructors.
This episode is for CEOs who are scaling headcount quickly and have lost direct visibility into what employees are actually experiencing.
Key Takeaways
- CEOs who time-block conversations with group managers, even at a high level, create a direct feedback channel that shapes product roadmap and company direction.
- Medical insurance claim data is ROI sitting in front of you. High diabetes, mental health, or musculoskeletal claims tell you exactly where your employees are struggling and where targeted wellness investment pays back.
- Empathy is not a leadership liability. A CEO who feels the weight of a reduction in force and still makes the call cleanly, while treating people well on the way out, is exercising a skill most leaders lack.
- Hiring decisions made too fast and too expensively, without a 30-60-90 day accountability plan, cause disproportionate pain in bootstrapped companies where there is no room for error.
- When CEOs take care of themselves physically and mentally, they get more done in fewer hours. That is not a wellness claim. It is a productivity argument.
Why CEOs Lose Sight of Their People During Fast Scaling
Johnson put it plainly: “CEOs get so busy and so consumed in the next thing to do that they forget about their people and their needs.”
That is not a soft observation. It is a structural problem.
At Fitprose, Johnson’s 1,000-plus certified instructors deliver programming directly to employees at client companies worldwide. Those instructors hear what employees actually think, feel, and need. If Johnson is not listening to what her instructors are hearing, she said, “how are we truly roadmapping our product the right way?”
The same logic applies to you. Your employees talk to your customers. They see where the product breaks. They feel where the culture is failing. When you stop talking to them, you lose a critical intelligence channel.
The fix is not a massive cultural initiative. Johnson’s recommendation is straightforward: time-block with group managers. Even in a large company, deliberate time with the people closest to the work will “really help navigate where the company’s direction is going to go.”
CEOs Use Medical Claim Data to Build the ROI Case for Employee Wellness
If you are skeptical about wellness investment, your CFO is more skeptical. Johnson knows this and addresses it directly.
“The very first thing in front of their face is look at your data claims. Your medical insurance claims are telling you that your employees are struggling with high diabetes or mental health or MSK problems.”
This reframes the conversation entirely. You are not being asked to fund a yoga class. You are being asked to look at where your insurance spend is concentrated and ask whether a targeted intervention would reduce it.
The ROI argument is not complicated. If high diabetes claims go down because employees have access to nutrition coaching and movement programming, you spend less on insurance. That is a number your CFO will read.
Johnson is also candid about what wellness companies struggle to prove: individual health outcomes are hard to measure directly without HIPAA-compliant data collection. What Fitprose does measure is attendance, registration, and engagement within their platform, paired with employee survey feedback. Pair that with your claim data, and the picture gets clearer.
If your CFO asks for the business case, start with your claims data. It is already there.
Empathy Makes CEOs Stronger in Hard Decisions, Not Weaker
Johnson described empathy as something that comes naturally to her but can “come off as a weakness sometimes.” She is working through how to lead with it while still projecting confidence.
Gow pushed back on the weakness frame: “I believe empathy is a huge strength. As long as you recognize you have this skill, if you don’t let it affect your judgment and the way you make decisions, then keep it.”
The distinction matters. A CEO who is afraid to feel the weight of a difficult decision is not a stronger leader. A CEO who feels it, makes the right call anyway, and treats people with dignity on the way out is exercising a rare skill.
Johnson’s example of reductions in force is instructive. When she has had to let people go, she offers to speak to their strengths on LinkedIn. She believes in making space, not burning bridges. “If you are holding space for something that doesn’t serve us, then we can’t let something else in.”
Gow extended that framing to the scaling context: as companies grow, the people who built the early company sometimes stop being the right fit for what the company is becoming. That is not a judgment of the person. It is a recognition that different stages require different skills. Making that call, clearly and compassionately, is what good CEOs do.
Closing Framework: What Scaling CEOs Learn from Lindsay Johnson
| Principle | What it means in practice | Named evidence from this interview |
| Employees are your product intelligence layer | The people closest to customers know what is breaking. If you stop listening to them, your roadmap suffers. | Johnson built Fitprose’s programming model around instructor feedback — and credits that channel with keeping the platform aligned to what client employees actually need, rather than what leadership assumes they need. |
| Claim data is the wellness ROI argument | Medical insurance claims show exactly where employees are struggling. Addressing those conditions reduces claim costs. | Johnson uses insurance claims data as her opening argument with skeptical CFOs — because it converts a wellness conversation into a spend-reduction conversation using numbers the finance team already owns. |
| Empathy and clear judgment coexist | Feeling the weight of a hard decision does not cloud it. It makes the execution more human without compromising the outcome. | Johnson’s practice of offering LinkedIn endorsements to former employees after separations has kept professional relationships intact and her talent network clean — a direct operational benefit of leading with empathy rather than avoiding it. |
| Hire deliberately when bootstrapped | Without VC runway, bad hires are expensive. A 30-60-90 day plan with accountability built in protects against moving too fast on expensive people. | Johnson’s early experience at Fitprose — moving too fast on high-cost hires without structured accountability — produced avoidable cash strain in a company with no investor buffer to absorb it. |
| CEO self-care is a productivity lever | When CEOs invest in their own physical and mental health, they work more effectively in less time. | Johnson manages two children under four alongside a global company. Her deliberate investment in physical activity and AI education keeps her output high — not by adding hours, but by making the hours she has sharper. |
Quotes from This Episode
- “CEOs get so busy and so consumed in the next thing to do that they forget about their people and their needs.” — Lindsay Johnson, Founder and CEO, Fitprose
- “If I’m not understanding what they’re hearing, then how are we truly roadmapping our product the right way?” — Lindsay Johnson, Founder and CEO, Fitprose
- “If you are holding space for something that doesn’t serve us, then we can’t let something else in.” — Lindsay Johnson, Founder and CEO, Fitprose
- “I believe empathy is a huge strength. As long as you recognize you have this skill, if you don’t let it affect your judgment and the way you make decisions, then keep it.” — Glenn Gow, The Scaling Executive Coach
Frequently Asked Questions
How do CEOs make the ROI case for employee wellness investment?
Start with your medical insurance claims. High rates of diabetes, mental health issues, or musculoskeletal problems in your employee population are already costing you money through elevated insurance spend. Lindsay Johnson — who founded Fitprose in 2016 with no outside investment and reached profitability in six months — argues that CEOs who address those conditions through targeted wellness programming reduce claims costs in a measurable way, and that this is the most direct ROI argument available without needing HIPAA-compliant individual health data.
How should a CEO handle empathy without letting it weaken leadership decisions?
Empathy becomes a liability only when it prevents a CEO from making a necessary call. Glenn Gow, The Scaling Executive Coach, draws a clear line: feeling the weight of a hard decision and still making the right one, while treating people with dignity, is a leadership strength. A CEO who lets go of someone who is no longer a fit, offers a strong LinkedIn endorsement, and makes space for the right hire is not being soft. That person is running a tighter, more honest organization.
What is the biggest hiring mistake bootstrapped CEOs make when scaling?
Moving too fast on expensive hires without a structured accountability plan. Lindsay Johnson learned this directly at Fitprose — bootstrapped with no VC runway, where limited capital made each hire consequential and there was no room to absorb a bad one. Glenn Gow’s recommendation: give the new hire a 30-60-90 day plan, hold them strictly accountable to it, and keep your candidate pipeline warm until that person proves out. Do not assume a new hire is a winner on day one.
CEOs Work with Glenn Gow to Scale Their Companies and Careers
Glenn Gow is The Scaling Executive Coach. He coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
