About Todd Stiefler
Todd Stiefler is VP of Enterprise at WHOOP, overseeing the company’s B2B and B2G business lines. He brings an unusually cross-functional background to the role: a decade as a Senate defense staffer focused on missile defense and strategic nuclear deterrent, followed by product and commercial leadership roles at GE’s industrial IoT division, LMI, and Palantir. A self-described “tech nerd” and ultra-marathoner who finished the Leadville 100 in 27 hours, Todd found WHOOP the way most people find things that change their lives — by accident, scrolling LinkedIn late one night. He’s been building the company’s defense business ever since.
About WHOOP
WHOOP is a Boston-based wearable technology company focused exclusively on human performance and health optimization. Unlike general-purpose smartwatches, WHOOP does one thing: continuously measures high-fidelity physiological data — heart rate variability, resting heart rate, respiratory rate, skin temperature, and strain — and translates it into actionable metrics around sleep, recovery, and readiness. Its early customers included elite professional athletes, and it has since grown into a mass-market product worn by hundreds of thousands of consumers and, increasingly, military personnel. WHOOP is actively pursuing the DOD enterprise market, partnering with programs like SOCOM’s POTD and the Army’s Holistic Health and Fitness (H2F) initiative. The company’s enterprise division, led by Todd, handles everything from individual unit programs to large-scale institutional deployments.
Key Takeaways
1. Build for your most demanding user first.
In contrast to the “minimally viable product” framework, WHOOP’s early decision to build exclusively for elite athletes — with LeBron James and Michael Phelps among their first 100 customers — wasn’t a marketing stunt, but a product strategy. By targeting the most demanding performance environment, they built something rigorous enough to eventually serve everyone else. That same logic attracted special operators before conventional forces, and conventional forces before institutional DOD programs. They solved for the “edge cases” first rather than the average user, because they were solving their distribution challenge through their product design.
2. But the right product alone isn’t enough… you still have to solve the process.
Todd was direct about what WHOOP got wrong in its early defense push: they had a best-in-class product but hadn’t built the surrounding infrastructure. No contract vehicles. No data sharing agreements. No pricing architecture tuned to government procurement. “The DOD buys from people that solve their process, not their problem.” Getting that right — not just shipping a great device — is what actually enables scale. So while many of us laugh at high-ceiling IDIQs without real funding, the vehicle is a key ingredient.
3. The wearable itself is actually not the intervention.
This was one of the most important points from the episode: motivated, self-selected consumers who buy WHOOP on their own are signaling their desire to change their behavior. Warfighters handed a device in a conference room, with no context, no coaching, and no program design, often won’t. Even though the average warfighter may be more attuned to their body than the average civilian, in this case, if the warfighter doesn’t opt in, the product won’t deliver. This insight is why Todd never sees WHOOP going to a “push to all” rather than a “pull” based sales motion. If it’s foisted upon people, it will not produce the desired effect.
4. In federal sales, relationships and strategic partnerships beat conference booths.
Todd assesses that in the defense market, niche events where you can have real conversations, and partnerships with athlete management system providers who can pull WHOOP into their stack, have been the most valuable sources of leads. Trade show booths? Much less effective. As always, your mileage may vary, but it’s another reinforcing data point suggesting deep, niche relationships beat a larger breadth with high impressions.
5. Sell sustainable programs, not hardware deployments.
Todd’s north star for WHOOP’s next 12 months is helping customers build programs that will still be running in five years. That means bringing in WHOOP’s human performance experts and solution architects early, co-designing integration with existing data platforms, and being the vendor who asks, “What are you actually trying to achieve?” before taking the purchase order.
For more Crossing the Valley: valleycrossers.com | LinkedIn
For more on WHOOP: WHOOP.com
Follow Todd: https://www.linkedin.com/in/toddstiefler/
Follow Noah: https://www.linkedin.com/in/noahsheinbaum/
