Leader Spotlight: Driving digital transformation inside a legacy culture, with Ben McAllister
Ben McAllister is Chief Product and Technology Officer at CrossFit, where he leads digital transformation across products for athletes, gym owners, and trainers. Previously, he spent six years at Under Armour overseeing MapMyRun and Connected Footwear, scaling “shoes that coach you” from zero to over $100M in revenue. Earlier in his career, he held product and strategy roles at frog design, Comcast, and Boston Consulting Group.
In our conversation, Ben talks about driving digital change inside a legacy culture, proving success with data, and extending CrossFit’s mission through digital tools. He shares how he balances intuition with evidence, builds and mentors empowered teams, and approaches opportunities in AI, wearables, and community. Ben also reflects on the advice he’d give his younger self about separating identity from output and focusing on fundamentals.
Driving digital transformation inside a legacy culture
You’ve driven digital innovation in very different environments — from a stealth startup to scaled platforms like MapMyRun and now CrossFit. What’s it like leading digital transformation in a more established company like CrossFit?
At Under Armour, working on MapMyRun felt like a hybrid environment. We were physically separate from the main business, mostly spread between Austin and San Francisco, so it often felt like we were in a little tech company. Over time, we became more integrated, and that created tension. The cadence of a company that sells shirts and shoes is seasonal — big launches every six or three months — whereas we were shipping continuously.
I would always tell people on the shirts-and-shoes side of the business, “If you launch a shirt that doesn’t sell well, you can put it in the outlet and flush it through the system and forget about it next season. If we ship a feature that’s unsuccessful, we’re going to have to live with it or go in there and do the work to rip it out.”
There’s also this idea you have to combat — that because it’s software, it’s just bits, it’s infinitely flexible, so you should be able to move really quickly and make rapid changes. There’s truth to that, but you still have to make careful calculations.
At a startup I was part of (it’s still in stealth mode), things were different because we were all on the same wavelength. We shared the same assumptions about what “good” looks like. When you have that alignment, it feels like you can drive 100 miles-an-hour down the freeway. You can move so fast.
Whereas if you’re in those hybrid environments, or where not everybody shares the same familiarity with software or approach to decision-making within software, you have to slow down and build a lot of that basic trust and those assumptions.
Before I arrived at CrossFit, there had never been a true product management function. The basic premise of CrossFit had such an incredible product–market fit that the company experienced meteoric growth and also grew as a cultural phenomenon without a lot of typical business decision-making processes and operations.
If you think about CrossFit as a training methodology, it was about overturning conventional wisdom. By extension, that applied to the way CrossFit ran its business, too — not the MBA-with-spreadsheets approach — and that worked really well.
Is that antithetical to product management? I don’t think so. Product is contextually sensitive to who your customer is, what the product is, and what problem you’re solving. What works at one successful company may not work here.
My CEO said the same thing when I joined: what really doesn’t work at CrossFit is coming in and running a playbook from somewhere else. You need to be tuned into what has made this company successful and stay true to that while you layer in some product management techniques and best practices. It hasn’t been totally straightforward, and I still feel like I’m in the early innings of this transformation.
Defining success and building alignment
How do you demonstrate if a new digital initiative is working at CrossFit?
With my startup mentors, we had a shared sense of what would work — even if it was hard to prove in advance. That level of alignment is rare. At CrossFit, the approach has been: listen, respect the culture and history, and — where possible — show rather than tell.
I lean on data — ship features, measure the effect, and use those results to persuade people that a customer-centric, product-oriented approach can work. It’s the old adage: the proof of the pudding is in the eating. The onus is on me not just to have a good debate, but to get things out there that make a difference that everyone can agree on.
What approach do you take to align product innovation with broader organizational goals?
We usually talk about three main lines of business, and now really a fourth. One is the sport of fitness — the CrossFit Games season, including the Open, a mass-participation event that 300–400K people compete in each year. Then our education business where we train and certify coaches — four levels you can work through. And our affiliate business: CrossFit is not a franchise; affiliates are independent owners who license the name CrossFit and operate very independently from HQ and from each other. On top of those, we now have a nascent merchandise business — at the Games and via ecommerce.
With a relatively small product and engineering team, we can’t split into four separate teams. The way I’m orienting the roadmap — and this is a long-term transformation — is to build foundational technologies and features that can support all these customers rather than one-off things for each business. Some will be customer-facing, some internal tools, some enterprise systems.
We spend a lot of time with each business, ensuring we understand their goals. On the margin, we try to be a connector among them so there’s a greater strategic fit. A simple example: merchandise opportunities coincide with the Games season. Another: education and affiliates are tightly connected — you need to be credentialed to run an affiliate, and we want affiliates to have highly trained coaches.
A very common conversation with stakeholders is: you want a feature — if it’s successful, what opportunity does that set up next? If it’s unsuccessful, what are we left with? Can we dial this down and validate with something smaller?
Before I arrived, each business sometimes directed its own tech teams to build bespoke tools, which can work but also leads to complexity. Part of our job is deciding what to build with our in-house expertise versus what to buy or partner on. Usually it’s a mix.
One example we’re working on now: the ability to communicate with a private group inside our mobile app. Gym owners talking to each other, coaches to coaches, members to members, or people not in a gym — all viable. Even if the first use case doesn’t work out, the capability should be useful elsewhere.
We can’t afford big bets that miss; the opportunity cost is huge. So we validate, start small, and try to build fundamental capabilities that are useful in multiple places.
Extending CrossFit’s mission through digital
An important mission of CrossFit is to combat chronic disease. How does that shape product decisions?
Greg Glassman characterized CrossFit as “a cure for the world’s most vexing problem”: chronic disease. Anyone who works in fitness — definitely people at CrossFit — has seen how it can transform people’s bodies and lives. We want as many people as possible to experience that. There’s a common misperception that you have to get fit before you start CrossFit. We need to dispel that and make it comfortable to walk into a gym.
Two truths I keep coming back to: people want to get better, and consistency is key. Community helps both. Digitally, we have potential to extend and amplify that community.
Maybe you and I are in the same gym and I travel — can we maintain our camaraderie and encouragement? If I move gyms or build a garage gym, how do we support that? If I’m a gym owner, it can be a lonely job — how do I lean on the support of other owners when I can’t travel to a conference? These are upstream of the ultimate mission, but they support it.
Does digital play a role in CrossFit’s education business too?
Absolutely. You start with the Level 1 seminar — a weekend, then a test. If you pass, you’re certified for five years. We’d love for you to get experience coaching and take Level 2 — that’s a big leap forward. But if you wait four or five years, there’s so much potential in that time.
Are you getting mentorship? Feedback? If you have questions, where do you go? There’s a lot of opportunity for more learning — not only top-down but peer-to-peer — across those years. We haven’t solved it yet, but the opportunity is there.
Balancing data, intuition, and trends
Are there times when you lean on qualitative insights versus quantitative metrics?
People who work at CrossFit love CrossFit. Many have been doing it for 15–20 years. That depth of experience is a strength, but it can also mean you’re less in tune with what a 19-year-old might be looking for. I don’t want to ignore qualitative insight — I want to complement it with data to bring balance.
There are also times when intuition is all you have. Tracking is a good example. CrossFit emphasizes measurable, observable, repeatable results — the whiteboard culture — and yet, in practice, it’s uncommon for people to deeply track.
The workouts are complex; capturing a rich picture of the work involves friction. And at the end of a workout, you’re lying on the floor recovering, your phone isn’t nearby, and the idea of typing a bunch of data isn’t top of mind. To tackle tracking, we’ll have to think about it differently.
And, I suppose, long-term members may not reflect new audiences?
True. Fitness is subject to fads and trends, and CrossFit has been remarkably enduring. Retention in the CrossFit Open year-to-year is astonishingly high from a digital product perspective. You always want it higher, but it’s remarkable.
Still, tastes evolve. You don’t mess with the essence — constantly varied functional movements executed at high intensity — but how you appeal to a 19-year-old versus a 47-year-old who’s been doing it for 15–20 years might differ.
Coaching PMs through transformation
You’ve said you love building teams even more than building products. When you’re mentoring PMs through a digital transformation, how do you help them develop the vision and the grit to see it through?
A basic principle for the team is: say what we mean and mean what we say, and follow through. It’s easy to say, “We’re building this feature to move retention.” We ship it, and then someone says, “You can’t really measure that.”
If you say success will be measured by retention, I expect that you’ll be able to measure it and attribute the measurement to what you did. If not, that’s okay — just say so up front. Agree on a proxy, be disciplined about it, and avoid success theater where shipping becomes the goal and you start majoring in the minors.
We focus on fundamentals at both ends of the lifecycle: articulate up front why we’re doing it and what customer problem it solves, and then follow through after launch on what happened. If we get those bookends right, PMs and engineers can hash out the middle.
I don’t need to dictate exactly how we write specs; the feedback loop between PM and engineering should drive the right level of specificity. We’ve had conversations about PRD templates, documentation, and process, but I always want to avoid bureaucracy for its own sake. It’s about rigor, not red tape.
Promoting a culture of experimentation
Has there ever been anything your team built or suggested that really surprised you?
We recently did a hack week. A clear theme was AI. By the end of the week, engineering had internal tools stood up and in use.
On the product side, PMs learned a mobile-app feature we assumed was constrained by the backend was more flexible than we thought — so improvements are now on the roadmap.
And we took an old, thorny piece of tech — our trainer directory — that lived in our old stack and had been a pebble in our shoe, and we basically fixed it. It’s not quite deployed yet, but it will be soon and it’s going to be better than ever.
The surprise was how much progress came from being freed from the usual process. Even at a small team, there’s some bureaucracy. Hack week let people just do it.
The challenge for me now is how to capture more of that on an ongoing basis — understanding degrees of risk and where we can empower small teams with broad permission to move without creating chaos.
AI, wearables, and the enduring power of community
How do you see AI and/or wearables influencing the future of fitness?
I’ve worked on wearables — a wristband, heart-rate strap, connected scale, and later a connected shoe. The question after the first few weeks is always: does it still tell me something new? Does it help me get better and sustain the habit?
I remember talking with researchers at Johns Hopkins who were studying sleep, and one of the challenges they ran into is that tracking itself stresses people out. That doesn’t help sleep quality. It’s a good reminder that more data isn’t always better — it has to help people improve and feel better, not just measure for the sake of measuring. With any device, week-one motivation can become week-two annoyance.
AI will be a massive part of fitness — programming, coaching, personalization. But nothing replaces doing fitness with friends. Technology should strengthen in-person connections and make new ones possible; it shouldn’t replace community.
Do you think personalization really matters in fitness?
I remain bullish on community. My controversial hot take is that personalization is overrated. If you look at what the average person in the United States is doing in terms of health and fitness, they don’t really need a lot of personalization. They need to address the fundamentals. They need some degree of physical movement, some degree of resistance training.
Not to diminish personalization — I think it can be great for engagement and retention when you talk about digital products. But at the end of the day, we all need to get stronger, improve our cardio-respiratory fitness, keep moving, and eat a healthy diet. Those things aren’t going to change, and you don’t really need a high degree of personalization to make it.
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