This interview is with Brian Root, Fractional Chief Product Officer at Rooted In Product.

Brian Root, Fractional Chief Product Officer, Rooted In Product

Can you introduce yourself and share a bit about your leadership experience that has shaped your expertise in this field?

I’m the founder of Rooted In Product and work as a Fractional Chief Product Officer, partnering with companies to build high-functioning product organizations that drive business outcomes. More broadly, I’m a product executive with a track record of leading high-performing teams across product management, design, research, and analytics. My focus is helping companies unlock real product leverage, where product isn’t just shipping features but shaping business outcomes. That work starts with leadership.

I’ve led organizations at a range of scales, from scrappy startup environments to companies with hundreds of millions in revenue. In every context, the common challenge is the same: how do you align people, process, and priorities in a way that drives compounding impact over time? I’ve built that alignment from the ground up, restructured orgs mid-flight, and guided teams through periods of high growth, existential crisis, and post-acquisition integration.

What sets my leadership apart is a systems-level mindset. In college, I majored in game theory, and that foundation has stayed with me. I see product organizations as networks of people, incentives, feedback loops, and decisions. My job is to make that network healthy, scalable, and self-correcting. That means investing in strong decision frameworks, building connective tissue across functions, and creating the conditions where judgment can flourish at every level of the team.

The proof is in the outcomes. I’ve driven product strategies that resulted in successful acquisitions, rebuilt core user journeys that were blocking scale, and established foundational product practices in companies where none existed. I don’t lead by charisma or control. I lead by creating clarity, setting standards, and raising the bar, then giving people the tools to reach it.

What was the pivotal moment or experience in your career that led you to focus on leadership, and how has it influenced your approach?

I pursued and was fortunate to become a part of leadership teams extremely early in my professional career, so I actually have to go much further back than that. To be perfectly honest, the pivotal moment that shaped my focus on leadership happened on a tennis court in high school. My doubles partner and I were one of the top-ranked teams in Michigan. We had built real chemistry over the season, and we came into the state tournament as one of the favorites. But in the quarterfinals, with the match slipping away, something changed. My partner started to freeze up. I could see it in his body language, the hesitation in his shots. I knew we were in trouble.

What happened next wasn’t a conscious choice. It was a surge of determination I didn’t know I had. I covered more of the court. I made riskier plays. I spoke with more intensity between every point. It wasn’t anger or frustration. It was a refusal to lose. And somehow, we didn’t. We won the match. But what stayed with me wasn’t the comeback. It was the realization that I played my best not in spite of my partner’s struggle, but because of it. I was better under pressure because someone else was counting on me. And I was still only able to carry that weight because I trusted he would show up when it mattered. That interdependence shaped me.

Years later, when I became a manager just a few months into my first job, that mindset came back into focus. I didn’t want to be a leader for the title. I wanted to build the kind of team where people made each other better. Not through hierarchy or control, but through shared trust, clear purpose, and mutual accountability.

That’s how I still think about leadership today. The best teams aren’t built on individual brilliance. They’re built on context, communication, and alignment. My job is to create an environment where people know what matters, know how they contribute to it, and feel a sense of urgency and pride in getting it right. Not every day will be your best. That’s why teams exist. But if the structure is sound and the relationships are strong, your worst day doesn’t break the system.

You’ve mentioned the importance of empathy in leadership. Can you share a specific instance where practicing empathy significantly impacted your team or organization?

Several years into my time at Amazon, I got sick. It wasn’t a cold or something routine. It started with a severe cough, progressed to recurring pneumonia, and eventually reached the point where I couldn’t breathe properly. My blood oxygen levels dropped into the high 80s and low 90s. That meant constant fatigue, brain fog, and an overwhelming sense of something being seriously wrong. Just a few months before, I’d completed my sixth or seventh ultramarathon. Now I was struggling to climb stairs.

At the same time, the product initiative my team had been building was suddenly deprioritized by leadership. The entire org was being reshuffled, and I was staring down a double hit: I didn’t have a team, and I was physically unable to think clearly, let alone compete for a new role. Under Amazon’s internal transfer policies, I would’ve had a narrow window to find another team or be out. On paper, I was unassigned and nonessential.

What happened next has stayed with me ever since. The VP I reported to called me in for a 1:1. She acknowledged the value I had brought to the team but didn’t dwell on it. Instead, she told me to focus on getting healthy. She said she’d protect my spot at the company for as long as it took to recover and find a new role. I was stunned. I remember asking her, “Why? We didn’t even successfully launch.” And she looked at me and said, “I’m not doing this because of what you’ve done. I’m doing this because of who you are.”

That moment redefined empathy for me. It wasn’t performative. It wasn’t conditional. It was a human decision inside a very high-performance, metric-driven culture. And it changed the way I lead. I saw firsthand what it meant to put the person before the employee, to treat someone as more than their latest output. In every comparable moment since, whether someone on my team is going through illness, burnout, family crises, or just struggling to find their footing, I’ve drawn from that example.

Going through severe illness myself has made me more empathetic by necessity. I understand now what it means to feel like you’re falling behind through no fault of your own. That experience, combined with the way my VP handled my situation, gave me a blueprint I try to follow. Not just to be kind, but to lead in a way that makes space for people to stay whole while they find their way forward.

How do you balance being a visionary leader with the day-to-day operational demands of running a business? Can you provide an example of how you’ve successfully managed this balance?

One of the most vivid examples of balancing vision with operational execution happened at Fundera during the onset of COVID. At the time, Fundera’s business was centered on helping small businesses access capital through a curated set of lender partners. Then the pandemic hit, and that model fell apart almost overnight. The products we offered disappeared. Lenders pulled back entirely, even though demand from small businesses had never been higher. At the exact moment our customers needed us most, we had nothing to give them.

That’s where the vision came in. We saw early signs of the federal government rolling out the Paycheck Protection Program (PPP). There was no clarity, no documentation, no infrastructure. But it was the only game in town. A few of us across product, engineering, design and operations grouped up to form a task force. The long-term vision was simple but urgent: make Fundera a trusted, go-to partner for small businesses during the most volatile financial moment in recent memory. But the day-to-day reality was chaos: personal and work-related uncertainty, conflicting guidance, customers in crisis.

We didn’t wait for clean specs or polished requirements. We made educated bets and stood up a fully digital PPP application flow in days using no-code tooling and fast, cross-functional decisions. That balance, between speed and direction, between making something work today and ensuring it would hold up tomorrow, is what made the initiative successful. It kept Fundera alive. We brought in over $1M in net new processing revenue from the PPP program, enough to stabilize the company through the uncertainty of 2020 and ultimately help enable a successful acquisition by NerdWallet.

Balancing vision and execution isn’t about cleanly separating strategy from tactics. It’s about knowing how and when to shift altitude, to connect the urgent with the essential. That’s what leadership demanded in that moment, and that’s how I still operate today.

In your experience, what’s the most challenging aspect of leading a diverse, cross-functional team, and what strategies have you found effective in overcoming these challenges?

One of the most challenging aspects of leading diverse, cross-functional teams is the way people’s roles subtly shape what they believe “good” looks like. Engineering might prize system elegance and maintainability. Design may center on consistency and emotional resonance. Operations might push for speed and predictability. None of them are wrong. But the real challenge is aligning people who are all solving for different things without flattening those differences.

I’ve stepped into more situations than I care to count where those differences had hardened into hierarchy. Research was seen as nice-to-have. Design was a downstream support function. Operations was reactive support. Engineering had to fight to be a part of strategy, not just implementation. In those cases, I’ve found that the only way to restore balance is to reframe what the team is actually there to do: solve problems, not ship tickets.

That shift starts with how you define success. Instead of committing to features, I anchor teams around user and business outcomes. Then I build the structure to support it: regularly scheduled synthesis between research and analytics, clear problem briefs, shared rituals that include all functions from the start. In some cases, that’s meant slowing down initial execution to make space for co-creation. In others, it’s meant protecting room for deeper discovery work even when stakeholders push for velocity.

One approach I’ve used with success is intentionally flipping the room dynamic. Instead of a PM walking into a design or research review with a baked proposal, we start from an open question, often with data or research insights as the entry point. I’ve seen this create far more ownership across functions and defuse turf wars before they begin.

None of this is fast. But it works because it treats alignment as something you build through trust and shared context, not something you enforce through process. That’s the only sustainable way to get people with different incentives and vocabularies rowing in the same direction.

You’ve talked about the value of ‘interests and skills’ sessions. Can you walk us through how you implement these sessions and share a success story of how they’ve improved team collaboration?

The “interests and skills” sessions I run are group sessions, and their value goes far beyond simple team structure or work allocation. They’re designed to surface what people actually care about, not just what they’ve been hired to do. Everyone in the room shares what topics or problems they find genuinely interesting at that moment, whether or not they fall inside their job description.

Over the years, I’ve had conversations in these sessions about woodworking, independent game development, particle physics, classical piano, and wilderness survival. The point isn’t to translate all of that into relevant project work. The point is to build connective tissue between people. When you hear someone talk about the thing they get lost in, you see them differently. And when a team shares that kind of context, the collaboration changes. People are more willing to interact, quicker to ask for input, slower to make assumptions, and more willing to help their peers.

I ran these sessions regularly during my time at Walmart Labs, and they were especially important during some of the more difficult moments the team went through. It was a high-pressure environment with shifting mandates and little room to catch our breath. These sessions became a place to re-anchor, to remind people that they were surrounded by talented, multifaceted humans, not just coworkers pushing tickets.

More than once, connections made during those sessions led to unexpected but significant wins. Sometimes it was uncovering a skill that filled a critical gap. Other times it was two people realizing they shared an interest and teaming up to solve a problem in a new way. None of it would have happened through the usual channels.

The structure is simple, but the effect is real. It creates space for people to be more fully seen, which in turn makes them more willing to step up, speak up, and show up differently in their work.

How do you approach failure or setbacks in your leadership journey? Can you share a personal example of a leadership mistake you’ve made and what you learned from it?

I was twenty-two, three months into my first job out of college, when I was promoted into a management role at a high-growth retail startup. I was now responsible for a team of other twenty-two-year-olds, most of whom had been hired at the same time I was. The company was fast-paced and chaotic. There was a clear sense of internal competition, and the structure of the job made it easy to compare performance. It didn’t take long before I realized I had no idea what I was doing.

I assumed I’d been promoted because of how I personally drove results, so I made the mistake of thinking that my job as a manager was to get others to do things my way. That mindset led to constant micromanagement. I second-guessed their choices, rewrote their work, and constantly inserted myself into things I should have delegated. I thought I was being helpful. I wasn’t. We didn’t hit our goals, and the environment became toxic. One of the people on my team openly undermined me in front of my boss. I tried to paper it over with rah-rah speeches and surface-level positivity, which only made things worse. I hadn’t earned their respect. I was trying to lead by control instead of credibility.

That experience taught me a hard but lasting lesson: getting promoted doesn’t mean you’ve earned trust. Authority is given, but leadership is earned through consistency, clarity, and integrity. The best outcomes don’t come from getting everyone to copy your playbook. They come from helping people figure out their own. Since then, I’ve learned to approach new teams with far more humility, to listen before I direct, and to treat influence as something that has to be built brick by brick. That first experience was rough, but it was an essential lesson.

In today’s rapidly changing business environment, how do you ensure that your leadership style and strategies remain relevant and effective? What’s your approach to continuous learning and adaptation?

You ensure leadership remains relevant not by tweaking tactics on the margins, but by rejecting the idea that any single approach will work indefinitely. The environment changes too quickly. New technologies, shifting employee expectations, volatile markets — none of these wait for a leader to catch up. The only model that holds is one where you build feedback, introspection, and course correction into the operating system of your leadership.

I use three mechanisms to do this in practice.

First, I design for feedback. That means actively soliciting critique from all directions: direct reports, peers, executives, clients. It’s not enough to wait for feedback to surface. You have to go get it. And you have to make it safe for people to tell you when you’re off. Some of the most valuable feedback I’ve received has come from people two levels down, who were only willing to share because I’d shown that their input wasn’t just tolerated, it was expected. I treat misalignment between my intent and the team’s experience as a data point to investigate, not a narrative to defend.

Second, I conduct structured retrospectives, not just on projects but on my own decision-making. After a launch, a hire, a strategy pivot, I ask myself: What did I expect? What actually happened? Where did I go wrong? I try to make my reasoning explicit before the result is known, so I can later evaluate whether I was correct for the right reasons or just lucky. This builds discipline around learning. Without it, your conclusions tend to justify your ego rather than improve your approach.

Third, I stay committed to intellectual breadth. For work purposes, I tend to read subjects like behavioral economics, organizational psychology, and profiles of successful individuals and companies, because the best insights often come from outside the immediate context. I find ways to connect frequently with operators across sectors. I try to hold beliefs loosely and subject them to disconfirmation. The more honest you can be with yourself about what you believe and why, the more resilient your leadership becomes.

This mindset applies to teams and organizations as well. Any strategy, process, or structure I put in place is provisional. It works until it doesn’t. So I focus on creating teams that can notice that inflection point early, and leaders who are comfortable discarding what no longer serves them.

Looking ahead, what do you believe will be the most critical leadership skills in the next decade, and how are you preparing yourself and your team for these future challenges?

The leadership edge over the next decade will belong to those who excel at sense-making, adaptability, and ethical judgment.

Sense-making is the skill of extracting clarity from chaos. Data will never be scarce again, but meaning will be. Leaders will need to scan across disciplines, identify patterns before they become obvious, and help their teams navigate ambiguity without paralyzing them. This isn’t something you can outsource to AI or wait to resolve itself. Interpretation is a human skill, sharpened by context, experience, and judgment.

Adaptability will be non-negotiable. The half-life of any strategy is shrinking. Markets shift, tools evolve, and entire industries are being redefined in real time. Leaders who cling to what worked yesterday will find themselves dragging their teams into irrelevance. The job is to foster a team environment that can adjust quickly without losing its bearings, and to do it without drama.

Ethical judgment will be under more pressure than ever. As technology amplifies impact and increases the speed of decision-making, leaders will face more consequential choices with fewer clear precedents. Long-term trust, reputation, and internal alignment depend on being able to make hard calls when the answer isn’t obvious and the cost of getting it wrong is high.

To stay ready, I build structures that force intellectual honesty. That includes pre-mortems to confront what could fail, red-teaming to intentionally challenge favored strategies, and disagreement rituals that create space for dissent before we commit. I reward people not for being right, but for helping the team get to a better answer.

I coach my teams to see learning speed as a core competency. We track feedback loops, test assumptions, and run post-mortems even on wins. Every project is treated as a chance to improve the system, not just the output.

I also study beyond my domain. I read about design and behavioral science. I study decision theory and systems thinking. I push myself and my teams to build range, not just depth, because the problems we’ll face won’t come in neat categories.

Thanks for sharing your knowledge and expertise. Is there anything else you’d like to add?

I’ll leave you with this: most companies don’t suffer from a lack of ideas or talent. They suffer from a lack of alignment and clarity about what good looks like. Strategy drifts into decks, priorities pile up without friction, and teams execute while quietly wondering why it matters. That’s not a resource problem. That’s a leadership and product discipline problem.

At Rooted In Product, I work with CEOs and founders who recognize this pattern. They don’t want another roadmap filled with incremental features. They want their product org to become a lever for business transformation. That requires more than better processes. It requires creating the conditions where the product team becomes a trusted interpreter of customer needs, a driver of focus, and a force multiplier across the company.

If there’s one thing I’ve learned, it’s that product can’t just be the function that builds what’s asked. It has to be the function that helps the company ask the right questions. And that shift only happens when product is grounded not in guesswork, but in rigor. That’s the work I care most about.