Leader Spotlight: Product as a superpower in a turnaround, with Jill Kellett
Jill Kellett is VP of Product & Marketing at Root, Inc., an insurance company using data science and technology to revolutionize the industry. She began her career in graphic design at Express before being promoted to Associate Art Director. Jill then joined Ologie, a marketing and branding agency for higher education, before transitioning to Lane Bryant and, later, Root.
In our conversation, Jill discusses how she leverages design thinking as a superpower rather than just beautiful screens. She discusses how she’s helped plan and execute a business turnaround at multiple companies, including in her current role at Root, and the lessons she’s learned from these experiences. Jill also discusses qualities of good leadership during a turnaround, including transparency and fear mitigation.
The value of the creative ecosystem
Most of your career has been in design, retail, and ecommerce. You were brought into Root as Executive Creative Director. What led you to transition to product?
My journey into product goes back to my time at Express. I started as a graphic designer and I worked my way up to an associate art director role. It was a really amazing environment. At one point, we were facing problems with how efficiently we could get assets to our website. Product and engineering were trying to fix the pipeline, but I was sitting on the creative side and observing from a distance.
Then it hit me like a ton of bricks: the design we’re making and the copy we’re writing only have value if they get to the internet. They have no value sitting on my computer, so if there’s a massive broken technology pipeline, I should care about that.
Express had a culture of radical ownership — if you felt like something was broken, and you had the ideas, means, or hypotheses to dig into it, you were encouraged to investigate it. I was invited into conversations with my VP of Creative, Jay Borman, and the VP of Product and Engineering, Jude Reter. Because I understood the flow between a photo studio, SKUs, digital metadata, and digital asset management software, I started writing requirements and, eventually, started dotted line reporting to Jude on the product side. It was really fun. I ended up having a heavy hand in Express’ digital asset management product, as well as the content management system.
Fast-forward to Root, I came in looking at how the creative ecosystem adds value to the business. Thinking about creative processes as a product is naturally where my brain goes. The more I leaned into the business and the problems, the closer I got to product over time. It all stems from what I learned at Express – that whatever I’m doing, it only has value when it gets to market.
At Express, you were part of an ecommerce push during the Great Recession to re-IPO. Can you talk about that experience and share the hypotheses that drove your work?
Express was part of L Brands, which included Victoria’s Secret and Bath & Body Works, and was split off to private equity during the Great Recession. In 2008, Express didn’t have an ecommerce website, so the big hypothesis was to start one. Could we actually turn around the finances of this 30-year brand in and of itself? Could we separate it from this bigger public entity (Limited) and have it stand alone?
We had a sound hypothesis. If we could cut the fat and focus on ecommerce, the math made sense. Ecommerce launched in late 2008, and I joined the ecommerce creative team in 2009. To be honest, I didn’t fully know what I was doing at the start — it was a lot of trial and error, testing, and learning as we went. The whole team moved fast, iterating and adjusting in real time.
What made it work was the leadership around us. I was lucky to watch our CEO, Michael Weiss, lead through this major shift — he was decisive, disciplined, and deeply focused on execution. And day to day, I was especially influenced by our CMO, Lisa Gavales. She carried the pressure of making ecommerce work and somehow made it look effortless. I still think about her mix of clarity and drive as the model for how to lead through uncertainty.
Preparing and executing a complete business turnaround
As you mentioned, your time at Express coincided with the Great Recession. How did this experience shape your thinking about how product fits into the repositioning of a business in a turnaround?
During the Great Recession, it felt like everything around you was crumbling. That environment naturally evoked a different pace — a kind of heightened urgency that, whether real or perceived, forced you to move faster and decide faster. Looking back, I’ve realized that tempo wasn’t just a product of the economy; it was the right operating mode for a turnaround in any context. The presence or absence of macroeconomic pressure doesn’t really matter — that sense of momentum and decisive pace is what helps teams find their footing again.
That pace is what ultimately delivers the turnaround. Once you latch onto it, you channel it into action — testing, shipping, learning, and adjusting in real time. You can’t afford to bet everything on one big move; you need multiple shots on goal and the discipline to keep iterating.
Product teams are built for that. We’re wired to move fast, test ideas, and adapt as we go — and that’s exactly the muscle a company needs during a turnaround. Sometimes, the product itself is the repositioning. In higher education, for example, the product is the degree or the alumni network — the core value proposition. If you can clarify that value and improve the customer experience, whether online or in person, product becomes the engine of the turnaround, not just a support function.
How do you think about the basic anatomy of a turnaround? What’s the first priority, and what happens if you get it wrong?
The first priority is financial, full stop. Every business is an equation, and every business is a funnel. Where in that equation are things not working? Is it the cost? Is it the revenue? Is it a nuanced part of your business model? Is the equation itself wrong? That is the first priority.
Once you know that, focus on daily actions that move the equation. Every day, ask, “What action can I take today to materially improve this?”
Something businesses get wrong is that when they face hard times, they say, “We need to reinvigorate morale and set a new strategic vision. We need to look to the future and inspire people.” Yet, every day, they make poor decisions on where they’re spending their money or how they’re acquiring customers. Turnarounds fail when vision gets in the way of execution.
Making an impact and searching for repeatable signs
You’ve described product as a superpower in a financial turnaround. How do you help product managers reframe their role so they can create value in less traditional — but business-critical — ways?
At Root, we describe product as the group of people responsible for making things worth making. In a turnaround, that means asking, “What is worth making today? “ Sometimes that’s not a new feature at all — it’s rethinking billing practices, cutting costs, or reorganizing the budget.
For example, during Root’s financial turnaround, we analyzed our budget through a product lens. Instead of organizing by department, we looked at dollars by “jobs-to-be-done.” Each dollar had a job — and when we saw duplicate tools or overlapping expenses, we treated those as inefficiencies to eliminate. That exercise alone created a prioritization funnel and clarified what was truly worth building or funding.
Do you have examples of products that you built at Root that made a measurable impact on the success of the turnaround?
A major one was pricing and underwriting. In insurance, accurate risk pricing is everything. The more precisely you can price, the better the outcomes for both customers and the business. Much of that work was still manual, so we built a configurable underwriting management system alongside an automation layer for pricing, which together allowed us to move faster, make more precise decisions, and improve our overall financial performance. Separately, we built a configuration system to manage fees, giving us more flexibility and control in how we applied them across markets.
It wasn’t glamorous, but it was transformational. Though this wasn’t as exciting as rebuilding an app or creating a beautiful customer experience, they were amazing pieces of technology that advanced our market position and allowed us to adapt fast.
How do you move out of a financial turnaround and into a more strategic phase? What’s your process for pivoting and making sure the company doesn’t get stuck in short-term financial triage?
Short answer: It’s really hard. Once you stabilize the business, there’s huge inertia toward profit-optimal work. The key is to look for repeatable signs of stability before you pivot. Move too early, and you risk sliding backward.
In our case, we were looking for stability in our loss ratio. This was a lagging indicator that took time to develop. In hindsight, could we have pivoted to growth and strategic work a little earlier? Maybe. But we wanted consistent, durable signals first. Once we had them, leadership had to consciously lift its gaze and reorient the organization toward growth.
Then it becomes about leadership. The CEO and executive team must declare, “We’re stable.” That gives teams permission to think forward again. After long periods of austerity, people can forget what growth feels like.
The reality is, at this point, you’ve probably lost years of business time being so heads-down focused on unit economics. So once you pick your head up, it’s important to ask, “What’s changed in the past year or two since we were last in growth mode?” From there, think about where your people are. Making the pivot from the financial to strategic phase can be scary for people, especially if reductions in force are involved. It takes a lot of empathy, coaching, and check-ins.
Tactically at Root, we use OKRs to make that shift explicit. They help us define what must be true to look forward. We focus on two questions: Can we 10x reduce cost? Can we 10x differentiate? If the answer is yes, that’s where the next wave of investment goes.
Good leadership and mitigating fear
What does good product leadership look like in a turnaround vs. in a growth environment?
In a turnaround, leadership is about message consistency. Every conversation reinforces the same idea: our job is to add value and hit specific financial outcomes.
It’s also important to give your teams explicit tools. At Root, we created a tool called an impact analysis. This was a specific framework to gauge whether a new feature or product idea was going to move the needle of our specific financial goals. Introducing this tool gave the team confidence and focus that aligned with leadership’s consistent message.
From there, when the business shifts back to growth, the message shifts too. You celebrate the win — we did it, we stabilized — and then set new targets for what’s next. Leaders have to be clear that what got us here won’t get us there, and provide new tools and language to support that evolution.
Many PMs enter a turnaround with half their team gone and their roadmaps blown up. Did you see any fear in your team, especially with AI, that they’re going to be asked to do more with less?
Absolutely. The fear of being stretched too thin was real. If downsizing is part of your turnaround strategy, the key is to keep your strongest business thinkers — those who can see the business as an equation and who fully understand the financial goals you’re out to achieve. Tell them: you’re not being asked to do more with less. You’re being asked to do something entirely different — to help save this business. That framing changes everything.
The two biggest fears in any turnaround are overwork and overgrowth. People worry they’ll be buried, or that the company will hire too fast and end up cutting again. You have to name both fears out loud and explain how your approach will prevent repeating the past. Transparency builds stability.
Protecting vs. hoarding resources
As a leader standing in front of a room of people who have these fears, what tactical things do you lean on to help the culture?
Root’s product org is small but central, which makes transparency easier. When we entered the turnaround, I was direct with the team: you can trust that I’ll tell you the truth, even when it’s hard. I won’t overwhelm you with every detail, but I’ll make sure you have the context to understand decisions. Over time, integrity and consistency rebuild trust.
Early in a turnaround, nobody trusts leadership — and rightfully so. Your words only matter if they align with your actions. The question to keep asking yourself is: what transparency does my team need to see to believe me?
You’ve said that keeping one designer was the best decision that Root made during the financial turnaround. What can that teach leaders about protecting design and customer experience even in austerity?
There’s a big difference between protecting and hoarding resources. If I were hoarding, I would’ve kept a lot more designers on staff. But protecting means being intentional about what stays. For us, design was one of those things we knew we had to protect.
The designer who stayed understood that pricing, in and of itself, was a user experience. And that kind of business thinking in a designer was essential. They helped us see which challenges were truly visual and which were operational or service-related. And they never used design as a blunt instrument, but rather focused on work that they could truly move the needle on.
It came down to using design thinking as a superpower, not just for beautiful screens but for how we solved problems. Protecting design wasn’t about keeping headcount; it was about preserving the discipline that helps a company see problems differently.
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