Leader Spotlight: How new product functionality re-engages users at checkout, with Sean McAuliffe
Sean McAuliffe is Director of Product Management at Shop Your Way, where he leads checkout payments and credit strategy across online and in-store experiences. With nearly a decade of experience spanning fintech, retail, and regulated financial services, Sean focuses on building products that balance speed, compliance, and meaningful customer value. His work centers on integrating credit seamlessly into checkout flows, helping teams navigate complex ecosystems while delivering intuitive, high-impact experiences.
In this conversation, Sean breaks down how product teams can re-engage users by adding new functionality that collapses time to value. He shares how to distinguish KPIs from outcomes that actually drive the business, how misaligned funnels can hide massive opportunity, and why the most effective re-engagement often happens when users are given immediate access — not just approval. Sean also explores the realities of competing in crowded checkout environments, designing frictionless experiences in borrowed UI, and shipping quickly in highly regulated systems without losing sight of the customer.
Sean is the author ofAutonomy Lost: The Silent Crisis in Product Management, which explores how product teams can reclaim ownership, clarity, and impact in complex organizations.
Defining engagement that actually drives the business
Can you give us a high-level overview of what KPIs, OKRs, and a North Star metric look like in your product ecosystem?
When I think about KPIs, I actually start at the very beginning. At a high level, Shop Your Way lives at the intersection of a few different markets. You have BNPL, express payment, credit, and rewards solutions, and we’re trying to offer prime credit at fintech speed.
There are two things I look at with KPIs and OKRs. OKRs are the outcomes the business needs to see and how it ultimately makes money. KPIs are the signals that tell us how the app is behaving from a user engagement standpoint.
We have a very narrow window at checkout to educate users. There’s a lot going on in that moment. A KPI might tell me that someone saw something or clicked something, but an OKR is about how many people applied, got a card, and actually used it — because that’s how we make money.
None of this matters if the business doesn’t make money. For most companies, clicks cost money, so we measure them. KPIs tell you how the system behaves. OKRs tell you whether the business is winning. Our North Star is collapsing time to value: you see it, you click it, you become a cardholder, and you start using the card.
What’s your process for identifying that North Star?
It’s very much driven by how the business makes money. Engagement and member statistics are important because they show trends in usage from our most loyal customers, but the business ultimately thrives or dies on someone seeing an opportunity to apply and actually getting the card.
There are two sides to that. My side is more card acquisition. My job is to get your attention and get you a credit card. Then your lifetime value to me is how often I can get you to pull that card out of your wallet, whether that’s a digital card through instant provisioning and tap-to-pay, or when you eventually get the physical card.
How do you help teams distinguish between interesting KPIs and the ones that actually drive business outcomes?
KPIs can be separated into what’s vocally interesting and what’s globally impactful.
You might have someone in marketing who’s very interested in how often people are exploring the experience, learning about the product, or reviewing terms and conditions. But what really matters is whether someone makes it through the entire funnel.
You always start from the business outcome and work backward. Any KPI that meaningfully increases the number of people who even get a chance to convert usually creates more leverage than squeezing incremental gains at the very bottom of the funnel.
When metrics lie: finding the real opportunity
Can you give an example of when KPIs and OKRs were misaligned?
This is a real example, but I’ll keep it general. One of the most impactful moments for us was realizing we weren’t fully connecting the dots between KPIs and the actual magnitude of the business outcomes.
We were starting the story in the wrong place. Our analytics stack began with users landing on our homepage, which meant we only knew about people who had already clicked. That became our assumed addressable audience. From there, we knew our conversion from landing to applying for a credit card was around 60%, which is excellent in the credit card industry.
Because of that, we became very focused on how to capture the remaining 40%. But when we took a step back, we realized impression volume was massive. Our click-through rate was around half a percent. To be competitive with a credit product, you want checkout conversion around one to one and a half percent, which means your click-through rate needs to be closer to two to five percent.
Conversion is bounded. If you’re at 60%, you can only get to 100. Even in a best-case scenario, you’re looking at maybe a 35% increase. Meanwhile, the upside from increasing click-through was enormous. Improving that number could drive tens of thousands of new applicants, compared to only a few thousand from conversion gains.
That’s when we realized it wasn’t that there was a hole in the net — it was that we didn’t realize how wide the net could be. Conversion felt loud and obvious, but click-through was the real problem. Checkout is a crowded space, and when you connect the right user with the right value proposition in that moment, that’s where you can really differentiate.
How did you reframe that conversation with your team?
We used a visualization. The funnel started very narrow with the number of people who were approved and got a card. Then it widened to include people who applied, whether they were approved or declined. It widened again to include people who completed the first login of the application.
From there, it widened to the people landing on our homepage. And at the very top, it showed impressions.
That top section was massive; it looked like the Earth next to the sun. You could see this enormous population of users who were there but never entering the funnel. We had been focused on keeping people once we had them, instead of realizing that for every one user we captured, there were tens of thousands more we were never reaching.
Winning back users at checkout with new functionality
In a crowded checkout space, how do you translate acquisition OKRs into something actionable?
There’s a lot of economics that go into building a credit card. Some acquisition costs can be absorbed by merchants, some by the credit card company, and sometimes by an intermediary offering membership or co-branded credit. Ultimately, you need to find the balance between how much value you can give the consumer based on what they’re buying while still remaining profitable.
When you’re competing at checkout with PayPal, Apple Pay, Google Pay, and BNPL providers like Affirm, Klarna, and Afterpay, they all have instant brand recognition. Most people have used them recently, and they’re comfortable with them. But those products are primarily about simplifying payment.
If we can offer a streamlined way to access credit, present a compelling offer, and move through checkout without friction, that’s how we compete. For a big-ticket purchase like a $1,500 sofa, extended financing or a stronger credit value proposition can be far more compelling than a simple pay-in-four option.
Where we stand out is accessibility. Many regional or middle-market retailers don’t have access to prime credit. By offering an alternative with a stronger value proposition than BNPL, and by provisioning the card instantly, you can win at checkout.
How do BNPL and express pay shape user expectations?
BNPL is an intrinsic competitor to credit, and it has disrupted the space significantly.
Younger consumers in particular have been conditioned by express pay and BNPL experiences. They expect speed, simplicity, and immediate access. When you build your roadmap, you have to account for that conditioning. People expect checkout to be fast, intuitive, and nearly effortless.
Designing frictionless experiences in borrowed UI
What are the unique challenges of operating on third-party checkout pages?
You don’t control the space — you rent it.
You need something generic enough to scale across partners, but natural enough to fit into their checkout experience. Consumers are conditioned to ignore anything that looks like a third-party ad. If it feels like an ad, no one touches it. But if it’s too custom, you lose speed and scalability.
So you operate on a very fine line. You have to move quickly while still looking native. That constraint forces discipline and creativity at the same time. At the end of the day, they own the UI. You’re borrowing attention in a very crowded space.
How does observing real behavior change how you think about engagement?
Traditional analytics tools do a good job of telling you what happens after someone clicks. They show you what people engage with, where they linger, and how quickly they move through pages. But watching users in real time is completely different.
It’s like the difference between reviewing a report and watching CCTV footage. You can interview users, which is critical, but watching real behavior lets you see hesitation, pauses, and breakdowns in the experience. That’s how you build a truly customer-centric product team.
Collapsing time to value with functionality
How does functionality like instant provisioning or passwordless flows change outcomes?
Approval isn’t the same thing as value. Access is.
If someone gets approved for a card but can’t use it easily, the experience breaks down immediately. If you ask them to type in card numbers or jump through extra steps, you’re going to lose them.
We’re competing in an environment where people are already logged in, already trusted, and already paying in one click. Asking users to do anything more than that just isn’t going to work.
You also lose trust. If I go to checkout today and it asks me to enter card information without Apple Pay or Google Pay, that feels outdated. Those experiences have become the baseline.
When you build software, you’re not just competing with direct competitors. You’re competing with the best experiences people use every day — Netflix, Instagram, Airbnb. If your experience isn’t intuitive, users won’t come back.
What signals tell you that time to value has actually collapsed?
You need to know exactly where users drop off. Which fields cause hesitation? Where do people stop and think?
Social security numbers are a big one. Nobody likes entering them. Field freezing, where users pause and sit, is another strong signal.
Pre-qualification makes a massive difference. Nobody likes getting declined. When you allow pre-qualification and clearly communicate that someone’s credit won’t be impacted, you see major lifts in engagement and meaningful reductions in drop-off.
Operating under regulation without losing velocity
What have you learned about building products in regulated environments?
Credit cards are heavily regulated. There are rules that determine what you can and can’t say and how much you need to disclose. BNPL and express pay providers don’t deal with all of those constraints, which means you have to build a runway.
As a product person, you need to understand the regulations as well as the customer. Your job is to advocate for the customer while working within legal boundaries. That means doing the work upfront, building systems that can evolve, and minimizing rework for development teams.
Regulation isn’t friction — it’s the cost of durability and consumer safety.
How do you position your product relative to infrastructure players?
We’re a platform with a prime credit offering. We’re not the creditor ourselves; we distribute a co-branded card on a partner bank’s behalf.
That distinction matters because we’re responsible for the end-to-end member experience. We’re not just facilitating payment — we’re accountable for access, trust, and ongoing usage.
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