ENIOLA IBISANMI: Every year, Sears Home Services sends thousands of technicians into American homes to fix fridges, HVACs, washers, and more. And before very recently, this experience ended in a very clunky, outdated experience that did not match the trust the customers put into the brand. Today, we’re going to dig into exactly how that changed. My name is Eniola Ibisanmi from Stripe’s professional services team. And today, I’m joined by BJ Naedele of Transformco. He is the president and chief commercial officer of Transformco, the business behind iconic brands like Sears, Shop Your Way, Kenmore, DieHard, CRAFTSMAN, and more. BJ, thank you so much for being here with us.

BJ NAEDELE: Thank you, Eni. Thanks for making time today, team.

ENIOLA IBISANMI: All right. Well, this is a fireside, so let’s get a bit cozy.

BJ NAEDELE: Okay.

ENIOLA IBISANMI: I love your shoes.

BJ NAEDELE: Thank you. Thank you.

ENIOLA IBISANMI: All right. So I heard that you have over 500 pairs of Jordan, 400, 500? And can you tell us a little bit about that, and also what brought you to Transformco?

BJ NAEDELE: Yeah, that may be true. I got to figure out who shared that with you. Look, it’s a real artifact of my career history. Prior to joining Transformco, I spent 10 years at Nike. One of the things I did at Nike was lead our sneaker culture. And so working with Brand Jordan, the Nike brand, Converse, really trying to bring innovation and inspiration to the marketplace. Part of that before was really leading all things digital at Nike. And so Nike.com, Nike Run Club, Nike Training Club. We actually cofounded and launched Nike+ here in San Francisco almost 20 years ago to the day. Before that, I spent a bit of time in pro and college sports, working in Moneyball at the NFL with Duke Athletics. And I started my career at GE Capital in the late ’90s, right as the dot-com bubble was growing. So yeah, definitely have 400 pair, but a good reason for it.

ENIOLA IBISANMI: Yeah. If there’s anything I know is that maybe I need to upgrade my shoe game.

BJ NAEDELE: We can do it.

ENIOLA IBISANMI: All right. Well, today, you all are going to learn three things. First, how Sears Home Services transform the payment experience for when a technician is standing in your kitchen. Second, how moving into a new payment system transformed and made company-wide change. And then third, how you felt leading this transformation and maybe some tips and tricks for others facing similar decisions.

BJ NAEDELE: Sounds good.

ENIOLA IBISANMI: All right. So let’s get into it. I want to hear a little bit from you about, for those who don’t know the business—maybe they know the brand—what was happening internally that led you to making this decision?

BJ NAEDELE: Look, I think it says Transformco up there. We’re called Transformco for a reason. We talk a lot about internally, turnarounds are hard. Turnarounds are challenging, but turnarounds, you’re just fixing what’s already broken. Transformations are something completely different. It requires a radical rethinking of your operating model, your tech stack, your go-to-market, and even business models. And so when you think about transformation and Transformco, most people don’t know where you’re trying to get to. And so for us, the amalgamation, we are the old Sears Holdings company, and we bring a lot of pride with that. You talked about the brand—trust, pride, reliability. And so, but that holding company of the brands you mentioned—Kenmore, CRAFTSMAN, DieHard, Sears, and Kmart—those are all amazing businesses for us.

The real growth engines right now as we’re looking forward, and I think John talked about the acceleration earlier this morning—it’s really our Shop Your Way loyalty program. We’re one of the largest loyalty and credit card providers in the country. And as you mentioned with Sears Home Services, we’ve got almost 4,000 technicians that are committed to going into someone’s home. That’s a really private and personal moment. It’s a moment typically of need, when a refrigerator or stove is broken before a holiday. And so the Sears Home Services business is the largest home services platform in the country. 4,000 technicians, over two million home visits, hundreds of thousands of subscribers. And so as we sit here and we think about what Transformco was and really where we’re going, our aspiration is to become America’s home manager. And when you think about that, the home is typically the place you spend the most time. It’s also the single biggest financial investment. And emotionally, it’s where you create the memories for life.

And so our mission really is: let’s make homeownership easier, less costly, and more rewarding. And so when you talk about kind of, what was going on in the business or the brand, all those businesses grew up as independent operating entities. That meant we had seven businesses, six different commerce experiences, five different processing experiences. None of it hung together. I would buy an appliance from Kenmore, and I did not connect it to my warranty or to my repair. And so for us, really aligning on the mission and the vision for where the brand is going, we knew we had to make a change. It wasn’t really just a payment processing project. It was really a transformational initiative that allows us to get a single view of the homeowner and connect everything that they’ve done with us. And so again, the brand and kind of where we’ve been, it goes back.

I was telling someone earlier, we first sold the first Sears home in 1908. We had the first Sears mortgage in 1911. And so you think about that heritage and trust. And so trying to go back to where we were, just using technology to kind of get us there. True transformation, which is kind of what we’re here to talk about today.

ENIOLA IBISANMI: Transformation and also unifying all of your different systems.

BJ NAEDELE: Yeah.

ENIOLA IBISANMI: So I want to dig into the in-home experience a little bit more. What did that payment experience look like before, and what does it look like now?

BJ NAEDELE: Let’s start with the journey. So if you’re a homeowner, it’s the day before Thanksgiving or it’s Thanksgiving and your range breaks. You got to call someone. It’s not Ghostbusters. It’s Sears. And so you are pressed for time, you’re stressed. And so you’re relying on the technician to be on time, to get into the house, and to be an expert in what they do. And I would tell you, our 4,000 technicians—extremely committed to serving the homeowner, first with the expertise and the knowledge to do that, but really with a commitment to the experience. And if I had to summarize it, while they were experts in appliances, over the last five years, they really became our payments help desk, which is not what we hired them to do.

And so they’d be there with their iPad taking a picture of the appliance or in with their tools on the HVAC. They’d have to put that down to then get a different tablet and system to be able to show you the quote and the estimate. You’d then have to go to a different tablet or screen, or your own device, to confirm the estimate. It was too many screens, multiple handoffs, and the repair would take 45 minutes, but that interaction of estimate to payment to exit sometimes took 15 minutes. And I don’t know about you, but whether it’s Thanksgiving or just any Saturday, I’d rather be back with my family or doing something else.

And so it was really, really clunky. And I think for the technician, we had to equip them with the toolkit to do what they really, really wanted to do. I’d flip it back though a little bit, and it goes back to kind of what I said a couple minutes ago around America’s home manager. We exist to serve the homeowner. And now if you’re on the other side of that, all you want is the appliance to be fixed, the protection agreement to be in place. And so for our homeowners, it was a really, really fragmented experience. One that when the technician left the house, they were left with a really bad taste in their mouth, which is not what we wanted to deliver.

ENIOLA IBISANMI: So it looks like moving to this new system allowed for faster checkout as well as maybe more payment methods were unlocked?

BJ NAEDELE: It’s been game changing. And so, let me start with the homeowner side since we’re right there. We talk a lot about trust and reliability and expertise from the technician side. As a homeowner, what we want to deliver is value, choice, and convenience every day. And so what we’ve been able to do by kind of moving from the legacy stack with five different endpoint solutions into one integrated is to unlock the rest of our capabilities. And what I mean by that is it starts first with our rewards currency. We’ve had over $3.5 billion… $3.5 billion of Shop Your Way rewards redeemed since we launched. And so we’ve got tens of millions of homeowners with rewards in their account that previously, they were unable to spend or use. We’re not talking about rewards that you save up for a holiday vacation or a gift card.

It’s really purpose-driven rewards. And so what we’ve been able to do is enable pay with points. And so while the technician is standing there at your kitchen counter or at the kitchen table, you can use the value that you’ve worked so hard to be able to pay for that repair today. Number two, and I talked a little bit about our credit card program. And so if you think back, the Sears credit card program, the first and largest retail co-brand product in the country, at one point was bigger than American Express. Our Shop Your Way credit card program is one of the largest co-brand programs in the country. Previously, those products, if you come back to making homeownership easier and less costly, those products were not available in the in-home experience. And so that meant that our homeowners could not take advantage of the industry-leading offers that we had.

They had to use some other form of tender. And so we’ve been able to integrate what we’re calling “apply, buy, and save now.” And so it allows our homeowners to get the new credit card, use our bank partnerships to get up to $200 or $300 off their repair, and then use the promotions and the incentives of our business to really help the homeowner in their time of need. It’s been game changing for us. I would say if you’re an existing cardholder, what we’ve been able to build with your team’s help, the card is on file everywhere. And so it goes with you in the home, out of the home, anywhere you interact and engage across the Stripe network. And I’d say third in this, if it’s a $50, $100 appliance repair for a part, you don’t want to pay with points. You maybe want to save them.

You don’t want to get a new credit card. And so we’ve been able to implement buy now, pay later. And so with like one week of work, being able to offer alternative financing really delivers to the homeowner that value, that choice, that convenience. So game changing from those three pillars, I think again, to where you started: the technician is the expert, the homeowner is served. It’s a win for the brand. It’s a win for the business. It’s a win for our partners.

ENIOLA IBISANMI: Amazing. And I want to dig into a little bit about the technician side of it. After talking to the technicians and making this change, did you hear any surprising feedback that you weren’t expecting?

BJ NAEDELE: Yeah, it’s interesting. And if you guys seen that episode of Seinfeld where Costanza’s walking around with all the papers and junk—that’s what the technicians were doing. They had like more devices than my kids. And so what we’ve heard is really a simplification and a focus, and it allows them to focus on A, what they’re passionate about and B, what they’re experts in—passionate about serving and experts in repair. And so I think what’s been interesting in that feedback over the last three months since we’ve gone live and scaled, we actually haven’t heard about payments, which is good. It kind of reminds me of what my grandma would say, which is, the meal that’s amazing, no one’s talking because it’s so good. And so the technicians are truly immersed. What we’ve heard from them and the homeowner is more about time and more about satisfaction.

And so, I used the analogy before that that payment experience could take five minutes, 15 minutes. If you’re now cutting that out, the technician is saving over 150 hours of work a year. That’s one extra week of productivity that our business and our technicians get back. The homeowner then gets their time back to go do what they need. So the feedback’s been really encouraging. Almost no news is good news, but the feedback is higher satisfaction from the techs, better brand affinity and satisfaction from the homeowner.

ENIOLA IBISANMI: That’s always what we want to hear. Okay. So that is going to be the transactional moment. But as you’ve kind of touched on a little bit before, Transformco is more than just Sears and Sears Home Services. You also have Shop Your Way. So I want to hear a little bit more about that.

BJ NAEDELE: For sure.

ENIOLA IBISANMI: Can you tell me a little bit about how moving to Stripe and onto a new payments processor unlocked system-wide transformation for your company?

BJ NAEDELE: Yeah. I mean, look, as I said, Shop Your Way has been around since 2009—literally tens of millions of active members and billions of dollars of rewards redeemed. And so we’ve been in the fabric of American homes for literally almost two decades. One of the things that when we were embarking on this transformational initiative, not a payments project, was really thinking about what else could it unlock, and how do you bring this idea of affordability and financial services together with homeownership in a really unique way? What it meant for my team at Shop Your Way was home services and Sears was just a partner and a client. And it allowed us to really rethink the foundation of what we are. And from day one, Shop Your Way was, number one, about a universal currency, and number two, everything-as-a-service. And so the opportunity for us, with the replatform and the transformational work, unlocked three things for us that we were really trying to do over the last, let’s call it 18 months, but we hit a blocker.

Number one, it’s to take the rewards and really democratize them. And so take them from out of the retail box, out of the home, and bring them everywhere. And so one of the things you’re going to see us continue to do here with Shop Your Way and Stripe is think about wallet-to-wallet integration and really giving the points the opportunity to go to more places every day, everywhere. Number two, and I mentioned the credit program, and we just relaunched the credit program as a service back in November with a new bank and new partners. The idea is that we can serve every franchise owner, every mom-and-pop, every regional provider, every local provider in the home space, in the retail space, with a loyalty and a credit program—we call it LCAS, loyalty-card-as-a-service—that only the biggest brands typically have access to, but then really bring it down and democratize it. Give the big tools to the little guys.

And so it’s one of the things we’re really excited about, especially getting this live and scaling it with Sears and Sears Home Services. It’s the blueprint for where and how we scale up that side of the business. And I think third, not knowing how many are our partners or clients here, the idea that the member is ours is really antiquated. Or that the homeowner is ours. They’re interacting with Instacart, they’re interacting with Uber, they’re interacting with a marketplace. And so every one of those transactions historically was closed off from us. They would happen on the merchant platform. And so now what we get to do, we truly get to know and serve 365. We get to partner with other brands and connect our members to their products and services. And the fact that both pay with points or the credit program or the Stripe payment platform connects it all back together is a game changer.

It’s a game changer for the member and the homeowner. It’s a game changer for us, but it really does create a force multiplying effect with respect to the ecosystem. So I would tell you, for us, we’re really, really excited about the foundation that’s built, but the opportunity ahead, it’s a completely different business model. It’s not even a different product set, and it wouldn’t have been possible without the core platform that we implemented here.

ENIOLA IBISANMI: Yep. We have so much to scale with you all on, and we’re excited on the journey ahead. You talked a little bit about before how one of the most difficult parts here is moving onto a new platform, a new [payments] system. So there’s [the] technology, and then there’s also the transformation. The technology was the easier part, but actually transforming the system and all that comes with it is a little bit more difficult. And I know you know that by being on some of the calls that we have. So I think a lot of people in this room would benefit from hearing some of your tips and tricks on how you worked with the change management to make this whole transformation happen.

BJ NAEDELE: Well, I tell you the technology today and with you and our team has been easy; the technology of the past was absolutely cumbersome. And again, I go back to some of this stuff had been around since 2003. And so you’re talking about as antiquated and legacy of systems as possible. What I think really helped us at Transformco, and it comes back to what I said about our mission and vision around the home and becoming America’s home manager and the relaunch of the cart-as-a-service platform: once we made that decision 12, 18 months ago, the infrastructure we had was just not viable. And so it really allowed me and the team first to look for partners, not vendors. I think second, a platform that could scale and adapt and be configurable, not an endpoint solution. So I think for us strategically, that was where we started.

If I think tactically, which is maybe kind of day-to-day and how things get done, there’s maybe a couple things I’d share. Number one, and I get this from my Nike days. At Nike, the Olympics didn’t move, the World Cup didn’t move, the Super Bowl didn’t move. At Transformco, we’re a date committed culture, and you set a date, you hit the date, come hell or high water. And so we set a very aggressive date. We started with you and the team late October. One week later, all seven business units were up and live in Stripe Connect. Three weeks later, we had a first sandbox environment, and like two months later, the first business unit was live on the new platform. And so it was really the date, hard date commit. And what happened when we did that, because again, we’ve got people and processes and systems—that wiring and that muscle memory is really hard to rewire.

And I would tell you, and you know it, there were a number of people early on: “But this is how we always did it.” And, “I’m running this day-to-day, so I don’t have time for this.” And all of that disappeared when you said, “We are launching on November 15th. We are launching on January 31st, and we’re launching on March 30th.” And so everything in that first tranche was about date, what needs to be decided. The second thing I’d say maybe is, and I get this a little bit from both sports and special forces, we created speed pods—not a committee. Committees are where initiatives go to die, and we are anti-committee. And so a speed pod is a team of eight. It’s one person per function. They are accountable and they are empowered to move with speed and purpose, which means the decision-making, the bureaucracy in a holding company with seven different business units and five different stacks immediately fell by the wayside. Because again, it was that group and that team that was ultimately both responsible and accountable for it.

And so again, that was really game changing for us. The idea that an enterprise transformation has a executive team, that’s got a committee, that—we didn’t do any of that. And I think the third one was kind of parallel pathing. And I say that because we got the technicians, the business operations, the technology team, all of that was working while we’re building and integrating the technology stack. And so we didn’t wait till the end. It wasn’t kind of a waterfall, let’s test it, alpha/beta, then roll it out. It was truly all three things working in parallel. And so, I said earlier about transformation and understand that it’s a fundamental operating system change. The partnership angle, and look, your team was amazing, right? The professional services team facilitating workshops. But those four things of having the right partner focused on the platform, having that date—World Cup’s not moving, our launch is not moving—getting empowered speed pods, and then activating and inspiring the front lines in parallel? Couldn’t have gotten it done without those four things.

ENIOLA IBISANMI: Yeah. And we really enjoyed the partnership with you as well. Being able to work with you all day-to-day, come up with new ideas to bring you onto the platform, especially with your aggressive timeline that you all let us know was not moving from the jump was really amazing.

BJ NAEDELE: Yeah. It’s awesome when teammates both internal and external share the same values, and all are marching to the same objective. So it was great.

ENIOLA IBISANMI: Yeah. And you’ve probably heard through a lot of talks today, we always say here at Stripe, “We haven’t won yet.”

BJ NAEDELE: Yeah.

ENIOLA IBISANMI: So, we haven’t won yet here, and we continue to aim towards reaching new and new heights with Transformco. But before we can do that, let’s take a step back and look back at our journey together. If you could go back and change one thing that would make this whole process smoother or maybe easier towards this transformation, what would you say it was?

BJ NAEDELE: Start sooner? Yeah, I would say start sooner, right? The analogy, the best time to plant a tree was yesterday, second best time is today. The reason I say start sooner is, and it goes back to my narrative around America’s home manager and our new credit platform—those decisions and that strategic transformation was made in early 2024. And so, I would’ve in hindsight kicked the engagement off and the replatform work off co-terminously with all of the other things we did. It may have been too much at the time, but I think given what we know to the prior question around your team’s engagement support, the ease of the technology implementation, and kind of the operating system that we had, we could have done multiple things concurrently and been faster on our transformation agenda. I’d say go faster.

ENIOLA IBISANMI: Okay. Very, very ambitious, which does match Transformco’s personality. So I love that. Next time, start earlier, start faster, get to the goal quicker.

BJ NAEDELE: Yeah, absolutely.

ENIOLA IBISANMI: All right. Well, thank you so much, BJ, for being here with us today. You’ve allowed us to learn how you actually moved onto Stripe, what were the intricacies of that, how you actually changed this process and deploy new tools and devices on Stripe. So before we part here, is there anything else that you want to share with the team today about this process and how it’s been for you?

BJ NAEDELE: Yeah. I mean, what I’d say in closing, to Eni’s support and help—we’re just getting started. And the opportunity that we have ahead of us, whether it’s new products and services, whether it’s new partnerships, I think a lot about—and we think a lot about one wallet, one currency, one identity—and really if you can take that everywhere, every day, what does that mean? And so I’ll just give you one example that’s top of mind for us. Right now, most products are created at the one-size-fits-all level. And so the idea that every single one of you here would get the same appliance, the same protection agreement, the same home warranty—where we’re going is to a version of this where it’s a segment of one. You can customize your plan, you can customize your payment method, you can customize your tender.

And so again, I think back to what you hear from us, the transformation agenda continues to be aggressive and opportunistic, but we’ve got the right support, the right platform, and the replatform in place. So it’s all about what’s coming next and continuing to push the transformation.

ENIOLA IBISANMI: Great. We’re excited to continue this partnership together. All right. Thank you everyone.

BJ NAEDELE: Thanks, team.

ENIOLA IBISANMI: And enjoy the rest of Sessions.