How to balance a two-sided marketplace

Note: Transcripts are automatically generated from episode audio, and are not fully corrected for spelling, grammar, and formatting.

WILSON: At the end of the day, these people are here to serve and help your family and other families, and we want to make sure that they get the best and fairest pay. It may not be obvious, even for the people who are hiring the caregiver, but you do have other care-related things in the home that you’re already likely paying money for. Home care and housekeeping are one example. Many people have pets — 70 million people have pets in this country. So I can assure you, most of those caregivers would love to take some of those duties on because, again, it prevents them from having to figure out the scheduling and the calendar Tetris of going to other locations, and they can actually earn those wages in the home. So it’s actually a way for families, in most instances, to keep the cost down.

BERMAN: This is Masters of Scale.

[THEME MUSIC]

I’m Jeff Berman, your host. This week on the show: Brad Wilson. Brad is the CEO of Care.com. That’s the digital marketplace that connects caregiving professionals with people who need help with kids, seniors, pets and more. With more than 45 million people on the platform, it is the market leader in an area where the need is constantly growing. We talk with Brad about how companies can create more loyal employees by supporting caregiving, why the future of work needs to be flexible, how he’s leading through transformational technology change at the company, and how some very difficult circumstances in his personal life have informed and inspired his commitment to Care’s profound mission. Brad, welcome to Masters of Scale.

WILSON: Thank you for having me, Jeff.

BERMAN: I’m thrilled to have you. I just want to start by acknowledging, on a personal note, that I’m so sorry to learn that you lost your wife.

WILSON: Thank you.

BERMAN: I know that you stepped in to lead Care when your wife was sick. I’m curious how that came to pass and how your personal and professional lives came together in that moment.

WILSON: I appreciate that. Thank you. It was an interesting time. This was back in January of ’23, when I first started talking about the role with IAC and Barry and Joey and company. I’d followed Care.com for years. There are only so many marketplaces at scale, and for me, I’d done 25 years in consumer brands, so I have a little bit of pattern recognition about what I think ticks. It’s a brand I always loved. When I looked at it professionally, I saw a great brand. I saw a clear market leader with the largest caregiver pool and supply, which is extremely important when you run these companies. And we’re still on this journey today, if we’re being honest: it wasn’t a great experience. So when I took a look at things that I thought I could be good at, influence and help improve, this was a great fit.

WILSON: It just so happened that, at the time, as I was interviewing, we learned of my wife’s diagnosis and we started to go through it. Care became a part of our story, too, because I needed that help. This is a deeply important mission for me personally. I’m living it today. I’m a single parent. I have three wonderful children. I have a great support system, which we all need as well. But I also go through what a lot of parents and communities go through today, and I’m trying to stitch together my own care community to make our family go, get to all the activities and events, and make sure that we can show up for work, do great jobs, and be part of our communities.

Copy LinkWhy caregiving has become a defining challenge for modern families

BERMAN: A lot of people who are of our generation are very much in the sandwich generation moment. I’m curious, as you look at the trends both nationally and globally, how you think about the mission of Care.com and the problems that you’re solving, and the scale at which they have to be solved.

WILSON: We view our vision as, number one, we want to help families find the care they need. Most families have four care occasions in the home, whether that’s senior care, pet care, child care, home care, or even tutoring, camps and activities, et cetera. So there’s a lot that families are working to stitch together.

WILSON: The other thing is, we really believe we have to be a leading advocate for families and caregivers. There’s a lot that families go through today to bring the cost of care down, but the reality is our caregivers aren’t making it up either. So that’s a very tricky equation. Just to give you a little bit of what families are facing, it’s a very overwhelming and stressful time. Work is more demanding than ever. For most families, the cost of care means 20 percent of income goes to child care-related expenses. If you’re dealing with senior care and other care needs, that escalates to about 40 percent. Ninety percent of people report losing sleep, 89 percent report feeling burned out, and they really want enterprise and/or some federal support — by way of tax credits — to help ease the burden of this cost of care.

WILSON: We have about 700 corporate relationships today, and we’re finding more and more that companies are coming to us because their employees need that support. Employers are happy to give it because they know that if that support is right, they find happier employees who stay longer and are much more loyal to the company. So we enjoy both aspects of that equation.

Copy LinkHow AI can reduce busywork and improve care support

BERMAN: I’m curious, as you look at your team, especially on the nontechnical side — or even on the technical side in terms of prioritization — how is the nature of work changing at Care with these new AI tools?

WILSON: I’d put it in two, if not three, buckets. One is what I’ll call the mundane tasks. Not every engineer likes to debug their own code, so I think AI can do a lot of that for you today. We do get a lot of people calling in because we don’t always get it right, but all of a sudden, now, sifting through the notes and the cases and actually looking through the experience to see what we can learn that can serve that customer better and fix that problem right away — it’s not 100 percent AI, but there’s a lot of assistance that helps gather the information and even make a recommendation to the agent.

WILSON: But there’s still a lot of research that has to happen behind the scenes at times. We have this concierge platform, as an example, where people call in, and there are hundreds of use cases. One of them may be, “How do I think about getting my aging loved one into a facility or an in-home caregiver? How do I pay for it? What happens in the first three weeks?” So we put together these tailored, personalized plans. Research for those cases used to be very manual and very hour-intensive. Now, a lot of our researchers and master’s-level social workers can rely on AI and reduce days into hours. So that’s just one example.

Copy LinkBalancing family affordability with fair pay in a two-sided marketplace

BERMAN: On the point of a two-sided marketplace, and in particular where you have a tension between serving both sides, you want to not only provide the highest-quality caregiver and care for your family customers at the best price possible, but you also want to get the care provider the best job at the best price possible. There’s a tension there.

WILSON: Right.

BERMAN: How do you balance that tension, particularly in this kind of two-sided marketplace?

WILSON: I’ll take you back two years ago. When I joined, and a lot of the new management team joined, you had a product, frankly, that was quite tough when you measured it by any kind of marketplace metric. I always think about conversion, meaning how many people are actually willing to pay you. A lot of the time that comes through: did you match them to the right caregiver and home? That rate, let’s just call it, was far lower than you would typically see from marketplaces.

BERMAN: Were you seeing that drop-off at the match point, or were you seeing it earlier in the process?

WILSON: It’s a freemium product, so you’re allowed to post for free, and we charge at the point of access to communication. Most marketplaces, I always say, convert between 2 and 6 percent. We were south of the 2 percent number. The second thing is responsiveness in the messaging. Let’s just say that number was astonishingly low, and then that leads us to the match rate. But all those metrics were substandard.

WILSON: To your point on the tension, on the caregiver side, when we got it right, they’re happy, they’re great. But the reality is we weren’t getting it right a lot. The piece we really have to solve for, which is tricky, is you have to keep the cost low for the family and get wages higher. That’s a very complex thing to solve, and you really can’t do it fully without some support. Again, I think there needs to be subsidy from the government and/or, mostly, enterprise. That’s where we’ve seen a lot of benefit, because enterprises come in and help take care of those costs for families. Some of the recent legislation, too, with the One Big Beautiful Bill and 45F, has lifted the tax credits for companies and caregiving-related expenses.

WILSON: I go back to the fact that most families have four care occasions in the home. They all stitch together things from pet care to housekeeping to senior care. If you think about most caregivers — and mine’s a great example — they’d prefer to do as much as they can because it saves them from driving and going to different jobs, which therefore can lift the wages and the well-being, and really what you can make in that particular household, without having all the stress of going to multiple places.

WILSON: The enterprise side of the business and the consumer side were, in part because both were scaling, a bit separate and federated. I think what we’ve tried to do is really say: one brand, one team. We also want to create what we’re calling this ubiquitous Care platform. The way we think about that is, rather than having separate supply serving the enterprise side and the consumer side, which it did, we’re now merging that supply and thinking about other forms of supply, like locations. We want one common delivery tech platform so we’re not shipping eight different things. We want that efficiency.

BERMAN: Because it’s complicated. You’re selling into HR, you’re selling into finance — not channels that generally have the budgets for the bigger spends.

WILSON: Yes.

BERMAN: So what’s working for you there?

WILSON: Generally, we make money three ways and serve our clients in three ways. One is backup care. Most companies will come in and say, “Hey, we want all of our employees to have 15 backup care days for when their primary care falls through.” I can tell you, I’ve had a caregiver — a lovely caregiver — and she’s needed three days off in the past month, and we all need it. So it’s a great benefit for employees and for those companies. They do find it as a vessel for, I call it, well-being because people are more loyal and they have the stress relieved by knowing, “I have a safety net here.” So backup care is one way.

WILSON: The other way is through our care concierge. This is a service where we have master’s-level social workers, and we get people calling in about everything from, “I just need parental guidance. How do I think about getting my father into a senior assisted-living facility?” to legal guidance. There’s a whole gamut of things. The third way is our digital membership. You mentioned small businesses as an example. Not every company can afford a backup care program, so perhaps we can just give them the digital membership at a reduced or wholesale rate and help them find that caregiver.

BERMAN: Are the enterprise customers — I have to imagine that they, on some level, can understand that if their team members have better support for the care that they need to provide, or need help providing, they’re going to be better team members. They’re going to be more engaged, be happier.

WILSON: Better team members. We have a lot of data showing that they’re more loyal. They’ll stay longer. In fact, when they don’t have the benefit, in our future benefits report, we see that there’s often a very high burnout factor and a little bit of disdain for the company they’re working for.

Copy LinkWhy care benefits can boost loyalty and reduce employee burnout

BERMAN: Twenty-five-ish years in consumer, largely in tech, largely in marketplaces: what drew you to the space to begin with?

WILSON: Business school in, gosh, ’99 to 2001. Now we’re really dating ourselves. It just so happened this thing called the internet was burgeoning, and I was super interested in the technology. I was in Dallas, Texas. I graduated from the Cox School of Business at SMU, and everyone was doing oil and gas or going to their investment banking jobs. I just said, “I’m very interested in that. I want to get into that.” And lo and behold, I was lucky enough to get into Match.com, which was an IAC company at the time, in Dallas, Texas.

BERMAN: In Dallas, yep.

WILSON: And so you very quickly learn internet economics at the time. You learn consumer behavior very fast, unlike how we’d ever learned it before. I was very fortunate to learn from and study under great leaders. At the time, we had Tim Sullivan, our CEO, who I felt was a great leader. Over time, I got to Expedia and was fairly close to Dara Khosrowshahi. I really worked under Aman Bhutani, who was just a fabulous CEO at GoDaddy, and then ultimately through HBO Max and WarnerMedia, Jason Kilar, and at 84Sells, just incredible men and leaders. But at the end of the day, this is what I tell our team: You have to deliver delight. That’s something I took away from all those leaders. Deliver delight, constantly innovate, and drive people directly to your products and brands.

BERMAN: Yeah. You mentioned Jason Kilar. I don’t know if he coined the term. I always give him credit for it because he’s the first person I heard it from, which is this term, automagically, where it feels like magic and it’s just happening in the background and it delights you.

WILSON: That’s a good one. I don’t know if I’ve heard him say that.

Copy LinkBuilding direct trust as AI reshapes search and discovery

BERMAN: Yeah, back in the Hulu days, that’s where I heard him say it. What lessons did you learn from that era that you’re applying to an era where Google is really being meaningfully displaced by AI search, effectively, or where agentic search feels like what’s coming? How are you preparing for that future, given what you learned in that time?

WILSON: Yeah. Everyone in our company is measured on delight, literally. We try to drive it through the organization. We’re not perfect. We’re far from where we need to be, but we want to build experiences where people know us, they can trust us, and they’re going to come to us directly. But I think first and foremost is how we go to market. For Care.com in the past, it was a lot of the old traditional ways. You would put some things on TV, you would play in the Google space. But with AI having a huge disruptive effect on search, we’re really trying to make sure that we are playing and meeting audiences where they’re at, publishing a lot of authoritative, educational, and entertaining content, whether it’s distributed through social media, through our own influencers in the company, or through anyone else who might find that content interesting. That’s the way the game’s got to be played now. Everything’s so fragmented.

Second, we reshaped our brand. We got a fantastic brand leader, Mae Linton, who reshaped our brand. We really want to go to market in a way that speaks to care beyond childcare and to care holistically as an emotional ally for our families and our caregivers. I would just say we’ve completely revamped go-to-market.

I think the second thing is we have to make sure the product is really delivering and works. In fact, we want to build AI into the product. Then the last thing I would say is, if you think about care on the consumer side, for 18 years it was mostly a transaction experience veiled in subscription. Why do you need a subscription after you find your match? So we’ve really thought about how we make these products work within the lifestyle of what we’re trying to do. Again, we want to match first, then we want to be a part of the entire journey. The way we think about that is before, during, and after the hire. Then we want to build an always-on platform, which is a couple years out. I’ll save that for a later conversation. It’s really hard, but if we get it right, we’re going to do a lot of good in the world. That’s the fun part about what we’re doing every day, and I’m very privileged. We have an incredible team.

Copy LinkWhat it takes to modernize legacy systems without losing momentum

BERMAN: When you take a new role, and particularly when you take a role leading an organization as a GM, as a CEO, you kind of think you know what you’re getting into. Then you get in there and it’s a covered dish, and you take that top off and you’re like, “Why is there cilantro in here? This makes no sense.” What surprised you coming into the role?

WILSON: The sales cycle is a bit longer than I anticipated. I knew it was long, but I figured it’d be six to 12 months. But what ends up happening is 12 sometimes becomes 18, becomes 24, particularly now because one of the challenges we’re seeing in our country and many companies is rising health care and dental costs. And so when that happens, care benefits become … We’re kind of a 1B benefit today, and because they have to meet the needs of those rising costs in companies, sometimes we get pushed maybe another half year to a year. So those sales cycles have been a little more challenging.

The second thing is, and I’m super proud of the team for working through this, when I joined, the number one thing I always talked about in the company was you’ve got to have a great brand, which means you have to deliver to your customers and, in our case, both sides of the marketplace. But you also have to have speed. Dara and Aman at Expedia did this better than anybody I ever saw. To have speed, you really have to have the testing apparatus in place. You have to have a very clear mandate on what you’re going after. You have to have total transparency in the culture, and you really have to give people permission to break things and move fast.

I knew we were slow. We’re still catching up to par, I would say. And the reason for that was the back-end infrastructure. This is probably not uncommon in a lot of these technology stories. We just had very outdated code. It was very federated. We made the very hard decision early on, and I said, “We’re going to pull it all together. We’re going to go through what I’m calling the infrastructure era. It’s going to be 18 months to 24 months of really hard work.” We basically took everything commoditized on the back end, from authentication, where you recognize users and where they are in the experience and can provide feature benefits to the package they’re in, to messaging, payments, and the entire back-end trust and safety systems, and completely replaced it.

Now we’re moving into that true transformation era where we can do fast-twitch retailing, merchandising, and testing. So we’re just now embarking on that. But I would say that was a little more complex than I originally anticipated.

BERMAN: And did paying down that technical debt limit your ability to launch new features and new products?

WILSON: Most certainly, sure.

BERMAN: That’s got to be hard. People want to build. People want to do cool things.

WILSON: That was tough. That’s tough.

BERMAN: How did you keep the team motivated and focused around driving toward that, to get to a place where you could launch the new things?

WILSON: Yeah, it’s a fantastic question because we do spend a lot of time thinking about culture and how to motivate people. We want this to be a really great place to work, with people equally excited about the mission as we all are. I think what worked for us was a couple of things. One is we’re just constantly in front of our teams, whether it’s town halls, biweekly standups, or our weekly operational meetings. It was very clear what we were marching toward and the vision that we were painting for the future. So I think that was really motivating and enticing.

The other thing I would say is that kind of midterm in this first period, we did take a very bold swing on a new go-to-market. We kind of unchiseled that subscription. We had an access-pricing model. I will tell you, it didn’t work particularly well, but I found that it was a very hard thing and a big thing for the company to do, which motivated the engineers and product people and technical people in ways that probably hadn’t been done in quite some time. Even in the last six months, I always tell people this company’s had more innovation in the past six or nine months than the prior 18 years combined. So I think you have to give people these big challenges and big problems to solve together. I think people have been invited in on the mission maybe in ways that they hadn’t before.

BERMAN: Yeah. And sometimes, as paradoxical as it may seem, you have to slow down to be able to go fast.

WILSON: We had to. Almost every answer I got when I came in on, “Well, why aren’t we doing this? Why aren’t we doing this?” was, “Well, the tech is outdated.” So we made the right decision. We’re not fully through it. I don’t think you’re ever done. But what’s promising is now you’re in this world where we’re all reading about the same things, from vibe coding to generative AI. There’s the promise that it’ll eradicate this in a short period. I actually believe it will. I think we’re going to work our way out of it over the next year.

Copy LinkLeading through regulatory pressure while staying focused on the mission

BERMAN: One of the things you inherited coming to the company was an FTC investigation that you all settled. I know it happened before you came in, and the settlement happened on your watch. Could you just frame up what happened there and how you led through that?

WILSON: Yes. I will state very plainly, and stand on my head if I have to: I violently disagree with what they claimed. In fact, the FTC attorneys got to know me quite well. And I will acknowledge one thing: the FTC, particularly under Lina Khan, was doing something good that we should all want, which is removing what they call dark patterns on the web, where people are being forced or coerced to click down a path maybe to buy something they didn’t want to buy, or where it’s really hard to cancel. One of the three things that the FTC asserted was that our site, being a subscription or membership service, was hard to cancel. Guess what? I agreed with them. Before that claim was even there, we had already started to change it and did change it to the point where they actually said, “You guys are far better than everyone else.” So we were already down that path. We were going to fix it.

The other things they asserted were that our jobs aren’t truly jobs. So there was language on the site that essentially called them job posts, and they wanted us to change the language around that. There was another piece where they challenged whether the rate caregivers were making was a fully accurate depiction of that rate. We don’t know how they could have claimed that because that was actual real data that we would get off our transactions on the site. And, of course, there are people who take those jobs off-platform and negotiate their own rates and deals.

For us, with all that we had to undertake, we felt it was better to settle and move on, probably against my better wishes. People persuaded me that that was the right path, and it was the right path. We worked with outside counsel. It was probably more of a time investment from me than anyone else. But we really tried to keep people focused on the mission of what we were trying to build.

BERMAN: Speaking of mission, you’re involved with the World Economic Forum and the future of care globally. How did that come to pass, and what’s the mission there?

WILSON: Yeah. I was invited on very graciously by the World Economic Forum, and I was reluctant to join this forum, in large part because anytime I see these caucuses, I worry about a lot of talk and no action. It’s been a good, healthy start to the dialogue. I think we’re bringing a number of different perspectives and solutions to the table. My role inside that is I’m one of the few, if maybe even the only, commercial heads who actually runs a business.

BERMAN: Because everyone else is a philosopher? Is that it?

WILSON: Researchers, maybe, or people who are very well studied, or professors. And so I think what’s attractive about having me on board is we see a lot. We have a lot of data. We can support, especially because we’re across 16 countries in Europe as well, a lot of the data they need to help enhance the dialogue around solutions, not too dissimilar from what we talk about. For us, I think there has to be a technology player, or players, that can help simplify this for caregivers and families. There has to be a policy effectuation that helps subsidize care for families, and enterprise must play a role. For them to understand and see the data on why it’s compelling and important, and actually how hard it is to get the match effectiveness and get people the proper care they need, that’s the role we play inside of WEF.

Copy LinkWhy solving the care crisis requires business policy and new models

BERMAN: Just focusing in on the U.S., where we seem hopelessly gridlocked on almost everything, we can’t even agree whether the sky is blue today or not. The need for quality care across the four vectors that you mentioned doesn’t matter if you are far left, far right, somewhere in the middle, or completely off the spectrum on this. I spent four years on Capitol Hill. Most people who work with companies that might engage with Capitol Hill will tell you basically to stay away until you absolutely have to. But it does seem like there’s a real opportunity for Care to play a significant role at both the federal and state level in making care more accessible, more affordable, and higher quality. Is that part of the strategy here, to proactively engage government and try to make things better for both sides of your marketplace?

WILSON: Yeah. We want to really advance that agenda at the federal level. We’re also going to take a look at the state level, too, and we haven’t fully tackled that piece just yet. But one of the big things I think about is that, if you look at how the federal government has approached this, they view accessibility and quality only in the form of a center. A center is something they can wrap their brain around as, “I can go check that location. I can validate that they have the right teacher-to-student ratio. I can validate that it’s clean, and the safety measures are right.” But the reality is more than 50 percent of the country lives in these childcare deserts, and there’s not enough childcare in the region, even if it’s a densely populated area, or there’s just nothing for the rural population. You have to have in-home caregivers as part of the apparatus to really solve this problem. That’s where we come in. We’re seven, eight, nine times larger, depending on the week, than any other next provider.

BERMAN: Yeah. Is there anything happening at the state level that is potentially a model for other states or for the federal government, where there’s been a real innovation in regulation or legislation?

WILSON: Yeah. I mean, New Mexico has universal childcare. Of course, we’re all waiting to see what Mr. Mamdani does in New York here. But what I would say is there’s no one single solution here. It is such a challenge for families. So when we see things like universal childcare, it’s really an acknowledgment for us that, yes, this has to be a bit of infrastructure and education, and it’s going to take a lot of different solutions. Technology does have to play a part in that. And I think the thing that we’re most optimistic about is enterprise, and that companies truly value it as well. So we’re not just relying on government. We do have enterprise players that want to play a part and make sure that their employees, who have families of all kinds, also have benefit equity.

Copy LinkHow families can create better caregiver relationships from the start

BERMAN: Brad, from the data you have, both qualitative and quantitative, what’s a non-obvious piece of advice for a family who’s hiring a caregiver, or is engaged with a caregiver, to create the best possible relationship and experience?

WILSON: Well, I can give you my personal experience, too, because I’ve gone through a few of them.

BERMAN: Great.

WILSON: First off, they’re looking for consistency. That may sound obvious, but I’m often shocked by the stories I hear around discrepancies in pay, and it’s usually tied to consistency of hours. Which leads me to say: Make sure there’s some kind of contracting up front, even if it’s informal, around what that looks like. I went through it myself. I had to learn a couple of times, too, where I thought it was understood what was needed by way of hours, and whether they get paid for driving, whether they don’t, whether they get paid for mileage. At the end of the day, these people are here to serve and help your family and other families, and we want to make sure they get the best and fairest pay.

BERMAN: Yeah. It’s a really interesting relationship because it’s one of the more intimate employer-employee relationships you’ll ever have, maybe the most. They’re in your home. If you’re lucky enough to be able to afford that kind of help, they’re in your kids’ lives, they’re in your lives, they know intimate details of your life, and you may know intimate details of theirs. But it’s still a business relationship.

WILSON: Yes.

BERMAN: So is there counsel on how to set those healthy boundaries in those dynamics, beyond getting things contracted up front?

WILSON: Yeah. I think it truly is unique. The other thing I would say is, I go back to the stat I shared earlier: It may not be obvious, but even for the people hiring the caregiver, you likely already have other care-related things in the home that you’re paying for. Home care and housekeeping are one example. Many people have pets — 70 million people have pets in this country. I can assure you, most of those caregivers would love to take some of those duties on because, again, it prevents them from having to figure out the scheduling and the calendar Tetris of going to other locations, and they can actually earn those wages in the home. It’s a way for families, in most instances, to keep the cost down if you consider the aggregate of the other care services, while also making sure the caregiver is appropriately paid.

BERMAN: Right. It’s a way to actually spend less as a family while the caregiver can make more and have a simpler schedule in life.

WILSON: Correct. That’s right.

BERMAN: That’s a great note. I love that. Brad, such a pleasure. Thanks for being on Masters of Scale.

WILSON: Jeff, thank you so much for having me.

BERMAN: Thanks again to Brad Wilson for joining us. As our needs for caregiving continue to grow, it is essential to have compassionate leaders like Brad tackling this incredibly important issue. I’m so grateful he’s taken on this challenge, and I’m so eager to see what Care.com does next. I’m Jeff Berman. Thank you for listening.