How to balance a two-sided marketplace, with Care.com CEO Brad Wilson

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0:44Creative planning where wealth works together. Learn more at creativeplanning.com slash mastersofscale. Hey folks, Jeff Berman here. the speaker lineup for Masters of Scale Summit 2026 is coming together. And I'm thrilled to share some of the absolutely iconic speakers. We're going to have the incredible Kara Swisher, Danny Meyer, Anjali Sood from Tubi, Cloudflare's Matthew Prince, Adam Grant, our very own Reid Hoffman, and some folks you might be less familiar with, but who, well, they're going to blow your minds. It's this October 20th to 22nd in San Francisco. Our theme, our agency now could not be more timely.

1:29Applications are open, but spots are limited. Apply at mastersofscale.com slash apply25. That's mastersofscale.com slash apply25. You know, 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 most fair pay. It may not be obvious, even for the people who are hiring the caregiver, you do have other care things in the home that you're already likely paying money for. Home care and housekeeping is one. Many people have pets. 70 million people have pets in this country. And 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.

2:15So it's actually a way for families in most instances to keep the cost down. This is Masters of Scale. 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.

3:11Brad, welcome to Masters of Scale. Thank you for having me, Jeff. I'm thrilled to have you. I just want to start by acknowledging on a personal note, I'm so sorry to learn that you lost your wife. Thank you. And I know that you stepped in to lead care when your wife was sick. And I'm just curious kind of how that came to pass and how your personal and professional lives came together in that moment. Yeah. Well, I appreciate that. Thank you. Thank you. And yeah, it was an interesting time. You know, we, this was back in 23 in January when I first started talking about the role with IEC and Barry and Joey and company.

3:51And, you know, I'd followed care.com for years. Marketplaces are only so many at scale. And, you know, for me, I'd done 25 years in consumer brands. And so I got a, I have a little bit of pattern recognition on what I think ticks. And it's a brand I always loved. And, you know, when I looked at it just 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, you know, and we're still on this journey today, if we're being honest, it wasn't a great experience. And so when I took a look at things that I thought I could be good at and influence and help improve, this was a great fit.

4:34It just so happened at the time, too, as I was interviewing, we learned of my wife's diagnosis. And we started to go through it. And 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 and go to all the activities and events and make sure that we can show up for work and do great jobs and serve and be a part of our communities.

5:14A lot of people who are of our generation are very much in the sandwich generation moment. I'm just 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. You know, 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. And whether that's senior care, pet care, child care, home care, even tutoring camps and activities, et cetera. So there's a lot that families are working to stitch together.

5:54The other thing is we really believe we have to be a leading advocate for families and caregivers. And 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 enough either. So that's a very tricky equation. You know, just to give you a little bit of what families are facing, it's a very overwhelming and stressful time. I mean, you know, work is more demanding than ever. You have most families, the cost of care, 20 % of income goes out to child care related expenses. And if you're dealing with senior care and other care pieces, that escalates to about 40%.

6:3490 % of people report losing sleep, 89 % report feeling burnt out, and they really, really want enterprise and or some federal support for, you know, by the way, of tax credits to help ease the burden of this cost of care. We enjoy 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. They'll stay longer. They're much more loyal to the company. And so we enjoy both aspects of that equation. I'm just curious as you look at your team, especially in the non-technical side or even the technical side of the prioritization, how is the nature of work changing at care with these new AI tools?

7:24Yeah, I'd put it maybe in two, if not three buckets. So one is, I'll call it 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 call 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 can we learn that can actually serve that customer better and fix that problem right away. It's not 100 % AI, but there's a lot of assistance that helps gather the information and even make a recommendation to the agent.

7:57But there's still a lot of research that has to happen behind the scenes at times. So we have this concierge platform as an example where people call in and there's hundreds of use cases. But one of which 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? And so we put together these tailored, personalized plans. So research for those cases used to be very manual, very hourly intensive. And now a lot of our researchers and master's level social workers, they can rely on AI and reduce days into hours.

8:34So that's just one example. On the point of a two-sided marketplace, and in particular where you have a tension between serving both sides, right? You want to not only provide the highest quality caregiver and care for your family customers at the best price possible, but you want to get the care provider the best job at the best price possible, right? There's a tension there. How do you balance that tension in particular in this kind of a two-sided marketplace? I'll take you back two years ago. When I joined, 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.

9:13So I always think about conversion. So meaning how many people are actually willing to pay you? And a lot of time that comes through, did you match it, match them to the right caregiver and home? And that rate, let's just call it, was far lower than you would typically see from marketplaces. And we were seeing that drop off at the match point or were you seeing it earlier in the process? Well, it's a freemium product. So you're allowed to post for free and we charge at the point of access to communication. And so, you know, most marketplaces, I always say, convert between two and six percent. We were south of the two percent number.

9:49The second thing is responsiveness in the messaging. And let's just say that that number was astonishingly low. And then that leads us to kind of a match rate. But all those metrics were substandard. And then to your point on the tension on the caregiver side, you know, when we got it right, they're happy, they're great. But the reality is we weren't getting right a lot. And the piece we really have to solve for, which is tricky, is to your point is you got to keep the cost low for the family and you got to get wages higher. And that's a very complex thing to solve. And you really can't do it fully without some, again, I think there needs to be subsidy from the government and or and mostly enterprise.

10:35And that's where we've seen a lot of benefit because enterprises come in and help taking care of those costs for families. And some of the recent legislation, too, with the one big beautiful bill and 45F have lifted the tax credits for companies and caregiving related expenses. I go back to most families have four care occasions in the home. They all stitch together things from pet to housekeeping to seniors. And 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 from the 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.

11:17The enterprise side of the business and the consumer side were, and in part because both were scaling, they were a bit separate and federated. So 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. So the way we think about that is rather than having separate supply serving the enterprise side and the consumer side, which it did. Oh, wow. We're now merging that supply and thinking about other forms of supply like locations. We want one common delivery platform. So we're not shipping eight different things. So we want that efficiency.

11:53Because it's complicated. You're selling into HR. You're selling into finance. Yes. Not channels that generally have the budgets for the bigger spends. Yes. So what's working for you there? Yeah. So generally, we make money three ways and serve our clients in three ways. One is backup care. So 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. 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.

12:29And they do find it as a vessel for, I call it well-being, because people are more loyal and they're just, they have the stress relieved of knowing I have a safety net here. So backup care is one way. The other way is through our care concierge. So this is a service where we have master's level social workers. And we get people calling in from everything from, I just need parental guidance. How do I think about getting my father into a senior assisted living facility? legal guidance. There's a whole gamut of things. And then the third way is our digital membership. And so you mentioned small businesses as an example.

13:08Not 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. And are the enterprise customers, I mean, 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 they need help providing, they're going to be better team members. They're going to be more engaged. Better team members. We have a lot of data. They're more loyal. They'll stay longer. And in fact, when they don't have the benefit, our future benefits report, we see that there's often a very high burnout factor and there's a little bit of disdain for the company they're working for.

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14:39It takes about 10 seconds to find. Just search Rapid Response wherever you listen to podcasts and hit follow to make sure you never miss an episode. I hope to see you there. humans will never be more intelligent than ai there's gonna be two types of companies those are great at ai and those that went out of business because they weren't how do we build a future that is human-centered i'm rana el-khaubi and on my podcast pioneers of ai we answer that question and so many more as an ai scientist entrepreneur and investor i know what it takes to build AI that works for everyone. Every week, I sit down with the pioneers shaping our future, and we take you behind the scenes of the AI that's transforming our lives.

15:29Find Pioneers of AI wherever you tune in. 25-ish years in consumer, largely in tech, largely in marketplaces. What drew you to the space to begin with? Business school in, gosh, 99, 2001. and now we're really dating ourselves. And it just so happened, this thing called the internet was burgeoning. And I was just super interested in the technology. And, you know, 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. And I just said, yeah, I'm very interested in that. I want to get into that. And lo and behold, I got, I was lucky enough to get into Match.com, which was an IEC company at the time in Dallas, Texas.

16:17And so you very quickly learn internet economics. I mean, at the time to, you know, you learn consumer behavior very fast, unlike we'd ever learned it before. I was very fortunate to learn and study from great leaders. And so at the time, you know, we had Tim Sullivan, our CEO, I felt was a great leader. Over time, I got to Expedia and, you know, was fairly close to the dark house of Shahi. I really worked under Amon Bhutani, who was just a fabulous CEO at GoDaddy. And then ultimately through HBO Max and Warner Media, Jason Kyler and 84 Cell, just incredible men and leaders. But at the end of the day, you know, I always, this is what I tell our team is you have to deliver delight.

16:57Something I took away from all those leaders. Deliver delight, constantly innovate, which should drive direct to your products and brands. Yeah, you mentioned Jason Kyler. 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. That's a good one. I don't know if I've heard him say that. 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 agentic searches?

17:38It feels like what's coming. How are you preparing for that future given what you learned in that time? Everyone in our company, we're measured on delight, literally. I mean, 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. And 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 in 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 and or through our own influencers in the company or through anyone else who might find that content interesting.

18:38Christine, pardon. And that's the way the game's got to be played now. Everything's so fragmented. Second part of that is we reshaped our brand. We got a fantastic brand leader, Mei Ling Tan, who reshaped our brand. We really want to go to market that speak to care beyond childcare and care holistically as an emotional ally for our families and our caregivers. But 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. And in fact, we want to build AI in the product. And then the last thing I would say is if you think about care on the consumer side, where it was for 18 years, really, it was a mostly it's a transaction experience failed in subscription.

19:28And why do you need a subscription after you find find your match? Right. And so, So we've really thought about how do we make these products really 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. And the way we think about that is before, during, and after the hire. And then we want to build kind of an always-on platform, which that's a couple years out. I'll save that for a later conversation. And it's really hard. But if we get it right, we're going to do a lot of good in the world. And so that's the fun part about what we're doing every day.

19:59And I'm very privileged. We have an incredible team. When you take a new role, and particularly take a role leading an organization as a GM, as a CEO, you kind of think you know what you're getting into. And 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? Like, this makes no sense. What surprised you coming into the role? The sales cycle is a bit longer than I anticipated. And, you know, 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.

20:41And so when that happens, care benefits become, you know, 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 just pushed maybe another half year to a year. So those sales cycles have been a little bit more challenging. And then the second thing is, and I'm super proud of the team for working through this, but when I joined and the number one thing I always talk about in the company is you 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 have to have speed.

21:16And I mean, Dara and Amman at Expedia did this better than anybody ever saw. But to have speed, you really have to have the testing apparatuses 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 were still catching up to par, I would say. And the reason for that was the back-end infrastructure. This is probably not uncommon from a lot of these technology stories. We just had very outdated code. It was very federated. We made the very hard decision early on.

21:54And I said, we're going to pull it all together. We're going to go through what I'm calling the infrastructure error. It's going to be 18 months to 24 months of really hard work. We basically took everything commoditized in the back end from authentication, where you recognize users where they are in the experience, and you could provide feature benefits to the package they're in. Messaging, payments, the entire back end, trust and safety systems completely replaced it. And now we're moving into that true transformation era where we can do fast twitch, retailing, merchandising, and testing. And so we're kind of just now embarking upon that.

22:31But I would say that was a little more complex than I originally anticipated. And did paying off, paying down that technical debt limit your ability to launch new features and new products? Oh, most certainly. Sure. And so, I mean, that's got to be, people want to build, people want to do cool things. Like, 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? Yeah, it's a fantastic question because, you know, we do spend a lot of time thinking about culture and how do you motivate people. We want this to be a really great place to work and people equally excited about the mission as we all are.

23:07And 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 stand-ups, and our weekly operational meetings. It was not unclear what we were marching towards and the vision that we were painting for the future. And so I think that was really motivating and enticing. The other thing I would say is kind of mid-turn of where we were in this first period, we did take a very bold swing on a new go-to-market. And, you know, so we kind of unchiseled that subscription. We had an access pricing. I will tell you, it didn't work particularly well.

23:43But 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. And even in the last six months, I always tell people, this company's had more innovation in the past six and nine months than the prior 18 years combined. And so I think you have to give people these big challenges and big problems to solve together. And I think people have been invited in on the mission, maybe in ways that they hadn't before. Yeah, and sometimes it's paradoxical as it may seem.

24:15You have to slow down to be able to go fast. We had to. I mean, almost every answer I got when I came in on, well, why aren't we doing this? Why aren't we doing this? Well, the tech is outdated. 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, you know, what's promising is now you're in this world where we're all reading about the same things from vibe coding and generative AI. There's the promise of that it'll eradicate this in a short period. And I actually believe it will. I think we're going to work our way out of it over the next year.

24:45One 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 settlement happened on your watch. Could you just frame up what happened there and how you led through that? Yes. And I will state very plainly, stand on my head. In fact, the FTC attorneys got to know me quite well. I violently disagree with what they acclaimed. And I will acknowledge one thing. The FTC, particularly under Lena Kahn, I think it was a good thing that we should all want to remove what they call dark patterns on the web, where people are being forced or coerced to click down a path, maybe to buy something that they didn't want to buy, or it's really hard to cancel.

25:33And so one of the three things that the FTC asserted was our site being a subscription or membership service was hard to cancel. Guess what? I agreed with them. And before that claim was even there, we already started to change it. It 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. You know, the other things they asserted were we – our jobs are truly jobs. And so there was language on the site that essentially called them job posts. They wanted us to change the language around that. There was another piece where they challenged that the rate that caregivers were making was maybe not fully an accurate depiction of that rate.

26:19We 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. So, you know, for us, we just felt with all that we had to undertake, as I mentioned earlier, it was better to settle and move on. And probably against my better wishes and people assuaged me that that was the right path. And it was the right path. We worked at the outside council. It was probably more time investment from me than anyone else. But, you know, we really try to keep people focused on the mission of what we were trying to build.

26:56Speaking 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? Yeah, so I was invited on very graciously by the World Economic Forum. And I was reluctant to join this forum. And in large part because anytime I see these caucuses, I worry about a lot of talk, no action. And, you know, 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 of that is I'm one of the few, if maybe even only, commercial heads that actually run a business.