S3E2: SJ Sacchetti of Cleo

Welcome to The Room Podcast. My name is Madison McIlwain and I'm a partner for seed stage investments at DefyVC.

And I'm Claudia Laurie, a co-founder of Pryve. We're a founder and funder who are in the room where it happens. If you're a first-time founder or an emerging venture capitalist, we're glad you found us. We share inspiring, authentic, and insightful stories from founders, funders, and operators who have been in the room and provide tactical feedback on their early aha moments and learnings along the way. Before we dive into this week's episode, we have a short message from our partners.

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Cooley is a global law firm built around startups and venture capital. The firm has been devoted to entrepreneurs and investors, partnering with both to transform breakthrough ideas into successful companies. Cooley works with thousands of entrepreneurs and newly formed companies to ensure that they are structured for growth and long-term success. Since 2005, Cooley has been ranked the number one most active law firm. Representing VC-backed companies going public. Learn more about the firm at cooley.com and also at cooleygo.com, Cooley's award-winning free legal resource for startups. This week on The Room, we are thrilled to be sitting down with Sarah Jane, or SJ, Siketty, CEO of Clio, a working parent family benefits platform for employers. What was so refreshing about today's episode was that SJ didn't always think she was going to become a CEO and chats with us about her career path, her learnings along the way, and what it's like coming into a company as a CEO just months before COVID and work from home. SJ started her career in politics and policy, cutting her teeth in the world of political fundraising, which set her clock for the startup world before she even knew it. SJ made her way into tech as a marketing consultant at Formspring, landed a role as SVP of marketing at Collective Health, and then ultimately became CMO of a pivotal step towards her career at Clio. After nearly 5 years at Collective Health, SJ joined Clio as CEO in late 2019. This episode is particularly well-timed as Clio just announced their $40 million Series C round. Today we dig deeper into themes such as leadership during unfamiliar and unusual circumstances, overcoming imposter syndrome, and being a boss amidst uncertainty. Let's open the door.

S.J. Sachetti, thank you so much for joining us today here in The Room. We're really thrilled to have you.

I am so glad to be with you guys today.

You're the CEO of Clio, but you didn't always start as a CEO, and as you alluded to in our pre-convo, there's likely a fun story on how this came about, but we always just start at the beginning of our guest's journey. And so taking you back to undergrad, you studied political communications at NYU and started as a political campaign manager in San Francisco after undergrad. What initially drew you to politics and policy?

Yeah, I think it's interesting to go to the Wayback Machine because I'm certainly the accidental CEO if there ever was one. It was not by design, but it's a position I'm really honored to have today. So when I actually came out to California, feels like 150 years ago, I did start in politics and that was actually my trajectory throughout my early adulthood through college at NYU. I was really focused on two things. One was social impact and another was political organizing around that. So I actually studied city planning, political communications, et cetera, NYU. And in any spare time I had, I was actually working with many different nonprofits, oftentimes in environmental work and doing some really interesting, very local-focused work in New York. And so when I made my way to San Francisco, unlike most people at that time, I wasn't focused on tech. I was really focused on how do I pursue a job that could pay my bills, pay my but keep me close to this impact that I was seeing when I was in New York in community organizing. And political consulting just happened to be this open door. I started at the bottom. I literally started as a temp. Just for people to think about designing these moments, it— I found any job I could, and it ended up being a temp job at this group called the Lou Edwards Group that is still crushing it across California with finance measures and healthcare districts, education districts, and candidate measures. And started as a scheduling for the CEO, doing anything she needed. Within 6 months, she was sending me out to Kern County and Fresno County working on local campaigns. And so it was really the nature of just following my gut and intention to do something meaningful in these communities. And it was really exciting because I started in education measures. So that's where it began.

So clearly you've had this thread of wanting to make an impact throughout your career, and we're going to touch on multiple, uh, jobs where that is proven to be very true. But the switch from political consulting to marketing consulting, walk us through what that transition was in and how you switched sectors, so to speak, in that way.

Sure. For anyone who's been in both the fields of what I think of as startup tech and political campaigns, I think they'll well understand this. And for those of you who haven't, you'll probably see it from the outside. I always say that my job in startups and was really helped by creating the pain threshold that I had in political campaigns. And so I just wanna start there because there's actually a connective tissue to me with political campaigns. The pace, the fact that you actually win or lose on a single day after months or years of work is really interesting when you think of startup winning and losing, because I've found in startups you get a second day most of the time, you get a bridge funding, or you get another opportunity. So I want to start with actually just on the one side of it that wasn't obvious to me at the time, but I think politics really set my clock speed, my focus on impact results, my competitiveness on winning or losing, understanding of these small things coming together. So that, that's more on what I would call the backside of this, the soft skills that I had developed in political campaigns that I didn't think of at the time. And then the second piece was the hard skills, right? Why was I able to go from political campaigns to marketing? It was a really natural jump. First and foremost, I was planning to take a short break from the campaign trail. I was planning to go right back into politics. But even at my really young age, I think I was 25 at the time, I was exhausted. The honest goal was I wanted to have friends and see people and not work. I was working probably 18, 20 hours a day at the peak of campaign season, flying everywhere. The job I had in political campaigns was convincing people, persuading people. We did a ton of polling, understanding grassroots. I did door knocking door to door. It's not a glamorous job, but really listening to people and finding those connective tissue between How can we bring those people along? How can we get, right, that 65-year-old who has no interest in paying more for schools where her kids have already grown up to find this connection to the teachers, et cetera, in her community? It was a perfect place to find marketing skills. I hadn't thought of it that way at the time, of course, but that's really what I was doing is listening, synthesizing, and connecting people. At the time I jumped into a tech PR role, Fascinatingly, it was some similar skills, right? So listening to them, transferring it to relatable content, relatable persuasive, right, techniques to get journalists and others to follow us and connect the pieces. So, so I went from, right, political campaign measures and ballot measures to press releases, but it was actually quite transferable, which is actually interesting.

Thank you for drawing those parallels for us. I don't think that the average listener or, you know, individual would really think, oh, political consulting, marketing consulting, they make sense together, but I see that path and I see that thread for you.

You eventually found yourself in a less consulting role at a, at a Formspring, which I have to say Claudia and I have not heard the Formspring name probably since maybe 10 years ago.

And you guys were probably users.

We were Formspring users. I'm gonna tell you that right now.

How funny.

So some things come full circle and just tell us about what it was to, to land your first official role, non-consulting role in tech.

I've ridden so many waves in tech, so I really started enterprise software and hardware, conductors and service-oriented architecture, etc. Then I moved into ad tech. So it's all these waves I've seen over my last 20 years of being in tech, and those waves brought me into outside of my PR firm that I was working at into being a consultant, to your point. And then landing at Formspring was really interesting. It's probably the headline of my career. It was just the connections I had built and relationships I had built. So they called me in, into the role they were looking for Formspring. For those of you don't know, was actually one of the fastest-growing social networks at the time. It grew wildfire. It was an anonymous social network that let people ask questions of one another. It was both used really well, but it was unfortunately used and sometimes abused, right? And it— the power of anonymity online. And so they were looking for someone who understood policy and politics, who also understood marketing and tech, who could be part of this founding team. And so one of the investors was— had seen me working at some of these other startups and had actually pulled me into the conversations. And so that's how it all happened. I met the founders, and to that point of impact, I really wanted to help address the issues that we had as well as really build this company into what it could be. And it ended me, funnily enough, right back in DC. I think within 6 months it was really on the policy side, so it all came full circle with that first role.

It's incredible to hear just sort of how many varied experiences you've had in tech, but also How many varied experiences you've had from marketing to political fundraising and how those experiences have really informed your skillset, which probably gives you an edge as a CEO, especially in the startup world because everything is moving so quickly and you have to— the common trope of wearing so many hats and really hearing you talk about selling someone on voting for someone is truly a marketing role. I was just reflecting on a sales call that I had earlier today where I was also thinking that skills from previous industries and school clubs were more helpful to me in that call than a lot of my formal product manager training at Uber. So that's really interesting. But let's talk a little bit more around your role at Collective Health, which was an incredible stepping stone to Clio. You went on to be SVP of Marketing and ultimately CMO of Collective Health. What were some of the key learnings you took away from your time there?

I owe so much to my time at Collective Health. It was first and foremost the, the dream job, if you will, because I had been in all of these tech companies. And I had just missed this impact that I had experienced in my early part of my career in politics and nonprofits earlier than that. And, and health tech was this opening. It happened about 10 years ago that we started to see so much funding, so much exciting innovation in health technology, and Collective was that place. The first thing I learned is that is the perfect place for me and many folks who want to do well while they're doing right by others. And I think that's why we're seeing so much exciting innovation come to fruition. It truly is a mission-driven part of the market in the technology landscape. The second thing I learned beneath that is the culture, right, attracts incredible talent. And that's been true of both Collective Health and Clio and so many of these incredible health tech companies. So just advertisement for everybody, come to health tech. The weather is wonderful and the people are great is number one. And number two is more on skill level and market level information that I learned at Collective Health. I call it Collective Health University because we were really in the middle of how healthcare is paid for in America. So Collective Health has built this remarkable transformation technology around supporting one of the largest payers in the US, employers, in managing their healthcare spend and also innovating around all of the potential solutions that they could bring to their members. Employers sponsor healthcare for over 150 million Americans today. In my 5 years there, I just learned the intricacies, the complexities, the obstacles, and the opportunities that are really, I think, drive both the progress and the failures of our healthcare system. So, that was number 2, is just how much I learned there. And number 3 is more the bright side, which is, I think, then foreshadows my time at Clio. Is I learned that employers are certainly, I think, one of the bright spots in the healthcare market today in the US. It's an accident of history that employers, right, are in this position to figure out all of these gaps in our health system as well as our social safety net. But they are actually showing up and they're really driving remarkable innovation and as well as transformation of things that are really core to destigmatizing in our culture. Transgender reassignment surgery or mental health have been really shaped and shifted by employers in the last decade. So that's the bright thing that I learned is just how much is possible within that market.

When I was working at Uber, we used collective health, and I'm originally from Australia, and my parents are always incredibly confused about the US healthcare system, and I've been through so many different health insurances, and I remember just how easy it was to understand what my plans were, how to navigate this whole system that now as a startup founder myself, I'm trying to think through the best ways to provide healthcare healthcare and benefits to my employees. And seeing a lot of our listeners are founders and are starting to think about healthcare for the first time, especially coming out of this pandemic, do you have any tips or guidance for how early-stage founders should start thinking about providing healthcare and benefits?

That's a big question because there's unfortunately not a lot of choice, especially in the smaller side of the market. So the larger the employer, as Uber and others are self-funded, and so through that vehicle, just have the opportunity to have more control and choice over the experience and the products that they could select for their people. So if I were gonna back up into what you should think about, if as an early stage employer in this space, I think number one, understand the mechanics of the healthcare system and how it operates and why. I think it's always useful versus just doing a check the box benefit. So you can ask some really good questions about why things are priced the way they are. Understanding, right, that brokers make a lot of money on you as an employer is really helpful to understanding some of the fundamentals as you— because you don't have a lot of choice, but you can be an informed buyer. I think there's so much about our system that takes away our agency and makes us— I want to say almost because it is so opaque and so complex, we don't actually ask good questions. You can still be an informed buyer. You can still ask good questions of your broker. You don't have all the power that a self-funded employer does, but you could still ask, why is that rate that way? Why are my rates going up 30%? How do we shift that? So I think just you would with a SaaS product or a CRM platform, asking good questions and doing the research is one tool that I think you should employ, which oftentimes we don't. The second one is, and this is, this is true, by the way, not just of health benefits, but general HR. I firmly believe that the best startups will think about HR benefits and the investment there fundamentally differently than we did the last decade. I think investing in your people, investing in their healthcare, not just thinking about the check the box on core benefits, but actually thinking about what you stand for and how you can not just attract and retain, but also really improve the lives of your people is a huge opportunity.

We talk a lot about this with our companies. Of course, Claudia's amazing company is one of those, but someone, one of ours, post their Series A, just hired a head of people and culture. And I love that just right when they had the capital to invest in that, they, they started doing it. And I, and I hope to see more of that investment, to your point.

Oh my God, 100%. My favorite analogy around this is so many people think about HR as the umbrella. Oh, it's raining, let me go run and get an umbrella and protect us now. And they, as a compliance or a check the box or fixing something, I think about it as the weather report, right? This should be someone who's ahead of you, who's strategically driving your culture, your initiatives, your performance. One of the people I've worked with at two companies, Jude Komoves, is now the chief people officer at Affirm, and I couldn't be a bigger fan of hers. She always talked about her role in people operations and HR as she was building a product of her own, which was the people and the organization that would ship the products that everyone needs. I think you should add, I think you celebrate those companies. I think VCs should ask that question because I think we see really compelling returns from companies who are intentional around that strategy.

And speaking of not ticking the box, I think this year has— or past year in 2020 has been a year where families were really starting to rethink wellness, their care. And I'm sure for a workforce of working parents, it was really quite, quite the trial. And I think that sort of brings us to what you're doing at Clio today. After nearly 5 years at Collective Health, you left in late 2019 to join Clio as their CEO. Madison McIlwain, for our listeners, what does Cleo do?

Absolutely. Cleo is a family benefits platform that supports large employers with ensuring that every part of an employee's journey who's a working parent is supported, advocated for, and driven by one fundamental belief that working families should be able to thrive, not just survive and get through the day. So we think about things in three dimensions: health, career, and parenting. And so much of that has been not only fragmented but unsupported along all of these, right? We think of the big moments, a fertility journey or having a child or having a neurodiverse or an acutely ill child. We think about these big picture moments and they're oftentimes so unsupported. So we bring incredible set of experts who we call our Clio Guides, who are essentially the partner to each of these member families throughout their journey. So you have an expert support system in your pocket, but we also then connect all of the many, many pieces that are a puzzle for so many families to connect, whether it's their local support system, school decisions, childcare decisions, as well as the employer's own benefits, right? How does your FSA support your childcare goals? How does your leave work? And so by connecting this as one platform, we've really transformed the working family's experience to being a massive gap and frustrating issue that drives huge, huge attrition, especially among working mothers, to actually an incredible perk and supportive system that drives retention as well as better household health for the whole family.

Thank you for sharing that. I think as young women in our careers, I think I'm even having conversations with friends of mine who are starting to think about, should I freeze my eggs? What's going to happen in 5 years?

I'm—

my career is just starting.

I just had this conversation this weekend with my friends. We literally spent 2 hours talking about, is egg freezing a good idea? What can it cause? What are the risks?

And none of us are medical professionals, but we were just debating it.

And there's so much speculation, not only just on the science part and whether that's something that we should be doing sooner rather than later, so on and so forth.

And there's also a lot of profit-seeking entities that want you to go ahead and do that right now. Right. And so there's so much conflicting information and it can be equal parts empowering and disempowering. It's this really bizarre map. And so I think that's where, and this is by the way, not just true of your journey, right? How do I think about egg freezing? How do I think about future fertility? But it's the same around childcare. It's the same about talking to your manager about taking leave while you're still gunning for the promotion. There is no map, right? There are no examples. I am too many people's exception to every rule, right? As a mom of a 4 and 7-year-old running an early stage startup that's growing, right? Faster than my kids are. Right. I have so few examples myself. And so if we look back, then what does that look for all these others? And I think there's so much conflicting advice, and I think that's where this concept that our co-founders had in the very early days. Our co-founder, Dr. Kailaswaran Chitra, is remarkable and is a practicing OB at a safety net hospital in Alameda County. And she saw this, right, in the healthcare system, you can't even get the attention and advice you need. And so I think that's what's really brilliant about Clio's model of putting these expert advocates who stay with you. It's not a hotline. Literally, you get a coach that stays with you. You would with Noom or some other incredible, right, coaching app. That gets to know you and your goals and also takes some of the pressure off of figuring it out on your own.

I hear the passion that you have for this problem space, and it's incredibly important. And so it makes sense that becoming CEO of Clio was something that really made sense for you. Would love to double-click into sort of that journey to being CEO. What was the process of being approached to join Clio as a CEO? Tell us about sort of that recruiting process. You mentioned that becoming a CEO was potentially an accidental part of your career. Tactically, what does that look like?

It was not on my bucket list. We'll put it that way. Especially after working with over probably 20 early-stage startup CEOs in my career and seeing their trajectory, seeing both their, right, successes and failures, I saw it very up close and personal. And it, it was always something I greatly revered but never saw myself doing. And so to that point of what was my path here, I'll, especially for listeners who are earlier The number one is early-stage startups. When you perform well and are a focused team member on the results of the business, you build incredible relationships. I'm quite— my path was circuitous with consulting, with having my own business, with going into venture capital firms, helping them with going into startups. But one of the things that was true all along is there were always the next person or the next role always brought me in, if that makes sense. And so building these relationships with early-stage startups and boards was really, I would say, the theme that then also held true into this position into Clio. And I'm a big fan, especially for those who are really, really passionate about what they do and want to learn a lot. Early-stage startups can be an incredible training ground. And then Clio specifically, I had known since it was a little early-stage product called Lucy, because at Collective Health, we actually saw many of our clients thinking about this issue 5 years ago, where they were seeing women leave the workforce, they weren't seeing women, right, make it through the path between manager and executive, right? They were seeing so many women drop out, which we still see. Unfortunately, COVID has made that even more disastrous. And so at the time, and as a collective, we actually integrated a lot of these emerging creative new solutions in these vertical areas. And Lucy was one of them that came up often. And I actually had, I remember an early marketing campaign for Lucy. Oh, they put these boob cookies on my desk and I was very pregnant with my second child, Leo. And so everyone, of course, just thought I'd be interested in them. I wasn't. I'm a prude from Massachusetts. I was not interested, and I'm still such a nerd and a prude, but it certainly was attention-grabbing. It clearly worked for Cleo at the time. And so I had known them from the early days, and people on my collective health team were asking me, you should talk to them. Maybe we could bundle their solution into our products. And being this massively pregnant woman in the room, everybody obviously thought I would put two and two together. I didn't. I was very busy and I was, well, that's interesting. Oh, that's interesting. So I had seen them for a long time. That was 5 years ago. And then as my got later stage at Clio, I started to build a great relationship with a remarkable investor, Sarah Glo at Greylock. And she would just ping me time and again about different roles that she had open or wanted to talk to me, but she would always bring things back to Clio. And so she actually introduced me to the then CEO, Shannon, co-founder, who's remarkable and really created Clio from the ground up. Up through sheer willpower and vision. And so she had connected us. And so I had known the company through many dimensions and was informally helping them here and there, help them think about their first marketing hires, help them just as a friend of the company, but nothing formal. And so when it came time to the CEO transition that occurred, I was just on the list as a friend of Clio. And they had 3 things they were looking for. One was someone who understood employer health benefits and employer healthcare. The second thing they were looking for is they would have preferred a woman. They wanted you to be in the Bay Area, and it would be extra credit if it was a mom, right, who really felt this.

So I always joke, there's about 30 of us that got it to the executive position, maybe 25 in the Bay Area.

So there was just a short list of women, and many of us knew each other.

They started recruiting for the role, and we would text, and, oh, they're calling me, or they're calling you.

And it just didn't occur to me, it was not obvious why they were calling me about about this role, not because of Clio or my understanding of the market, just the CEO position itself was not obvious to me because I hadn't been excited about it in the past. And so it took some convincing, a few different coffees and lunches with the board, and it was actually a great conversation with Sarah where I said, "It's just really not for me. I don't see myself in that way." And she said, "Well, what do you want to do in 5 years' time?" And I said, "Well, I'm going to be making a massive impact on the lives of hopefully hundreds of thousands or millions of Americans in issues around working, around women." around all these things. And, and, and she said, well, that's Cleo, right? It's right in front of you. Why aren't you connecting the pieces? And it was really this getting over this hump of the CEO title and not identifying with it, which I think is truly structural. Misogyny was so baked into me. And also the fact that there aren't a lot of examples of women doing this successfully. We've seen a lot of younger women starting companies before they have families. We see some women right in the Fortune 500 that are much later stage and probably have many, many more dollars to spend on childcare. Care than I do and other structural supports. So I have to say my, my missing link was how would I do this and still be the involved mom I am, and how could I get over that hump? And then when I realized that the opportunity was to shape the product and the team to support that and essentially practice what we preach, was being handed the Rubik's Cube and saying, well, if you solve this here, you might be able to create that carbon copy for, for many more companies and women to follow. So I finally said yes. Yes, and I'm glad I did. That was a long answer, I'm sorry.

No, it's awesome to hear that, and I'm sure many of our listeners are going to resonate with that quite a lot. You mentioned that you, throughout your career, having been at so many startups, having seen so many different leaders go through their journey, that you saw the struggles, the pitfalls that they had been through. Could you give us maybe one thing that you really had to overcome in your path to sort of executive leadership roles?

It's something I'm constantly working on, and I think I've managed it. I think it's gone, and then it sneaks its way back again. And it's the one you guys probably think about and talk about a lot, which is imposter syndrome. I thought I was cured of it, and a week ago I realized in talking to a remarkable coach I'm really lucky to work with— I've worked with him on and off actually since I was at Collective— I still have it. And I think, I think it's just a constant undercurrent. Thinking that everybody else knows exactly what's happening next or what's supposed to happen. And of course startups are by definition not knowing what's supposed to happen next and being creative. And it's so funny that I know that through 20 years of working with startups, but still hold myself to that expectation, which is of course not realistic.

I think imposter syndrome is something Claudia and I feel transparently, and we've talked about it with some of our other guests, men and women alike, but unfortunately more often women. And I appreciate you sharing that because it's easy to look at you and hear you speak on this conversation and just be wowed by how poised and thoughtful you are.

To hear that you sometimes still doubt yourself, you shouldn't, but the fact that you do just is a comfort to me.

The best part is that I thought I was done with it.

That's the most frustrating. I was talking to him last week. I was like, "Oh my God, I'm not done with that yet." So of course, and I think we should obviously talk about it more and more. I'm sure you guys saw the— there was a great HBR article, was it? About 3 or 4 weeks ago about women don't have imposter syndrome. They're women in the workplace, right? It's essentially wired into our existence because we don't have, we just don't have as many examples. We, and I certainly, right, we, I strive to find them and create those connective tissues, but they're not obvious. And there isn't a club. There isn't on the other side of the fence.

Well, you're clearly figuring it out as you go. Clio has successfully just announced recently their Series C round, which was, I think, about $40 million in capital from new investors. Transformation Capital, Glen Capital, Proven Capital, and existing investors such as Greylock, who you mentioned, and NEA and Felicis. First of all, congratulations.

That is no small feat.

What were some takeaways for you going through this process as a CEO for the first time and doing this in a global pandemic?

Yeah, I wish I had the, a way to compare, right? Doing it in person versus on Zoom.

So I'll have to extrapolate just from from the experiences I've had watching my other CEOs do it when we weren't doing this in this little room on a box. I think the takeaways I had are, number one, the obvious one, which digital health is exploding, but there's a lot of big questions about essentially the subcategories of digital health and telling a really compelling narrative and vision around what the future looks like in our specific space. Is it takes a special investor who sees that thesis outside of the non-obvious thesis. Mental health, I would say, has become an obvious thesis And so finding that connection to an investor who sees some patterns that are not obvious at a growth stage and a Series C stage, them coming with a thesis, I think was a lesson learned because we ended up working with the folks who had a strong thesis before they sat down with us. So that was number one. Number two was, gosh, it's so crazy to do this on Zoom. And I think one of the things that I remember from my last CEO, Ali, who, when he was fundraising, is he could blow off steam and come to the office and talk about it with others.

And I didn't really have that connectivity with adults. It was my children and my husband who's like, I'm over it, we don't need to talk about this again. So I'd say there was a— there's always a loneliness, I think, in doing the job. But I'm really excited that this thing is over, this pandemic's almost over, because for the next fundraiser, I'm looking forward to having some people to have a laugh in person or, or blow some steam.

And then the third lesson for me was involving the team. And that's probably an interesting thing for later stage companies of how much, especially as a new CEO, I learned about the business during the process and how to, which is fascinating for me, right? Because I came in 2 and a half months before the pandemic. And so didn't have a ton of time even with my executive team in person. And so while we were running the business day to day, some of the bigger strategic pieces or some of the larger data questions we actually uncovered during the Series C process.

Thank you for sharing those insights, especially your first point as an investor and where we try to create delightful conversations with entrepreneurs and try to get, say, please come work with us. I didn't realize how much sales there was in, on the investor side of the table. Quite frankly, when I joined, uh, I thought everyone was, oh yeah, we'd love to work with you. But no, you have to say, we're really unique and we had this thesis and we believe in you. To hear you say that, um, really resonates and I think is helpful for both sides of our listeners, both founders and funders. Taking a step back more thematically, as we look at the future of work and especially what the future of work looks for women and families, you alluded to this, but I'm just gonna hit us over the head with some unfortunate reflections made recently that progress for quote, women at work, uh, is likely back to 2017 levels by the end of 2021 as a result of COVID-19. And this analysis was done by PwC's annual Women in Work Index. So, gonna go ahead and say it, yikes, that is not good. And the work that you're doing with Clio is becoming more and more vital to empowering families and caregivers everywhere. Would love to touch on what you think is the most powerful part of the Clio community and product that is helping to change these numbers.

Yeah, listen, the state of women in the workforce was unacceptable. Before COVID and it is an emergency post. And I'm uncomfortable with how comfortable people are about it. And I just want to say that and light us up because the fire burned in our— it was burning in our backyards for probably a decade, and now it's in our front yards, and we're still— it's okay, right? It's okay because we're, we're privileged. Many of us are having these conversations aren't part of that truly marginalized group of especially BIPOC women and others who are shift workers or others who have already been outside that safety net and now are just completely underwater. So I think number 1, let's all talk about it. Let's be open about it. Let's not be cavalier about it. Number 2, let's have metrics about it around not just did you keep women in your workforce? How many women are on your board? How many women are on your executive team? If I see one more person, and I won't say names, put a all-white male leadership team and celebrate on LinkedIn, I think I'm going—

you guys will know why I've lost my mind if I start going crazy.

And so number one, let's just really talk about it. Let's not be careful about it. And it's enough is enough. And if COVID didn't shake us up enough, let's make sure we shake everybody up so they talk. And then to the point of Clio, right? This is 5 years in, we have over 100 enterprise customers. We have incredible renewal rates. So most of our customers stay with us, right? They didn't just buy us once. Months they're keeping us in. Why? Because working women, but also now all working parents, need someone to talk to. They need someone to support them through these gaps in the system. They need to figure out what solutions work for them, and they most often need a coach to get them to that next stage so they don't just stay, but they go for that next promotion post-family leave or other. So I think the difference for us is that 93% of our members, right, come back to post-leave, right? That they're, say, they say that they're 90% more confident in their career because of Clio. And now remarkably, health-wise, they're getting now mental health support, which is very specific around parenting. So there's a unique vertical around what parents go through around burnout, but also perinatal and postpartum depression that we're seeing huge impact on of essentially treating within a 6-week program. So I'd say our impacts are both really dramatic on the health side, as well as making sure that we drive better organizational health and prioritization within these companies to not just keep people at work, but actually get them to that next stage. And I think that's what we should measure people on, is not just percentage, right, of women in your workforce and how many are there, but how many do you have in your leadership positions? And I think this is the biggest problem to solve.

Thank you for unpacking all of that for us and highlighting the ways in which Clio is making an effort through actionable technology and change to hopefully provide employers with more resources to both have better retention and empowering the emerging managers in their communities. In the interest of time, I think I'll skip over my next question and bring Claudia on to wrap us up.

Yeah, absolutely. Well, you mentioned that it's been a crazy period of time for working mothers, families, really everyone. We can only imagine the craziness that was joining a company 3 months before a global pandemic as CEO and navigating a successful fundraise within that following year. As we look towards a more open second half of the year, what are you looking forward to personally?

Oh my goodness, all of the things. My kids, just yesterday my oldest got to go back to school, which is remarkably important for her mental health, her development, and our sanity as parents. I'm so excited to get outside of the Zoom box and brainstorm and build with the Clio team. It's remarkable to me, not only did we get the fundraise done, build the team, I've hired 4 or 5 executives in this time, most of whom I haven't met in person. And we've also shipped remarkable products. We've built over 12 partnerships. We've sold our biggest clients to date. We've done that all in this little box that I stare at all day, and I just cannot wait to get outside and brainstorm and think even bigger, because I think that's been the biggest limiting factor, even though we've gotten a lot done.

Thank you for sharing that. We have a hero question for our podcast, and we ask this to all of our guests. Who is a woman in your life that has had a profound impact on you?

Okay, there's so many because I'm so lucky. I have a short list of folks that I go to, I would call it daily or weekly, that are my compass. But I'll go one level above that of someone that I model and look at as is a complete, what I would call a change agent. My dream of if I could have even a quarter of her impact on the world and how she works with others, and it's Kay Foster. She is incredible. If those of you aren't aware of her, she had an incredible career in pharmaceuticals and biotech, in HR and organizational development. She's now an advisor at Boston Consulting Group, and she runs Glide Memorial in San Francisco, impacting the lives of thousands and thousands of people daily. She's really knitted together these two things that I think we often disconnect, which is social impact. I think she's on the board of Spelman College as well. She's just remarkable because she's put these two pieces together of great business and organizational development and entrepreneurial leadership with social impact. I was lucky enough to work with her. She was an advisor when we were at Collective Health. I only get to talk to her once every 6 months, but she's She's that person that I keep in my constellation of, "Kay did it. How did she do it?" As she brought up two remarkable kids as well. So that's my person.

That's awesome. Super important stuff. Well, thank you so much, SJ, for spending the time to sit down with us.

It's been such a treat.

Of course, it's a pleasure to meet you guys, and someday hopefully I'll meet you in person. And Clio's hiring. Do I get to say that?

Absolutely.

I have a feeling there's some listeners who want to make a huge impact as well. So come on over, HiCleo.com. We're hiring.

Thank you for listening to this episode of The Room. If you enjoyed our conversation, please like, follow, subscribe, talk to us in Clubhouse, and share with friends. We'll be back next week with an exciting new guest, airing Tuesday, May 18th at 10:00 AM Eastern, 7:00 AM Pacific. See you in the room.

All opinions expressed by Claudia Madison and podcast guests are solely their own opinions and do not reflect the opinion of The5AC. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

Cooley is a global law firm built around startups and venture capital. The firm has been devoted to entrepreneurs and investors, partnering with both to transform breakthrough ideas into successful companies. Cooley works with thousands of entrepreneurs in newly formed companies to ensure that they are structured for growth and long-term success. Since 2005, Cooley has been ranked the number one most active law firm representing VC-backed companies going public. Learn more about the firm at cooley.com and also at cooleygo.com, Cooley's award-winning free legal resource for startups.