She Built a SaaS Company Accountants Love, Without the Title, Degree, or VC Backing

He's really successful. They've raised multiple rounds. They're absolutely crushing it. And he's still learning every single day and growing as a leader. And so, you don't have to have it all on day one to start your business. The adventure of life is go do cool things and make friends along the way. Why would you want it any other way? We made some very expensive mistakes. We were kind of told that was the norm. And we realized after we take a few steps back like what is actually true to us as an organization, true to our users and maybe it's not

applying this more standardized play. Welcome to Ambition Align. Today I talked to my good friend Claire, CEO and founder of Kipsy. So I've known her for almost 10 years now. She was a accounting professional with me over at Deote. Then she moved her way to Blackline and then ultimately another startup and then started her own startup after going through an incubator like event. And she talks about her whole journey, how she went to found her own company, speed dating through founders and ultimately the challenges of being a founder and leading with value and

integrity throughout it all and self-leading as well. It's just an awesome awesome interview. I think you get a lot of value out of it and I really want to thank Claire for coming on. So stay tuned, subscribe, watch and let's dive into it. Hey Claire, it's so good to have you on Ambition Aligned. It's just really my pleasure. I can't believe it was what it must have been 10 years ago when you and I or eight to 10 years ago when you and I were working at Deote together on impulse. You finally reminded me the name right before this. So and now you're a founder and you own

your own company and you're a founder and CEO. How did that happen? Like what what what was that what happened from being that audit assistant with me and then now you're a founder of Kipsy? Tell me the tell me the story. Yeah, it's uh it's been a while uh since then. Um let's see. Well, I I I love working with you. I didn't entirely love working in audit. So, I knew I wanted to make a career uh pivot out of uh accounting. And luckily, a recruiter reached out to

me asking if I wanted to go join a uh software company. You're building accounting software uh out in LA, company called Blackline, also female founded. Super cool. Oh, I remember. I remember Blackline. Yeah, I remember the referral process for that. Yeah. Yeah. Yeah. They're they're super cool. Um I had some great mentors working there and I joined the product management department. Got really passionate building software and felt like, you know, if we knew how to even better tools at Deote, I probably would have had a better experience working in audit

there. and it kept me really passionate wanting to build for the accounting space and kept growing my career in product. Flash forward a few years later, I get this opportunity to start my own company. Obviously, I'm going to pick accounting software. Um, and I really I think relied on my background as an accountant, but also as a PM to help scale up the early stages of our software product to where we could actually start selling it. Um, but I think like from early time on, I always knew I wanted to start something. It just back when we first started working

together, I always thought I wanted to like make partner and go go that route, but like have a large impact on a culture in some way, an organization, whether it was a brand new organization or one that's been around for a while. Um, it just so happened that my path took me into actually starting my own company from the ground up. But yeah, it was all kind of centered around I'd say want to build a healthy culture for people to grow their careers like I was able to grow mine. Yeah, it's really interesting. You said something there that it'd be fun to unpack a bit because you said that maybe if I had a tool like this in audit, I

would have stuck around. And it's something I've talked to other professionals on here before that it's unfortunate the culture we have in audit and the unsophistication of the tools because it makes a unnecessarily harsh environment, right? Like it's fun to learn. It's fun to have mentors. And did you mean I guess my question is do you mean that seriously? Do you think was there something that would have kept you there was there something you liked about audit or was that transition I want to say about like audit as a as like a like a workflow? Um, but I liked

admittedly I actually liked traveling to go on site for clients like you got to touch all these different industries, work with a lot of different people. And so I really enjoyed those aspects of Deote and now that I'm at a startup, I still do miss some of like the benefits you got working at a really large company like you don't have to worry about running payroll, right? Or like HR compliance and stuff like that. It just like just taken care of for you. And I think um that was like a benefit that I definitely appreciate more now as a founder. But yeah, I think there would

have been some things that definitely would have kept me there if you know it would just been a better experience earlier on. But ultimately I'm really happy where I'm at. I wouldn't even be where I'm at without Deote and so it all worked out. Yeah. I I I mean I'm I'm super proud. I mean super impressed. I know proud is the right word or impressed the right word. You too. You've been crushing it on your end too. like you run his podcast, you're writing a book apparently. So that that was awesome. So yeah. Yeah. But it's still it's still the risk of running payroll and starting

your own company is just amazing. So how does that go? So what did you learn at Blackline and what was the kind of the inclination that oh I'm going to go start what was the catalyst to start your own business? Yeah. Um well I was working at Blackline and I felt like I was getting exposed to a lot of other parts of a company that we didn't really get to see working in audit like we mainly talk to just people in the accounting and finance function at Deote and at Blackline I met or I had to work with on the daily basis like engineers

um you know a lot of people in operations even sales actually too they're very salesled um technology company and so there was a lot of go to market motions that I would be involved in more passively on the product side but I still get exposure room and I felt like I could kind of start piecing together like how they came to be and I had immense respect for um Theres Tucker who's the CEO and founder of Blackline. Uh just you know she built this really large now publicly traded company and different types of people were welcome to work there. It was very um friendly

for working parents which I have a lot of respect for just in terms of like the health benefits and the flexibility which I think especially precoid wasn't super common yet. Um, so I always say it's like, hey, like that's super cool that you did this. You built something from the ground up and you've had this monumental impact on all your other employees. Like when the IPO, people were able to send their kids to college, buy a house, like these big milestones in their lives, and I was like, I want that. Like I want to do what you did. Uh, the only problem was, uh, when I

joined, they were already this massive company. And so while I was still kind of piecing it together, I felt like there was still a really big gap between like starting out and like how did you get to where you're at now, right? Um and that's when I ended up leaving Blackline to go work at a Sequoia backed startup called LILT uh in the AI space and that were a little bit smaller at the time only about 100 employees to get more hands-on experience at an earlier stage company. So So let me recap it. I want to make

sure I'm hearing you right. It was intentional to go to LILT. It was how did you didn't see clearly how you can get to a blackline size? You're already at Deote which is the as big as it gets and then Black Line's still pretty huge and you're saying I want to see how to build it. So you're already having the building mindset going into Lil. Is that right? Yeah, definitely. I think that's I realized that that was where like my gap really was. Um I was lucky that Black Line and that like I got a really good um product mentor. Um so the director of of product was like this

really really smart um product expert who I think guided me a lot early on my career also taught me to like make more space when I enter a room and just like I think being a woman in tech you need to learn how to navigate that and ironically he's not a woman in tech but he was a really great advocate for me in my career and I benefited a lot from that now as a CEO um but I learned the really great basics of how to be a good product manager um got a lot of certifications took a lot of classes all provided through Blackline and I also

had the opportunity to work on a product that was um kind of selfisolated. So we actually got to operate a little bit like a startup inside of a publicly traded company and that was super fun but ultimately we still had the growing pains of big company bureaucracy and stuff like that that you had to deal with all the red tape multiple layers of management that ultimately realized I was going to slow my growth if I didn't stretch myself and go to a smaller company where there were less layers of management um and that that's exactly when I decided to leave and go work at Lil. Can you can you tell me a little

bit more about the creating space? That's kind of interesting. He said so he taught you one thing is really big. Same for me as like being an advocate. If you're not a woman, you can still be an advocate for women, right? It's really important and support your female colleagues uh especially. What what did he do or what did you learn from him about creating space if you don't mind sharing? Yeah, definitely. So, I think for starters like just being present like having regular check-ins especially like I was coming from Deote. I had no idea it was normal, very young in my career. And he was like, "We're going to

have dedicated time, one-on ones, and like we're going to check in, see how you're doing. We're going to give you certain goals to execute on." And I responded really well to that structure. And then just again working in office, he would notice certain things in our meetings. Like if I was running late from one meeting to another, um I was coming into the room, even though I was one of the presenters, I might come in through the back or like just try to be very quiet when I come in. He's like, "No, like he's like you're one of the main reasons that this is even happening. you help from this initiative like take more ownership, speak up more,

command the room more, like just garner more attention. And so he really pushed me in certain ways. I don't think I got that experience while working in audit at Deote cuz it wasn't really something we would get much experience doing there. Um, but he was just very observant and noticing like my behaviors, I think, in physical spaces, but also how I present and carrying myself around other colleagues. and then he would give me really good, healthy, constructive feedback that was very objective on how I could make improvements to just kind of better present myself.

Well, I think there's two sides there. I mean, thank you for sharing that. That's that's great feedback and I completely agree like confidence especially with uh is with women and certain I'd say certain ethnicities too like certain cultural right there's certain cultural boundaries where you just don't feel comfortable speaking up or asking questions but there's that perception if you are kind of louder and more in charge in a room it it's noticeable and people are looking for that they're looking for someone to add value that's why you're there in the first place um but I'm curious

what trying trying to think of the right way to ask this. You It takes I guess it takes someone to be coachable. Like the fact that you were open to that advice that's quite confront there's a bit of confrontation with that advice, right? Like someone comes to me and like hey I noticed you came through the back room. Next time go through the front room. Part of me wants to be like screw you buddy. Who the who the hell do you think you are? But but what got you in that mindset? Was it like did he build some trust with you beforehand? Um yeah I think so. like the

I I could feel it during the interview process. I remember being pretty nervous leaving Deote to go work at this technology company um that I admittedly didn't really know much about and a career that I didn't know anything about either for that matter. Uh but it was pretty obvious when I was going through like the um the series of interviews of different people on his team that people were really approachable um very empathetic just like generally cared about getting to know you. And that sense continued on if not only got stronger while I was working at Blackline over the years. And so I think

like that definitely just helped like this is a really weird analogy but it's just something honestly that I still remember to this day. I was wearing really comfortable shoes one day at work and so I I didn't notice but apparently I was walking with like a slight limp because I had a blister at the back of my heel. My boss noticed and actually asked he's like oh like are you okay? Did you injure yourself? I notic like you're walking a little bit differently when we were coming out of one of the elevators, but he was just like very observant and in a very thoughtful way. So when he would give me that kind of criticism, I always knew it was coming from a place of care and he wanted what

was best for me. And so I never had, I think, any defensiveness whenever he would bring anything like that up. If anything, I was hungry for more feedback like that because I knew he just wants me to be better and it was coming from a really positive place. And so the intention was definitely there. I just had to be ready to receive it. Yeah. And I think you you bring something really powerful there. And I can already see it and how you've you've structured your language around your your company of KFC is the importance of putting people first and that is really

leadership, right? To to build trust by actually caring and giving a crap about your people. Yeah. That's that's how it it sounds silly. It sounds so basic, but that's what you need to do. And it it's pretty rare. You and I know it's very rare actually to have a leader who cares to see that you have a blistered foot and make wants to make sure you're okay. Most people just want to see outcomes and kind of don't want to deal with the hassle. But that's the best part of leadership in my view or the best ever since it is just working with people and seeing if you can make their lives a little better while you build something do something cool together, right?

That's the whole point of life is that the adventure of life is go do cool things and make friends along the way. Why would you want it any other way? Um, so that that's interesting that you had that with someone and you mo that modeling you you're carrying that forward into your other companies. Seems very powerful. Um, so how does LIILT so you're there now so you went from Black Line, you wanted to get the exposure to a smaller company. What did you learn? What was that experience like? Uh, it was great. I mean I think has an amazing product.

They're in the language translation space. um they use AI to help localize um all sorts of different content and it was a much smaller organization and so I had a lot more reach from day one and I just I loved that it was basically like if you don't get this done it just it's not going to get done kind of mentality there. So very humble people would just pick up whatever need to be picked up. There was really like no ego about like this isn't my job description. Everyone was kind of there to help out each other. Uh it was very much a hustle mentality and I really honestly picked

that job not necessarily because I was particularly passionate language translation space although I I did become more excited about it while I was working there. Um I picked the job because of the hiring manager. Um I thought was like a really experienced product leader. I really again appreciated the way that he communicated uh very clear direct but again coming from a place of care and also very objective. So, I think I had to like worry about politics or things like that, right? It was just like, "Here's what you do. Here's what I recommend and

like I trust you." And it was also a leader where I could go and push back on and say, "Hey, I don't think we should do this." And he would just like look at me for a second and be like, "Okay, yeah, you explained why that makes sense. Sure, let's not do it." And like, no ego, nothing about it. He's just very rational. And that again helped boost my confidence even more about executing which you know when you're starting your own business you have to be very very good at execution to survive especially that that first year of starting like a technology startup. Um so he was great ended up having a baby and then um after

the paternity leave um didn't come back to the company unfortunately um he started his own his own thing which actually makes a lot of sense given his background. Um so I was bummed about that but ended up actually becoming a really great opportunity because I then end up reporting into um the CEO for quite a while um from my ring of time at LUL actually I spent a lot of time working directly with the CEO and seeing how he operated um how you interface with some of the investors other um heads of different departments and it just felt a a bit more real I guess cuz

again it was a smaller company they're still figuring things out um obviously everyone's super smart and amazing product. But like again, he was just very humble about like, oh, I didn't know this how you could approach product management. I didn't know this. And there were certain conversations I realized where like actually I knew something more than he did, which wasn't really something I got to experience working at larger companies. And I appreciated that cuz it made me realize, okay, like he's really successful. They've raised multiple rounds. They're absolutely crushing it. And he's still

learning every single day and growing as a leader. And so you don't have to have it all on day one to start your business is basically where like that kind of light turned on in my head. I was like, "Okay, like I think I could probably I could probably do this." Um, and then a few months after that, that's when I I I left a little and started Kipsy. Wow. So it was something that's an interesting jump. You kind of got that promotion, battleground promotion, battlefield promotion, whatever you'd call it, from your hiring manager who

luckily had a kid but unfortunately left even though you're very close and sounded to them or respected them and then worked with a CEO directly and gained confidence through that that exposure, right? But how do you translate that? How do you translate that to that? Okay, I'm it's not like money comes up from thin air or like some great idea. How did you how did that spawn into and I know a little bit about this but I'm just for the audience. How did that spawn into building Gypsy? So I guess one thing that was probably worth mentioning is in between Blackline and Lilt um I've been

approached by a recruiter to interview to be a founder through like an incubator program and I was super excited about it. That was really really great experience because they're basically going to give you like funding on day one to launch an idea and they'll help you uh find your technical co-founder. It was like this really great again structured program that would kind of help you get past like the initial hurdles of starting a business which for me as someone who'd be a brand new founder I I found very appealing. Um and I interviewed for it and I didn't

get it and I remember being super bummed about that. And the feedback from that was I didn't have real like startup experience because Blackline was too mature at the time and it showed when I was going through the interview process. And so that was really a major catalyst. I was like okay now's that was like this is now the time like I need to go to a smaller startup and like you know really like learn the ropes and everything. Uh can we pause there for a second because that's really I can't tell you how many times I get that note from recruiters or

I have throughout my career is like hey you have too much big company experience like me I've done the Google thing I've done the uh deote thing and I've done but I was at a boutique consulting firm but they still that perception having that brand it's actually an interesting thing to get over of like hey that's a different brand you actually being at a startup's a little a different game and you really won't understand it unless you've done it right. And so it sounds like you that that's the feedback you got. Yes. Yeah, that was exactly it. Like they could just see that like I I

didn't have like enough like on the ground experience probably to to start from going from like zero to one ultimately. And so I was like well like that case I got to go get that experience somewhere. I need to I have to go to a smaller company like this like this is what I need to do if I want if I want to take advantage of an opportunity like this again in the future. may not that exact same opportunity, but something like that. I need to be prepared for it. So, let's take control of my career and move on to the next thing that where I can help kind of level up my my role as a as a product manager. Um, took a senior PM

role at LILT and was like a great great confidence boost like you know building things from the ground up very hands-on with engineering team. They were much faster in how they released software updates as well compared to Blackline. Again, just apples to oranges. Clearly different comparison of like how these organizations are structured. Blackland's publicly traded company. They do all these investor updates. You know, Wilt's still private, much smaller, probably like a tenth of the size at the time. Um and I was like just

having to like run all these different initiatives and engineering. I was like, "Okay, cool." Really comfortable executing at a fast pace. And it just so happened that um the job at LIILT brought me back to the Bay Area which is where I grew up but you know we we were working down in LA stayed in LA for quite a while after that too. Um, but LIIL was hybrid, so I had to come back up to the Bay Area. And I was working in the Bay. And the recruiter from that program that rejected me had a post on LinkedIn uh, saying that they were going to do a like women in tech event in the

city one night. And I was like, you know, I'm going to go to that and reconnect with her. And I did. And we reconnected. And she's like, I really liked you. I think you should try applying again for the program. And I was like, "All right, you know, I got rejected once. Like, let's try it again and see how it goes." It been like a year, I think, at that point. Um, and I interviewed, you know, prepped a lot and I think also the experience at built really helped. And I got in the second time around and that's

what ultimately was the catalyst for me leaving LOL and starting the company. Well, pause there. That's so brave. I I can't even just imagine going and seeing someone who already rejected me and just connecting with them again. I I I mean that not imagine is not the right word. I've done it, but it's like it's not an easy thing and especially after something as but not in in that capacity where you're really applying for a big program and then go meeting after. That's that's not easy. That was a really brave thing to do. Thank you. I appreciate that. Um and luckily the

Bridget is her name was awesome. Um, she's super approachable. I loved her. I thought she was super cool and I think that also helped a lot. And then the people who interviewed me through the process were really great. Um, and just kind of honestly coaching me through the interviews too, which is really, really sweet. Um, and I end up getting in, joined the program, and that's how we got started. But I've been very grateful to the program itself and everyone I met through it, including my co-founder, because part of their structure is the five people who are really good at executing. So again, I learned how to

execute through Lil. Um, and you either get in as like a future CEO, like a business founder, or a CTO, like a technical co-founder. So I got in through the CEO track. The next step was to get you matched with your CTO, which is a very strange emotional experience, kind of like speed dating in a way, almost worse or harder, I guess. Um, it was very, very tough for me to make a decision. And luckily I met my co-founder Shaolong um in that

program and he's like the best engineer ever worked with and I didn't even know he existed until we both got like the bachelor or what was what was the like like a little bit like like it's it's very structured which for someone who like myself who has like really bad ADHD I I loved getting these instructions right um but you would have like these different rounds of like almost like dates with these different potential like co-founders. Um, and they

even gave you like it was like a talk track, but like a list of like these are good topics or things to ask on the first call and like you should do like a 30 minute to an hour long and if they make it to the second call and you're both kind of vibing like you get a little heavier and you talk about this and then there's the third one and the last one you need to meet in person and see who really like can click, you know, have that chemistry in person with your co-ound. Yeah, it's like dating. It's very similar. Yeah, it's very funny. At least you got instructions for it. So I

there's dating it's like you don't know where it's going to go kind of a thing. Um but it's that's what I did. And one thing I really loved on my co-founder was I I had talked to a lot of these other engineers basically. And most of them just cared about product development and that was it. and they're like, "Yeah, this seems like, you know, a good thing to build for. Requirements, check, check, check." Kind of they all just kind of center around building the software. My co-founder comes in like guns ablazing and he's like, "Do you think this will make money? And are you

the one who can actually sell it? Like, are you able to sell?" And I was like, "Okay, I like you." Um, because like this is all something you need to care about. You could have the best, most amazing product ever, but if you can't actually take it to market or the market's not there, you're going to die because you just won't make enough money. and he had that business mindset while still having again big company experience coming from like Apple and Netflix from engineering. So he had um this really great background of like how to build best-in-class software at scale

um but then also he went to work at a startup before joining Kipsy with me. So he had that startup kind of scrappy experience as well. So it was a really great combination. Um, and he at the end of the day was very business-minded like it wasn't just about building a cool feature or building in the certain architecture. It was about how is this actually going to drive real business value for the company for our customers to where we can take it to the next level. And that was something I feel like I didn't see in all of the CTO

candidates that I was interviewing. And I I've I've also seen I've advised quite a few different startups throughout my career and uh it's a shame that too many people aren't thinking about the customer. They're thinking about their idea and I always say like do you think you could sell this tomorrow is can you sell this idea and that means you have to have a good product and someone who's reputable that can sell it for you. You need those two. So I like that CEO CTO founder model. it sounds like a great I want to pick I want to ask more questions around there

but so many people just like oh I have this great idea there's this great product it's like well if no one's going to pay you for it then it's not that great I'm sorry like someone people still need to use it even if it has cool functionality if you can't figure out how to monetize it then you don't you're going to falter and it's not going to be sustainable for the long run um so it sound that sounds really cool that you met someone who was like that and had that mindset that's so helpful and so first what so what did that program look like what did you But so you win the application, you meet this founder, co-founder, and then what happens on day

two? You go to Lil and say, "Hey, I'm going to start my own company. Screw you guys." What what what goes on next? Yeah. Um like a little bit. I mean, luckily, um so this the CEO, Spence, um who I actually still talk to the last few years, he's let me borrow their office space when I want to get out of my house, which has been really sweet, too. Um Oh, cool. He was really understanding about it. And you know, he was telling me he's like, "I hate when people leave, but the reason that you're leaving, like I can't even be upset

about like this is a great opportunity and as a as a CEO and as a founder, I am so proud of the fact that like the experience that you got at Lil led you to be able to do this because that means I'm doing the right thing as an employer, which I was just like, that's you're you're so perfect." Like, who says that? Um, but that was like that was a culture at Lil and like I still talked to a lot of like my old engineering team and people that I worked with and I missed them a lot actually. They're they're all phenomenal people. Um, but starting my own company was just too good of an opportunity to

pass up. So luckily Lil was super understanding about it. Um, and there were people even afterwards who were like, "Oh, hey, like you want like the sales leaders, um, Sylvia, she was like, I'm happy to, um, give you advice on how to hire your first, uh, you know, salespeople when you get to that point and what to look for." And she even shared like this kind of like rubric of how she evaluates candidates and stuff like that. And that was super sweet. Um, lots of people in the engineering design side offer to be um, kind of resources. We're first getting started. And it was just really nice to see that kind of

culture. again very lucky to work at great organizations like Lil and Blackline to then start my own company and see like okay this is what I want to grow it into is have a culture that's like this where people are supporting one another. Um, yeah. So, Lil was like, "All right, cool. Like, we understand that you're, you know, tendering your resignation. We get it. Please stay in touch." And I did because they're great people. And yeah, it was super weird. Like, one day you have all these teams of people that you work with and like the next day you're kind of on your own because I think I I quit before I

matched with my co-founder. I think was how the timing of it kind of worked out. Um, so I left Lil in June of 2022 and my co-founder joined in mid August. So there was kind of this weird in between phase. It was really just me and the people um who were part of like the program they launched out of um kind of coaching me like here's what you do to get started like you got to you know get like a website domain, you got to like incorporate your company and here's all other things you got to do like the paperwork side of things. um you should

also start doing market research which luckily given my product background I was like okay like I can actually wrap my head around that part more than all the legal junk. Um, so I started doing that and getting a good understanding of like what would we build for our MVP? And that was helpful in the conversations I ended up having while vetting out these CTO candidates because they're also vetting me, right? Like I'm not the only CEO that they're interviewing. They're interviewing other CEOs in the same program who are building other types of companies to decide if they like this person as a co-founder and if they also like the

idea that this co-founder is going to build for if there's enough, you know, kind of market to support growing a company for that space. And um luckily my co-founder Jalong thought that there was and we end up matching. But before that, it was kind of weird. I was like just alone in my house basically taking a bunch of video calls and trying to to get organized and taking lots of notes and things like that. And then he joined. Um and then we brought on a UX designer and some engineers a little bit

after that. Okay. So they gave you some seed capital and then you you kicked off. How long how long between getting seed capital, ramping up teams? There's a lot there, but ramping up teams and then having a product in the market and selling selling it. Um, Xiaolong is like an absolute beast. So, we were very lucky in that regard. Um, we started I think building in October is when we actually really started building the product. Um, before that it was like

market research, getting the designs mocked up and then we actually executed on it. and we signed our first customer late December and they onboarded to the software the very beginning of January 2023. So we had enough of MVP to go to market within a few months. Um and that was I think because we had very strong design requirements set up. I think I had very good user empathy and then my co-founder is just an absolute machine of an engineer. Like it's it's insane

like how much code even today the team will push out on a daily basis. And that's because we have a very very strong engineering leader and engineering culture within the company. That's it's a testament to you that you speak so so well of the team. You know, it's that's great to hear. There's not enough not enough of that in leadership. So, good on you. Um what does I guess what does getting your first customer look like in that like it sounds interesting to get your first customer be while you're building the product, right? Yeah, they were pretty

openminded. We're very very lucky. Um, it's an accounting firm out in the Bay Area. Although, ironically, the people that we work with are based in Indiana of all places. Um, but they're an accounting firm called Sensiba. So, they're headquartered out in the Bay Area. Um, top 100 firm. They're growing great organization if you know anyone who's looking for an accounting firm to work with. And I met um one of their like R&D tax like leaders within the firm. Uh we were introduced I think

through the I think it was the CFO of the like incubator that we launched out of. Um I think that's how we got connected. And I remember talking to him cuz I I was taking a lot of like informational interview types of calls at the time. I remember leaving that call being like I'm never going to talk to that guy again. He did not seem to want to talk to me. I felt like he was just doing it as a favor for the CFO. Um, and then in no it was November um of 2022, so like probably

got to be like two months maybe after I I I talked to this guy. Um, his name's Cole over at Sensa. Um, I got an email from him and I remember cuz I was about to board a flight and um it basically just said like, "Are you guys still alive?" And I was like, "Yeah, yeah, we are actually." And like, "And this is we're working on this. We're building this." And he was like, "I think we have a need for this. Do you want to reconnect?" Um and we reconnected and that was also part of the reason why we were able to execute so quickly on building the MVP is we met with um him

and some other people on his team um who gave us a lot of feedback on the software that we were designing like okay hey what if we do this have this feature here like no you should do it this way or think about this edge case and here's what we see like in the day-to-day work that we do and it was really generous of them to give us so much of their time and we really just had mockups in Figma And that was a but I think they were willing to do that because they saw like how excited we were to be working with them and also how quick we were to incorporate their

feedback and respond. And I think you know we're still doing that today. Whenever we we get feedback from any of our customers we're very quick to execute on it and that helps build a lot of trust at the end of the day. Um I think you were telling me right that you're like your northstar before is if someone gives you feedback you're going to try to get that out ASAP, right? You're like you're and your team does it in remarkable amounts of time. Yeah. Yeah. Absolutely. We're very very big on user feedback at our company. Um the way I see it, especially for accountants, like they're not usually type of people who like to speak up a whole lot. You

think about like the traditional archetype anyway for an accountant. They're a little bit more timid. Um not the people we work with, they're pretty passionate about what we build. That's just great. I feel very lucky for that. Um, but it's like I want to encourage that type of culture. People are comfortable speaking up and people aren't comfortable speaking up and giving you feedback or sharing their thoughts if they feel like it's actually being received well and you're you're considering the type of feedback that they're giving. And I think we show them that really by doing, which is okay,

hey, you you mentioned this thing that you thought was really important or you felt like was a gap in the platform. Well, now we've built it. Here you go. and now please give us your feedback on the new thing that we built based off of your original feedback and let us know if we can make it better and they responded really well to that. Um so Senso was a huge um you know huge contributor to our initial MVP development and they were just really generous with their time and meeting us multiple times a week to help kind of flush out those design requirements. And so I think that also helped build a lot of trust with that process to where they

were comfortable signing that contract with us early on and being our very first customer. And how many calls before they were your first customer? Like how many pro almost first customers were there? Uh, you know, that's a good question. I mean, there were other firms that we were talking with. So, Kipsy is a software platform built for accounting firms, I guess, for background. Um, that's a good question. I'm trying to think of how many people I I probably

talked to like over like a hundred people probably. That's right. By that time, some of it were like they weren't the right fit, but they would be really good for informationational interviews. Maybe like the firm themselves wouldn't be a good use case for like the platform that we were trying to build. Um, but Senso definitely for like the size, the volume of clients that they deal with, how they're growing as a firm, perfect, perfect use case. And also just like their mentality

about software, like they're not your average accounting firm. They're they're much more open-minded to adopting new technology. Um, they have a really great product mindset. Like they know when to ask for something or they're asking for multiple things at the same time. They'll actually say, "Okay, out of these five things I'm I'm giving you feedback on, this one's the highest priority, and here's why." Which is a really smart way to kind of present that information, whereas other people would just be like, I need all these different things with no rhyme or reason as to

like why they're asking for it. Sensible was smart enough to always give the why. And again, that helped us from an engineering perspective build with better empathy for the end user. Um so again just they were a perfect fit for us whereas a lot of other firms that we work with or even don't work with might have more old school approaches and as we come more mature we definitely widened our reach in the market. Um but in the early days we definitely wanted more like those like early adopter personas and we found that in firms like Sensa.

Yeah. Wow. Well, it's it's interesting because you brush over the hundred people pretty quick, but you had a hundred calls and that takes a lot of confidence, a lot of perseverance. And through all those calls, you still maintained a customer first curiositydriven mindset of, hey, I'm here. I want to build something special for you and we're we're trying to customize it to your needs. And they even came in, it felt like a no and they came back later with the yes, right? And that just goes to show and I think

everyone can copy that model. I think that's something to replicate in business to like care about your customer, not to build assuming you know what they want, figure out what they want, listen and to have perseverance through the process because you never know who's going to be the right fit. But if you put your best foot forward and with a listening ear and and really try to customize to it and take customer feedback into consideration, who knows what can happen, right? Yeah. It's pretty ironic actually. a lot of the um the firms that I had initially reached out to even some of the ones that didn't respond to like my cold emails um are

customers now funny enough. So it it really kind of came back full circle. Uh but Sensible was the one that like very early on was willing to take that risk on us and we're very grateful for that. Yeah, that's great. And accountants should take more risks like that. There's great software out there. No one should be using, you know, what was the old uh like the QuickBooks predecessor. Like no one wants to use old software. Like there's a competitive advantages to using new stuff. So why why are we stuck in the past as a

profession? There's great products like what you're making. Um Okay. So that's amazing. So you got your first customer. I'm grilling you a ton. I hope you're doing okay. I'm not wearing you out yet. Yeah. It's just fun getting to hear about what is that? You've you've been there for three years now. So, what's been that journey like? I'm not going to ask you every day of every week, you know, but um even though I want to. Uh what is that what has that journey been like? Where are you guys at now from getting that first customer? That what's that change been like? Uh it's been a lot. I

mean, the first really I want to say like year, year and a half in some aspects. I almost feel like it was a little bit easier because it was just me and a bunch of engineers at the company. So I really got a play in what I felt more comfortable doing, which is predominantly product management with like a light sprinkling of productled sales. And so I was like, "Oh, like this is this is great." Like I go into a sales call and I would forget to talk about pricing and I would just go into the demo and want to get feedback for the entire hour that call lasted.

Luckily for the type of user we were selling to, they reacted really well to that because they felt like that made us look more trustworthy and they could tell we really cared a lot about what we were building. Um it's not great when you actually want to scale like you need to get a little more organized when you go to market. And after we so we basically then the money that we got through that incubator program was essentially like our preede and then we went and raised a seed round a little bit over a year after getting that that initial preed funding. Um, uh, the firm's Harlem Capital, so they're a DEI

focused VC, which is really cool, very values based. And, um, the main focus of using that funding, uh, was to to grow the team and primarily the go to market area. So, we brought in a customer success manager who's an absolute rockstar and a really great, um, founding sales team. And then I had to learn how to manage people. This is like early kind of middle of 2024 at this point. Uh, and that was like super hard adjusting to that. And I can't just hang out with engineers and focus on product

as much as I wanted to or was used to. Um, and build out new processes internally and stuff like that. And luckily we've, you know, ironed out some of the kinks on the go to market side of like how to stay organized and also like learning a to let go a little bit for certain things and not always be in that kind of icy mentality, but also try to think of being a good manager. um we're in a really good good place where everyone's able to run autonomously on the go to market side of things and that allowed us to book more meetings, you

know, book more demos, close more deals at a much faster rate because we had more people now in the team to do that. Uh and that's been really great for us now. We've grown a lot um kind of in the accounting firm space across different sizes of firms. We're primarily I'd say focused on larger firms for the most part, but we do have some really small even like solar practitioners who use our platform. Um, but ultimately I'd say we we tend to play more like in the top 100 to 200 kind of ranking and we haven't had a lot of traction in that area in particular. So much so that some

of the firms we work with are international and we're now expanding international and building out um our product for the United Kingdom for their R&D tax credits. We're not just going to do the United States anymore, but we're also going to go Wow. across the pond. Yeah. Wow. That's that's amazing. So what's how many people do you have now? What and what does that what does the future for Kipsy look like? What's your plans for over the next year? We are What is Claire up to too? Like what is or is Cla kipsy as a or have they merged to make Clarypy or something? You know, that's a good one actually. I'm going to use Claripy. Uh I definitely merged

where most of my personal life was focused on work. I'm now learning to unmerge that. Um it turns out that's not sustainable like physically, mentally, and emotionally to do that for multiple years. like you actually have to get regular sleep and exercise and have relationships outside of work ones. Um so I've been really trying to strike a healthier balance just in general with that cuz I do think it has an impact on my ability to perform at work. Um so that's I think something for us like my

co-founder and myself to work on. We, fun fact, never really hung out socially um until this year. Even though we meet all the time virtually and we've been working together for insane hours for years now, we never really like hung out as friends, I guess. Um even though I like to think I think we both really like each other, we get along well with each other. Um it was just like laser focus on like again

executing just work work and we're realizing it's work can also be more wellrounded. Um and you know just it's going to be a lot more meaningful that way too and so I think that's been a kind of a big area of focus just for us as individuals. Um as a company you know we've grown our headcount about 10 people right now and I'm very happy with that. I think when we were first modeling out our growth, it was very much a you add a headcount, you get this much in growth

kind of model. Um, turns out you can also optimize more for certain individuals on your team. And if you can do things to better prioritize their time or train them, you can actually get even, I think my opinion, more ROI per head that way. So, I'm very happy with our our group of 10 right now. We'll probably keep it around that size for the time being before we make our next big push. Um, but we've been able to optimize our resourcing to be very capital efficient. Um, which is as an exac accountant I find very appealing because it allows us to control more of

our timeline as a company when it comes to fundraising and um, things like that. So that's been pretty good and stable for us. So it's mainly just I'd say around overall revenue growth. um m maturation of the product is a big one going up market and maturing the product for more enterprise level features and part of that is that that international expansion that I mentioned earlier is providing more coverage for again those really large clients that some of these accounting firms are serving where they have R&D all over the world um and a lot of other um just maybe reporting

requirements that they need to be aware of or keep track of that our software could help with you know what I love about everything that you said is that once that I hear like a dollar which is just awesome and something you've mentioned throughout the entire conversation is values like you're values driven you've talked about you know recognizing having the self-awareness to recognize that you are looking for some kind of balance not because you're missing out on the work but because you can perform better if you have that balance and um and you

keep talking about like optimizing for the team and it doesn't sound and I know so many founders I've met who optimize for headcount optimize for dollar growth trying to get their go IPO, but it sounds like you're doing everything right. Like you're trying to optimize for outcomes for your customers. You're trying to out optimize for your team's dynamic and still like be have financial rigor like not just to make decisions based on optics but actually on outcomes and hats off to you. That's awesome. That's a very rare combination in leadership and I'm sure it took a lot of

sacrifice to get there. So we made some very expensive mistakes to get to that that realization. um probably overhired a little too quickly. we spent a lot of money that we didn't need to spend in certain areas of the business um because we were kind of told that was the norm or you know you you're on LinkedIn you kind of see all this dialogue and it's it's like a playbook right um and we realized after taking a few steps back like what is actually true to us as an organization true to our users and maybe it's not applying this more standardized

play that could work really really well for like maybe other B2B SAS companies but doesn't necessarily work well in space because admittedly selling into an accounting firm is going to look really different than selling into some other type of organization and we need to know our space well enough to have the confidence and how to execute off of that type of a playbook and recognize that it might be different. Um, but we definitely went through some growing pains I'd say in 2024 to figure that out and make adjustments and then get comfortable

with like what actually is going to be like our approach to selling and also building the company. So, it was intentional to stay lean to stay to not get more capital, stay in that seed space, right? Yes. Yeah, definitely. Um that that was one thing like I fundraising is a very unique experience and um some some aspects I really enjoyed other aspects I did not enjoy. Um, it was a just a very different

experience in like building software and the day-to-day and the shift from having to like step away from building the product and talking to your end users to going and pitching all the time to investors um was just like you spent your day doing very different things fundamentally. And I'm very happy that we got the funding that we did. I love our current investors. Um, but it was also very distracting to fund raise. Be perfectly honest. It's really hard to just try to run both things in parallel. Something something has to give somewhere to make room for the bandwidth

for me to fund raise. And I feel like where we're at right now from a development perspective is so much more crucial for us to stay focused and executing on than for us just to go and raise capital right now. And the good news is we we don't need to raise the capital. So if I were to prioritize my day, I'm going to prioritize what can I do to make the product better so I can make the lives of my employees and our end users better as a result. Yeah. And not enough people focus on that. Not so many people I know are chasing funding. And my only my

challenge to everyone is why chase funding if you can finance it yourself? If you can figure it out how to make money in your own business in order to not need financing, generally financing is going to be the most expensive way to get raise money to get money in your in your pocket. So look at look at just building it organically after you have your initial preed funds or seed funds, right? You're doing that, right? And it's not easy. It's not easy because the world's everyone else is telling you something different, right? Everyone's like grow fast. Throw money on the throw

like throw money into the engine and just watch it burn and it'll go faster. But that's not honestly that's not right for most people. It honestly burns a lot of people out. Um yeah. So what are you doing from that from that from that lens? What are you doing uh to take care of yourself? Like it sounds like that's a priority upcoming. And taking care of yourself, I want to be clear actually helps businesses because then you can operate better, right? Like having a CEO who has some time to exercise and like take care of their health and mental health is like it that's how you can think better and execute stronger. So

what are you doing for yourself? Um, ironically actually one of our investors um the for Harlem who led our round for the seed round has been very good about like pushing me or also co coaching me to like think more holistically about my life. Um, and that's something I've been been working on is like making more time to like I block time in my calendar to work out. Um, I disconnect pretty much entirely on Saturdays from work. So that's also been good too. So just again building in space for yourself um to

have to just have the disconnect or time to focus on areas of your life um have been I think really really helpful for me. So I wouldn't say like I've picked up like a great hobby that I do consistently. Um although I do like to do random projects like we got a custommade claw machine um for the company just cuz I thought it'd be fun to have at a conference that we were sponsoring. Um, so I feel like I do fun side projects. They happen to be interrelated to work, but I get to flex in different ways. And that's part of

the reason why I love my job so much. Um, is I get to wear different hats every day and do different things I wouldn't otherwise get to do at like a company like Deote. Like I I wouldn't need to touch anything related to to sales or marketing or even product development for that matter. Or build a claw machine. Yeah. Exactly. Yeah. Or like find a random dude on Etsy to make you a claw machine. Right. Like so that's awesome. Can you send me that? Because I am strangely addicted to claw machines. Like do not give me money in my pocket around a claw machine in Taiwan allow like a hundred bucks when I

was in the night markets. I was like go through money. I don't know why I love those things so much. Especially collecting like little stuffed animals for my kid is like the best. It's it's so fun. Well, I got a bag of like 200 of them that we have left over from the event. So, if you're in need of any little plushies, we have a plethora. Um Okay. But yeah, it's pretty fun actually. I've learned all these different things that you can do like you can code the machine to give like a certain like payout rate make it easier or harder for the user. I knew it. I

that's what I was wondering why. Yeah, there has to be a payout rate because these things are impossible half the time. No, it's uh you're you're like probably guaranteed to lose money if you if you go into like an arcade and try to use claw machine. But um if you already come up, you can practice to really hone your We got to go on a hike on the mental health like on the values-based uh health note. Let's go on a hike. I would love to play some claw machine, too. Funny enough. Yeah, that'd be a blast. It's so funny you made one, right? But yeah, I mean like that that part's been nice, actually. Um and so I will

say like even like we're kind of like anti like we're not fundraising right now because we don't need to. um like we wouldn't exist without the capital that we raised from multiple investors and like the relationships with those investors that open up new doors for us. So I guess it all kind of comes back full circle in a weird way. Um and like I I just feel like with fundraising you should be intentional like you should know like there's a reason a strong reason like why you're doing the raise at that time and it's really to kind of

level up or go to the next step with your company. Uh but for us like it allowed us to to you know one exists MVP development was the first round second round was really to scale go to market um which was huge for us but I I've really enjoyed kind of like developing I guess my relationship with some of our investors. Um like I said like Harlem we have a monthly check-in. the first thing they always open with is like like what's going on in your life and they've been pushing me to not open by talking

about work but like something else that I'm looking forward to in my personal life and like almost like kind of coaching me on that. Um they've also encouraged me to like find a coach uh to help with things like learning to get to delegate or public speaking or certain areas that you know I could level up in as a founder of a growing company. And so that all again has a trickle down effect I think in my again holistic personal professional intermingled life at this point and that's been I think really really positive to see.

Yeah that's amazing and I'm glad you're getting that coaching and everyone can everyone use that and you're leading any organization. I always wish because I I joined an executive coaching program and I learned the old executive coaching arm but I met so many people who were like ex CEOs who who do something similar and it's so valuable. I wish I learned these things years ago. I had people in my corner who were challenging me to mentor better, lead better, take care of myself, look at like having people to give you the right questions to work through things yourself and challenge you to think differently is so valuable

and can like span and improve your ability in all areas of your life. Yeah. Yeah, definitely. And like that could be through like you know finding a good coach recommendation like from your investor for example, right? like they're talking to so many different portfolio companies on any given day and a lot of the founders in similar stages as you probably deal with similar problems. Um they've seen that right or you have a network of like maybe like repeat founders that you know um in a similar space you could go to for

mentorship um or a coach right that's been a founder before who could help you know share their experiences and lessons learned and kind of help guide you through that process you're going through now. I think there's a lot of great opportunities for different people in your life or people you can bring into your life to help guide you through this process. Yeah. Well, we almost had an hour already and I've been talking your ear off, so I don't want to waste your whole day. You're very busy and you need time for yourself, too. I'm curious what what do you wish I asked that I didn't is

Oh, I don't know. I think this is pretty great. I mean, I just hope it's useful for people. I think it's inspiring and people are going to learn. I think people are going to learn a lot. There's a ton there a lot of takeaways. I I just wish I your brain I feel in mine could just meld with some of the take like great takeaways. Maybe it's the accounting background, but like seed money investors are great, but make sure it's more than just money. Make sure you're building relationships. Make sure you're getting the right coaches in your sphere. And don't just chase the dollars. customer first mentality,

product market fit, like make sure that your customers actually want to purchase uh want to purchase something that you're offering and make sure you're constantly thinking about them. Making sure you're taking care of yourself as a leader um and making sure you're looking out for your people. Something that stuck with me is like that your valuesdriven leadership and I really admire that that throughout the conversation you kept talking about like values and how you care about your team and the de DEI focused investors that you found like all that stuff. I think this has been a hugely valuable conversation, Claire. So, Oh, thanks.

No, I appreciate that. Yeah. I can't think of anything else like really maybe that would stand out just like Yeah. If you're the founder listening to this, you have a really good employee or you found like that really special hire, like take good care of them. It's hard. It's really hard to find good people. It's hard hard to find good investors, good employees, good customers to work with. And if someone's willing to be honest with you and vulnerable and share their feedback, like that's a really special relationship. Um, and like that type of truth is immensely valuable when you're building a product. So I feel

like that translates directly to dollars on my end. And as long as you can maximize getting more input from a larger group, that's one of the best ways you can kind of aggregate all the feedback to build a really great solution that people will find and love. Oh, that's great. It's a great place to end, but I got to fire drill three questions for you and then we'll be done. Okay. Sweet or savory? Oh god. H. Oh. Oh no. It's dinner time, too. Yeah, it's

it's Yeah. Uh, it's hard. I love boba and I love fruit, but I think savory has to win because cheese like any like just cheese crisps, like any anything like just cheese related wins. So, I'm I'm going have to go with savory just for that. Okay. Okay. Good. What's your favorite dessert? You seem like a sweet person based off that second question. Yeah, I know. I know. I'm just trying to keep you on your toes. I'm You're in the savory mind. I'm going to flip it.

Man, that's really hard. I really like the berry chantelli cake at Whole Foods. Oh my gosh, that cake is Okay, maybe I'm having a sweet tooth today, but maybe you called me on it. That cake, that cake is delicious. Yeah, I like 700 calories a slice and it is so worth it. 700 grams of sugar a slice, too. It's just cond Oh, but the p Yeah, that flavor I nail. So many people love that cake. I don't know what they did

there. They put crack in it or something. Um, what is one piece of advice that everyone gives that annoys you or you wish they didn't? Ice baths. I don't know if that counts. That's like too weird. But no, it count. You know what's so funny is I got I was in that ice bath kick for a while doing cold showers in winter here. No, don't be sorry. I did it one morning to where I was feeling a little off. Turns out I had COVID really bad and I did an ice

bath that morning and it totally almost KOed me. I had to go to the hospital and the doctor was like, "What? What did you do?" And I was like, "I went in an ice bath." Like, "What are you, an idiot? Don't don't go in an ice bath when you're sick." I'm like, but they it's I suppose the YouTubers, you know, they told me that it increases immunity and they're not doctor. What are you crazy? Don't be in cold water. Yeah. Yeah. So, I'm with you. Lesson learned. Don't take ice baths unless you really like want it just to kick up. Yeah. Yeah. Yeah. It it will not solve all of your problems. Some of them it probably

can actually, um, but it will not solve all of your problems. So, that would be the one piece of advice that I find a little a little annoying. Yeah. Fair. I I think that's a good place. It's a good place to close. Claire, I really appreciate you. This was a ton of fun. I'm serious. I want to find time. I put a reminder to keep bugging you about going on a hike sometime the next time in the area. And I'm just rooting for you. So, if there's anything I can do, would love to have you back on and see where you're at in a few years, even just keeping your 10erson team, but just global. Who knows where you'll be, but I'm so excited for you and so impressed to see where you've

landed. So, thanks for coming on. Thanks for having me, Devon. I appreciate it. Yeah, of course.