The art of the pivot: Max Greenwald on finding PMF and scaling Warmly

0:00To make the transition from founder to CEO, you have to go from solving problems to sharing problems. Welcome to the SaaS Revolution Show, a podcast by SaaS.com. Here we interview SaaS founders from around the world who've been there and done that. They share the ins and outs of how they built their businesses, their operations, their path for securing investment and more. Our mission with the podcast is to help you, the founder, learn how to scale your SaaS, maintain your well-being and navigate the complexities of this ever-changing industry. I'm your host, Alex Thiemann, and together we'll explore the good, the bad, and the ugly in the journey to SaaS success.

0:45All right, welcome back to the SaaS Revolution Show. I am your host, Alexander Thiemann, CEO and founder of SaaStock, also general partner at BackFuture Ventures. Delighted to be joined today by Max Greenwald, who's the CEO of Warmly. Welcome, Max. How are you doing? Thanks. Doing well. Thanks for having me. Is it warmly or warmly.ai? What do you say? Is Warmly on the t-shirt? Yeah, I say Warmly out loud, but the website's warmly.ai. Very cool. And we'll get into a little bit soon about what Warmly does. And I noticed before we were recording, it seems I thought like either you had a themed office or you were perhaps in a Airbnb or by the beach somewhere.

1:24But can you share a little bit of light? Maybe the picture actually gives it away. I don't know why I thought beach. Yeah, no worries. I'm skiing in France right now. And what's great about actually working American hours in Europe is I ski in the morning, start work at noon, and then work till midnight and kind of rinse and repeat. And it's pretty fun to do for a few weeks when away from San Francisco. I was going to say living the dream until you said work till midnight. And then I was like, I don't know. It's a very long day. But I guess if it's a couple of weeks. It's doable when you don't have a spouse and kids.

1:56But it's part of the grind to get it done. And I'm just feeling grateful that I can get some shredding on the slopes in addition to building the business. So skiing, not snowboarding? I'm a skier, yeah. And, you know, no judgment if you're a snowboarder, but I've been skiing my whole life. And I actually just switched to Telemark skis this year. So it's been fun to, as they say, free the heel and take on the extra challenge. Very cool. Very cool. Good stuff. Well, skiing, I haven't been for 20, 30 years. So I'm not sure I'd be very good if I join you on the slopes. But do enjoy it whilst you can, Max.

2:31And very cool stuff. And obviously, hopefully you enjoy France and Europe as well. And so, Max, we'd like to get the audience to get to know you a little bit better, right? So often I ask, you know, who the guest is. So if perhaps you can share a little bit about who is Max Greenwald? Yeah, well, I'm just a kid from Colorado in the United States, and I grew up skiing and horseback riding and kind of stumbled by accident into the whole founder tech coding world. I went to Princeton University on the East Coast where originally I was going to study like politics or policy economics. And then I had my first ever hackathon and I loved coding and I kind of took over my life and I became really into engineering and product management and then left Google to start my career.

3:21I left Princeton to start my career at Google in product management. So I worked on Google Maps, Google Photos, Google Chrome for a couple of years, but was kind of sold the dream that Google was the best place in the world to work before finding out that it kind of sucked. It was full of a lot of people who were lazy and slow and didn't work that hard. Nobody wanted to get anything done. And it was just a lot of bureaucracy. And I feel like I learned how to be a politicker more than I learned how to be a executor and builder of things. So I met some co-founders, including my co-founder Karina, who's now the head of customer success here at Warmly.

3:53And we quit to start Warmly. And it was funny because at first we had no idea what we were doing. And we pivoted for three years and really just struggled because we were in the sales and marketing space. We were not sales and marketers. We're engineers by design, but we figured it out over time. And so it's been a really fun journey the last six years. I turned 30 last week and in my free time, I love to ski, as you can probably tell. And I've been freestyle rapping for about four years now. So that's another fun thing that I do. Very cool. It's made me think, should we get you to do a freestyle rap at some point in the podcast?

4:28But I might not do it to you, but it's up to you. You put on a beat and I'll freestyle for you. Okay. Well, putting on the beat might be the challenge, but I'm sure we could get there. But perhaps if you're just tuning in, obviously it's the beginning of the podcast, maybe wait to the end to see if Max does freestyle rap. I'll tell you what, if you remind I'll put on a beat and we'll get it done. Okay. All right. Well, I think let's just do it. So stick on to the end of the podcast for a freestyle rap from Max. And so you mentioned, so you found your co-founders, you came out of Google, decided to start Warmly, but there's been a couple of pivots, but was it always in the sales and marketing kind of space?

5:07And what was that first version? Well, the first version of Warmly was actually my co-founders and I struggled to find each other. We couldn't find co-founders. So our first problem we wanted to solve was an app to help people find co-founders. And it was kind of like Tinder for co-founders. You know, you'd sort of swipe on a person and all that. It was a terrible idea. It didn't make any money. No users only wanted to use it. It was horrible. But it got us thinking about how to connect people. And then we really got advice from a lot of mentors, like you got to make money. How are you gonna make money?

5:36And we said, okay, well, who will pay money to connect to people? And that's So we stumbled into sales and marketing. People will pay money to be able to connect to prospects for sales. And that stumbled us into the sales and marketing world where we really just thought, man, like we love sales and marketing people, but they're really using manual stuff and they're not really automating or using AI or maximizing their ability to succeed. What if we brought an engineering mindset into sales and marketing? And so that brought us on our next four or five pivots. Awesome. Awesome. And so in terms of then you had your next four or five pivots.

6:14During that point, had you taken on venture capital or was it until you kind of landed on what the product is today as to when you went on to the VC path? Yeah, the first money that we took was from Techstars and we were crazy enough to get in with our Tinder for co-founders idea. They helped us mold it and shape it a bit and then we pivoted entirely during the batch. and then COVID hit. So we were two months into a four month program. We had left our homes and moved to Boulder, Colorado, and then COVID hit. So we think the world's ending. Why do we leave Google? Oh my God, we're not going to make any money.

6:48So we applied to another accelerator program, Y Combinator, out of the fear that we wouldn't be able to raise money because of COVID. And we ended up not only getting into Y Combinator, but also raising a seed round for our then idea at the time, which was to help salespeople get more warm leads by tracking the job changes of their existing customers to new accounts and then reselling them there. And that was good. We got up to about 100K in ARR, but at the time we were trying to scrape LinkedIn, which you're not supposed to do and we don't do anymore. And so we kept getting banned by LinkedIn and just sort of failed.

7:20So we couldn't scale the system. And so we had to pivot again, but we were able to raise a seed then and then brought on the money from YC. And then we raised a bit of more money in an extension, but sort of the seed stage, we were well capitalized to be able to suffer through several pivots until we kind of figured out what we were doing, raised our Series A. Lo and behold, we pivoted again nine months later, kind of going back to where we started, but pulling together many of the pieces of the prior pivots. And our Series A investors and our seed investors were super supportive. And then I think they picked right because we've been on a tear ever since.

7:54And we recently announced our Series A extension, bringing our total funding to about$20 million. And I think we're well capitalized and growing quickly. but it took a lot of iteration and our investors had to come along for the ride. Yeah, I guess it's a good story to share, which is probably quite commonplace. You don't always land on the, like, this is what the product is going to be. I remember numerous stories around this, even if you're familiar with Segment, which got acquired by Twilio. I think it went through a couple of pivots until they really landed on what the product is. but I think just highlighting and certainly if you're, you know, that super early stage that, you know, that initial idea doesn't always necessarily have to be or mean that, you know, this is going to be the product for the long term.

8:47You've got to figure it out. But also when you're getting to that point of like, okay, you identify, maybe we can't make money from this. Maybe people are not paying for this. You've got to pivot also at the right times and like, don't wait too long because then you will likely die, you know, as a business. So I think just the fact that you're able to sort of like identify like through numerous pivots to get to where you are today and then see it take off, right? I've also heard kind of the counterpoint, which some VCs have told me, which is we shouldn't capitalize businesses very heavily to sort of force them into a situation where they only have a year of runway.

9:23And that kind of catalyzes them into action to hopefully, you know, figure their shit out, excuse my language, but actually like sort of depriving them of capital was a forcing function for driving, you know, results. And sure, some will die, but some will really figure it out. You could argue that because we were well-funded, we could handle five or six pivots. Now, I'm grateful for that because I was able to learn all about sales and marketing. And even one of my investors said to me, he said, we're about to pay for your business school degree, your real life business degree. And I am okay with the fact that you're going to burn a million dollars of our money between the co-founders and your engineers and customers, et cetera, for the next two years.

10:02So you can become absolute savages in business building and then be able to grow from there. And at the time I was like, that's so generous, sweet, awesome. Who cares if we live or die or fail, whatever. But actually that business degree in, you know, real life business degree was, was fantastic. And it really allows my co-founders tonight today on that sixth iteration to be able to move like, you know, hot knife through warm butter. Yeah. And I, I can tell, and I bet you're not regretting the decision to stay in Google and now being the founder and moving at a faster pace, running your own business.

10:37When I joined Google back in 2017, on day three, I snoozed an email to myself for two years from then and said, if you're still here, get the fuck out. And that email came back to me two years later and I was like, I got to follow through. And yeah, I haven't looked back. Good, good stuff. And what other data can you share about the company? So we know that you're VC backed, raised roughly 20 million, remote organization. What else can you share? Yeah, so we're about 60 people, about 40 on the go to market, 20 on engineering product and design. Our biggest bulk of folks are SDR team based out of Eastern Europe.

11:16We have a Brazilian team for engineers. And then we're, you know, we're global, but we're actually about to start our first office. So as of two months from now, you'll see us in San Francisco with our first office because things are doing well. We're growing and we're kind of like nine to 12 months in advance of our series B. We're about 3.3 or 4 million in ARR, growing about, you know, something like 10 to 12 % per month and are seeing pretty good renewal data with our customers, which is exciting. um what else uh yeah about 300 paying customers and are learning a lot and moving up market awesome and why san francis why choose the office in san francisco so originally from colorado you're remote could go anywhere uh why sf uh well our head of engineering and my co-founder karina are based there so uh you know sort of easy to go there my other co-founder alan has always wanted to move to san francisco and i started my career there so i've been there for three years um yeah I'm happy to do it in many places, but it's a pretty good place to sort of grow a tech business.

12:17And is it coming back? I know it had some struggles like during and after COVID, but like, I guess from your recent visits, do you feel SF is getting back to its best? I think people say yes. Yeah, especially for some of the AI boom stuff. The truth is, you know, it was dead for years and I thought I'd never come back. I didn't want to come back. You There was a lot of things I didn't like about the city. But yeah, I think for the time and place where we are in the business's life and existence, it's a good time to get an office, you know, get building our first headquarter location. But I'm open to basically, you know, New York.

12:52I'm open to Austin, Texas, my home roots of Denver, Colorado. We're all pretty good tech hubs that I'm open to. And, you know, I've been living in Europe the last few years before moving to San Francisco. And I was living in Berlin and I saw both London and Berlin have pretty strong tech hubs. Looking to London, where it sounds like you're pretty close to, is two VCs of ours that we think are fantastic. One's Harry Stebbings at 20VC, who just launched Project Europe. And the other one is RTP Ventures, who is global but based in London. And their partners there led our Series A extension to help us expand into Europe.

13:28So lots of great cities to be able to build offices around. But we're going to start with SF. Sounds like a good choice and plenty of options there. and then in terms of once you landed on the version of what the product of warmly is today how did you get those like initial 10 customers and what was that journey like to you know getting to that first million in ARR yeah so actually this is sort of this you know lovely thing about us being able to have multiple pivots and iterations before is we sucked to getting our first 10 customers the first three times around and then we became total savages at it so you know We're really good at landing page design, email iteration, cold emails, LinkedIn direct messages.

14:10We'd also built up a following in the community. So we had kind of hundreds of businesses and people who tried our earlier products and seen no success. And then we said, hey, this is kind of the latest version of what we're doing. We think it's going to work. And some people said yes. So yeah, I think your first-hand customers typically are friends and family, design partners in a sense. willing to sort of take a risk. They like earlier stage stuff, probably smaller companies in general. We probably can't, you know, make it into the enterprise from first customers. But yeah, so I think, you know, we had a design partner program.

14:45So basically said, money back guarantee, three months to try it, give us feedback, meet all the time. And we were careful to really listen to those customers and build for their happiness and not worry so much about things like, you know, will they pay as much money as we can possibly get from them? You know, are they going to refer us right away? But we did need to verify. I think it's important that most people do this, especially in B2B, that they did have a willingness to pay. So we did require money down. And it was money back guarantee, but it was money down. And I think that was something we learned from earlier iterations where we were just like, oh, you try this thing for free?

15:22And they're like, sure. And then we were like, you like it? And they want to make us feel good. So they're like, yeah, I like it. But that wasn't the hard hitting feedback of like, I'm going to charge you$10 ,000 now, give me your credit card. And they're like, no. And it was like, what would make you give us your credit card? And they're like, well, okay, like, here are the things that are truly need to have. So yeah, I think your earliest customers should be, you know, your customers that you can get money from, but also are willing to give you feedback. And for those people listening, I actually did a long post with Alex Poyer over at growth unhinged.

15:54And so if you search growth unhinged warmly, I actually break down our first hundred customers, one to 10, 10 to 25, 25 to 75 and 75 to 100, exactly how we got them and what tactics and tools we use for success. On the design partner point, so I see a lot of venture back companies, you know, sort of like pre-CT stage sort of do this. Do you think it's a viable option for bootstrap companies to go down that path? Probably. For some, you kind of got to get into it. But yeah, I think, you know, bootstrap company has to be profitable from day one, unless you're digging into your own funds a bit. So I think there's an even greater emphasis on are you willing to put down a credit card?

16:40And in terms of your go to market, so you've got those first design partners, first 10 customers on board. And also, you know, check out the growth unhinged interview as well to see the path to the first 100 and you're at 300 now. In terms of your go-to-market motion at the moment, how are you acquiring customers? What's working for you? It sort of varies at different stages. As a tool in go-to-market technology, I see lots of go-to-market technology and I use a ton of it and we use our own product, of course. But again, things have kind of gone in phases. So the first year of the business in 2023, we went from zero to a million in ARR.

17:21It was all about the sales motion. In 2024, last year, it was all about building our first marketing motion. But for the sales motion, basically the tactics we were using were cold email, cold LinkedIn messages, and cold calls. But then with our product, which basically is a warm lead tool that generates warm leads, we started factoring that in and reaching out to those warm leads, which generated much better and higher results. And so, you know, kind of the first couple of quarters, it was like the design partner program. And then when we moved to real sales, we actually wanted to remove the design partner program and even not reach out to the warm leads to prove to ourselves that our product was so good and our messaging was so tight that cold emails would actually get responses.

18:04And once we figured that out, then we did layer in the warm reach outs because we were able to be a lot more targeted and use intent data, first, second, and third party intent signals to essentially prioritize our outreach given our capacity constraints. And then by the end of that first year, we were hiring our first couple AEs and then SDRs. Now that my sales leader and I had proven out that we, the two of us, could hit quota on a recurring basis. And we were also starting to get some inbound at the end of the first year. But the whole first year was all hardcore outbound, just trying to get people to respond.

18:33Obviously good to hear. And I'd be surprised if you weren't using Warmly and drinking in your own champagne. But outside of Warmly, like perhaps within your sales and marketing tech stack, like what is your favorite tool to use to help grow the business? Great question. So to grow the business, I mean, there's some bigger ones that are more well known, but I'll call it some of the up and comers that I think are doing well. One's called loyee.ai, L-O-Y-E-E.ai. They do AI AI-based lead scoring for your ICP. And so they help you get a good account model, a good account list going, scoring your leads on things that you can't typically filter by in like big platforms like ZoomInfo or Apollo.

19:15Another one that I like is called Default.com. Default is a inbound routing and scheduling program. So when you do start to kick off your inbound, you can make sure that goes to one of your reps very easily and seamlessly. And then from an outbound perspective, I like letterdrop.com. It specifically focuses on social intent on LinkedIn. And so it sort of allows you to command and pull LinkedIn likers and commenters to essentially like find leads and also give you suggestions on AI post writing and maximizing your social content. Okay. Good stuff. Thanks for sharing those. I'd heard of one of those, which was Lawyee, but we'll definitely check out the others as I'm sure the listeners will as well.

19:59And then, so you'd only been going a couple of years, but then I understand that you had an offer from private equity to buy the company. I think this was last year, right? Tell us a little bit about that. How did the offer come about? You know, you're sitting there one day, you get an email, we'd love to buy warmly or, you know, and then what happened? So we were, I think about two and a half million in ARR. That's probably like eight or nine months ago, I got an email from some private equity firm that said, we have an interested buyer doing a roll-up of sales and marketing tools. We'd like to talk to you.

20:32I typically ignore most inbound term investors and private equity firms. You know, when I'm wanting to raise, I go to the ones that I think are good. But this one intrigued me. And I also wanted to get some comps in the market for what private equity exits might look like, especially as the, you know, we move past series A stage more towards series B. Yeah, I'm doing a lot more like financial modeling and I'm doing a lot more kind of like exit scenario planning and thinking about how to triple, triple, double, double. And so I'm doing a lot more, I don't know what, what, what it might've seemed boring to me in the beginning and probably useless.

21:03Cause I really advise founders against building a financial model in the first year of the business. You have no idea what's going on. Just focus on building something that works. Um, but yeah, as I was doing that, I wanted to get some, some benchmarks. Uh, and I got some good benchmarks for series B fundraising and what we needed to essentially like achieve. Uh, and then, um, the, on the private equity side, I kind of had no idea because my first business, I didn't even know what kind of exit scenarios we could have. So I took the meeting. And yeah, they basically just said the buyer that was interested in buying a tool like ours was looking at based on our ARR, about 2.5 million would pay about five to six X ARR.

21:38And you know, we've raised 20, burned 10, getting sold for 15, roughly, let's say I'd, you know, modulo some fees and taxes and problems and things. They'd like really get more like 12, 12 plus remaining 10 in the bank is 22. I've raised, you know, basically to have raised 20 and then sold for 22, like kind of only spending 2 million in profit. So it wasn't even close to worth it, especially because I think Warmly can be a billion dollar business and we're growing fast and it's super exciting. And so I want to really rapid blitz scale this thing. So it didn't quite make sense for us then, but it was cool to hear about what they care about.

22:13And it was interesting because investors care a lot more about ARR growth and less about net revenue retention. Whereas there's the flip for private equity firms. They want to see that you have not just good NRR, but good GRR, gross revenue retention. Whereas they didn't care so much about growth rate. So you want to blitz scale this thing. Do you spend a lot of time thinking about how to do that? But also maybe the challenges that come with that, right? Because certainly there are a lot of success stories around blitz scaling and there are some failures. rights and uh and also maybe just thinking about your your time in google and i wouldn't say i don't know obviously it's a huge successful company at the moment not necessarily blitz scaling like right now um but just the the impact that it has on culture uh as well okay so first addressing the like what are we doing to blitz scale situation uh we turned on paid ads at the beginning of this year in 2025 so that was pretty new for us to test that out and uh we had a couple months of like early testing, but we, yeah, we turned on paid.

23:16Uh, that's been exciting for us. Uh, we basically doubled our marketing team and put real investment behind marketing dollars as well as got our sales team ready by hiring a few more sellers. Uh, we have a, you know, a desire to triple the business this year. Um, whether you call that blitzkilling or not, I think it's pretty fast growth. Um, and, uh, we'll basically it'll be going more or less like two and a half to seven and a half or two and a half to eight will be kind of our goal. And I think it's doable given the plan and the runway we have. And we have, you know, month over month sort of check-ins to make sure we're on path.

23:51Roughly, it's like kind of still growing at about 10 to 12 % a month. And I'm excited about it. I think as long as we're continuing to hit our metrics and our goals, we'll do it. But, you know, we have an off-ramp level, right? We could turn off paid. We could, you know, sort of right size the team to be focused on a more conservative approach, but we're doing great. So I want to keep up the good work on the team, take some risks. And then to be able to blitz scale, we talked about two main things from our company this year. One is everybody needs to be AI efficient and everyone needs to be AI efficient and everyone needs to uplevel their game in terms of being much more focused.

24:26And so on AI efficiency, we're kind of mandating daily use of AI within the company. We're an AI tool as well, but we're talking across all departments. We're going to have speaker series on AI and we're going to sort of have people give talks on what they're using AI for. But I think I can essentially offset the pressure of the blitz scale on our employees by offering them efficiency with AI. So that's kind of like the hopeful trade off. But yeah, it's more stressful. And I think people who join fast growing startups know what they're signing up for or should know what they're signing up for.

24:57and hopefully they can handle the heat. On the AI efficiency topic, so hearing that a lot of VCs are saying to their companies that you've got to become AI efficient and up to something like 30 % and show those efficiencies, is that something that you're also getting from the VCs or is this something that you just think, look, we just have to do, we're an AI tool, we're in this world, we've just got to do it? More coming from within. I think our VCs trust our judgment. We've been able to, 18 months in a row, hit exactly what we said we were going to do and going to keep doing it. So I think we're in a position where our VCs are helpful and sort of offering good suggestions.