S13E1: Reinventing Work Through AI-Native Communication with Craig Walker, Founder & CEO of Dialpad

when we started, we did— we didn't need a lot of money, we didn't need a big team. And so we raised a Series A, I think we raised $4 million. We had the team at its largest size was 22 people, um, and then 18 months later we get acquired by Google and off to the races. And it was like all the pain and struggle of the 5 years before that were replaced by nothing but sunny skies and happy times.

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All right. Well, first off, Craig, thank you so much for joining us in the room today.

Yeah, totally happy to be here.

We're delighted to have you. And we like to start at the beginning with all of our guests. Rumor has it that you were born and raised in Cupertino, so you're a Bay Area local.

Absolutely.

How did growing up in the heart of Silicon Valley shape your view of the world?

Well, first of all, there was no Silicon Valley when I was born and growing up in Cupertino. It was primarily apricot orchards. And interesting fun fact for you, um, uh, lived on this little street called Presidio Drive and had just our orchards all around us. And pan the houses down on the same street, um, one of my childhood friends, this great gal Kara White, moved to Virginia. In moved Steve Jobs. So we had The same, we were on the same street, but this was in when I was, what was that? I was like 6th grade, 7th grade. But yeah, he had already started Apple and there was the early days and they were in that, on that street. So, but yeah, it turned into a very intensely focused high-tech area as you can imagine. And it was great. Every year, every summer in high school or summer in college, I pretty much worked at Apple, which was right there. And I just saw it grow and sprawl and all this other stuff. So it was a really cool place to grow up.

Absolutely. Well, you were exposed from such a young age from one of the most iconic founders of all time. So in that vein of early identity, did you yourself always think you would become a founder?

I'm not sure I understood it well enough at a young age. I was always scrappy and somewhat entrepreneurial. Always worked, had a paper route, loved, you know, having the freedom to be able able to buy things and, and work hard for stuff. And so I kind of always was. And then, then it did— I will say though, like, those early— that early Apple era when it was Apple against, you know, like Apple against Microsoft or Apple against the IBM version of, of personal computers, it did shape my mindset of, look, the best product— but it's being the best product is just the best place to be, even if you only have a small percentage of the market share. And I think Apple's still on the desktop is still single digits or maybe low double digits, but it's just such a better product and such a better experience. And it was kind of like David versus Goliath, good guys versus bad guys type of a thing. And over the long run, that's the winning strategy because they ended up having the world's best products. And now they're, well, for a while there, they were a lot more valuable than Microsoft. Microsoft's done a great job lately, but they're certainly more valuable than IBM and and the other things that they were competing against.

I love that. Like, once you know what true product market fit is, right? What— once you know what customers being obsessed with you feels like, uh, you can't fool yourself into thinking that you have it when you don't, right?

You're exactly— and that's one of the things that I like. This is my third, you know, company where I've been CEO in the business or in the communication space. And like, I get to actually be a consumer of the product. And so I don't have to go ask customers. I like, I can tell you when it's, when it's amazing and delightful. And I can tell you where, where we need to sand down the edges. And so it's been really, that's been awesome to be able to be work on something that you use every single day because you are the best patient zero there is out there.

Absolutely. Well, your background then took a bit of an interesting turn. So if I have this right, you got your BA from Berkeley, stayed in the Bay Area, went across the country to Georgetown to get your MBA. Then came all the way back for law school, also at Berkeley, and started your career as an M&A lawyer representing clients from Cisco to Kleiner Perkins to Sequoia. Did I get that all right?

That is right. That is right. That was, that was the arc. Some people would say I was just avoiding reality for a while. I would, I, I say I was adding capabilities and skills. But yeah, so it was, it was a, uh, it was a really interesting journey. And I'll tell you also, this is where I I truly understood the value of Apple is when you go to the East Coast and everyone's on Windows machines. And at the time, it was like Windows 3.1. I literally could not believe what a generational step back that was to have to use stuff like that. And to think that 90% of the world was doing that was just mind-blowing to me. So anyway, yeah, that was, but that was the career progression. And then after law school was, yeah, was down in Palo Alto at this great law firm and we had great clients and it was like the late '90s and the internet was coming of age and Marc Andreessen and Netscape had just gone public and it was just, it was just a great, incredible, special place in time to be in the center of.

Absolutely. I, I can feel that and have heard many of those stories. I think, you know, reflecting on that time, there is so many parallels to today, or at least people are saying that there are in terms of how quickly things are moving and having that energy back here in the Bay. I'm curious if you can peel back the curtain a little bit on some of the crazier stories you might have observed, of course, which you can publicly share from that era.

Oh, um, there were a lot. I mean, first of all, like, the dot-com boom, and it, it does kind of parallel here quite a bit, um, in that, I mean, there were, there were companies, you know, like, there were companies going public and being valuable with no real business plan whatsoever, right? Like in Pets.com and I mean, like, I'm trying to think what was the other one? There was, yeah, I think Pets.com was a good one.

Mary Meeker. Love Pets.com, by the way. Like that is lore.

There was another one that was, gosh, not just Pets. There's another one that was the toy one. I can't remember it, but I remember like it was a public company, was trading at like 90. And it was like down in the single digits. And Mary Meeker was the analyst at Goldman Sachs at the time. She's like, look, if I liked it at 90, I love it at 3. And then it went to zero. And like, there were just all these crazy things, and everyone was getting funded if you were internet. And even though it didn't make any sense, or like it was totally unproven, or there were 100 others just like you, money was flowing. The, the excitement was crazy. Um, it's very similar to when you see the AI-powered startups, you know, coming out today. I'm trying to think of the craziest stories back then. There were a lot of individual crazy people stories, like people who had made a ton of money. I won't say his name, but I worked with him. He was a client of mine when I was at Provec. And like, you know, drives, driving through Marin County one day and finds a house he loves, pulls up to the front door. He's like, How much should it— how much is it going to take for you to get out of this house? Like, I just said, name your number. I'm going to write the check. You walk out and I keep all your furniture and everything. Just you just leave. And that was a pretty crazy story. But there were a lot of kind of banana stories like that back in the day.

Well, what a crazy time and an interesting time for you personally as well. You shifted from lawyer to CEO during this era. So back in 2001, you were named CEO CEO of a VoIP company called Dialpad Communications. Tell us, how did you make the transition from getting deals done on the M&A side to becoming the CEO of a communications platform?

Uh, great question. It was— and then I don't mean to offend anyone here in this answer, but being, being a lawyer in Silicon Valley, working on, working on deals, and it was the great thing about— I wasn't just an M&A lawyer. You worked on IPOs and you worked on founding companies, you worked on private venture financings. And when you're in the middle of all that, it's awesome because you're literally at the table where things are happening. But after a couple of years, you realize I'm at this side of the table. Like, I'll do a good job fighting for my client and getting the good deal and making sure there's a win-win and stuff like that. But you really want to be further, kind of further on the other side of the table and like making the decisions and having the strategic ability to decide on buying a company or raising money or doing things like that. So the way I looked at the Valley was kind of a 5-step ladder. And no offense to accountants, but accountants were step 1, lawyers were step 2, bankers were step 3, VCs were step 4, and then founders were kind of like the pinnacle of this mountain. Or the top of the ladder. So, I was at step 2. I wanted to get to step 3. Like, that was my mission. And so, after 3, 4 years of being an attorney, the path for a lot of attorneys to get the next step was to go to investment banking. And so, I had gone and interviewed with a couple of banks, got an offer, was going to go join Piper Jaffray. In their Menlo Park office. And then I started telling all my clients that, hey, I'm leaving, I'm going to go be a banker. Like, here's the transition plan for your, you know, for your matters and stuff like that. And one of them was this client that I had literally just, just got, and he was starting a venture fund focused on investments coming out of the 1996 Telecom Deregulation Act. So, so super interesting. I learned a lot about that in representing Cisco and being in the middle of the Valley. And he's like, "Look, don't go there. Come join me at my fund. We're halfway through raising the first fund. We're going to get it sponsored as the SBIC. So, we have a lot of legal stuff we got to deal with the SBA to get that process done. And this is the right time to be investing in those types of companies. It's super hot, late ball." Anyway, so he was a dynamo, this guy, Arjun Gupta. The fund was Telesoft. Partners, but he was an absolute one-man wrecking crew. And so I joined Arjun, basically in the process got to skip over the third rung, and all of a sudden I'm up at the VC level. Full disclosure, I wasn't a great VC. I really, like, I did just like personally, it was really hard for me to get really excited about other people's ideas. Narcissist, whatever you want to call me. But like, it was just, it was just hard. And then the other part was like, you'd be in these meetings all day long, hearing pitches all day long. And half the time I thought they were the dumbest ideas in the world and they turned out to make a ton of money and they were great ideas. And the other half, I had no idea what they were talking about. So it was like all, all honesty here. Um, but anyway, so, so Through a chain of events, I ended up at another venture fund under this guy, Bob Smilic, who was awesome. He used to run First Boston's investment bank on the West Coast, but he was fantastic. And they had invested in a company called Dialpad, which was this early-stage voiceover IP company before Skype, you know, using the internet to make phone calls and literal phone calls to phone numbers. And it was super revolutionary. Had a ton of users, raised a bunch of money, hired a bunch of people. Dot-com bubble crashes. And then the fund is like, look, someone's got to go, go shut this thing down or try to sell it before we have to shut it down. And, you know, lo and behold, we have an M&A attorney in the firm. I get put in as interim CEO and literally it was supposed to be like a 3-month journey, end up being a 5-year full-time job. We, we like totally totally turned it around, changed the business model entirely, shrunk the team incredibly. Instead of losing $3-4 million a month, we got it down to $100,000. We were able to find an investor who gave us $5 million. And out of that $5 million, like $3 million went to the creditors. And it was just so much stuff. But it was a really exciting time, particularly if you've never been CEO before. It was a little bit like operating on a corpse. Like, everyone expected it to die and do nothing. So, like, the fact that I could keep it alive was magical. And so, then we grew and we became profitable and then we got acquired by Yahoo in 2005. So, it was literally like this— in a normal chain of events, no one would have put me in as CEO. But in desperate times, I got an opportunity and turned out that, you know, like just out of necessity became pretty good at it. And, uh, from that point onward, you know, there's no looking back.

Well, it sounds like over that kind of 4 or 5 year period of time, you went through it all, right? Like you had to cost cut, you know, make sure the team stuck around but not grew too much, like drive, you know, a profit and then, you know, go through an acquisition to, you know, an internet giant. Um, so I'm sure you learned a lot, um, in that first stint as CEO. And then, you know, in 2005, you co-founded and were CEO of Grand Central Communications. Um, tell us, what were a couple of lessons from Dialpad Communications that really informed your co-founding journey of Grand Central Comms?

Yeah, it was— first of all, it— I was absolutely convinced that a small team could do could do a ton of stuff. Like a small— you don't need to be a big, heavy-bloated, expensive team to do stuff. Because we, we were— when you're— when you literally don't have money to have more than a certain number of people, that's it. And so like everyone was wearing 3 hats, everyone was working like 14, 15 hours a day. There was no traffic in the Bay Area for us because we'd leave at, you know, 10 o'clock at night. Like it was, it was one of those types of experiences. So when I started Grand Central with Vincent Pacquet, who's currently my chief product officer, but he was also one of the few people that, that I kept around to rebuild Dialpad the first time. Um, when we started, we did— we didn't need a lot of money. We didn't need a big team. And so we raised a Series A. I think we raised $4 million. Um, we had the team at its largest size was 22 people. and then 18 months later we get acquired by Google and off to the races. And it was like all the pain and struggle of the 5 years before that were replaced by nothing but sunny skies and happy times at Grand Central. It was just, was just kind of a magical journey. So, so I think like the, the lessons that you learn of like You end up being completely confident that you can figure anything out. You end up realizing that there's, you know, even though someone's an expert at something, that doesn't mean they can't be wrong. Um, and you always have to kind of trust but verify. Um, and, you know, hard work and having people with you who are like-minded makes it really like, it just makes for a much easier journey. And so then a lot of those same people then left Google when I left Google. Now we're here at Dialpad. So it's been this kind of like step, step, step.

I just, I want to do like a prediction moment because you sold one company to Yahoo, one company to Google. So is Dialpad in conversations with OpenAI?

Ah, no, Dialpad, like, yeah, if we were, I wouldn't tell you. But, but I, I, yeah, I, we do a lot of We do a lot. Google is a very strategic partner of ours. We're, we're built in Google Cloud. We use a lot of their, their AI underpinnings. We have partnerships with them where we go to market together. So, so probably not OpenAI. Fair.

Well, many of the lessons, you were just reflecting on, have never been more relevant. You know, it's easier to build than ever. Keeping a lean team is actually what wins, kind of in this environment. Um, and so, yeah, it's, it's really cool to hear that some of these entrepreneurial lessons are certainly evergreen.

Right.

Um, so let's just double-click a little bit into, um, sort of the acquisition with Google. Um, Grand Central Communications really became the foundation for Google Voice. You were acquired in 2007. Um, and then right after that, you were Google Ventures' first EIR, an entrepreneur in residence. Tell us, what is an EIR for folks listening that may not be familiar with that term? And tell us a little bit about sort of your time at the fund.

Yeah, so, so exactly right. So we get acquired by Google 2007 and it's, it was amazing. So Google was a big company back then, 20,000 people. It's now 10 times that size. But for a 20,000-person company, it was chaotic. You know, like it was like a startup. Like they threw us in there. There's no like, hey Craig, welcome aboard. Here's how we build things. Here's all our documents. Here's this. It was like, figure it out. There's all these different ways you can go. We have all these different stacks. You get to decide, you know, pick who you want to partner with, all this type of stuff. So that was really interesting to me. And for the, you know, for a company that provides a product for consumers for free that you're going to launch for Google, like scale becomes the number one issue, right? So it's like, how do we take Grand Central, great feature product idea implementation, and then how do I scale that to 100 million users? And that was like this, the first 18 months there, Everyone left us alone. We were, we were just working on that and it was awesome. The chat, the, once we launched 18 months later and we had a ton of users and tens and tens of millions of users, then it's, then, then it becomes less fun because now everyone wants a piece of, uh, this, there's a little bit of like knife fighting of like, okay, is it, do I, does it go over here? Does it go over there? And like, we think it should. and you end up going from being left alone to being in the middle of a ton of things that are kind of like just big company things. So, so as it became a little bit, little bit too big company, I was having a hard time getting things done. And we wanted to build an enterprise version of Google Voice. We wanted to build what Dialpad has become. And in 2010, Google got very obsessed with, uh, Facebook and wanted all of us to work on Google+, their next-gen social network product. And by— you've probably never even heard of it, but it was a big deal. Or it was— it wasn't a big deal. It was a big effort to try to go, you know, build their own social network. And so that's when I realized, like, okay, I have nothing to add to the social network. Stuff. I want to do the business version of Google Voice. So I went to Google Ventures. They had just started their venture fund, and they hired me as basically their entrepreneur in residence. And that— it's a really— it sounds great because basically you get paid to hang out at a venture fund and think about what you're going to do next and, and just think big thoughts. And, and like, there was no pressure from them to come up with something. Like, you can hang here for years, like No, no worries. For me, I've kind of felt like I was stealing money every day that I wasn't doing something, you know, so, so I wanted to get out of there as quickly as possible just because, just because I didn't feel like I was accomplishing anything. So we came up with the idea for what has become this version of Dialpad, which really was, okay, let's put some real thought behind how would you make an enterprise version of of Google Voice. And how would you make it from outside of Google when you don't have access to all the tools and infrastructure and stuff that you have at Google? So it was a— it took probably like— I was there for about 6 months working on that and working on designs and working on other idea, kind of like other ideas. Um, and it was like, it was just special because it was a new fund. There wasn't like you know, you're going to Kleiner Perkins or anything like that. It was literally like a new fund of really smart people given the freedom to do some really cool stuff. And I was just very, very fortunate to be there in the early days. Now it's a big, massive, you know, structure and they figured it all out. They're killing it and they have this awesome fund and they were awesome back then, but it was like, it was Wild West and it was really, really a cool experience.

Well, It's a circuitous path to get to where we are today, but the learnings along the way have built you into this incredible founder and CEO. Um, and you know, I agree, like, venture is not for everyone. Uh, but sometimes, every once in a while, there is an incredible investor who believes in you early on and sees the vision and becomes a true champion. So we'd love to ask you, who was maybe one of those first people who said yes to you, who believed in you early on?

Yeah, I will tell you that. And by the way, not to disparage venture capital, we have great ones like Marc Andreessen on our board. Like, we have— I see the great ones. They're amazing. And God bless you. You can see around corners and you have such, you know, pattern recognition and connectivity. Like, you guys are amazing. I just was terrible at it. The person who had the biggest impact was a product manager at Google called— named Wesley Chan. So Wesley Chan was like the, you know, first 500 employees at Google, worked for Marissa Mayer, MIT, brilliant, smart guy, had his own lab at HP at one point, like just super, super smart with no fear whatsoever. And I met him at a voice over IP show in Boston in like 2003, and I had no idea he was even like paying attention to the meeting I had with Google at the time. Or man, that's probably 2005. I'd started Grand Central. So there's 5 people from Google, they're all product managers. I give 'em a demo. There's one guy who's paying absolutely zero attention. That's Wesley Chan. But apparently he was listening very closely. And then I go to Consumer Electronics Show a couple of months later, he's there, comes to see us. And then like within a month, they're talking about buying us. And so Wesley led the acquisition. And then I worked side by side with Wesley to build Google Voice. And then Wesley left to go start Google Ventures. And so he was like, hey, come on over. So then, because he knew my frustrations and he shared them. And so I went with Wesley there and then Wesley drove the investment from Google Ventures and was our first venture capitalist. And then funny enough, Wesley left to go to Felicis Ventures, and as soon as he got there, he's like, okay, Felicis has got to invest in DowPad too. And so then he got Felicis to make investments, and then he was on our board for a long time for Felicis. Then he left to go start his own fund, now FPV Ventures, but Along the way, Wesley did the entire Series A and the entire Series B of Canva. And so like, if you want to talk about returning funds multiple, multiple times over, Wesley's the man. So for whatever reason, Wesley and I like were thick as thieves and thought the same way. And he's just been this incredible influence on my career. And hopefully I haven't let him down and I've never lost him money. Um, but yeah, it, it was, it was just an incredibly fortuitous, you know, relationship that happened kind of like just by giving a demo at a trade show in Boston.

That's incredible. And you never know when you're going to meet your next connection, your next Series A investor. And I would say that it's been going pretty well. Um, my numbers have you guys having raised, you know, over $170 million in venture dollars. And most recently at a $2 billion plus valuation. If you have any updates to those numbers, let us know. But, you know, it's really incredible to see all the traction and progress.

So, yeah, we've actually raised $418 million. And there you go. Perfect.

Yeah, you were correct.

You were right on that. Certainly right on the valuation. And it's been like the, the cool thing is like it started Google Ventures did the entire Series A, Andreessen Horowitz came in, did effectively the entire Series B, but for the pro rata of Google Ventures. And then Marc Andreessen joins your board and then it just kind of continues this rolling thunder. And then Iconiq Capital led our Series D, Will Griffith runs their growth fund and one of the greatest B2B SaaS growth investors, not even growth, just B2B SaaS investors firm world, what have you, just phenomenal. And then as we got bigger and we needed more scale, T-Mobile came in and made a sizable investment and their president of T-Mobile for Business, Kelly Field, joined the board and, and like big pension fund in Toronto, the Ontario Municipal Employee Retirement System, OMERS, made a big investment and the head of their growth, their growth investing is on our board. So it's just been like, I've been so blessed to, to have great investors every step of the way and been able to, you know, have people really help guide me in guiding the company. So, so it's like it's, it takes a village for sure.

That's incredible. With all of these really iconic folks in the technology industry supporting you and kind of helping Dialpad grow, a lot went right. But as we know from your earlier journey and just the journey of a founder in general, things are not always a straight path. Could you maybe share a moment in kind of the second iteration of Dialpad's sort of journey of growth where things didn't quite go as planned?

Yeah, it's, it's funny because you take a step back and you're like, okay, you started, you started here with zero revenue. You're now over $350 million here. And it's just like you can go like this, like, boy, wow, that must have been fun and easy, just crushing it. But if you zoom in, you know, like you guys know, it's a series of ups and downs and ups and downs and ups and downs and ups and downs and overachievement and underachievement and things you think are going to work out and they don't. You spend a lot of time on them. So they've, you know, I've been doing this now. I call it Dalpad too. And just so there's no confusion, I just bought the name back from Yahoo 10 years later. It's an entirely different company and people. But I've been running Dialpad now for 14+ years. A lot of things have gone wrong along the way. A lot of, a lot more have gone right along the way. Um, trying to think like some major missteps. I don't think we've ever had any major missteps. I think it was probably a little slow to, um, to lean into video conferencing. You know, we had audio conferencing, we had business phones, so sometimes we had a halfway decent video conferencing product, and then the pandemic hit and video conferencing just became radically, radically important. So luckily we acquired, um, HighFive, which was a group of ex-Googlers who were really good at video conferencing, and they built it basically on the same GCP Google backend platform the way we would have built it too. So we were fortunate to make that happen right at the beginning of the pandemic. And bam, all of a sudden we had really top-level video. But that was almost a pretty big miss by me, had I not been prepared for it or had I not found HighFive. And then, you know, like along the way, there's just like, there's ups and downs and there's, you know, hiring, you know, HR hiring people, Picking the right people, picking the right leaders for the right phase of the business, knowing when the business has moved on and you have to find someone to come in and replace someone who'd already been there for the next phase of the journey. That's really hard. You know, that's, you know, you hear people talk about like if you're thinking about making a move or changing or letting someone go, just do it because, you know, no one ever And by the way, like, it's almost like this was written for me. Like, never in my life have I ever been like, you know what? I totally, you know, should have waited a couple more years on that. Like, it's usually darn, like, like I should have done that a little bit sooner. So there's things like that, but it's a, you know, like it's a, it's a 1,400-person company, right? There's, there's gonna be plenty of ups and downs and highs and lows and, and things like that.

Thank you for sharing a bit of that. It's so easy to look at a company like yours and a trajectory like your career, and young founders say, gosh, I'm never going to get there. But when you take a step back and say, no, no, this was a journey, it's been 14 years, and here we are, we're an overnight success, right? Um, it really, um, it, it refocuses, uh, the effort that's ahead, um, and the exciting effort that's ahead.

Um, yeah, and it's— it, it doesn't get any easier. Like, let me tell you, like, I, like, I, like, wear this Whoop because I'm trying to track you know, how much sleep I get, it's, it's not a lot. You know, it's still, it's still not a lot. So, so, uh, yeah, it never gets super easy.

We should open this call with a sleep score check, like how's everyone doing. Well, you know, we talked so much about your personal journey and the business moments along the way, but I'd love to get in a bit more to Dialpad and its product and its mission and its scaling journey. So, um, you know, Today it is the AI-powered communications intelligence platform. Big words. I was playing around with the product experience page, um, on your core website, and it seems like you have a few offerings. There's Dial Connect, there's Dialpad Support, Dialpad Sell. For someone who maybe is less familiar with this broader communication space, could you just give us the layman's version of the core product functionality and how you sell into an org?

Yeah, yeah, well, I'll tell you. So it, it hit me. So I was working at Google. Vince Bacquet, who was my co-founder of Grand Central, we were running Google Voice and we shared this tiny little office. And both of us had— here we are running, building, developing, launching, supporting Google Voice, which is a phone system for individuals, basically all virtual stuff. And I had like a Nortel desk phone on my desk and Vincent had one on his and we had like cell phones in our pockets. Like we shared that office for 3 years. That phone didn't ring once, you know what I mean? And then I remember we came home or I came back from lunch once and like a red light was flashing on it. I'm like, like, I don't even know what that means or how to turn it off. And apparently someone had left me a voicemail somehow. I didn't even know what the number was. So like the epiphany was every business in the world needs to communicate with their customers. With their, with their partners, with their suppliers, with, you know, like, you're, you're the people you're trying to hire, prospect. Like, so the thing that I always thought about communications is it's universal. Everyone has to do it. And so we said, look, let's just go, let's make a modern cloud-based, software-based, work from anywhere, use any device, beautiful business phone system. Let's put these Avaya, Cisco, Mitel, Nortel dinosaurs out to pasture. Like it was just so obvious. And those things were just so expensive and so brittle and so manual and so on-prem. So it was just like, it seems so obvious to me, but in 2010 when we left to go do this, or 2011, like no business of any decent size was going to trust their phone system and they're this crucial link to communicate with, with just to put it over the internet, right? Because like they, they needed the reliability, they needed the perfect quality, they needed all this stuff. But in order to get that, they traded so much away. You traded away flexibility and, and being able to be productive from anywhere. And at the time, you know, like that whole mobile revolution, this is kind of like in the first third of that. It became clear that people were willing to trade mobility, quality for mobility. Your phone, your mobile calls back then didn't always sound great. They dropped quite frequently, but they were taking over the world because people loved the accessibility and the flexibility. And so tying all that together, we're like, okay, even though no business today would put their phone calls over the internet, the internet's only gonna get, continue to improve the codecs and the processes and the stuff. That we get to innovate on are gonna continue to improve. And then it's a no-brainer once it gets to a certain quality level, everyone has to because your business will be so much more productive. So that was the original idea, one software-based solution, all-in-one, beautiful, modern, and it'll do video conferencing, audio conferencing, phone calls, business phone system. And then we're like, hey, you know, like we should, let's get same thing, let's get into contact center, let's get into, you know, support use cases. Let's build a version for a sales team or for recruiting teams. And when you have that foundation of this platform that is just so reliable and high quality and accessible from anywhere on the planet, wow, you're cooking with gas. You're not beholden to all this legacy stuff. And then along the way in 2018, I got a demo of a real-time artificial intelligence capability that the startup called TalkIQ came and pitched us and blew my mind. The only reason I took the meeting is their CEO came from Google and was friends with my co-founder, our CTO. He's like, you gotta meet Dan. He's been trying to get to meet you. He's got this AI thing that'll understand your business phone calls. Anyway, I take the meeting and they do a demo of two people talking with, and it was a fake sales call, but they had on the app, hey, ask these four questions. And, you know, like, what's the budget for this? What's the need? What's your authority to make a decision? What's your timing? And as the conversation went on, it was checking off that those topics were covered. Wow. And it was like, I walked out of there, I'm like, Hang on, that thing understood in real time what they were talking about? Like, this is like, this has gotta be the future. And it was a bunch of PhDs and the only way, it was kind of a flawed business model 'cause the only way it would work is if they were built into the core of a communication stack. So we came out of that, started partnering with them, they built it the right way, they were a bunch of ex-Googlers and then we acquired them 'cause we're like, okay, this is just too good to be true. And so then that gave us, you know, kind of like this head start on, AI, you know, 7 and a half years ago, and we were able to launch AI products where we could give you sentiment, or we could suggest like a battle card would come up in real time if someone mentioned a competitor, or how to answer a question. And then, then you bring in the generative capabilities, and then all of a sudden you can have— use all your training and all your PhDs to make even a greater greater generative solution. And then now the Agentic stuff, which I'm super excited about that we're going to launch, of how do you automate and not just have, you know, a generative conversation that can provide answers to questions and do it conversationally like a human, but now it can actually take actions and solve problems like rescheduling appointments or, you know, like checking your insurance or paying a bill or doing all these things that that now it can just all do. And to have the thing where we're really excited about is when we have all those AI folks, we have all this AI experience and pedigree, and now we build that Agentic piece into the core of this one beautiful communication offering that our customers don't need to go out and try to figure out which startup on the planet to use for this particular use case. We're going to give them the tools to build any use case they need. And then we're going to have pre-built ones that are pretty uniform across all the competitors or all the customers in certain industries and verticals. And we're off to the races. So I'd like— it's funny to be a 14-year-old company that feels like a day one startup, but that's really what this revolution is.

That's the mindset you have to have. And I had a question teed up about being AI native, and I love the story about the TalkIQ and the way that you even 7 years ago saw the shift was going to be happening in the broader voice space and began embedding these types of experiences and, uh, you know, really a product feature that has become a platform into, uh, Dialpad. And I'm just a bit curious, for those who were also facing this question of, we've been around a little bit longer, we see AI and we understand that it needs to be a part of our business, how have you guys thought about, um, kind of building your own LLMs versus partnering with some of the larger model providers? You mentioned close partnerships with Google. How has that informed your roadmap decisions in the last few years and going forward?

You know, it was— it's interesting because it's all like 3 years ago feels like ancient history, but, but you put, you know, like 2 and a half years ago when generative AI and OpenAI and ChatGPT first kind of like just exploded onto the scene, um, nobody had— there was, there was such a scant amount of resources and GPUs available to to use. And, you know, like, it was like, if you're a little startup and all you need is a little bit of capacity, that's fine. But if you're a mature business with hundreds and hundreds of millions of calls and you're trying to drive them all through this engine, the capacity just wasn't there. The ability to build your own models wasn't there just because the capacity to get to the training clusters wasn't there. And so what we did, we said, look, we got our own PhDs, we got our own training data, we can build our own LLM. And our LLM is gonna be entirely focused on business conversations, right? So whereas every LLM is trying to be, I will give you every bit of information on the planet throughout history and you can come, you know, use that to do things. We were like, if that's the Library of Congress, we were like the children's nonfiction section. Like we were like, but, and it's, but if all you do and all you want to do is business conversation analysis and understanding and what comes next and how to coach and things like that and sentiment, then you want to have a very specific model that is very, very accurate for those things. So that's, we did it a little bit out of necessity and a little bit out of just kind of the lucky, place we found ourselves having had so much experience in it.

Yeah.

But like today, like those, we continue to, we now are using a lot of combination of Google stuff and our own just because those capacity constraints are gone. You know, the cost of accessing generative has gone way down. Yeah. And how do we do the best of both worlds? Because like, I'm not a tech zealot of like, just because we built our own back then when we had to, doesn't mean that's the right answer forever in history. Like, if that's no longer an advantage, let's put those brains and all that resources to something else that is going to be an advantage. So, but it's a stunning amount of progress on the daily. And like, the funny thing is, like, I tell our team, like, everyone's blown away by demos that we're doing now. I'm like, yes, and also remember, this is as bad as it will ever be. Like, it will only get better from here, and it gets better really, really quickly.

And as we march towards that progress and continued innovation, just our final question as we talk about the product and a look forward is just thinking through finding that balance between, you know, automation, iteration, and then also preserving that authenticity to human connection that we do have person to person. And how are you guys just thinking about that in terms of your long-term strategy?

Yeah, that plays really well. I mean, like, that is our long-term strategy of we want to be the platform that no matter where you are on that journey, we're here for you. So, you know, like, you're a cutting-edge Bay Area company, you're probably further on the automation side than the vast majority of other businesses in the world. You know, if you're a massive insurance company in Milwaukee, you might be slower on that journey. And it's still like, you know, like, The fact that half of the business phone lines in the world are still on-premise tells you like this, the whole world doesn't move to the pace of, you know, a Bay Area startup. So our vision is we give you all the capabilities in this one unified platform that, and you can, you can use as much or as little of the Agentic stuff as you need. And by the way, everyone should be at least experimenting and trying to use Agentic to make their businesses more productive. But if you get down a rabbit hole and need to speak to a human, it gives you this perfect Agentic-human handoff because it's all on the same platform. It's not like I've went and found some, like, some Agentic-only startup solution. But hey, if it doesn't work and the customer's stuck, they have no way to get it to a human. So having it all in one unified system is, is really kind of like our strategy.

Well, Craig, it's been incredible to hear about your career journey, Dialpad twice over, and really kind of how you're driving the business to continue to be on the forefront of innovation in today's kind of AI climate. As we kind of come up on time today, I'm curious, what's next for not only Dialpad, but for you personally?

Yeah, I feel like my entire life has been building up to this moment. So, so, you know, even though like my kids are out of college and I'm getting a little up there in age, it keeps you young. So I'm, I'm in this, I'm in it till the end, right? So, so personally, this is, this is the most exciting time, space, opportunity in my lifetime. It's It is more dynamic and more exciting and more disruptive than even the internet was. That's the only thing that you can even kind of compare it to. But it's, it's moving even faster. For Dialpad, continue execution, continue making customers happy, continue to roll out the best product in the world. And we do love that, that one unified platform. Is still unique today. And even though like some of our competitors will say, we do these 3 things too, they're 3 different things. So they had bought something and it's janky and it's different interfaces or the different platforms. That's a massive differentiator when you put that AI capability core into it. So, so like my vision for the company is we go, we go public at some point, we continue to take market share. We continue to grow faster than all of our competitors, and we just continue to make the world's best products.

Well, we'll have to have you back for your, your IPO story when that inevitably happens. Well, Craig, we'd love to ask you our hero question of the podcast. It's a question we ask all guests, and we ask that the answer is not mom or, you know, another family member, although we do love them. And that question is, who is a woman in your life that has had a profound impact on yourself and your career?

Hmm. There've been a lot. I mean, there, like, throughout my career, like, and I was raised by a single mother. Like, my dad left literally when I was 1. And so she went back to school, worked nights, you know, became a very successful professional. But it was like, yeah, there were times on food stamps. There were a lot of stuff. So, I've always been radically impressed by working, particularly working mothers, like the amount of juggling and the amount of work that goes into it. And by the way, they're incredible employees because they don't have time to screw around. Like, it is so good. So I've been a ton of them. I'd say on our board, Kelly Field, who's the president of T-Mobile for Business, one of the most impressive executives ever. And I've only known her for a handful of years, but, but super, super like, like no one meets Kelly and doesn't come away impressed. Internally at Dialpad, our CHRO, Tasha Linegar, she's been here for 8 years. Incredible. Incredible hard workers, super smart. In other jobs, like even with my early jobs at Apple, like I was always like on teams that were, that had a lot of women leaders and they were just phenomenal. So, you know, I've been, I've been blessed to have a ton of people who could, who could fit that role, including my mom. So I'm just going to leave it at that.

That's amazing. Well, we'll have to tag all of those names when we release this episode. And incredible to hear that there are so many folks and so many women who have had such an impact on, on your career and Dialpad. Craig, it's been such a pleasure to hear your journey. This has been awesome. Thank you for being on The Room.

Yeah, thanks, you guys. It's been a lot of fun.

Thanks, Craig. Thank you so much for joining us at The Room Podcast. If you want more from The Room every week, subscribe to our newsletter at theroompodcast.com/newsletter. We'll be back next week with a new episode, an inspirational guest Tuesday. See you in the room. Perkins Coie supports the most innovative entrepreneurs and investors in fast-moving and high-growth sectors, addressing their myriad of legal needs. But the firm doesn't just provide end-to-end legal and business counseling to its startup clients. It also facilitates introductions to key advisors and sources of capital. Perkins Coie's interactive website, Startup Percolator, offers access to programs, resources, and rich dynamic content designed to assist entrepreneurs on their startup journey. To learn more, Go to startuppercolator.com and perkinscoie.com.

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