Zach Dunn On Raising $60 Million To Build The First Hybrid Workplace Experience Platform With AI Capabilities

Zach Dunn’s entrepreneurial story is unique and intertwined with his twin brother, Sam. This blog explores their journey from starting a blog, scaling an agency, pivoting to product development, raising millions, and thriving through a pandemic—all while doing it together as twins.

Zach and Sam’s company, Robin, attracted funding from top-tier investors like Atlassian Ventures, Tola Capital, Allegion Ventures, and Accomplice. They are also building Rally.

In this episode, you will learn:

• Building a company with a sibling can be challenging yet rewarding, leveraging complementary strengths like vision and execution.
• Transitioning from a service-based agency to a scalable product business requires identifying reusable solutions and pivoting strategically.
• Success often hinges on timing, as Zach and his brother capitalized on the early days of social media and tech innovations.
• Overcoming biases against service-to-product founders, they raised $60M across four funding rounds by demonstrating adaptability and vision.
• Pivoting their office software business during COVID-19 turned a crisis into an opportunity, leading to rapid growth in desk-booking solutions.
• Each venture, including their latest company, Rally, builds on lessons learned from solving pain points in previous businesses.
• Balancing short-term execution with long-term vision is crucial for convincing investors and achieving sustainable growth.

 

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About Zach Dunn:

Zach Dunn is the co-founder and VP of Customer Experience at Robin, the first workplace platform to put people before places. Prior to Robin, Dunn co-founded and led product development as Chief Product Officer at One Mighty Roar.

Dunn has served as an Adjunct Professor of Computer Science at the University of Massachusetts and graduated with a B.A. cum laude in Multimedia Web Design and Development from the University of Hartford.

Connect with Zach Dunn:

• LinkedIn
• Crunchbase
• Zoominfo
• PitchBook

Read the Full Transcription of the Interview:

Alejandro Cremades: All right. Hello, everyone, and welcome to The Deal Maker Show. So today we have a really amazing founder, a founder that has done it also a couple of times. you know We’re going to be talking about how it’s like to start a company with your twin brother.

Alejandro Cremades: Also transitioning from doing something in the service space to then maybe like thinking about productizing it and launching a product, rolling something out of that that is more repeatable and scalable. And then also about weathering the storm via the pandemic or raising money you know through different rounds. Again, the episode today is going to be packed with very inspiring stuff. So without further ado, let’s welcome our guest today, Sak, Dan, welcome to the show.

Zach Dunn: Thank you, Alejandra. Happy to be here.

Alejandro Cremades: So originally born in Connecticut and then raised in Western Massachusetts, which is a very important distinction from Massachusetts. So tell us about growing up.

Zach Dunn: Yes.

Alejandro Cremades: How was life for you?

Zach Dunn: Oh, fantastic. um the you know Like most folks, I spent a brief time in Connecticut. Didn’t actually stay there. And Western Massachusetts is, for those of you from Massachusetts, know the distinction.

Zach Dunn: It’s very rural. I had an alpaca farm in my hometown, and it was a very different experience than Boston, which is now ah where I’ve lived and worked for the last 12 years.

Alejandro Cremades: So how did you get into the whole thing of, let’s say, design and and and development? Because that’s in the end when you ended up studying.

Zach Dunn: Yeah, so ah my twin brother and I, ah have, despite but the odds, we’ve managed to do just about everything together over the last 35 years. You can’t get quite get the hint. It’s the weirdest thing, you know? But we both went to University of Hartford down in Connecticut I went for web design and development, which was basically ah graphic design meets computer science. And then he went for marketing. And so as a result of that, we figured out that, hey, there’s maybe some some work we could do there together. And while we were down studying there, we started what would later become one of the top 10 blogs on the internet for web design and development called

Zach Dunn: built internet. And ah through that, we were able to jump out of school and into the wonderful world of client services agency work, right?

Zach Dunn: You want a website?

Alejandro Cremades: and well And we’ll talk about that in just a little, I guess with with your twin brother, because as you were alluding to it, you know you guys do everything together.

Zach Dunn: We’ll make you a website.

Alejandro Cremades: How do you guys complement each other?

Zach Dunn: um So I am what people would call the rational one now. So he and I ah have learned how to how to work together obviously over the years. I would say he is probably the big picture guy and I am more the how, the execution side of it. and that ends up working very well. And ah those that we’ve been fortunate to work with over the years have learned that distinction, i’ sometimes trial by fire, but ah we’ve been able to to balance each other.

Alejandro Cremades: So that’s pretty cool, actually. you know I think I mentioned that I have twin girls too, so it’s amazing to see what it could look like in the future. Now, in your guy’s case, you know you were in university, and then and eventually you design, I mean, you you build up this block that started to get ah quite a bit of attention, and that, the way that you kind of like thought about monetizing it was via the service-based type of approach. So I guess,

Alejandro Cremades: How big did the blog get? And what was that the thought process of, hey, how do we make money from this?

Zach Dunn: So we lucked out on timing in a big way because this was right around the cusp of um social media really becoming a thing. So this was probably within the first couple years of Twitter and ah but also back in the day.

Zach Dunn: I don’t know. Do you remember when Facebook had like a Farmville in a tab?

Alejandro Cremades: Oh, yeah.

Zach Dunn: Yeah.

Alejandro Cremades: Oh, yeah.

Zach Dunn: Oh yeah. The golden age, right?

Alejandro Cremades: Yeah.

Zach Dunn: So, um, On the blog, a lot of the work that we were doing was writing tutorials on how to get into some of that sort of design, and we would have people reach out to us and say, hey, that thing that you talked about, can you do that for our company? And that was a new idea it to us.

Zach Dunn: But ah we were able to turn that into a handful of first $1,500 clients, $3,000 clients. And then I think it grew from there to 30, 50K projects. And so at a certain point, I think our senior year of college, we were like, I am pretty sure we can employ ourselves now. um So let’s just do this full time.

Alejandro Cremades: So how do you land into the, um let’s say, service-based agency type of work?

Zach Dunn: agency, digital agency. Yeah, so um at the time, that was it that was pretty big, ah where there were a handful of so-called digital agencies out there that were really helping shape a lot of the um consumer brands out there, for example, ah how they used social for the first time.

Zach Dunn: um because nobody had really figured it out. ye ah like What is a Twitter account actually um for ah for a business? And so one of the niches that we fell into was um helping these brands build in-person ah digital experiences um for their events. So an example of that would be if you go to a music festival and they would give you RFID wristbands as the ticket. We made ah work We made things that when you walked up to kiosks, tagged that in, things around you would change. Like the screen could change to something. It would take a photo, send it to you, that sort of stuff. Gimmicky in retrospect. But at the time, that was like a goddamn revolution, right? Like, cool. And so ah we were able to to build some interest and visibility through that.

Alejandro Cremades: So then eventually you go into um productizing, right? So you guys are you know doing the this whole agency thing, but that doesn’t scale. You have certain amount of hours in the day, and and I’m sure that at one point you were like, hey, maybe we can do something where we can make money when we sleep.

Zach Dunn: The dream. ah yeah One of the things that I think you you learn in a hurry if you’ve done the services business is it’s hard because a lot of your work um is temporary. That is to say like your portfolio is only as good as the last two to three things that you’ve done. And a lot of the earliest stuff that you’ve done is no longer anywhere on the internet. And um you’re constantly in a state of finding your next thing. And sometimes you get long-term customers, but more often than not, you’re constantly hunting.

Zach Dunn: And so while we were working with these these clients, we started to build stuff that we could reuse across clients. And that ultimately led us to what would later in 2014 spin off into our first venture backed company, Robin. Robin came out of an idea that we had a conference room table in our, ah ah conference well in our conference room, which um we made it so that when you sat down at it, it booked the room using using like motion sensors and other stuff. And this was like ah just a fun thing that we had built using some of the tech that we were developing.

Zach Dunn: And that it went viral at the time. And we were invited to go present it at NIACON, which despite the name is actually a furniture and architecture and design conference in Chicago. And that was really the first time where we were able to like springboard this idea of client work into, oh, maybe this is a product. And so Robin was ah over the but from on.

Zach Dunn: Basically, whenever you see an iPad outside of a conference room, ah that was probably us. If not, we would fix it and become the one who did it. And that really over the next 10 years, it became a full body workplace ah scheduling system.

Alejandro Cremades: So I guess saying, how are you guys making money there for the people listening to to get it?

Zach Dunn: Yeah, so a lot of the times in the early days, what people would come to us for is a problem of like, hey, there’s you have an office, you have dozens, if not hundreds of conference rooms. How do you make sure ah that you’re you’re able to ah book the right rooms, cancel meetings if people don’t show up to them? Everyone hates it when you show up to a, when you can’t find a conference room and they’re booked.

Zach Dunn: there’s nobody in and there. So there’s a lot of that sort of of air traffic control that we were able to do. And over the years that evolved into supporting a thing called activity-based work, which is a way of designing your office ah to support the type of work that you’re doing instead of ah just a number of people.

Zach Dunn: So like you might have an area that’s for brainstorming breakout space. You might have another area that’s for different types of work. And when you do that sort of thing, it has a profound impact on how you actually have to schedule and ah coordinate everybody.

Zach Dunn: so

Alejandro Cremades: So how was that the moment like as well when you guys decide, hey, maybe we got to scale this thing faster. Maybe we should take a look at the raising money.

Zach Dunn: Yeah. So the, it was, it was probably one of the best slash worst years of my life. The, the year that we decided to raise, um, the, the seed round, which ultimately ended up being around 3 million or so. And one of the the things that we decided was, hey, we’re going to start trying to fund this ourselves. Because that was just in our DNA. And we had a little bit of a war chest from the agency um that we had started. And so we were like, OK, we have people that are very good. We have an idea. There’s some interest. Let’s see how far we can get this thing on our own.

Zach Dunn: And we put in the first million, probably, out of that funding. And what we quickly realized is it’s just a different beast when you’re building a product. um And a lot of the growth that you want to have happen really comes from being able to like not just identify the opportunities, but also act on them. And I think identifying opportunities is often the sexy, easy part, but actually acting on them, seizing them. A lot of times, that’s where the constraint comes in. And you know when you only have about a dozen people, ah you got to move a little bit faster than just bootstrapping it allows. So we decided to go out, fundraise.

Alejandro Cremades: So how was the journey of raising money? Because all you know, you guys raised about 60 million bucks. So that was four different rounds.

Zach Dunn: yeah Across all the rounds. yep

Alejandro Cremades: yeah so So during those different four rounds, what did you see changing and shifting when it came to strategies or expectations to to be effective and to get it to to happen?

Zach Dunn: So a lot, I’ll go round by round. So with the seed round, a lot of it was ah around Sam, my twin brother and I’s ability to actually navigate ah the transition from a services business to a product. Because one of the things that we weren’t expecting as we were going out fundraising was ah how little ah

Zach Dunn: interest people had in our backgrounds. It almost was like a ah black mark, so to speak, because you know we had a number of VCs where we would ah seemingly have a great conversation. and But at the end of the day, what it came down to for them was like there’s two types of people in the world, people who do services business, people who do product business. When you choose one, you can’t go to the other.

Zach Dunn: And I don’t believe that, still don’t. But that was, I think, a pattern that had emerged in the fundraising environment at the time, around 2014. And so a lot of it was convincing folks that we could ah actually build a product and not just a services-client relationship.

Zach Dunn: And we were able to find a handful of folks that fortunately believed in that and us and ah go from there.

Alejandro Cremades: Okay, and then and then what would you say was the toughest thing or the biggest lesson that you got from from capital raising?

Zach Dunn: I think the the may it’s important to balance the aspiration that you have, like where it could go with short-term goals, even. Because like it’s really easy to look from the outside, I think, with a venture and think, OK, the type of people that get funded in tech are the people who go into a room and all right you know there’s this amazing opportunity and here it is and let’s do this. And you can get people excited about an idea um and that’s enough. But the fact of the matter is most of the people that you’re meeting with, ah they are partners war ah in the the firms and they are only funding maybe like three, four companies a year.

Zach Dunn: conservatively and sometimes more in earlier stage but really the question that you’re not just competing against other people trying to do the product you’re trying to build you’re basically you basically got to convince the person you’re talking to is this worth one of my four or five for the year and um so in that way you’re competing against anything that could raise money and ah that was not something that ah we really fully appreciate it until maybe midway through the process. um Because there’s a lot of folks who would, with unlimited budget, sure, invest, but that’s not the criteria. It has to be, you know of all of the ones I’m likely to see this year, is this is this one that I’m into.

Alejandro Cremades: I know as well that the um COVID a period was a little bit rough um when it came to um to scaling and pushing Robin. ah so So I guess, say what what do you i actually not Robin, one mighty run.

Zach Dunn: One mighty roar was the agency you were right the first time, Robin.

Alejandro Cremades: yeah Yeah, so you’re right. So so then basically Robin. so So with Robin going through the pandemic, you know after you guys had raised this money and everything, how was how was that like for you guys? I mean, that sounds like a crazy, crazy you know murky waters to go through.

Zach Dunn: I definitely wouldn’t recommend selling office software during a pandemic, especially when offices are closed. ah Not so fun, at least, you know, compared to other things. So we had, for some context, right before the pandemic, we had just closed a series B, I believe that was about 20, 20 million. So at the time we had ah basically closed 30 million across the first few rounds. And so we were really ramping up and starting to develop our second

Zach Dunn: ah product line. So the first one being conference rooms. And then the second one, we were getting into hot desking, hoteling, that’s like where you can book desks instead of just rooms, right? So you don’t have assigned seats in an office. And that was early days. And we, we knew that it would be probably a couple years before that really took hold, but we were making the investment. And then the pandemic happened.

Zach Dunn: And ah at first, it was awful because 100% of our customers were not able to actually use the product that they had purchased from us. But as more people started shifting into the how do you return to the office, that actually became a major ah driver for us. and We saw over that ah time period, we grew three to four times over and what we thought would be multiple years ah ended up happening in a matter of like six to 12 months as far as growth goes because at hot desking solution,

Zach Dunn: at like desk booking thing, turns out that that actually was a pretty critical thing for returning to the office. So it ended up being a fascinating turn of events.

Alejandro Cremades: Love it. so um So then for you guys, you know at what point does it become evident that maybe it’s time to um to shift gears and and turn page and and get going with something new, which would end up becoming rally?

Zach Dunn: Yeah, so um we, so I, we did, Robin for about 10 years. It’s still going. And, you know, attend the board meetings. Love it. And really ah continuing to see that move forward. But about a year or so ago, um we started a another company and decided, hey, this is this is a good opportunity to take some of what we learned with um our time at rally er Robin and start another company, ah Rally, which ah now targets ah some of the storytelling and team communication around product marketing and like how people actually announce and present product-related demos, updates to their customers, those sorts of things. ah It was a direct pain point, felt at Robin, and it was one that I think

Zach Dunn: we had a ah perspective on ah that we could bring. So that’s where we’re now.

Alejandro Cremades: So Riley, what’s the business model there?

Zach Dunn: So you know typical SAS until it isn’t. um Of course, I feel like the right answer at this point is everything has to be AI. right you know Otherwise, what are you doing? um The business model is basically per seat with a ah secondary business model of ah AI credits. That part’s in the work still. But it just as we sell into go-to-market teams, so think people who are on the front lines talking to customers, prospects, and the people who support them. So think product marketing, sales enablement. And the motion here is actually,

Zach Dunn: Unsurprisingly, very different than selling workplace scheduling software where you’re talking to facilities and IT teams. Here, you’re actually talking to people whose job it is to explain and present the product to not just prospects, but also an existing and growing customer base. And a large part of that has to do with is the product that you have actually the product that you’re selling and the product that your customers know you have. And it turns out that there’s a pretty big lag in um building the product versus letting people actually experience the most cutting edge version of the product that you have. And that’s what we’re we’re trying to close.

Alejandro Cremades: Was it a little bit the easier to raise money this time around or not?

Zach Dunn: Oh yeah, yeah. I think that the for a second time around founder, there’s certain um credit, and I think you can, in good will, that you’re able to leverage, especially with the early days. um So I think it was much more of a, hu which folks do we wanna work with again, um conversation?

Zach Dunn: and ah you know Fortunately, we were able to to pull together almost exclusively previous investors from Robin, and then we involved you typical angels. and you know It was, all things considered, very smooth.

Zach Dunn: um and You know, in some ways that’s a relief, but ah you know for those of you out there who have done it one time around and you’re worried about round two, if you’ve had a decent outcome, it’s a very different experience the second time through.

Alejandro Cremades: That’s how amazing. like ah Obviously, investors, they bet on a vision. So when it comes to a vision, if you were to go to sleep tonight and you wake up in a world where the vision of Raleigh is fully realized, what does that world look like?

Zach Dunn: I think that ah the experience that a customer has in and ah learning about your product, using your product, they it’s consistent from start to finish. like The way that your sales team talks about the product and presents your product is the same as the way your customer team is able to present your product. there’s this um There’s this real challenge with ah the product that you have is not often the product that your customers think you have. And ah the better that we can do at helping people present and display their latest product updates,

Zach Dunn: the more ah we can help people ah get that feedback loop needed to build ah a great product faster. Which is, if you think about some of that AI coding stuff, the rate of change is going to go up. And so it’s not really practical to expect that it’s going to take three to six months once you ship a feature for your customer base to actually realize that it’s there.

Alejandro Cremades: So, we’re talking about the future here. I want to talk about the past, but doing so with a lens of reflection. If I was to put you into a time machine, and I bring you back, you know let’s say, to around 2011, where you and your brother were starting to play with having a blog and you know maybe think about a world where you could do something of your own,

Alejandro Cremades: And if you could go back in time and have a sit down with but your younger self and your brother to win, you were able to give your younger selves one piece of advice before launching a company. What would that be and why, given what you know now?

Zach Dunn: I think the, well, first of all, if I had a time machine and specifically for 2011, I would buy as much Bitcoin as possible and just get that out of the way. But you know once I’ve made the correct financial decision there,

Zach Dunn: um the when you’re going through this for the first time, it’s really easy to over index for people who have to hire people who have skills that you don’t. And when when you’re hiring somebody for the first time who has financial accounting background or operations, um everything that they do will feel like magic.

Zach Dunn: Like, oh my gosh, I had no idea how the Microsoft Excel worked that way. And so you can end up hiring people that may not be the, um that may be better than you, but may not be the best pick for the stage. And ah this is, I think over the years, being able to hire people who know how to do things that you don’t, but also ah are able to have that lasting impact over a number of years and scale with the company. ah that’s That’s a process to learn. And I think that’s where a lot of the wisdom I would share is. Also, ad revenue is probably not a good source of income. That was mostly how we funded the blog days early on. And there’s some you know banner ads. or

Zach Dunn: A few thousand dollars a month at the time, which was college years. Oh, amazing. But, you know, there’s some other opportunities too.

Alejandro Cremades: Yeah, no kidding. Well, hey, it’s a trial and error, like everything in life, eh, SAC? But that’s right.

Zach Dunn: Life is risk. Yes.

Alejandro Cremades: That’s right. So um so hey, so really amazing. you know I got to really thank you on behalf of everyone that is listening. Also, on my end, you know for really taking the time to come on to the Dealmaker Show today and and share your super inspiring journey, SAC.

Alejandro Cremades: So thank you so much.

Zach Dunn: Thank you, Alejandra.

*****

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