Michael Sacca is the CEO and Co-Founder of Gigantic. He previously sold two companies, Crew to Dribbble and Brandisty to Brand.ai. For the last six years, Michael has held various roles inside Dribbble including GM and Chief Product Officer. During his time as GM the business revenue grew by 70% year over year. He oversaw all product, design, data, and engineering initiatives across Dribbble’s suite of brands including Creative Market, Fontspring, and Font Squirrel. He has led growth initiatives across Dribbble including a transition of Creative Market from a transactional to subscription platform, developing a native ad unit on Dribbble, and building Dribbble Education to a multi-million dollar business line in under two years.
Chloe Oddleifson started her career at Tiny Capital supporting all aspects of the venture capital firm. Prior to joining Gigantic as Co-founder and COO, she was the VP of Operations at Dribbble for 6 years. She was one of the co-founders of Dribbble’s education business line. Chloe speaks internationally on the topics of distributed teams, leadership, and the future of work. She regularly mentors HR and operations leaders through her personal consultancy.
Working in a startup brings the concept “CEO of the product” to a whole new level. Suddenly, as Gigantic CEO Michael Sacca and COO Chloe Oddleifson know well, you’re responsible for every aspect of your product’s development, launch, promotion, sales – and everything in between. Fun fact: there’s plenty to take away from the startup mindset for all us product managers.
In this episode of Product Momentum, Michael and Chloe share their journey, from 6 years of working together at Dribbble to now building Gigantic from the ground up. Gigantic is a product- and marketing-focused training institute that aims to fill knowledge gaps through perpetual learning.
“Michael and I were coming from a place where we knew our jobs inside and out,” Chloe says. “We knew exactly how to be useful, exactly how to bring value. And then we started Gigantic and moved into a world where it’s just us. There are no processes, there are no rules, nothing is set in stone, and there are no clear answers. We just have to pick up and figure it out.”
“It doesn’t take long to see the power of a brand,” Michael adds. “I don’t think I ever respected it before as much as I do today. We can have a better product than the competition out there, but it’s so much harder to get people’s attention” when you’re just starting out. “We can build whatever we want,” he adds, but getting the attention and going to market are much different and much harder.
“If someone wants to be the CEO of the product internally…,if you really want your head of product to be the CEO of the product, then they really need to understand those other disciplines and they need to be able to do them,” Michael says.
In many ways, that mindset becomes easier to execute when the culture that nurtures it is founded in joy.
“As we started thinking about the type of company we wanted to build, the type of culture we wanted to infuse, and the type of experience we wanted for our customers, joy was the term that best described it,” Chloe explains. “We should be able to find joy at and in the work we do because life is just too short for it to be any other way.”
Catch the entire conversation with Michael and Chloe to learn even more about that journey and their plans to deepen Gigantic’s impact.
Paul [00:00:19] Hello and welcome to Product Momentum, where we hope to entertain, educate, and celebrate the amazing product people who are helping to shape our community’s way ahead. My name is Paul Gebel and I’m the Director of Product Innovation at ITX. Along with my co-host, Sean Flaherty, and our amazing production team and occasional guest host, we record and release a conversation with a product thought leader, writer, speaker, or maker who has something to share with the community every two weeks.
Paul [00:00:43] Hey folks, I’m super excited to share the conversation that we just had with Michael Sacca and Chloe Oddleifson. Their journey on the road towards launching and bootstrapping Gigantic, their new firm, has been inspiring to me and most of all, I think, you know, people spend 40 hours a week, 2000 hours a year working, and the message that comes through to me is that if you don’t infuse joy into those hours, you’re missing the point. There’s so much to unpack in this conversation, so I’m just going to leave it there and hope you enjoy it. Let’s get after it.
Paul [00:01:15] Well hello and welcome to the pod. Today we are really excited to be joined by two very special guests, Michael Sacca and Chloe Oddleiffson, starting out a new adventure. And I’ve been following them for the past couple of months. I’m going to do a little bit of a different intro and toss it over to Michael and Chloe to introduce themselves a little bit just because they’ve got a lot of passion and have a real, I think, investment, in a literal and figurative sense, in where we want to take this conversation today. So Chloe, can you share with us a little bit about where you’re coming from and toss it over to Michael?
Chloe [00:01:45] Yeah, for sure. Thanks for having us. We’re thrilled to be here. My name is Chloe. I am today the Co-founder and COO at Gigantic. Prior to joining the team, I was the VP of Operations at Dribbble for six years. So Dribbble is a design platform, for those of you who might not be familiar. So supporting kind of all aspects of the business’s operations. Dribbble held a few different companies, so supporting those teams as well. And prior to joining Dribbble, I was at Tiny Capital, supporting the partners there. Michael, do you want to introduce yourself?
Michael [00:02:18] Yeah, yeah. I’ve got like 20 years in product. I host Rocketship.fm, which is another product podcast, for the last decade now. And then I’ve been kind of in between product and entrepreneur journey. I sold Crew to Dribbble about seven years ago now. At Dribbble, I led our sales team, our marketing team, our data strategy team, and then finally, our product team there as the Chief Product Officer. And we are now the founders at Gigantic, which is a product- and marketing-focused training institute for continued education.
Paul [00:02:50] Awesome. First of all, congratulations to you both for taking the leap. I know it must have been scary, and I was going to ask it a little bit later on, but since you mentioned Rocketship, I want to ask something that I know launched my sort of empathy and following of where you all have been over the past few months/ you shared a very personal Rocketship.fm episode back after Industry Dublin, in I forget what month it came out now, but it was the unpublished talk at Industry, or something to that effect, and it really resonated with me. And it sparked a real, I think, journey of reflection that, you know, you really have an endearing way to bring people along for the ride just in your tone and style and the work that Gigantic is doing, obviously. So I’m wondering if you can unpack just where you’ve been and, you know, if you wouldn’t mind, a brief synopsis of what that episode kind of catalyzed for you as you started on this journey?
Michael [00:03:42] Yeah, I’m glad it helped. It was kind of a weird transition time. I’d been at Dribbble for six years and I knew I was leaving. We did a long kind of off-boarding because I was the Chief Product Officer, there was a lot to kind of tie up and take care of. So we had been planning this for almost a quarter. My departure and Industry Dublin came right at the end of that. And so I had, I think, a week left when I got back from Dublin of Dribbble and we were prepping for the next thing, right? So we were prepping Gigantic. I was kind of in between these two worlds of being the Chief Product Officer at Dribbble, but then also wanting to express what was coming next, but not quite being able to.
Paul [00:04:24] Mm-hmm.
Michael [00:04:24] And I ended up going to Dublin and I rewrote the talk twice while I was there. I was on the phone with Chloe at midnight, trying to rework the talk into something that was more authentic to where I was. I was calling my wife, getting her advice, and ultimately I ended up just having kind of a breakdown and I didn’t give the talk at all. I was supposed to be one of the last speakers of the second day, and I called up Mike Belsito, who runs Industry Conference, and I told him I couldn’t do it. And they had flown me all the way out there. I felt terrible, but I really didn’t have a voice at that time to be able to deliver a message that was both honoring kind of the six years at Dribbble and my Chief Product Officer status there, but the reality of not really being in that role anymore and turning into a founder with a different mission.
Michael [00:05:20] So, yeah, so I released the talk on Rocketship that I never actually gave that I wanted to give there, but I never actually gave it. We finally did give a version of it in New York City a couple of months later when it kind of felt better, but it started kind of a self-reflection journey for me too, into yeah, what was this new phase? What am I now? Even, you know, you go from being a Chief Product Officer, everyone wants to talk to you, you know, you get emails all day long. And then you leave that and you don’t have that title anymore. No one really cares what you’re doing. You’re not useful to anyone anymore in the same way that you could be when you run a large product team. And so it was a moment of transition. And then that speech kind of came right at a key point where I just was not ready to be in front of people and really talk about it.
Paul [00:06:11] Well, just a few weeks later at New York City Product Conference, both of you on stage absolutely knocked it out of the park sharing your authentic story, so hearing that story from the beginning to sort of the kickoff. It really was a powerful moment to watch unfold and kind of see you both really share your journey. I want to kick it over to Chloe. I know as COO you’ve got a lot on your shoulders and there’s a lot of new kinds of experiences going from a somewhat large organization down to everyone as chief, cook, and bottle washer. What has the transition been like for you trying to build up and operationalize a company from the ground up? What’s it felt like for you, from your perspective?
Chloe [00:06:51] Great question. It’s been all at the same time, a total blast and very scary, I think. You know, like Michael said, we both spent six years at Dribbble and so we were coming from backgrounds where you know your job inside and out, you know exactly how to be useful, you know exactly how to bring value. You’re fully aware of sort of the different challenges and are working to overcome them in certain ways and implementing different strategies there to a world in which it’s just you guys, you know, and there are no processes, there are no rules, nothing is set in stone, there are no clear answers. And you just have to pick up and figure it out.
Chloe [00:07:34] And I think one of the things that I have maybe like initially struggled with a little bit is just being okay with throwing things against the wall and seeing what sticks. But that’s really, there’s kind of no other way to do it. You really just have to, like, jump in and give it a go. And Michael and I have been spending a lot of time talking about how we really want to build a company culture that is okay with a little bit of mess, a little bit less process, and just jumping in to try something, to figure it out and reminding ourselves to take that ownership, to take those risks and those leaps, and that as we start to grow our team eventually, that we want to build a culture where that is embraced and acceptable as well.
Chloe [00:08:18] So yeah, it’s been a wild ride so far, but it’s been so much fun and incredibly rewarding because, to your point, you are everything. You are the line cook, you’re the prep cook, you’re the person serving the dishes, you are the owner of the restaurant. Everything is going to come back to you at the end of the day. So it has been very rewarding and fulfilling for sure.
Paul [00:08:40] Thanks for sharing that.
Sean [00:08:41] So having such an incredible product background with both of you now starting your own business, kind of treating this new business really as its own product and having all of the responsibilities, it’s a big change. But you always hear this thing in the product industry about product leaders being kind of like the CEO of the product. Not really the CEO of product, like having all the responsibilities but none of the power and control. What are some similarities you guys are seeing, you know, in this complete startup phase again?
Michael [00:09:05] Yeah. So it’s different. You see the power of a brand. And I don’t think I ever respected it before as much. You see these big brands, they put out products, but when you’re launching to, like, millions of people, you forget how hard it is to get it right because there’s so much power and trust that’s built up over time. And I think when we step back into this, we can have a better product than what’s the competition out there. But it’s so much harder to get people’s attention than it was when we were at Dribbble. We can literally build whatever we want. We can kind of design the courses the way that we want them, but getting the attention and going to market is much different and it’s much harder.
Michael [00:09:48] And you realize, like, how important those other services are. Like, I used to just focus on product and getting that right. Now I know that I can get the product right, but if I don’t get the sales and the marketing right, it really doesn’t matter. And so you start to understand, I mean, we all have these departments internally of product and design and sales and marketing. We try to get them to work together and they never do. And everyone has like, you know, they all have their different goals. But really, it should all be the same thing. And I think my takeaway is if someone wants to be the CEO of the product internally, right, if you really want your head of product to be the CEO of the product, they really need to understand those other disciplines and they need to be able to do them.
Michael [00:10:33] Like, I’ve always done sales my entire life. I’m doing sales now. I talk to every single student. You know, Chloe and I have designed all the drip campaigns, we’ve designed all the communication. We designed how we talk to them, what we say to them, how we relate our curriculum to their problems. And all of that as product work. And we often forget that within larger companies when we become more distanced. A lot of our students, even, they struggle with this very same thing. “Sales is coming onto my roadmap and they want X, Y, Z feature, and I don’t want to build it because I’ve got this…”
Michael [00:11:05] The truth is we’re all really solving the same problem. And I think if product folks had more experience across, you know, the disciplines of a company to actually bring something to life, we would have a lot more empathy. When we get into these larger organizations, we’d have a lot more empathy for, we really are all building a product. Like, the customer service is the product, sales is the product, marketing is the product, right? And it’s not just the features and functions and user stories. It really is the entire experience. And if we can own that, then I think we as a product people can actually be like the CEO of a product internally. But I think it takes a much wider heuristics of an individual to truly be able to do that. And it’s not going to come from being, like, heads-down in a funnel of a product org ladder. You’re going to have to branch out and get uncomfortable in order to truly do it. And that’s the thing that I hadn’t done in a really long time, and I realize how connected everything is today when we have to do it all ourselves.
Sean [00:12:12] That’s profound. You know, you said something’s changed. And this is the second time you’ve done it, so you did it. Then you were acquired, you worked inside of this larger organization for a long time, and now you’re doing it again. So you get to see sort of the same problems just in very different time environments. And I would love to pull on that thread a little bit. What has changed?
Michael [00:12:31] I think there was this kind of mythology when I was coming up, and probably like many of us, that if you build a great product, it’ll win a market. An engineer alone can kind of do everything, and if it solves the problem 10x better than everything else, then no problem, go do it. It’s kind of the Paul Graham, kind of the Y Combinator early musings in like engineering-led product. And I think that was probably true early in software where you really could just kind of build a better widget and like Salesforce is a behemoth and yet it’s a giant crud app, right? Like, there’s nothing actually special that Salesforce does, but they did in the beginning take a manual task and make it accessible online. And they were the first to do it and they built a huge brand around it. And yeah, now they have like half a dozen tools that help you. But I wouldn’t say it’s an easier solution today. It’s a lock-in solution.
Michael [00:13:27] Anyway. The point is those were the types of products that could win early on. They didn’t necessarily have to be great. They just had to take this super painful process and automate it a bit. We’re probably coming into another phase of that with artificial intelligence, but for a long time, really what won was branded marketing. But we as product people are constantly told, “if you just build it better, you’re going to win customers.” And it’s come to a point where I don’t think that alone is true and it is valuable to have a more holistic skill set, although I’ll say there’s probably going to be a nice phase within artificial intelligence where if you can kind of do the same thing, if you can take Salesforce and automate most of it, there’s probably a whole nother giant brand and company to build out of that. But those instances come once every 20 years. It’s that in-between phase where we need to be more holistic, and if we’re not within that specialized industry, you can still build a great company, but you do need to focus on more than just product. It is the full customer experience that matters. I hope that answers.
Paul [00:14:35] Totally does. Well, a lot of the themes that you’re hitting on are reminding me of service design concepts. A lot of stuff that Mark Stickdorn and Adam Lawrence write about, about, it’s not just the product, it’s not just the design, it’s product marketing management and the go-to-market strategy itself, and all of this stuff all rolls up to the big E experience of what customers feel at the other end of all this stuff that we’re building.
Paul [00:14:58] I’m going to take us on a bit of a hard pivot because I have to ask this question because I hear one word come through in so much of your communication and so much of the journey and the talks that you shared. And that word is joy. You talk a lot about losing it and finding it again, and it’s had a big impact on me and just sort of the ethics and the decision-making process and building culture and leading a team. And I think, you know, that word it is, you know, it doesn’t feel comfortable in business circles very often, but the way that you bring it out, it just kind of snaps everything into focus. So I’m wondering, Chloe, maybe you could start us, if you wouldn’t mind sharing just kind of, this word seems to recur and it seems to be on purpose. Can you share a bit about what that means to both of you and why, you know, losing it and rediscovering it was such an important part of this decision?
Chloe [00:15:46] Yeah. So I think that one of the things that Michael and I are both just very passionate about is building things. And as we started thinking about, you know, the type of company that we wanted to build and the type of culture that we wanted to infuse and the type of experience that we wanted to provide for the people using our product, our students who are coming to our courses, that was what we wanted. You know, we sat down and had a big conversation about it, and we believe that we should be able to find joy at and in the work we do because I think life is just too short for it to be any other way, and that we should be able to work somewhere that brings out the softness in us rather than the survival in us, and that we knew that we were going to be successful if we were able to infuse that across every single layer. So across our company culture, across the way that we work together, and within our product.
Chloe [00:16:39] So I think when you talk about, like, hearing that word intentionally, like, I’m glad that that comes through because yes, that has been intentional. And I think that’s something that we have just really tried to kind of focus on as we’ve been building and kind of gut checking, “like, is this the right thing, are we on the right path here?” Michael, I’m sure you have more insights along that line.
Michael [00:16:59] Yeah, well, I think, you know, I burnt out, you know, and I burnt out through process. And I think, like, we both felt the pull on the team to, like, there was so much energy going into adhering to a process. And the process wasn’t producing great results. It was just a process and we were happy with it. But I burnt out on, the process didn’t give me joy and the process didn’t output joy and it didn’t output a better product than not having it. So it was like a good two years kind of in survival mode.
Michael [00:17:34] When I started to pay more attention to other things kind of around me, what can we do here? There has to be a better way to run a company than in survival mode, and there has to be a better way to motivate people other than deadlines and fear. Because you could see people check out, you could see them come into the org and then check out within a couple of months. Once they realized that, “I’m just going to do the minimum because everything else is just too much of a pain.”
Michael [00:18:01] And one of the things, like, I started looking for inspiration elsewhere. And I’ll tell just a quick story. My son, he’s eight and he plays soccer and we’ve been looking for different programs for him because it’s something that comes quite naturally to them. And he found this coach and the coach would encourage them. He would teach them soccer, but then he would only encourage them on the field when they did something interesting. And if they messed up, he would ask them, “What could you have done differently?” Or, “What other options did you have in that scenario?” And the kids are eight and in the middle of the game they turn to him. They’re like, “Well, there was a guy over there; I could have passed it instead of dribbling and losing the ball,” or whatever the situation was.
Michael [00:18:43] But the kids are now learning how to function in a game and they don’t feel this overarching pressure that most coaches, and honestly managers, put on their kids, which is telling them exactly what to do and screaming at them that they’re not doing it. And the kids are in a situational game. I don’t know the last time you’ve been on a sports field, but it’s different when you’re standing on the sidelines versus when you’re in the game. And all of our people at work are in the game, right? They’re doing the work. They have to do the output. They have to put in the cycles to get the output. And then we’re standing there screaming at them to go faster, do it different, change this. Right. And de-motivates them.
Michael [00:19:22] And his whole philosophy, which I guess comes from European football, was, let them experiment and then positively reinforce what they did well or help them understand when they could have made a different decision. But don’t be punitive, don’t punish them, don’t scream at them. And he’s a completely different coach than anyone else. All the other teams that we play against all have these kind of like coaches, they pull the team over and they scream at them at halftime, they scream at them after the game. They go through all the mistakes that they made. He just lets the kids go play, and his team is more talented than any other team that they play and they play freer and they’re just so much more fun to watch because they’re actually enjoying the game. And they mess up and they do crazy moves in front of the goal and they dribble for too long, but their skills as they develop are going to be incredible because they’re free to experiment.
Michael [00:20:13] You know, and if we take that same methodology into how we coach our teams and how we lead our organizations, these kids are playing with joy and they actually enjoy what they’re doing and their end result is much higher than anything else I’ve seen at the end of the day. But the process to get there is a mess. Like, you know, they’re doing rainbows in front of the goal when they should be clearing it. But he encourages them for taking a risk right? Great job, you know, the other team got the ball and scored and we lost. It doesn’t matter at this stage, right?
Michael [00:20:46] So I think when I started to realize that we were just, we were working against ourselves by trying to control every movement within the company. And that with a little bit of mess, we could actually produce better output if everyone involved was okay being messy.
Paul [00:21:03] Love that.
Michael [00:21:04] Right? And no great product has really ever been built through, like, a strict process. It’s these moments of inspiration that we were suppressing inadvertently. We didn’t know, but we were suppressing these moments of inspiration that they’re the ones that keep me up til two, three in the morning when you get it and you just have to execute on it. I’m not going to do that if there’s no benefit, but I’ll do that all day long if there’s a benefit and it’s accepted and it’s rewarded and it’s not punished. No one wants to stay up, you know, on an idea that they’re super excited about, only to be told, “Well, that was stupid,” first thing in the morning. Right. Maybe the idea isn’t perfect, but if we’re willing to get involved, get our hands dirty, and iterate, you can build a team that does actually operate through joy rather than building a team that’s too scared to take any risk and can only literally follow a process until you fall off the cliff.
Michael [00:22:01] And we’ve seen this in the companies that we acquired that had incredibly strict process. Their process was from Starbucks, their process was from these big companies, and they took it into these small companies and they ran the company off the cliff because there was no value being produced by the actual team. A lot of it because they were too scared to and someone had literally suppressed their joy for work to the point where everyone was just executing but there was no actual functional output at the end of the day. And we had to unwind all of that. But unwinding it was actually quite counterintuitive to me because the first thing you want to do is go in and just put in a different process, put in different rules. But what we realized was let’s actually unwind all the rules. Let’s try to take it as far back as we can to see if we can actually bring the human back into these organizations so that people feel free to work with joy. And with that, there will be great outcomes. The highs are going to be higher, the lows will probably be lower. But if you’re okay with that median, I think overall that’s how we build better organizations and better products. And moving forward, you know, hopefully, we are less burnt out as an institution moving forward if we’re able to start to allow humans to be human at work.
Chloe [00:23:15] And I think that speaks really well to what you were commenting on earlier around, like, encouraging that CEO of product mindset. When it comes to product in particular, the more that we can encourage people to think outside their function and to give them experience outside their function, the more that it creates that willingness to bring different ideas to the table, to iterate, to experiment, to be okay with a little bit of mess if it means getting to a better end result. We used to take the mindset of keeping everyone in their lane, following this really strict process, that that was going to give us better outcomes. But to Michael’s point, we’ve found that, you know, taking this perspective of, how do we infuse more joy, how do we get a little bit more comfortable being a little bit more loosey-goosey when it gives us better outcomes? We found that was kind of counterintuitive at first, but now that we’ve embraced it, it makes a ton of sense and we’ve seen some really, really positive results come about.
Paul [00:24:08] Yeah, what a great story. I think your son’s soccer coach might be named Ted Lasso, Michael. Great story.
Michael [00:24:16] It’s Sia, but. But, yeah, he’s real, I swear.
Paul [00:24:21] I believe it. I can hear it. It’s coming through strong. We’ve just got time for about one more question, and I want to make sure that you have an opportunity to share. What’s the future of Gigantic for you guys? How can people find you and why should they find you? What can you leave with our folks to understand a bit more about where you’re going and the journey ahead of you, as opposed to kind of where we’ve been talking about, which is what led you to this point in time? What’s in store for Gigantic?
Michael [00:24:44] Yeah. So what we really want to do is build more holistic and well-rounded product leaders. That’s the goal right now. We’d like to build more holistic marketing leaders, more holistic sales leaders. That’s the future. And what we see in the market is that people come up and there is a finite set of skills that we kind of intrinsically pick up. But to really be effective, we need to be much wider and we need to have these understandings of sales, of marketing, of inner organizational discipline, of, how do we actually scale outside of ourselves? How do we set goals that aren’t demotivating but motivating for our teams? How do we lead decision-makers in the most effective way? So we’re really focused at filling that gap right now for product folks. And so we’ve got several courses on that now.
Michael [00:25:30] Where we’re trying to get to is more of a perpetual learning cycle where throughout the year you can be upskilling and enriching yourself through Gigantic. And so we’ve got courses now, but we’ve got a lot more coming because we see the gaps that people don’t even know that they have. I’ll be honest, like, I did all the sales calls for the first cohort and the second cohort. Not once did data and KPIs ever come up as a weakness for everyone because everyone’s amazing at data. But when we got into week four and we started actually setting KPIs, cascading KPIs of the products that they were working on, there was not one student that didn’t struggle through it. Because I think we’re so used to looking at the mixed panel dashboard or, you know, the Google Analytics, and as long as things are going up, we’re good. But it’s really hard to start to associate those KPIs with each other.
Michael [00:26:19] And those are skills that people don’t even know that they don’t have. So as we identify more of those, that’s really where we’re focused is, how can we fill those gaps for you? So that’s kind of what we’re focused on today at Gigantic You can find us at Gigantic.is. We’ve got five incredible courses right now for you to take. And like I said, if you get on board, sign up, we’ll keep you updated as we’re actually working on a more perpetual learning environment.
Paul [00:26:45] Wonderful. Well, I can’t think of two more qualified people to be in the position and on the adventure that you’re on. I really appreciate you taking the time out of your busy days to share a bit of the experiences with us and our audience. So thank you so much. It’s been a blast hearing it straight from you and getting just a peek at the adventures that you’ve had and those yet to come. So thanks again for joining us today.
Michael [00:27:06] Thank you.
Chloe [00:27:07] Thanks for having us.
Paul [00:27:07] Absolutely. Cheers.
Sean [00:27:11] Well, that’s it for today. In line with our goals of transparency and listening, we really want to hear from you. Sean and I are committed to reading every piece of feedback that we get. So please leave a comment or a rating wherever you’re listening to this podcast. Not only does it help us continue to improve, but it also helps the show climb up the rankings so that we can help other listeners move, touch, and inspire the world, just like you’re doing. Thanks, everyone. We’ll see you next episode.