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Focus on What Matters Most: A Sit Down With the CDO of Sticky

Updated: Dec 14, 2022

Sticky is helping people focus on what matters most while killing busy work in the process. Who leads product design and how did the founding team come together?


Editor’s Note: As part three of our three-part Founder Q&A series, we sat down with co-founder and CDO of Sticky, Andrew Lassetter to learn more about the design of Sticky and how the product came to be. Parts one and two are available in case you missed them.


David Williams

The backstory on the CDO of Sticky


Why don't we begin with the defining moment in 2020 when many of us started working remotely? Where were you, and what were you doing at the time?


I started working on Sticky in the fall of 2019. Before the pandemic kicked off, I'd left my last job and begun working on Sticky full-time. I was months into the transition from working in an office to working from home and cafes.


Not only did you transition from working at an office to working from home but also from working on a team to working alone. What was that transition like for you?


Concerning the pandemic, I wanted to do my part by isolating and sheltering in place. I saw it as the right thing for the community and the people around me.

At my previous company, I helped assemble the whole team from the ground up. I loved the people on my team and really enjoyed working in that environment. To go from that to working alone in a silo, and in the situation we were in, was very isolating. I wasn’t used to working like that. I'm very collaborative and like to bounce ideas off others to make ideation easier.


I had to learn how to adapt to solitude when it was just me. I needed to give myself a lot of time to think about things and then also a lot of time to not think about things. The way I had an internal dialogue with myself was to get lost in the details of something and then step away from it for a while. By the time I came back, I usually had more clarity.


How did you maintain a sense of direction?


The big hurdle was to get seed funding for the company; that was my milestone. To do that, I needed to dig in to understand users' problems and validate an opportunity.


The next layer was uncovering why these problems exist. There are plenty of tools out there, so the question becomes, what is it about how we're working that leads to these problems?


Sometimes I thought I had my arms around it; other times, it evaporated right in front of me. It was all part of the process.

At the same time, I was also talking to potential technical co-founders. I'm a designer—a product design person, and don’t write any code or have the expertise to specify detailed technical requirements, so I needed that technical partner. But talking to people early on, when the idea of Sticky was still solidifying, folks would often come to those conversations with strong opinions and want to push the project one way or another.


At times it felt like I was wandering through a fog. I'd find a place that felt okay. I'd have some clarity, and then suddenly, I'd get pushed off the path and return to wandering. Sometimes I thought I had my arms around it, like I had something solid; other times, it evaporated right in front of me. It was all part of the process.


CDO of Sticky

You explored these problems before the pandemic, which accelerated when everything changed.


So many of us just weren't ready for that change, right? Organizations, schools, companies, and teams were not equipped to work in that way, which led to the mass adoption of digital tools and relying more and more on filling people's calendars and asynchronous communications. In many ways, it just made it all more challenging, right?


People are struggling with burnout—they go to the office for meetings and then home to get work done. We're all just frying ourselves.

We've written articles about context switching costs and how to defend from them. In talking to people about their work life, the amount of time spent on busy work emerged. But saving time wasn't as compelling as saving them from having to copy information from this tool and put it in that one. Then organize it in this way. Then communicate information back out to people. It's all so manual and lacks visibility.


As you add more meetings and communication, it's like, when is anybody actually getting work done? That's where the mission to kill busy work came from. The way we're working now is not sustainable. People are struggling with burnout—they go to the office for meetings and then home to get work done. We're all just frying ourselves, and for what?


If Sticky can help people feel less anxious about putting their work away at the end of the day to spend time with their family and people they love, that would be great. Because that's what really matters, right?

The founding of Sticky


You honed in on the problem but needed to make a functional prototype and bring in a technical partner. Where were things when Tamzin Selvi, your technical co-founder, joined?


By the time I started talking with Tamzin, a clear pattern had appeared: you take some notes, and your action items emerge from that. You follow up on those things communicate to others what work has been done, and go back and take some more notes. It was evident that the things people were doing all the time were taking notes and attending meetings. There was a high-frequency use case where the product could enter people's lives and immediately bring value.

I built a prototype and put it in front of some folks to see if it resonated with them. A good amount of the people I spoke to told me they'd use it every day if we could build it. So I hired a company to help develop the prototype and had a bunch of people using it. We iterated on the design to a point where it was evident that it needed to be built the right way so we could deliver a stable and performant experience to customers that would scale.


Hiring Tamzin meant we could take a step back to develop a strategy to take ownership of the code base, set up our infrastructure, and start rebuilding the app in pieces to make it work really well. That was the task at hand.


 

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What happened next?


The first thing I wanted to do was spend time working closely together and get Tamzin up to speed so we could start executing against our short term goals. Once we were moving, we knew we would be better positioned to succeed if we had a third co-founder, assuming we could find someone that would complement our skill set and align with our mission. It felt like a huge challenge that would take time away from building the product, but we knew it was really important and we had to do it.


What was the process like in finding your third co-founder?


I talked to a lot of brilliant people, and it was validating to have other intelligent people find Sticky interesting and want to work on it. But, what I was saying earlier, when you talk to somebody in the early development process for a product, they’re quick to say, “here’s what you should do.” They wanted to push it in a direction but their solution wasn’t compatible with the research or data I had, so there was a lot of that.


What stood out about David Williams as a product and business co-founder?


One of the clearest things about talking to David was the level of alignment around the pain points, jobs to be done, the need, the gap in the market and opportunity, and everything from a bottoms-up approach to the market as an entry point. There was just tons and tons of alignment.


Part of the way I evaluated my job at that point was by hiring people smarter than me to work on this. So, in that regard, check and check.

In that process, I gave David access to pretty much all my work—from the beginning to where I was then, the assumptions that I made along the way, and the input I got from users. I remember David saying something like, "I looked at all of this, and I pretty much agree with everything you've done so far."


From my perspective—the art school student—when a guy like David—successful career in tech, Stanford educated guy—goes, “this is good”, I was like, oh, shit, okay. It was a huge feel-good moment, for sure. Part of the way I evaluated my job at that point was by hiring people smarter than me to work on this. So, in that regard, check and check.

A timeless piece of wisdom, but you’re being humble. I’m sure it felt great to clear the initial hurdles. How did things change from that point?

David, to his credit, jumped right in and added to the process. He got up to speed very quickly and began taking on things like investor relations, and a lot of the administrative aspects, essentially tackling the things blocking us from working on our critical pieces. That was a really amazing moment.


In a future post, we'll get deeper into the product, but I have one last question for now. Given everything you've experienced and learned, if you were to go back to 2020, what advice or wisdom would you give yourself or others struggling with this new way of working?


One thing I'd tell myself and others is to be where you want to be. Take advantage of the opportunity to go somewhere else. I would have significantly benefited from being closer to nature instead of in a city.


The other thing would be to really think about what matters. One of my main takeaways from the pandemic was realizing how vulnerable we all are to things that are completely out of our control. It was a big wake up call regarding so many things we took for granted. We need to take care of ourself and others.


If Sticky can help people feel less anxious about putting their work away at the end of the day to spend time with their family and people they love, that would be great. Because that's what really matters, right?


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