Hiring a new CEO

I told the Dwolla team this morning that we are hiring a new CEO, whom I and the rest of the board are going to recruit. I’ve replaced myself in every role I’ve ever had in this company and this will be no different. Change is a required part of growth. I’ll stay involved but in a different capacity.

I also called my parents and let them know. Their tone was oddly similar to when I told them I wouldn’t go to college, when I was selling my first company to build another that moves money around with computers, an idea I was sure would work and reach its full potential by my 30th birthday. I’d describe their response as skeptical about my choice but supportive in a way that’s hard to explain.

It’s a little weird.

I told the team who works with me directly a few weeks ago shortly after talking with our board members. This is a thing which will likely become a thing after I publish this post but an untold truth is that, this is the order of things and it was the right way to do it. Some of you reading will understand that. Some of you will not. This was all influenced heavily based on an exhaustive COO search. After 6 months of discussions and interviews we realized collectively that we, myself included, are looking for a new CEO.

With this change the company is also changing. We modified our go to market strategy a few weeks ago and we reorganized the organization this morning as well. That means some really great people are out looking for their next adventure. I doubt many of them will be looking for long but if you’d like a soft intro to some exceptional people please send me an e-mail. If you’re a part of the Foundry or USV networks you should already have received roles and departments in your inbox. If you’ve found this blog entry because one of those people has applied at your company, please contact me so that I can give you my whole-hearted recommendation. I consider myself fortunate to have been a part of their story. 

Change can be hard. It can also open unknown doors.

As a founder I’ve walked into so many fortunate opportunities and I won’t act like I don’t know that. Some felt like opportunities and some didn’t as they occurred. As a result, I’ve served the company as VP Technology, VP Product, VP Marketing, and many others at one point or another that I didn’t always feel qualified to hold. At one point, I had 23 direct reports and the company wasn’t more than 40 people. It was an intense time, but we got through it with grit and I eventually replaced myself in the teams I was managing at the time. There is a time when the grit is what the company needs and there is a time when that’s not enough.

I’ve eaten copious amounts of humble pie over the course of this project and received accolades that I probably didn’t deserve but was in the right place at the right time to receive over the past decade.

But I’ve always worked hard, learning a lot as we solved problems together. Mostly though, I’ve been supported by incredible people and been fortunate to partner with and learn from many of them as I’ve served the company as the CEO. 

I’ve cared for so many people in a way I can only describe as love. It’s stumped me time and time again because that word and the care that goes with it is something we’re almost taught not to let seep into our work. Analogies about building sports teams and/or families have all come and gone but the fact that I deeply care for people has remained the same. A few people have used that love word for me over the years and it’s always emotional and I always struggle with being deserving of that. That care and struggle will always remain and doesn’t disappear just because I’m changing how I contribute to the company and the idea.

As I’ve said to countless people over the last few weeks, Twitter got a real boost when Dick Costolo joined the company, Jeff Weiner was an incredibly important addition at LinkedIn, and even an early mentor of mine, Chad Dickerson led Etsy to heights that just weren’t possible without him. If Google had an Eric Schmidt, it seems to me that we should all go into this with an open mind.

It’s really not that weird. It just feels weird at first.

One of my best qualities is my ability to proactively replace myself. I’ll give myself some grace by admitting that I’ve always looked for ways to do this and each time I’ve replaced myself the company has gotten stronger for it. I could write a book about the wonderful things I’ve learned from people I’ve replaced myself with.

Dwolla has been through a thing or two but that’s in the past. The company and its future are now much bigger than me. The company we originally launched quietly recapped 4 years ago, restructured the board, team, and the cap table to go all-in on what is now our platform product. We took the new company from essentially zero to a $10M+ revenue run rate supporting $10B+ a year in gross payment volume since then and we’re cranking on the new stuff like never before. We’re seeing client applications and growth exceed 100% y/y and in Q4 ~1M new users joined the platform. I’m so proud of what we’ve done and anyone new coming into the CEO role will have a powerful platform to enable the next 10X+ jump. There is so much talent, ambition, product, board support, and drive already in place… The future is ours to create and the right things are in place to create it. 

Now is the time to focus on the future.

I’ll continue to remain a part of the company and serve as a board member and probably even something else. My work at Dwolla isn’t done yet. Time will tell how that pans out but I’m not going to disappear. I actually don’t care about titles, I only care about the success and future of the idea. I’ve been the CEO of the company for so long because someone had to incorporate the company and open the bank accounts. 

Defaults are powerful, but that doesn’t mean they shouldn’t be revisited. 

I’ll continue to participate in product, technology, customer success, and wherever else I’m requested. I’ll continue in a lot of things and you can still reach me in the same places. Some things will stay the same and some things won’t. I’ll keep all my commitments externally. I’ll openly talk about all this as it’s occurring.

We are recruiting a new CEO who gets to partner with an exceptional team and knowing that I can set them up for success in that way is going to make this one of the most rewarding positions I’ve ever recruited for.

If you think you’re the CEO to lead our company I’d sure love to meet you. It’s not my company and the right person isn’t going to think of it as mine. The collective work of hundreds of people makes it theirs too… Some of whom you’ll meet and work with but an entire crew of Dwolla Alumni that we appreciate and helped us get here influenced our direction and in many cases are owners as well. You’ll represent shareholders past and present and enable a company to change the way programmable payments impact innovation globally if you do the job well. The best way to get this job is to find your way in through the network at Dwolla, USV, or Foundry Group.

A profound thank you to the Dwolla team for your understanding and patience through this process. We’ve done so much together and we’ll do so much more. The future is yet to be built and I look forward to building it with you. We are never done.

Gratitude to Albert Wenger for his own tireless partnership and support through the constant evolution of this idea and myself. To my partner Jami for trusting me when I said “It’s time.” To the team of exceptional leaders at Dwolla who, even if you looked at me like I was crazy at first, gave me the opportunity to explain and trusted me in the same way my parents responded, with skepticism and support that’s hard to explain.

Hard to explain or not. I am grateful. 🙏🏻

The best is yet to come.