(Almost) Everything is within your control at a startup

Jason works on onboarding - approving and activating customers quickly and safely, and fraud - building out the platform to prevent fraud across our products. He was previously at Plaid where we worked on international expansion and expanding their suite of credit products.

When I ask a candidate what they’re looking for in their next role, one of the most common things I hear is that they’re looking for more ownership and agency. The sentiment resonates with me and was one of the main reasons why I wanted to join Cardless in the first place. But it's been interesting to hear what that actually means to each person, since the answers have varied more than I originally expected.

I spent six and a half years at Plaid before Cardless, and by the time I left it had grown from a scrappy startup into a business with real scale - processes had been stress tested over years and an established bar for what "great" looked like existed for any given area. It was incredibly rewarding to help build both the processes and products that contributed to that growth. However as Plaid grew, while I still felt like I had a ton of opportunity for ownership, the scope of the ownership shrank. There was realistically little I could do myself to meaningfully move the needle at the company level or individually tackle an opportunity that spanned across teams in any given week.

Ownership at a startup

Ownership at a startup isn’t really about owning a specific system, or project end to end, or even getting to see a product from inception to production. Or more specifically - it isn’t just about that. I understood this to some degree but didn’t fully internalize how different it really is until I actually joined Cardless. It’s about the craft and care that goes into building a company from the ground up. It's about taking it upon yourself to make sure the business succeeds, not just your project. It’s about not settling for good enough when you think it’s important enough for something to be great.

Early on, I was tasked with improving the reliability in our end user onboarding flows. My first instinct was to have the team swarm on this issue. What could be more important than making sure every applicant could easily apply for a card? That was my assumption, at least until a team standup where an engineer genuinely asked if that was the right prioritization, and pushed for us to re-design part of our user model in order to better capture context around users who had multiple Cardless cards. For what it’s worth, they were right, and it would have been to our detriment if we didn’t kick off that work early as we were starting to see a rapidly increasing portion of users carry multiple cards with us. It was honestly a quick moment in one of hundreds of stand ups - but it stood out as a fantastic example of the ownership that the team embodies here.

Figuring out how to help run a sustainable business, with a strong culture and technical bar, while balancing against very real business constraints, isn’t just a one person job. Even so, you’d be surprised at how much each individual can really move the needle on that at Cardless. The things we’ve accomplished with such a small team are nothing short of remarkable to me - but it only works since everyone here cares enough that this genuinely matters to them.

How do you actually decide what to do then?

The level of ambiguity and urgency at a startup isn’t necessarily an environment everyone thrives in. Ownership and agency in particular can be a double-edged sword. It’s hard to overstate how empowering it can be. Everything that isn't working the way I want it to is within my control to fix. Transparently though, it can also be stressful. Everything that isn't working the way I think it should is, in some sense, my responsibility. I could have made it better, and the end result is directly correlated with my actions.

It’s not that we don’t have priorities or a roadmap - it’s more that no one is going to prescriptively map out how you should be spending your time at Cardless. Given the near endless opportunities and work that we feasibly can be spending time on, what’s the best way you think you should be spending your time?

Notice a part of the application flow that needs to be re-designed? Go scope it out. Think you can improve the performance or reliability of our systems and that’s more important than the product feature you’re working on? Carve out time to make the system work how you think it should - in fact we have a monthly Zero Balance Day built for exactly that. Don’t think our interview process surfaces the best candidates? Help us fix it. The interview modules are shared openly, and feedback is part of every debrief so we can keep iterating together. Heard feedback from customer, family, or friends that really resonated? Let’s figure out how to incorporate that feedback into how our products actually work.

Startups can feel chaotic at times, but that tradeoff has been more than worth it to me. It’s not for everyone, but given the choice, I'd choose to work at Cardless all over again even with the benefit of hindsight. If you want to optimize for personal and professional growth, there’s something to be said for being pushed out of your comfort zone and working so closely with a fantastic team to figure out how to grow a business together.