Top 10 Carta Memories

Memories and people worth celebrating. If only I were a better writer…

Ry Sullivan
7 min readDec 22, 2021

It’s hard to step away from something that’s been a large part of your life. Memories and smiles come flooding back. This blog is a celebration of some of the memories I’ve been thinking about from my last 5.5 years at Carta. For friends and colleagues reading this, I hope it brings a smile to your face too.

1. Cage matches

As teams endeavored to figure out what users wanted, we’d occasionally call a “cage match.” These events were pretty simple: everyone got together in a conference room to work on a problem, and we wouldn’t leave until the problem was solved. It was product development and collaboration in its purest form. We had one memorable Investor Services cage match that lasted an entire week before we delivered our breakthrough–a way to move money for investors and their LPs. Startups live and die by their ability to keep shipping product. Cage matches created the focus when we needed to deliver. And they could be a lot of fun when you saw how much could get built in a short amount of time.

Investor Services cage match, October 2016.
Private Markets cage match, October 2017.

2. Hackathons

I believe that every person is a creative being and a natural problem solver. But that spirit of creation can oftentimes be suppressed by silly things like job titles and overly strict adherence to roadmaps. Carta is full of problem solvers in every function and geography. Establishing an all-company hackathon was my way of celebrating my coworker’s inspiring spirit of creation. It also led to many valuable (and obvious!) product wins in a matter of days (vs. waiting months for it to come up on the roadmap). My colleague Mara Pritchard sums our hackathons best: Supporting unconventionality: Why we do hackathons at Carta.

Investor Services Hackathon, March 2017.
Private Markets Hackathon, January 2018.

3. Show & Tell

Carta’s weekly Show & Tell presentations are special. For an hour each week, every person has the opportunity to present to every other person at the company about a problem they solved or are in the process of solving. It’s a chance to collaborate and communicate at scale, while re-focusing teams on the power of being scrappy and inventive. My first S&T presentations were forgettable. Over the years I decided to hone my speaking and presentation skills by borrowing from what I liked (a lot from Henry’s presentations) and dropping what I didn’t (a lot from my presentations). I gained confidence and soon my name appearing on the S&T list became something people looked forward to. I grew to teach our class on how to present, but I never would have gained the confidence or repetition without a laboratory like S&T.

A slide from one of my favorite S&T presentations. I swear it made more sense in context.

4. Incubating 0 → 1 ideas

Many of my most memorable product successes (and failures) came from pursuing 0 → 1 product ideas. My first experience at Carta with Investor Services mentioned earlier was of this mold, but it wasn’t to be anywhere close to the last. Our Investors Services eventually found product fit with fund admin after iterating through myriad ideas over 15 months. IS is now the second largest part of Carta’s business. I was also involved with teams that ideated and released Carta’s mobile app, employee experience suite, free Launch experience, and liquidity products. Launch was a particular favorite as we introduced a software-only approach to onboarding new customers. In late 2020-early 2021, I led our Incubation teams that focused on new bets. This led to the creation of Carta Total Compensation and stock-based lending along with some of the purest product ideation I’ve ever experienced in my career (h/t David Lichtenstein, Max Estes, Laura Newton). Carta has always had a strong connection with Henry’s “Founder’s Wanted” mentality. It’s thrilling to look back at how many bets took off. Many of my proudest moments were watching teams and product leaders graduate outside my org.

Investor Services team when everyone could still fit in one conference room, September 2017.
Whiteboard session in Rio on what would become Carta’s Launch product, September 2018.
Carta Total Compensation team, January 2021. COVID sadly deprived us of more in-person hangouts.

5. Design

A favorite product exercise of mine is thinking beyond the function of software, and understanding its emotional and psychological impact on users. People aren’t robots. They don’t experience workflows as binaries of “I did the job” or “I didn’t do the job.” Instead, they think about whether they enjoyed the work or trusted that it had been done effectively. In 2020 I was asked to lead our platform design team, which built a world-class design system called Ink. In 2021 my responsibility expanded to leading nearly the entire design org. Over the past 1.5 years, this group of incredible designers re-inspired me to place our users at the center of everything we build. While I hope I’ve been able to bring some of my product wisdom to them, I got the better end of the bargain in how much I learned from this team bursting with creativity.

Design team, September 2021 (source: Carta Design Instagram).

6. R&D Operations

After having been Carta’s first PM, I was also asked to stand up the company’s R&D Operations team in 2019 to coordinate the numerous and disparate activities happening across the R&D organization. At first, I was confused by the assignment–why me? I honestly didn’t know much about operations. But I looked at the challenge as something new and took a product approach to building the org. First I hopped on my Vespa and visited numerous offices around the Bay Area to learn what other organizations had done for this role: what worked and what didn’t? Why? What would you do differently? I also learned immensely from the teams’ first few hires on how we can better define our scope (early, key hires make all the difference!). Today I’m proud to see that R&D Operations is a pivotal part of our development organization.

R&D Operations team, September 2019.
R&D Operations team (and Max), January 2020.

7. Rio team

In 2016 we began hiring Brazilian developers and designers in Rio de Janeiro. Quickly these creators became foundational to so many teams and enterprises. In 2017, I made my first trip to our Rio office (which just happened to coincide with Carnival 🎉). In the coming years, I’ve regularly looked to hire amazing new talent into the Rio office and made numerous trips back. In fact, by my estimate, I have spent more total time in the Rio office than any other US-hired employee. Our Rio team is exceptional–as creators and as humans. It shines through in everything they do from quarterly hackathons to everyday customer interactions. I humbly hope I have achieved even a tiny bit of Carioca status over the years.

First Rio visit with the new mobile team, February 2017.
Hanging out with some of our amazing Rio team, June 2018.

8. Kitchener-Waterloo team

In late 2019, we acquired the former Kitchener-Waterloo Kik team and welcomed them into Carta. As part of the deal team, I had the opportunity to travel and meet these amazing Canadians multiple times during the diligence and integration stages. Over the following two years, they’ve been extraordinary partners and teammates in every sense of the word. They’ve made Carta a better place to work and inspired me to be a better product leader too. It feels fitting that my last in-office Carta experience before we began working remotely was in KW in February 2020. I only wish COVID hadn’t limited my number of visits north.

Integrating the Kitchener-Waterloo office, September 2019.
Kik integration team taking a quick break for a telenovela-style photo, October 2019.

9. Betting on trajectory

I’m constantly impressed by the quality of people who join Carta. I’m equally proud when people take on greater scope or “mountain jump” to a new career path. I’ve regularly dedicated my time to identify and promote career changes for talented individuals. Many high trajectory people joined my teams as first-time product managers, designers, and program managers from external roles or Carta’s incredible Delivery and Valuations teams — particularly talented women. These high trajectory employees fulfilled their promise and more — becoming leaders within our development organization. Others rose to the challenge of greater responsibility with our products, businesses, and customers. These are some of my proudest hires and promotions, and I hope I’ve been a meaningful part of their career growth.

My favorite kind of feedback :)
Product, design, and engineering solving problems together, April 2017.

10. Company Days at 75 Federal St.

I think everyone who has spent a long stretch at a startup identifies a personal apex moment of company and culture. My Carta apex moments were our “Company Day” celebrations at our San Francisco office at 75 Federal Street (which we sadly outgrew before also outgrowing our next office at 600 Harrison St.). On these days, the entire company would gather for a day of presentations and comradeship, culminating with a cookout and beer in the parking lot. We’ve since moved into nicer officers around the world, but this was my favorite of the bunch.

White Elephant gift exchange at 75 Federal St., December 2016.

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