👋 Hiya, I’m Conor!
I design and build thoughtful software. Right now, I’m the Head of Design at Rewatch, helping teams make the most of their important meetings and eliminating the rest. Previously, I was at 37signals for 7 years — leading the iOS team for Hey and building Basecamp 3 from scratch. I was an early designer at Medallia, and before that worked solo on marketing sites and hobby software.
A few things that set me apart:
Most of my design work happens in code — it’s very fast both in terms of execution and how quickly we can see what does/doesn’t work. I’ve built Rails apps from scratch, been part of developing frameworks, and love engaging in deep technical give-n-take with engineers.
I’m adept at taking in various inputs and perspectives, distilling a set of options, and making the call to pursue what I believe is the best option. I’m comfortable with ambiguity, sometimes getting it wrong, and taking full ownership. I optimize for trying + learning, over making perfect plans.
Just-enough product management
I’ve worked without product managers the last 10 years, and I'm most comfortable thinking outside the narrow window of a task list or singular project. I love developing problems and ideas into pitches (a simple example), and enjoy balancing priorities and tradeoffs both at both a product- and project-level.
Rewatch / 2021 - Now
As the first design-hire at Rewatch, I was quickly entrusted with all product design by our CEO-designer. My role has evolved to Head of Design as our team has grown, but I've continued operating as an individual contributor on projects too. We've decided to forgo Product Managers, so I’ve also served as the de facto head of product — responsible for our roadmap, shaping projects, setting team direction, etc.
Managing design + product
As Head of Design, I've led all product and marketing design at Rewatch. I'm super proud of the team I've built with Mike Stilling on marketing design and Chris Schnaars and Jon Barber designing the product with me. I've worked closely with our designers to guide them toward proactively leading projects, actively contributing to our codebase, and regularly up-leveling their technical and product-management skillsets. This kind of generalist skillset and personal development allows us to get a ton done with a tiny team.
In addition to leading design, I'm also deeply engaged with our engineers. I help evaluate technical tradeoffs, coordinate projects, and drive the overall development of our product.
Over the last few years, we've reshaped our product by integrating with calendars, building automation workflows, and ultimately shifting to helping people get the input and info they need without having to attend or re-watch so many meetings. AI developments have enabled exciting new capabilities, and it’s been a fun new area to explore.
Rewatch’s screen recorder is a great alternative to meetings. You still get to enjoy the humanity of someone walking you through an idea, feedback, bug report, etc., but without having to do it live. It’s easy to create polished videos with a clean background, animated video avatar, and instant uploads.
While the web remains our primary product, we wanted to provide a fantastic mobile experience as well. Initially, we honed essential on-the-go features like viewing videos, getting notifications, and being able to comment. Later, our iOS app served as a proving grounds for new ideas, like our canvas recorder that we later brought to the Mac.
37signals / 2014 - 2021
Working at 37signals was hugely formative for me. It was incredible to work with and learn from some of the most prolific product builders in the industry. While there I helped create two incredibly successful products from scratch.
Hey for iOS / 2 years
As 37signals shifted attention from Basecamp to HEY (a new email service), I led the iOS team in building a standout iPhone + iPad experience. Along the way we went toe-to-toe with Apple’s app review, and got ourselves in the App Store. Within months of launch, iOS was the preferred platform of most HEY customers. Even John Gruber loves it:
“it’s really great, especially on the phone. I feel super efficient in every single aspect of using it on the phone — triage, reading, responding.”
Basecamp / 4 yrs
On my first day at Basecamp, I got to help kickoff a full rewrite of our flagship product, Basecamp. I worked closely with Jason Fried and DHH to prototype, build, and ultimately launch Basecamp 3 — the company’s most successful product ever. Post-launch, I worked on core features, while pioneering Shape Up methodology.
Basecamp for iOS / 1 year
After working on the web product for 4 years, I was asked to lead the iOS team. In addition to designing app UI, I refreshed how the team worked by fostering a culture of pitching ideas, and brought Shape Up’s product management principles to the team.
Medallia / 2011 - 2014
Medallia was my first opportunity to design and build software as part of a team. I was brought on as the second designer, and helped the company mature its product and processes as the team and customer base went through rapid growth.
My last year there was incredibly rewarding as I helped start a 3-person, in-house entrepreneur team where we designed, prototyped, and launched downmarket products — helping Medallia expand beyond its previously enterprise-only offering.
Working solo / 2007 - 2011
For me, it all started in 2007 when I became interested in designing and building websites — like my dad. Someone I knew had a growing podcast and needed a website — so I quoted them $1,000, bought a book on web design, and dug in.
I loved the combination of designing and building that the early web was all about. After working on marketing projects for a few years, I got the itch to build software, so I hacked together some early projects like recipe organizers, budgeting tools, etc. — first using CMS’s like ExpressionEngine, and then by self-learning Ruby on Rails. Bringing life to a functional tool was intoxicating — I never looked back.
I don't spend much time on social platforms, but I'm always happy to receive a good old-fashioned email.