Ryan Singer - Head of Strategy - Basecamp - airfocus Product Hero

Who is Ryan Singer? 

Ryan Singer is a jack of all trades and a respected name in the product world.

As one of only three employees who have been at Basecamp since its original iteration, he has helped the company grow, transform, and shape its future, as head of strategy. 

Singer isn’t the type of person to turn down a challenge and loves nothing more than to jump into something new, learning as he goes. This can-do attitude has allowed Singer to work his way up the corporate ladder as he tackled project after project to further the platform. 

In 2019, Singer released his first book, Shape Up: Stop Running in Circles and Ship Work that Matters. Despite having no idea how to write a book, he didn’t hesitate to take Jason Fried (Basecamp’s founder and CEO) up on the idea.

The book details how Basecamp develops its products, while also offering techniques and guidance to help companies improve their own processes. 

What is Ryan Singer known for? 

Singer’s resume looks surprisingly short for someone as accomplished as he is. Don’t be fooled though — for nearly 20 years he has been working hard to ensure Basecamp is leading the pack when it comes to web-based product management. 

After joining the company in 2003, he quickly set to work as the company shifted focus from web design to web-based application development.

Singer would be responsible for the UI design of the flagship Basecamp platform before advancing through the ranks and gaining a more diverse skillset. 

In 2012, Basecamp underwent a complete overhaul under the guidance of Singer, with another major update following in 2014 as the company shifted focus entirely onto the platform.

Singer’s time as head of strategy has been instrumental in protecting Basecamp’s competitive advantage — especially as competitors, like Slack, have gained immense popularity in such a short amount of time. 

What's the Basecamp approach to product management? 

As detailed in Singer’s book, Basecamp has adopted a methodology they refer to as “shape up” — conceived as a response to the various issues facing the company as they grew.

“Shape pp” looks to clearly define and prioritize projects before handing them off to the build or shipping teams. According to Singer, this helps product teams to avoid anything too vague (as stories can sometimes be) or anything too restrictive, like premature wireframing.

Key to the "shape up" method are some classic agile ideas — such as six-week work cycles (or sprints) — and a greater emphasis on autonomy. This empowers development teams to think carefully — and strategically — about the product and the user problems that need addressing.

Where can you learn more about Ryan Singer? 

Ryan has recently moved away from traditional social media platforms, to give a more contextual look at what he is doing and why. 

Fans of Basecamp, and Singer’s ways of working, can join his mailing list — which Singer hopes will build a closer community with fewer distractions. The semi-regular mailer promises insights on leading teams to realize a vision, shaping and designing solutions, and previews of Singer’s ongoing projects. 

Elsewhere on the internet, Singer hosts and has featured on a number of great podcasts. He’s also published a series of blog posts, available via his personal website.