How Underdog trained 30+ engineers in Rails without slowing down
The Challenge
Underdog Fantasy operates a suite of fantasy sports and sports gaming products across nearly 30 U.S. states, with a fast-growing user base and high product demands.
As the company consolidated its technical ecosystem from .NET to Ruby on Rails, leadership faced a critical challenge: how to upskill over 30 .NET engineers in Rails without stalling product development.
“We were looking for support to help onboard our .NET engineers into Ruby on Rails and help them hit the ground running. While we could have done it internally, that would have taken away from day-to-day priorities. We knew thoughtbot had deep experience not just in delivery, but in teaching.
VP of Engineering
The Solution
Over a 10 week engagement, thoughtbot built a customized training program tailored to Underdog’s goals, developer backgrounds, and product roadmap.
Two thoughtbot team members led the effort, designing a curriculum based on developer feedback and real-world product context.
Key outcomes
- Engineers were grouped into pods to foster collaboration
- Daily pairing sessions, hands-on exercises, and office hours supported every learning style
- The program was flexible, adapting to evolving needs in real time
“It felt like a collaborative thing, not a rigid playbook. The team was extremely receptive to feedback and willing to adjust as we went.
Principal Engineer
The Results
Underdog not only avoided delays, they launched more features than ever ahead of NFL kickoff.
“We met all our product goals during training. 95% of those who trained are still here and thriving in Rails.
Principal Engineer
What could have been a costly transition became a seamless, empowering experience for the engineering team.
“thoughtbot cares about helping clients become better engineers and more self-sustaining. They’re the gold standard in Rails consulting.
VP of Engineering