Training 30+ engineers in Rails without slowing down

Client

Underdog Fantasy

Services

Ruby on Rails, Ruby, Mentoring

Description

Built a customized training program, tailored to Underdog, to onboard .NET engineers into Ruby on Rails

Product users in

40+

US States

Over

30

engineers trained

Trained in

<10

weeks

thoughtbot cares about helping clients become better engineers and more self-sustaining. They’re the gold standard in Rails consulting.

A headshot of Amit Gulati

Amit Gulati VP of Engineering

How to upskill over 30 Underdog Fantasy engineers from .NET to Ruby on Rails

Underdog Fantasy operates a suite of fantasy sports and sports gaming products across over 40 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.

Image of a neon light that contains underdog fantasy's logo

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.

A headshot of Amit Gulati

Amit Gulati VP of Engineering

Over 10 weeks, thoughtbot built a customized Ruby on Rails 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.

  • 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.

A headshot of Jerrod Carpenter

Jerrod Carpenter Principal Engineer

Underdog not only avoided delays, they launched more features than ever ahead of NFL kickoff.

What could have been a costly transition became a seamless, empowering experience for the engineering team!

We met all our product goals during training. 95% of those who trained are still here and thriving in Rails.

A headshot of Jerrod Carpenter

Jerrod Carpenter Principal Engineer

What does success look like for your project?