Jason Garber
Software & Cloud Leader


I'm a software architect and consultant who started Promptworks in 2013. I grew the consultancy to 45 employees and $8.5M.

  • Job status Seeking employment
  • Working remotely from New Hampshire, USA
  • Generation "Oregon Trail"

About Me

Years as

Fascinated by technology, innovation, and user experience all my life, I was fortunate to turn a hobby into a career: For the last two decades, my occupation has been to create technology systems that make life better, first as a web developer, then as a team leader and software consultancy founder.

Understanding the inner workings of complex systems led me from taking things apart as a child to studying economics in college. From there, I found my way into software engineering and spent my 20s learning web development, contributing to open source software, and freelancing while traveling.

For the last nine years, I've focused my energy on building high-productivity teams of people who do things right. Through smart hiring and nurturing a community of practice, we create a culture of care for user experience, economy, security, maintainability, and extensibility.

Now, I'm ready to apply my management talents and experience on a new team, helping to make the best products even better and delivering quality software reliably and consistently.

Contact Me

My Resume

25 years advising companies on technology, most recently as a partner at Promptworks, a software development consulting company. In addition to my executive role, I advised the clients in my portfolio as to their technology choices, staffing options, product development, and user-centered design.

As a founder of the company, I interviewed, hired, and supported dozens of employees—from developers and designers to operations and finance. With my technical background, I always enjoy the chance to play troubleshooter-of-the-last-resort.

I'm also the author of Practical Pair Programming, a short book about this powerful XP practice.

2013 - Present
Promptworks, LLC
Chief Operating Officer

I started Promptworks with two co-founders and operated it for nearly a decade. As an owner, my responsibilities ranged from finance and strategic planning to IT and sales, but my software responsibilities included:

Consulting and Planning
  • Estimated and planned projects with Product Managers, UX Leads, QA, and client stakeholders.
  • Advised clients and team leads on architecture, UX/UI design, strategy, and product roadmaps.
  • Identified and solved technical and scaling issues.
  • Resolved problems with customers.
Engineering Management
  • Onboarded new team members and recruited subcontractors to meet project deadlines.
  • Developed an engineering ladder, set pay scale, and provided staff advancement opportunities.
  • Provided code reviews, and technical and architectural guidance to engineers.
Software Development
  • Wrote production code in Ruby, Python, and Javascript for web apps, mobile apps, and APIs.
  • Developed proof-of-concept applications to facilitate closing sales opportunities.
  • Supported team with DevSecOps: CI, CD, server orchestration, release management, security automations, automated testing. Cloud platforms: AWS, GCP, Azure, Salesforce Heroku.
  • Discovered and squashed bugs in iOS, Android, Ruby on Rails, and Python applications.
  • Established QA department to help developers with testing and troubleshooting obscure bugs.
Thought Leadership
  • Wrote a book on pair programming and advocated for XP practices.
  • Spoke at technical conferences and industry events.
  • Wrote blog posts and published articles about the nature of software development, best practices, patterns, and experiences solving complex technical problems.
2006 - 2013
Freelance Web Developer, Software Engineer
  • Consulted with clients on their software needs.
  • Negotiated scope, prioritized features, and groomed backlog.
  • Planned, designed, built, and tested web applications using dynamic languages.
  • Contributed to open source projects on GitHub and maintained RedCloth (Textile parser in C)
2001 - 2005
Eastern Mennonite University

Triple majored in economics, business administration, and computer information systems. Summa cum laude, honors program.

Download Résumé

My Book

The XP practice of pair programming is a fascinating way to co-create effective, maintainable software, but there was little guidance on how to do it well. By observing the pairs at Promptworks and from my personal experience pairing since 2012, I was able to compile a practical guide that explores:

  • What good pair programming is (and isn't)
  • Techniques to support personal growth and improve team cohesion through pairing
  • Criteria for deciding when to pair and how to share time, space, and power
  • Ideal hardware and software setups for pairing, whether in-person or remote
  • Convincing your team to adopt pair programming practices

Available in paperback or e-book from A Book Apart

Practical Pair Programming demystifies the logistics, benefits, and challenges of pair programming. It’s a must-read for teams new to the methodology pair programming and great for veterans of the practice, too.

Joe Moore

Principal software engineering manager at VMware Pivotal Labs

A practical handbook for developers everywhere! Jason’s book is full of great tips on how to master the art of pair programming.

Rachel Davies

Author of Agile Coaching

My Blog

16 July 2020

Pair Programming Book Launch

In 2012, I began collecting thoughts and learnings from pair programming in a long document that I thought could one day become a book. Last year, when engineers at Promptworks asked for some pair programming resources, I circulated the manuscript internally. Jon Long saw its potential and tipped off Katel LeDû, the CEO of A Book Apart, who got in touch about making it the next title in their Briefs collection.

09 October 2019

The Safety Inherent in Pairs

The last connecting flight between home and my college was on a comically small airplane. It was a 1996 Beech turbo-prop with no lavatory, no overhead bins, and 19 of the tiniest seats you’ll ever see. About 10 minutes into the 45-minute flight, the copilot would crawl out of the cockpit and serve drinks to the handful of passengers aboard. He could barely finish opening everyone’s cans of soda and handing out the peanuts before needing to return to the cockpit for landing.

22 August 2016

Why can't we tell when software is done?

Over on the Promptworks blog, I wrote a short piece on how software, by its nature, is never “done” because there are always new ideas and changing business requirements that move the goalposts—and that’s not a bad thing! What can be detrimental is to not accept the nature of software and expect it to conform to a construction project paradigm. By doing so, you miss out on a lot of value and create fragile expectations.

Contact Me

+1 (603) 255-3383
PO Box 1497
Glen NH 03838