Reginald Braithwaite

Who I Am

I am technical. I ship products. I lead engineering growth. And I foster collaboration. This is not my first rodeo, and I’m available for work.

I have led teams with as many as fourteen members. I have led product groups with as many as forty-five.
I’ve led through growth from startup, to IPO, to annual revenues in excess of $450 million.
I shipped features and products that were material to successful exits for Sitraka and PagerDuty.¹²
I wrote a programming book; I write technical documentation and essays; and I speak at both tech conferences and company-wide events.³
My experience is itemized in more detail on LinkedIn; my personal email is raganwald@gmail.com; and my résumé is available upon request.

Reg crossed role and organizational lines to constantly better the company and increase in scale our impact on the market, our products, and customers.

—Michael Cucci: Investor, Startup Advisor, ex-VP of Product and Marketing, PagerDuty

What I Believe

I am guided by my beliefs that:

All software is social software: I believe that to thrive, software must become the comunications medium or load-bearing source of truth for a critical process.
Improving productivity is the faster horses of enterprise software: I believe that transforming the way customers think about their work is fundamental to creating and dominating entirely new markets.

What I Do

I am technical

I have designed and built software for paying customers since the 1990s:

In the early 90s, I wrote and sold Tableau, classified advertising management for desktop publishers.⁴
In 1994, I shipped nCrypt Light, a message encryption tool for the Apple Newton.
In the early 2000s, I was the hands-on Technical Product Manager for JProbe Threadalyzer, the first tool to perform predictive and actual deadlock and data race detection on Java servers.
As Program Manager for the JProbe Suite, I wrote a little code, such as designing and shipping the suite’s first configuration tool.
In the mid 2000s, I led the web banking team for ING Direct (USA), with more than three million active users. I personally wrote features such as its first ATM and Café locator. I used Enterprise Architectural Patterns for integration with legacy systems and extending their functionality.⁵
As a member of GitHub’s documentation tools and front-end flow teams in the early 2010s, I shipped features such as rich prose diffs.
In 2015, I joined PagerDuty as the Principal Engineer for Applications. I was the hands-on lead for the insights and operational review features, and launched features such as response mobilizer. I created prototypes for features such as recent changes.

Reg was always my ‘secret weapon’ for getting a new initiative off the ground. He understood our code and our product and what it was capable of, and he understood our customers and their needs.

Reg was exceptional at translating a product manager’s vision for a new feature into an actionable technical plan and architecture given all of the constraints inherent in adapting working software to new capabilities, then getting the rest of the team on-board and executing.

—Jason Diller: VP of Engineering, Georgias

I ship products

My career-long focus is the complete product strategy and development process around the technical work:

As the Technical Product Manager for JProbe Threadalyzer, I performed user research, developed the value proposition, and designed the product.
As the Program Manager for the JProbe Suite, I collaborated with Sales and Marketing Product Management on prioritization and positioning, acted as the media contact for feature-detailed interviews and demos, and manned the booth at JavaOne.
At Github, I created the prose-specific heuristics, designed and developed the user experience, and shipped rich prose diffs.
At PagerDuty—working with Product Mangement and Marketing Strategy—I wrote the technical road map for schedules, identifying feasible and compelling features to establish strong differentiation from our competitors and value complements.
At PagerDuty, my teams ideated, developed, and shipped insights and operational review features, and launched response mobilizer.⁶

Reg and I worked together for a year and a half. During that time, he spearheaded the effort to produce JProbe Threadalyzer, and then shepherded the entire JProbe suite through two subsequent upgrade releases.

By that time, Threadalyzer had all but eliminated its competition in the Java thread analysis space, and JProbe had become the company's major source of revenue.

—Christian Jaekl: Software Engineer and Concurrency Domain Expert

I lead engineering growth

I grow engineering in headcount, in scale of operations, in process maturity, and in tooling sophistication.

I’ve led technical interviews throughout my career and partnered with Talent on initiatives. At PagerDuty, I was recognized for using the interview process to close senior hires.
As a member of PagerDuty’s Architecture Strategy and Front-End Architecture Strategy teams, I led or co-led the adoption of tooling, process, and language choices that supported scaling engineering capacity.
I helped PagerDuty’s engineering successfully navigate the product/market fit refinement phase, a rapid sales growth phase, and a post-IPO transition to efficient and predictible scaling phase.⁷

You were such an anchor and leader at PD! Thank you for the countless interviews, for the always interesting insights, for mentoring so many, and for shaping PD and just being a great person! You are a true PD Hall of Famer and Legend!

—Richard Hartshorne: Senior Talent Partner, PagerDuty

I foster collaboration

At PagerDuty, in addition to the product and engineering growth outcomes above, I also collaborated across group and functional lines:

I was awarded PagerDuty’s Breakthrough leadership award in 2019 and the Inclusively Leading and Learning award in 2022.
I developed an internal capability supporting refined product management shipping strategies.
I ideated and prototyped features and products in partnership with my Product and Leadership colleagues.
I led our own Incident Management practice.
I have MC’d the company’s annual kickoff, and co-hosted the company’s IPO Breakfast Party.
I launched and supported a more rigorous iteration of Engineering’s Design Review process.
I launched and led technical and organizational reorganizations and process iterations.

Extraordinary communication skills... Able to mentor and coach other engineers and make those less experienced comfortable and build their confidence (empowerment) at the same time.

Reg's communication skills transcended engineering to other parts of the businesses (Product and Executive leadership). And, it is natural leadership... Not forced in any way. He talks to, and gets respect from, the Interns to the C-Level.

—Richard Hartshorne: Senior Talent Partner, PagerDuty

What’s Next?

This is not my first rodeo

I bring forty years of product- and customer- centric business and technical experience to shipping on time, without drama:

I have experienced both the highs and the lows of the startup trajectory, and I guide my teams with a steady hand on the tiller.
My teams know how to ship “good” without being seduced by “sufficient” or derailed by “perfect.”

Reg is one of the finest software engineering professionals I have ever worked with. He has great vision for product development, a strong sense of cultural fit for complex companies, and the vision to help scale an engineering group. Any growing organization would be fortunate to add Reg to its team.

—Jonathan Poehlman, Senior Technical Recruiter, Elastic

I’m available for work.

If you are looking for a veteran to play a meaningful role in your breakout success:

My résumé is available upon request.
My personal email is raganwald@gmail.com.
I’m open to 100% remote or Greater Toronto Area hybrid roles that leverage my technical and product focus.

You were a huge asset to PagerDuty, and wherever you land next will be lucky to have you.