Reginald Braithwaite

Who I Am

I’m technical. I ship products. I am a strong communicator. I foster collaboration. And I grow engineering.

This is not my first rodeo:

• I have led teams with as many as fourteen members. I have led development groups with as many as forty-five.
• I have led through growth from startup, to IPO, to annual revenues in excess of $400 million.
• I have shipped software in organizations with dozens to thousands of employees worldwide.
• I have shipped software at B2C scale (millions of active users) and B2B scale (thousands of customers with as many as thousands of users each).
• I have customer-facing experience in Sales, Marketing, Financial Analysis, Consulting, and Customer Engineering.
• I have shipped features and products that were material to successful exits for Sitraka and PagerDuty.1, 2

I’m available for work.

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 Cucchi: Investor, Startup Advisor, ex-VP of Product and Marketing, PagerDuty

What I Do

I am technical

I have written and shipped software products and services since the 1990s:

• In 2015, I joined PagerDuty as its first Principal Engineer for Applications: I co-wrote features such as insights. I designed and wrote foundational code for response mobilizer, operational reviews, stakeholder communications, and round-robin scheduling.
  I made the incident page live and feature toggles fancy.3
• In 2013, I joined GitHub’s documentation tooling team and then transitioned to front-end flow: I shipped features such as rich prose diffs.
• In the mid 2000s, I led the web banking team for ING Direct (USA), with more than three million active users. I wrote features such as its first ATM and Café locator. I used Enterprise Architectural Patterns for integration with and extending the functionality of legacy systems.4
• While serving as Program Manager for the JProbe Suite, I designed and coded the suite’s first configuration tool.5
• 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.6
• In the late 1990s, I shipped a server-side templating language for Java.7
• In 1994, I shipped nCrypt Light, a message encryption tool for the Apple Newton.
• In the early 90s, I wrote and sold my own classified ad management application for desktop publishers.8

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 product strategy and development process around both technical and business tools:

• At PagerDuty, I partnered with Product to launch response mobilizer, operational reviews, stakeholder communications, and round-robin scheduling. I wrote the technical road map for schedules. Working with Product, I created prototypes for features such as recent changes. 9
• At Github, I created the prose-specific heuristics, designed and developed the user experience, and shipped rich prose diffs.
• 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.
• As the Technical Product Manager for JProbe Threadalyzer, I performed user research, developed the value proposition, and designed the product.

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

My approach to product strategy is informed by my beliefs:

• I believe that improving productivity is building faster horses. I believe that a tool that doesn’t redefine the way customers think about their work, isn’t worth building.10
• I believe that “table stakes” for product functionality is defined by similar features in mass-market products, not by market competitors. Text editing must be judged in comparison to Google Docs; calendars/schedules must be judged in comparison to Google Calendar.11

Loved the unique and always well researched and thoughtful invites that Reg brought to deep technical conversations and especially the way he showed up as a person, engineer and colleague. Easily one of those rare people that can go wide and deep on a topic. Reg supercharged an organization’s most elite thinkers and helps everyone do and get better.

—Ravi Singh: Serial Founder and ex-Senior Director of Engineering, PagerDuty

I am a strong communicator

I foster a culture of writing and structured communication in both my work and my personal pursuits:

• I write technical documentation;
• I write technical and product road maps;
• I write white papers and other marketecture pieces;
• I write pull requests and design review documents;
• I wrote JavaScript Allongé and other books about programming;
• I have created sales and software development training materials;
• I have delivered technical training to my colleagues and at technical conferences;
• I have been an essayist since 2004.

My books, essays, and talks are available on my creative works page.

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

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 recognized with two leadership awards at PagerDuty.12
• 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.

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 grow engineering

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.14
• 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 predictable scaling phase.15

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

This is not my first rodeo

† No longer active.

Reg was an incredible asset at PagerDuty, having been there early days in 2015 through the IPO. He helped level me and several other members of the sales team on the product and was always willing to hop on calls to help articulate value to them. Can’t wait to work with him again one day.

—Radz Mpofu, Head of Business Development, XGEN AI

I’m available for work.

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.”
• I’m ready to apply my experience and proven skills to growing another success.

I’m open to 100% remote or Greater Toronto Area hybrid roles that leverage my technical and product focus. I’m raganwald@gmail.com, and I’m on LinkedIn.

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

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

Footnotes

1. Sitraka was acquired by Quest Software in 2002. ↩
2. PagerDuty went public on the NYSE in 2019. ↩
3. Expression toggles are a domain-specific language for composing feature gating criteria. As the company’s launch process became more sophisticated, so did the complexity and configuration required to gate functionality through the entire launch cycle. Expression toggles are easily accessible to product and launch contributors, and sophisticated enough to grow with the company’s needs. ↩
4. Ask me about MUMPS and JDBC. ↩
5. I wrote the configuration tool in MetaCard and compiled it for both Windows and HP-UX users over a long weekend. This freed the teams to focus on core functionality. ↩
6. Threadalyzer was written in C++, Java+Swing, and used an instrumented custom JVM. It had a client-server architecture with plug-in analyzers for extensibility. ↩
7. The templating language was loosely based on Scheme, while borrowing some syntactic sugar from Smalltalk. Its defining feature was that HTML could contain code, code could contain HTML, and so forth all the way down. ↩
8. Long before Tableau from Salesforce existed, I wrote a classified ad application for desktop publishers. I wrote the code in 4th Dimension and the manuals in PageMaker. I did my own sales, and marketed the product at MacWorld. The product was named after Tableau I, a 1921 painting by De Stijl cofounder Piet Mondrian. ↩
9. Not everything I championed ended up shipping. Ask me about Schedules, Automation, and Collaboration.↩
10. My belief is a generalization of Dr. Alan Perlis’ observation that “a language that doesn’t affect the way you think about programming, is not worth knowing.” ↩
11. Yes this does mean thinking hard about supporting functionality like undo/redo stacks, real-time collaborative editing, comments, full-text search, full time zone support, flexible notification preferences, and other affordances that are table stakes for B2C applications. ↩
12. I treasure the tombstones for the Breakthrough and Inclusively Learning and Leading awards. ↩
13. Triskaidekaphobia (TRIS-kye-DEK-ə-FOH-bee-ə from Ancient Greek τρεισκαίδεκα (treiskaídeka) ‘thirteen’ and Ancient Greek φόβος (phóbos) ‘fear’) is fear or avoidance of the number 13.
14. Ask me about my experience adopting or migrating to Ember, React, JavaScript, TypeScript, Elixir, Java, and Copilot.↩
15. During my tenure, PagerDuty grew from approximately twenty-five million in ARR to over 400 million in ARR in the years following its IPO. ↩
16. Mobile Commons is now part of Upland Software. ↩
17. All that appears to remain of Devtopia is a page on LinkedIn.↩
18. Opalis Software was acquired by Microsoft. Ask me about engineering hygiene and The Inner Osbourne Effect. ↩
19. Ask me about The Mouse Trap. ↩
20. I retained this interview with the founder. The title of “Vice-President” was largely ceremonial: I was the head of development, but this was a team of three engineers and a product manager. Our incubator insisted that we needed a VP, so I got the title.↩
21. Sitraka Software was aquired by Quest Software in 2002. ↩
22. Codestorm is now AIgility Solutions. Our core business at the time was client-server business process automation for the financial services industry. ↩
23. Publishing Revenue Partners was my one-man ISV for selling Tableau, a classified advertising app for desktop publishers. I bootstrapped it with consulting and training, including working as a mentor for first-time entrepreneurs through the YMCA’s Enterprise Program and as a Financial Analyst for a boutique investment bank specializing in the food and beverage industry. ↩
24. Bonar Associates sold turnkey mini-computer-based classified advertising systems to large “penny-savers,” print newspapers that were primarily classified ads. I made its software customizable so that it could be sold at scale. It was written in TurboPascal with BTrieve, running on an MP/M-based tightly-coupled network. It supported as many as 16 simultaneous users. ↩