dylant@hey.com | Website | Consulting | LinkedIn | 415-657-6589
I am a leader with deep expertise in technical program management, partner ecosystems, and SaaS delivery. Nothing makes me happier than getting things shipped to customers with an appropriately high quality bar. I achieve that through clear goals, timely decisions, and scaled operations.
Skills #
- Core: Technical Program Management, Agile Delivery, Technical Partnerships, Balanced Leadership, Remote Leadership, Growing teams, Organizational Development
- Technical: Geospatial, AI Engineering, and get-it-done levels of Python, Go, Google Cloud, some infrastructure, and SQL.
Work Experience #
Consulting & Sabbatical #
Founder of AlwaysMap #
December 2023 to Present
- Contracted with the Head of People at SaaS company to improve Engineering hiring outcomes.
- Building a digital-to-physical Life Journey web app to create beautiful wall maps of life’s milestones.
Head of DadOps #
June 2025 to Present
- My voluntary DadOps sabbatical is a play on DevOps, with a focus on smooth and agile family operations. University tours, a structured approach to high school, and ensuring that the home network is up to the rigors of both gaming and the home office.
- Diving into AI fundamentals in the ByteByteGo AI Engineering course.
- Coding up agentic patterns, and teaming up with coding agents on experimental work.
GitHub #
Remote
Head of Technical Program Management (TPM) #
Jan 2022 to June 2025
- Mission critical projects staffed and running within hours. For example, I staffed a project within 60 minutes of getting an urgent CTO text message about an active security concern. TPMs were actively coordinating the response with 2 hours and seeing measurable improvements in key metrics (secret count) within single-digit days. I accomplished this my creating the Flex Team—a dedicated squad of 3 TPMs—to handle urgent, high-impact projects without disrupting ongoing programs.
- 100% of GitHub Enterprise Server (GHES) releases are on time, with high quality. GHES accounts for a sizable percentage of GitHub’s revenue. In early 2022 releases were not hitting release deadlines. I led a small team of TPMs to provide clear expectations and repeatable processes for all GitHub feature teams: timeframes, quality bar, and communication channels. Since mid-2023 100% of releases were on time and contained few regressions, enabling the GHES team to focus more on net new features for customers.
- GitHub products are compliant to sell in China (PRC). GitHub’s certification to sell in the People’s Republic of China (PRC) hinged on compliance with a country-specific UTF encoding. I recognized the gap in compliance coverage and spun up a program in conjunction with Microsoft, including budget and resource commitments across EPDa and Revenue. GitHub achieved GB18030 compliance each year my team ran the program, thus protecting our revenue stream in the PRC.
- Narrowed the focus from 20+ to just 5 business critical programs. By early 2025 GitHub TPM was running 5 major programs with ~30 TPMs focused solely on major company goals including security, Copilot AI, and enterprise data residency. When I joined GitHub, a team of 30+ TPMs was working on 20+ programs and projects. I introduced a regular review of strategic need against investments made, thus putting more TPM investment into programs with the biggest business impact. The cut line was painful, necessary, and agreed upon by VP+ stakeholders cross Engineering and Product.
Woolpert #
Remote
Cloud Solutions Director #
Jan 2019 to Jan 2022
- Technical delivery. Closed and delivered consulting engineering work worth $450,000. Established pre-award R&D goals, work estimation, co-authored the technical proposal, and led agile project delivery with Google as my client.
- Customer support from zero to scale. Pitched, budgeted, designed, and implemented a scalable customer support system with SLAs that customers could rely on. The guiding principle: the answer to every question is a public URL.
- Product. Formed and led the team that defined, built, and sold our first SaaS product. As product owner I defined the features, pricing, SLOs and SLAs, directed the engineering team daily, and landed the first customer.
- Establish and nurture a new team. Hired a team of 12 engineers in both team leader and individual contributor roles. Defined net new remote-first roles and ways of working within a traditional corporate environment. Established a repeatable hiring process with core and technical skill components and a high bar. Established a functional org chart that scaled.
- Acquisitions. Technical reviewer for two potential acquisitions. I provided key input related to technical risk, technical staff, and product roadmap feasibility. Key questions I asked: how quickly can you add another customer and how quickly can a fix be deployed?
- Open source mindset. Led the release of our first open source solution, GeoAwareness, which represented a very different mindset from the closed-source, pay-to-play model. Writing and promoting open data standards in an industry that is not known for openness.
Google #
Remote and Mountain View, California
Head of Partner Engineering, Android Automotive — 2014-2018 #
- From zero to 70 million cars in 24 months. Founding partner engineering team member 2014, and it’s global lead from 2015. I built and led a global hybrid remote team of 15+ technical staff. We got Android Auto embedded and jointly shipped with 75+ industry partners in 130+ head unit variants in the first 24 months.
- Technical clarity for implementors. Implementing the Android Auto Protocol (AAP) in a car left many open questions for automotive suppliers. I led the effort to codify requirements and guidelines via clear written documentation and testing procedures. Third party (supplier) engineering teams could now validate correctness on their own before attempting certification. Google’s own codebase also improved as a result, notably around audio management.
- Launch 3rd Party Labs testing for automotive. My team was the limiting factor in certifying and launching new Android Auto project (AAP) head units. First I established a reproducible certification process applicable to all partners and internal teams (learn and do) This enabled my team to outsource certifcation through a 3rd Party Labs (“3PL”) program to dramatically increase the reach of the product.
- Corporate citizenship. Sat on TPM hiring committee reviewing 50+ candidate packages for hire/no hire decisions, and personally interviewed 70+ technical and non-technical candidates.
Google Maps Program Manager — 2012-2014 #
- Program Leadership. Founder of Geo Customer Success Services; I provided leadership for the practice, including program management and project execution. On a day-to-day basis I served as a technical advisor and advocate for strategic Google Maps OEMs, touching 27% of Geo revenue and key name brands.
- 2013 Enterprise Operations Chief of Staff. As a successful program manager I was selected for one of four global spots on the OCS leadership rotation in Singapore. Covered six countries in six weeks with great international business exposure alongside Google’s regional leadership team.
Other Experience #
Stay at Home Dad — 2018-2019 (Denver, Colorado)
- Took 5 wonderful months away from corporate life to settle the family into Denver after a move from San Francisco.
- Did a lot of school-related activities, and finally got both of them confidently riding bikes.
- Learned to cook better, and about the benefit of mise en place a.k.a. prep!
Microsoft — 2010-2012 (Mountain View, California)
- Senior Program Manager on Bing. Defined and executed the plan by leading large (20+) teams across Eng and QA.
- I defined, scoped, and planned feature releases, and ran stand-up meetings.
- Prototyped, owned the product backlog, and was accountable for final delivery on user-facing features on MSN.com.
Woolpert — 2004–2010 (Denver and Seattle remote)
- As Consulting Software Engineer I provided technical leadership and coaching to 20 software engineers and system analysts.
- Delivered core business objects and persistence tier for $8M suite of applications and data at a major U.S. airport.
- As Project Manager I opened a new remote office in Seattle, Washington; I pitched, won, and delivered technical contracts in the $20K-$250K range.
Education #
- University of North Carolina
- 1993-1996
- Masters of Arts in Geography
- Charlotte, North Carolina
- University of Reading
- 1989-1991
- Bachelor of Science in Geography
- Reading, United Kingdom
Other #
U.S. and U.K. citizen