dylant@hey.com | Website | Consulting | LinkedIn | 415-657-6589
I build the teams and environments that make audacious business goals possible—PMOs, TPM teams, partner engineering teams, and professional services practices. I walk into ambiguity, bring the right amount of structure, and stay focused on impact.
Skills #
- Core: Operations, Technical Program Management, Agile Service 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 #
AlwaysMap #
June 2025 to Present
AlwaysMap helps tech-centric organizations shift from operational friction to scalable, clearer ways of working—across operations, programs, and teams. Brief sabbatical on family logistics, followed by:
- AI-assisted engineering hiring. Contracted by a SaaS company to overhaul engineering recruiting end-to-end: built an AI-powered screening pipeline that reduced 1,000+ inbound candidates to fewer than 40 requiring manual review, redesigned structured interviews and calibration, rebuilt the technical assessment process.
- gh-velocity. CLI tool to surface engineering delivery signals from GitHub data—helps teams act on patterns, not intuition.
- CalcMark. Open-source language and interpreter for structured calculations inside Markdown. CLI, VS Code extension, and AI agent integration—fills the gap between spreadsheets (opaque) and notebooks (heavyweight) for decision-making and planning documents.
GitHub #
Head of Technical Program Management #
January 2022 – June 2025
- Transformed a ~30-person org into a lean team of force-multipliers focused on critical programs. I defined and raised the technical bar, set consistent program standards, and cut the portfolio from 20+ programs to 5—each aligned to company-level goals with VP+ agreement across Engineering and Product. The result: TPMs that partners actively pulled into their hardest problems.
- 100% of GitHub Enterprise Server releases shipped on time. GHES accounts for a significant share of GitHub revenue. In early 2022, releases were missing deadlines. Led a TPM team to establish clear expectations, quality bars, and communication channels for all feature teams. Every release since mid-2023 shipped on time with minimal regressions—freeing the GHES engineering team to invest in net-new features for customers.
- Mission-critical response in under two hours. Staffed a high-urgency security program within 60 minutes of a CTO escalation. TPMs were actively coordinating the response within two hours; the number of exposed secrets showed measurable improvement within days. Made possible by the Flex Team—a dedicated squad of 3 TPMs I created to absorb urgent work without disrupting ongoing programs.
- Protected GitHub’s PRC revenue stream. GitHub’s certification to sell in China required annual GB18030 compliance. I identified the gap, built the cross-functional program (Engineering, Product, Legal, Revenue, Microsoft), secured budget and resource commitments, and achieved compliance every year the program ran.
Woolpert #
Cloud Solutions Director #
January 2019 – January 2022
- Founded a technical practice from scratch. Joined a pure-reseller organization with no technical pre-sale or post-sale capability. Built three new functions: Customer Engineering (pre-sale), Customer Success Engineering (post-sale), and consulting. Defined the roles, wrote the job descriptions, hired 12 engineers, established remote-first ways of working, and built the proposal and delivery motion from zero.
- Won and delivered a $450K Google engagement. Wrote the proposal, led agile delivery, and shipped the official reference application for Google’s brand-new logistics API—built from scratch, with Google as the client. First engagement of its kind for the practice; proof the team could perform at Google’s standards.
- Customer support from zero to scale. Designed and shipped a scalable support system with published SLAs. The guiding principle: every answer is a URL—every support response lives at a permanent, shareable link so the team scales without re-answering the same question twice.
- Built and shipped the organization’s first SaaS product. As product owner for STREAM Raster: defined features, pricing, SLOs, and SLAs, directed engineering daily, landed the first paying customer.
Google #
Head of Partner Engineering, Android Automotive #
2014 – 2018
- Launched Android Auto with 75+ partners across 130+ head unit variants in the first 24 months. Each one a distinct effort with a distinct partner—different hardware, different software stack, different OEM org. Joined as IC partner engineer on Google Maps automotive integrations and led the first two Android Auto OEM launches: Hyundai (first to market) and Audi (fast-follow).
- Scaled to 70M+ cars on the road—300+ car models from 40+ brands by 2017. Got my team off the certification critical path: documented the integration protocol and testing procedures so OEM and supplier teams could validate their own work, then authorized 3rd Party Labs to certify head units without Google in the loop.
- 15-person global team across 5 countries, accountable for every OEM and Tier 1 integration worldwide. Took global team leadership in 2015 and stood up engineering presence in Japan, South Korea, Germany, the UK, and the USA—co-located with the partner engineering teams across those time zones.
- Corporate citizenship. TPM hiring committee: reviewed 50+ candidate packages, personally interviewed 70+ technical and non-technical candidates.
Google Maps Program Manager #
2012 – 2014
- Founded Geo Customer Success Services. Established and ran the practice covering strategic Maps OEM accounts—27% of Geo revenue and key named brands. Day-to-day: technical advisor, advocate, and program lead across a complex partner landscape.
- 2013 Operations Chief of Staff. Selected for one of four global spots on the OCS leadership rotation in Singapore. Six countries in six weeks alongside Google’s regional leadership team.
Other Experience #
Stay at Home Dad—2018–2019 · Denver, Colorado
Took five months away from corporate life to relocate the family from San Francisco to Denver.
Microsoft—Senior Program Manager, Bing & MSN · 2010–2012 · Mountain View, CA
IC Technical PM with lead-by-influence accountability for EPD delivery: owned social data integration features on MSN.com and platform-scale identity features on Bing, coordinating across engineering and QA teams of 20+. Formative experience in big-company platform complexity, large-scale data integrations, and shipping at Microsoft velocity.
Woolpert—Consulting Software Engineer → Technical Leader · 2004–2010 · Denver and Seattle
Started as IC system integrator on complex on-premises ArcGIS enterprise deployments for local governments and public utilities—direct accountability for utilization, earned value, and % complete. Promoted to Technical Leader, providing coaching to 20 engineers and analysts. Opened the Seattle remote office; pitched, won, and delivered technical contracts in the $20K–$250K range.
Education #
- ByteByteGo—AI Engineering
- Cornell University—Leadership Excellence
- University of North Carolina—Master of Arts in Geography · Charlotte, NC
- University of Reading—Bachelor of Science in Geography · Reading, UK
Other #
U.S. and U.K. citizen