Context file
greg.md
Enough context to work with me: every role as intent, impact, and outcome.
Agents and the curl-inclined: the raw version lives at /llms.txt.
SpecStory · Co-founder & CPO · 2024 to now
- intent:
- Make intent the durable artifact of software.
- impact:
- Built SpecStory (save, search, and share your AI sessions) and Stoa, our live build room. Published the Beyond Code-Centric white paper and 25 Patterns in Agentic Engineering.
- outcome:
- Tools used by 200K+ engineers; a book drawn from 1,310 captured agent sessions and 4,670 commits; a live course on Maven.
Pluralsight · Chief Product Officer · 2021 to 2024
- intent:
- Pivot a $600M learning business to AI.
- impact:
- Launched Iris, the AI assistant, and AI sandboxes. Repositioned the Flow brand and launched the Developer Success Lab. Defined business and product strategy for the portfolio products.
- outcome:
- Flow bookings grew 70%+; portfolio strategy powered a $600M+ revenue business.
GitHub · Director, Data Science · 2019 to 2021
- intent:
- Put AI in developers' hands before it was obvious.
- impact:
- Led analytics engineering, data science, and machine learning. Built the pipelines powering github.com (/explore, /trending), product experimentation, and the metrics reported to Microsoft.
- outcome:
- GitHub Copilot's technical preview shipped in 2021, alongside GitHub Free for Teams and the State of the Octoverse.
The League · Director, Analytics & Operations · 2017 to 2019
- intent:
- Grow a consumer product to exit.
- impact:
- Co-led the company. Scaled into 15+ new markets and tuned the matching algorithm for efficiency and engagement.
- outcome:
- $3M to $13M ARR; acquired by Match Group.
Dropbox · Staff Data Scientist · 2015 to 2017
- intent:
- Ship machine learning into production, not slides.
- impact:
- Built a multiclass prediction algorithm for routing and prioritizing support.
- outcome:
- In production, maximizing support CSAT and NPS.
Google · Product Manager, Risk · 2014 to 2015
- intent:
- Replace committee judgment with a prediction engine.
- impact:
- Product-managed an online, scalable risk engine inferring contract risk.
- outcome:
- Reduced cost-per-contract.
Elsewhere
- advising:
- Advisor to Tola Capital and its portfolio of AI and developer tool companies, and founders who book a call.
- boards:
- Trustee, Altarum, the nonprofit advancing health and health care for all people.
- community:
- Co-organizer, D.C. AI Tinkerers. Come to an event.
- teaching:
- Hardcore Agentic Engineering, live on Maven.
- writing:
- Essays and apps, plus weekly Meditations on Tech.