Greg Ceccarelli - Watercolor Portrait

Greg Ceccarelli

Building with AI

I want you to win with AI

Get in touch

Hi, I'm Greg.

I co-founded SpecStory in November 2024 because I believe intent is the new source code.

Before that I was the Chief Product Officer at Pluralsight. And previously was at GitHub, Dropbox and Google.

The shift driven by frontier models, made useful by co-pilots and leading to agents will transform every business. I'm focused on accelerating that future.

I also advise AI and developer tool companies within Tola Capital's portfolio. Follow my weekly Meditations on Tech on Substack. Conduct superfast AI product discovery at gregslist.ai.

Read the O'Reilly Book I co-authored with Hamel Husain for free: AI Essentials For Tech Executives.

Experience

Co-Founder and CPO

SpecStory, Washington, DC

Nov 2024 - Present
  • You don't write prompts. You author intent. Save, search and share your AI chat history with SpecStory.
  • Get our VSCode extension for today for GitHub Copilot & Cursor: get.specstory.com/extension
C-Level ManagementAI Product DevelopmentPositioningGrowth

Chief Product Officer

Pluralsight, Salt Lake City, UT

Nov 2021 - May 2024
  • Pivoted Pluralsight to harness generative AI. Launched Iris: AI assistant and AI sandboxes to market.
  • Defined the business and product strategy for Pluralsight's portfolio products powering a $600M+ revenue business
  • Turned around the Flow business. Repositioned brand, launched Developer Success lab and grew bookings by 70%+.
C-Level ManagementAI Product StrategyP&L ManagementProduct Development

Director, Data Science

GitHub, San Francisco, CA

Feb 2019 - Oct 2021
  • Led analytics engineering, data science and machine learning.
  • Shipped GitHub Free for Teams, GitHub Co-Pilot's technical preview in late 2021, the State of the Octoverse
  • Built pipelines powering GitHub.com (e.g. /explore, /trending), product experimentation and metric definition reported to Microsoft.
AI Product ManagementMachine LearningData Science

Director, Analytics & Operations

The League, San Francisco, CA

Jun 2017 - Feb 2019
  • Co-led the company, a venture funded dating app. Was acquired by Match Group.
  • Scaled from $3M in ARR to $13M in ARR by launching across 15+ new markets
  • Increased efficiency of matching algorithm and overall product engagement.
AI Product ManagementP&L ManagementMachine LearningBusiness Strategy

Staff Data Scientist

Dropbox, San Francisco, CA

Dec 2015 - Jun 2017
  • Built and put into production a multiclass prediction algorithm to maximize support CSAT and NPS.
Machine LearningData Science

Product Manager, Risk Management

Google, Mountain View, CA

July 2014 - Dec 2015
  • Product managed the implementation of an on-line scalable risk management prediction engine to infer contract risk and reduce cost-per-contract.
AI Product Management

Content

From Meditations on Tech (Substack)