Greg Ceccarelli

AI Product Strategy

I advise executives on how to win with AI.

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For two decades I've been an operator focused on helping companies create competitive advantage with data. Most recently as the Chief Product Officer at Pluralsight. And previously 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.

Currently, I'm advising AI and developer tool companies within Tola Capital's portfolio.

Follow my weekly essays on Tech on Substack. Conduct superfast AI product discovery at gregslist.ai.

Take my free 9 day e-mail course on AI Mastery for Busy Execs.

Experience

Founding Evangelist & Advisor

SpecStory, Washington, DC

Nov 2024 - Present
  • Accelerating the shift to intent-driven development
PositioningAI Product StrategyProduct Development

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

Writing

Explore my latest essays on what we get right and wrong in Tech