Greg Ceccarelli

Co-Founder

Washington, District of Columbia, United States18 yrs 8 mos experience
AI EnabledAI ML Practitioner

Key Highlights

  • Co-founded a successful AI product company.
  • Led major AI initiatives at GitHub and Pluralsight.
  • Expert in data science and machine learning.
Stackforce AI infers this person is a SaaS and EdTech expert with strong data science and product management skills.

Contact

Skills

Core Skills

Product DevelopmentGrowthFull-stack DevelopmentMarketingStrategyBuilding C-level RelationshipsProduct ManagementC Level ManagementGenerative AiRevenue & Profit GrowthSales PerformanceMachine LearningData ScienceOperations ManagementRisk ManagementManagement Consulting

Other Skills

PositioningCommunity DevelopmentStorytellingLink BuildingC-level supportC-Level RelationshipsStrategic PlanningProduct VisionCompliance OversightRecruitingLeadershipEngineering ManagementTechnical RequirementsDesign of Experiments (DOE)Data Analysis

About

If experience has taught me a thing, it’s that adaptability is the greatest skill. Multiplayer AI for product teams → withstoa.com I write a weekly Substack → meditationsontech.com

Experience

18 yrs 8 mos
Total Experience
1 yr 9 mos
Average Tenure
1 yr 10 mos
Current Experience

Tny.dev

AI Engineer

Jul 2025Present · 11 mos · Vercel Edge · Remote

  • Shortening your hyperlinks hyper-fast MCP and API first → https://tny.dev. Best for those creating content with Cursor and Claude Code
  • Motivation behind building this: https://get.specstory.com/built-to-be-outgrown
Full-Stack DevelopmentMarketingStorytellingLink Building

Specstory

Co-Founder & CPO

Nov 2024Present · 1 yr 7 mos

  • AI should be Multiplayer and local first. Now it is https://withstoa.com
  • With Stoa ship decisions, not just code. Turn ideas into shipped product and measure it end to end for the first time. Find out more and sign up your team.
  • Our free extensions auto-save your AI sessions in Cursor IDE, GH Copilot IDE, Claude Code, Codex, Cursor CLI to markdown. Download them and sync to the cloud from https://withstoa.com/specstory.
Product DevelopmentGrowthPositioningCommunity Development

Tola capital

Advisor

Aug 2024Present · 1 yr 10 mos

  • Advising Tola’s Generative AI and developer tool focused portfolio companies on product strategy and positioning
Building C-Level RelationshipsStrategyC-level support

Pluralsight

2 roles

Chief Product Officer

Jul 2023May 2024 · 10 mos

  • Shipped Generative AI Assistant (Pluralsight Iris) and Generative AI Sandboxes
  • Led the integration and successful release of the Skills & A Cloud Guru single product experience
  • Oversaw an org of >350 people across Product Management, Design, Content & Research for the Skills, A Cloud Guru and Flow product lines
C Level ManagementC-Level RelationshipsProduct ManagementProduct DevelopmentStrategic PlanningProduct Vision+1

EVP & GM, Pluralsight Flow

Nov 2021Jul 2023 · 1 yr 8 mos

  • Repositioned the Flow brand "your engineering transformation partner"
  • Bookings, retention and EBITDA accountability for the Flow P&L
  • Grew bookings 70% YoY and shipped many new releases inclusive of DORA metrics, Investment Portfolio and Single Tenant
  • Oversaw an org of >160 across all functions: Sales, Marketing, Customer Success, Support, Product, Design, Engineering and Business Operations.
C Level ManagementC-Level RelationshipsRevenue & Profit GrowthSales PerformanceProduct DevelopmentRecruiting+2

Round

Member

Jan 2023Jan 2024 · 1 yr

  • Round was a curated community of technology executives and senior leaders who support, grow, mentor, and learn from each other.

Github

Director, Data Science

Feb 2019Oct 2021 · 2 yrs 8 mos · San Francisco Bay Area / Washington D.C.

  • Led and helped build the data functions at GitHub, inclusive of Data Science, Analytics Engineering and Machine Learning. Responsible for ML pipelines powering github.com (e.g. /explore, /trending)
  • Led the Experimentation process and harness across the company for shipping new functionality that impacted new user signups, conversion to paid, engagement on the platform, etc.
  • Notable ships included: GitHub Free for Teams, GitHub Co-Pilot technical preview in 2021, The State of the Octoverse, etc
  • Oversaw a team of >30
Machine LearningData ScienceEngineering ManagementTechnical RequirementsRecruitingDesign of Experiments (DOE)+1

The league - meet intelligently

Director, Analytics and Operations

Jun 2017Jan 2019 · 1 yr 7 mos · San Francisco Bay Area

  • Business ultimately acquired by Match Group (MTCH)
  • Co-led the day-to-day operation of the company with responsibility including P&L management and company goal setting
  • Scaled employee base 3X and revenue 2X
  • Increased efficiency of matching algorithm and overall engagement rates (DAU, MAU). Launched in 15 new markets
Data AnalysisOperations ManagementRevenue & Profit GrowthData ScienceTechnical RequirementsRecruiting+1

Dropbox

Staff Data Scientist, CX

Dec 2015Jun 2017 · 1 yr 6 mos · San Francisco Bay Area

  • Tech lead on a small but mighty team of 5
  • Built and put into production a multiclass predictive model to maximize support CSAT and NPS.
  • Responsible for MBR reporting.
Machine LearningData ScienceStatistical ModelingTechnical Requirements

Google

Product Manager, Finance

Jul 2014Dec 2015 · 1 yr 5 mos · Mountain View, California

  • - Implemented an on-line scalable prediction engine to infer contract risk and reduce cost-per-contract. Product managed the effort to structure meaning from a corpus of 1M+ contracts.
Data ScienceRisk ManagementSoftware Development

Alixpartners

Vice President, Applied Analytics

Feb 2010Jun 2014 · 4 yrs 4 mos · Washington, District of Columbia, United States

  • Selected Engagements:
  • Co-led the definition and sale of a $11M program to transform a gaming and
  • entertainment business’ data infrastructure. Re-architected the company’s enterprise
  • data warehouse and company’s ability to generate insights from their data. Reduced
  • contra revenue expense from comps by 250 bps.
  • Engagement manager on an assignment to improve the profitability of a global
  • vehicle remarketing business. Implemented initiatives improved EBITDA by 3%.
Management ConsultingData ScienceLeadership

Ibm global business services

Consultant, Business Analytics and Optimization

Aug 2008Feb 2010 · 1 yr 6 mos · Washington D.C. Metro Area

  • Selected Engagement:
  • TTMS: The Time Transit Measurement Service. Member of the statistical programming team that quality assured IBMs contract with the Postal Regulatory Service. TTMS fabricated First-Class test mail that was injected into the mail stream to measure the on-time delivery performance of the U.S. Postal Service as an input to Postmaster compensation.
Management ConsultingData ScienceLeadership

Lincoln financial group

Investment Associate

Jan 2007May 2008 · 1 yr 4 mos · Bethesda, MD

Education

University of California, Berkeley

Master’s Degree — Information and Data Science

American University

BS — Economics

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