Rob Mathewson

Rob Mathewson

Investor/Advisor at Clearset
Seattle, Washington, United States

Rob Mathewson is currently Investor/Advisor at Clearset and Director of Sales and Business Development at Deepen AI. He previously held leadership roles at CloudFactory, Conceivian, Construction Documentation Services, and founded Geedra and On The Spot Games. His expertise is in sales solutions and scaling early-stage teams.

  • Clearset Investor/Advisor 2025–present · current
  • Deepen AI Director of Sales And Business Development 2025–present · current
  • Conceivian Chief Revenue Officer (interim) 2024 · past
  • CloudFactory Director, Presales/Post-sales (AI and Data Services) 2021–2023 · past
  • ViSenze - AI for Visual Commerce Global Head of Presales for AI Retail Solutions 2020–2021 · past
  • Whispir Vice President Sales (Interim) 2019, Director Solutions Architecture (WSP.ASX) 2018–2020, Customer Success and Enablement Lead, Americas 2016–2018 · past
  • Geedra CEO, Founder 2009–2016 · past
  • Construction Documentation Services Vice President Marketing 2007–2008 · past
  • On The Spot Games Founder 2003–2007 · past

Education

  • Conceivian The Power Course, Changemaker · 2021–2022
  • Boston University BS Eng, Manufacturing Engineering
  • Seattle University Master of Business Administration (MBA), Entrepreneurship, Technology Management

Organizations

See all 9
  • Clearset Investor/Advisor 2025–present · current
  • Deepen AI Director of Sales And Business Development 2025–present · current
  • Conceivian Chief Revenue Officer (interim) 2024 · past

Education

  • Conceivian The Power Course, Changemaker · 2021–2022
  • Boston University BS Eng, Manufacturing Engineering
  • Seattle University Master of Business Administration (MBA), Entrepreneurship, Technology Management

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