Jason Stewart
Jason Stewart was CTO and Co-Founder at Skilljar. He previously served as Executive Advisor for Customer Education at Gainsight, and held software development and architecture roles at Amazon and Irdeto. He began his career as a Software Development Engineer at LockStream Corporation.
Skilljar raises $33M Series B led by Insight Partners as pandemic boosts demand for its customer education platform
Seattle-based Skilljar, founded by Sandi Lin and Jason Stewart, raised $33 million in a Series B led by Insight Partners as demand for its customer education software surged during the pandemic; total funding exceeds $50 million and the platform has delivered over 10 million instructional hours to 300+ customers including Tableau and Cisco. The company provides cloud-based training, assessments, certifications, analytics and integrations to help companies build onboarding and customer education programs.
GeekWire Awards 2020 Goes Virtual; Ally Wins Startup of the Year as Bill Gates and Celebrities Celebrate
GeekWire held a virtual GeekWire Awards livestream honoring top Pacific Northwest tech companies and leaders across 12 categories, with winners accepting via Zoom and special video messages from figures like Bill Gates. Seattle startup Ally won Startup of the Year, and the event included entertainment such as The Drunken Tenorperforming an "Opera di Zoom."
Organizations
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Gainsight Executive Advisor • Customer Education 2025–2026 · past
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Skilljar Executive Officer, Director 2020–2025, CTO & Co-Founder 2013–2025 · past
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Amazon Software Development Manager - Targeting 2012–2013, Sr. Software Development - AmazonLocal 2012, Software Development - AmazonLocal 2011–2012 · past
Education
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Carleton College BA, Computer Science · 1994–1998
