Diego Oppenheimer
Diego Oppenheimer is a Founding Partner at AITFund.ai and advisor at AI Tinkerers and Hyperparam. He co-founded Algorithmia and Guardrails AI, both of which were acquired, and is a co-founder at AITFund. His expertise includes technical company building, AI, and investing in AI startups.
Former Microsoft CVP Jigar Thakkar Named VP of Amazon Quick Suite as Chartis and Supio Announce New Leadership
Jigar Thakkar, former Microsoft corporate vice president, has joined Amazon Quick Suite as vice president, focusing on agentic AI platform development. Additionally, Sara Vaezy returned to Chartis as chief product and technology officer, and legal-tech startup Supio named new executives following a $60 million funding round.
Pioneer Square Labs Assembles Expert Technical Advisory Board Featuring Seattle Tech Leaders to Support Early-Stage Startups
Pioneer Square Labs has formed a new Technical Advisory Board comprising leading technology researchers, executives, and startup veterans to support its early-stage startups, with a focus on AI and technology innovation. The board includes prominent figures from the University of Washington, Microsoft, Google, and other notable tech companies.
Guardrails AI, co-founded by Diego Oppenheimer, raises $7.5M seed funding to improve AI safety
Guardrails AI, a San Francisco startup co-founded by Diego Oppenheimer, raised $7.5 million in a seed round to help companies manage AI application risks with its open source platform. The company aims to enable safer, more reliable AI development, led by CEO Shreya Rajpal and backed by investors including Zetta Venture Partners and Factory.
What the heck happened at Convoy?
This week on the GeekWire Podcast, we examine the market forces, debt, and other dynamics that put the digital freight marketplace Convoy out of business, bringing one of the Seattle region's top startups to the end of the road. Related coverage: ‘The markets crushed us’: In tearful farewell to employees, Convoy execs reflect on shutdown Convoy collapse: Read CEO’s memo detailing sudden shutdown of Seattle trucking startup Convoy raised $260 million just 18 months ago, at a valuation of $3.8 billion. Its investor list was a who's who of tech moguls and celebrities, including Bill Gates, Jeff Bezos, Marc Benioff…
Rippl Care Hires Jamie Sharp as Chief Medical Officer to Lead Senior Mental Health Program; Other Seattle Tech Startups Announce Key Executive Appointments
Seattle startup Rippl Care appointed Jamie Sharp, former Aetna VP and chief medical officer, as its new chief medical officer to advance its mental health care program for seniors. Additionally, Diego Oppenheimer joined Guardrails AI as co-founder, PitchBook hired Paul Stoddart as CMO, and Tasso appointed Monica Williams as CFO.
Numbers Station Founders on Applying Foundation Models to Data Wrangling
This week, Madrona Managing Director Tim Porter talks to Numbers Station Co-founders Chris Aberger and Ines Chami. We announced our investment in Numbers Station's $17.5M Series A in March and are very excited about the work they're doing with foundation models, which is very different than what has been making headlines this year. It isn't content or image generation – Numbers Station is bringing the transformational power of AI inside of those foundation models to the data-wrangling problems we've all felt! You can't analyze data if the data is not prepared and transformed, which in the past has been a…
Seattle Veterans of Urbanspoon, Crowd Cow, Algorithmia Launch Blueprint AI to Automate Product Team Tasks
Seattle startup Blueprint AI, led by veteran founders of Urbanspoon, Crowd Cow, and Algorithmia, develops an AI platform to streamline task management and communication in product development teams. The company, launched in December and recently revealed to the public, uses AI agents to automate routine tasks and provide insights to enhance team productivity.
Algorithmia Founder Diego Oppenheimer Joins Venture Firm Factory to Open Seattle Office; Expedia Appoints Brad Bentley and Tript Singh Lamba to Executive Roles
Diego Oppenheimer, former CEO of Algorithmia, has joined venture capital firm Factory as partner and CEO-in-residence to open its new Seattle office, focusing on AI startups. Additionally, Expedia Group hired Brad Bentley as COO of Expedia Brands and Tript Singh Lamba as SVP of consumer product.
DataRobot buys Seattle ML startup Algorithmia and raises $300M Series G at $6.3B valuation
Boston-based DataRobot acquired Seattle startup Algorithmia and announced a $300 million Series G at a $6.3 billion valuation; Algorithmia CEO Diego Oppenheimer will remain at DataRobot after the deal. Algorithmia, founded in 2013, had raised $37.9 million, served over 130,000 users, and employed 58 people.
Algorithmia CEO Diego Oppenheimer urges resilience amid COVID slump; startup has raised $37.9M including $25M Series B
Algorithmia CEO Diego Oppenheimer encourages professionals stuck in a COVID-19 rut to balance survival with seizing opportunities, citing family background and a focus on employee growth; Algorithmia is a 58-person startup that has raised $37.9 million, including a $25 million Series B last year.
Anu Sharma leaves AWS to join Madrona Venture Group as investor after eight years at Amazon
Anu Sharma left an eight-year product management role at Amazon/AWS to join Madrona Venture Group’s investment team, turning a long-standing personal interest in investing into a full-time career where she plans to apply engineering rigor to evaluating and growing startups.
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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AI Tinkerers Founding Partner - AITFund.ai 2026–present, Advisor 2024–present · current
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AITFund Co-Founder 2026–present · current
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Stanford Graduate School of Business Executive Fellow 2026–present · current
Education
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Carnegie Mellon University MS, Information Systems Managment - Data Analytics
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Carnegie Mellon University BS, Information Systems
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The British Schools of Montevideo International Baccalaureate, Science
