Founding CEO (Edtech)

Woodside AI is a venture studio based in Palo Alto, focused on crafting category-defining AI companies in partnership with world-class entrepreneurs and industry market leaders.

Founded by industry titans and a top AI researcher from OpenAI, Woodside AI combines a proven track record of venture building and technical innovation. Our team members have shaped companies such as TSMC, Canva, and DRW, as well as backing disruptors like Anduril, Instacart, and Palantir in their early days. Our unique model of venture building has produced industry shapers such as Digital Asset (raised $135M Series E in 2025), Novaprime (now partnering with Fannie Mae and Freddie Mac), ErisX (acquired by CBOE in 2022), and Hashnote (acquired by Circle in 2025).

We are fully self-funded and focused on tackling complex industry challenges unlikely to be solved by traditional startups. Our unique approach gives founders and early teams immediate market access, domain expertise, and ample funding to take bold swings with real impact, while saving precious time and energy by staying laser-focused on delivering valuable solutions.

The Opportunity

We’re building an AI-powered EdTech company from the ground up - and we’re looking for a Founding CEO to lead it. This person will take the concept, prototype, and research developed by our venture studio and turn it into a thriving company. You’ll have access to the studio’s technical resources, top-tier AI talent, and go-to-market connections, enabling you to focus entirely on building and scaling the business.

As Founding CEO, you’ll be responsible for assembling the team, executing the business plan, and taking the product from early prototype to full-scale deployment. You’ll work closely with the studio leadership and founding product and engineering team to define the company vision, drive product-market fit, and lead the organization through its first critical stages of growth. This is a rare opportunity to be a fully backed founder - no fundraising required - and to build something transformative in the education space.

You should have:

• Deep leadership experience in EdTech or education-focused software
• A proven track record of building or selling products to schools or districts
• Experience as a founder, co-founder, or early leader at a venture-backed startup
• Strong business acumen and operational discipline
• Comfort navigating uncertainty and achieving product-market fit
• Excellent communication and storytelling skills

Nice to Have:

• Technical or product background (CS degree or equivalent experience)
• Prior experience taking a product from prototype to commercial launch
• Strong network in the education and EdTech ecosystem
• Experience leading or working closely with AI-focused teams