Background
Bill co-founded Schoology, a K-12 learning platform used by schools and districts across the United States, and spent a decade there as executive vice president, the company's second executive. He led sales, customer success and partnerships, ran finance and board reporting, and worked on its acquisition by PowerSchool through close.
He was most recently chief operating officer at Gipper, where he redesigned the organization and rebuilt go-to-market, retention and the cost base. In between he co-founded a consumer software company, took it to market, and wound it down when the numbers said to.
He also invests in and advises early and growth-stage founders, and has been an investor in education technology since before it was a category.
How the firm is built
Outermost is deliberately small and takes a limited number of engagements at a time. The work is done by the person you meet, with AI systems doing the parts that software does better than people.
That is not a slogan. The firm runs its own operation on the same automation it builds for clients: software that handles email, scheduling, reporting and monitoring, checked against what actually happened before it acts.
If a project is not a fit, we will say so early and point you somewhere better.
Contact
Describe the work you have in mind, and we will tell you how we would approach it.
hello@outermost.us