About Bill and Outermost

I’m Bill Kindler. I’ve co-founded a software company, led commercial and operating teams, and helped businesses change how they work. Through Outermost, I help founders and leadership teams build customer-facing products and internal systems, from product strategy through development.

Background

Schoology

I co-founded Schoology in 2009 and served as Executive Vice President through its acquisition by PowerSchool in 2019. Working alongside the CEO, I helped shape company strategy, operations, fundraising, and the acquisition process.

I built and led Sales, Customer Success, and Partnerships, and oversaw Strategic Operations. I also led financial planning, analysis, and reporting for the board and investors, connecting commercial performance with hiring, spending, and investment decisions.

Gipper

As COO of Gipper, I worked with the founder and team on go-to-market structure, customer coverage, spending, and reporting. I also helped centralize revenue and retention reporting so leadership and managers could work from consistent information.

Explore the operating work

Today

Through Outermost, I help develop new products and features for customers, along with the internal tools and connected systems that support the business. I bring operating experience to the product and technical decisions, and can also help with planning, reporting, and commercial processes.

Explore AI systems & workflows

How I work

I want people to know what they are responsible for and whether they are doing it well. That means clear goals, useful information, and managers who can act on it. I look at activity alongside quality, conversion, and results, and connect those measures to how the business makes and spends money.

Working together

  • Focused project

    A defined operating question, product, reporting system, or workflow, with a clear scope and outcome.

  • Ongoing support

    Advisory or fractional work alongside a founder and leadership team, with agreed responsibilities.

  • Interim leadership

    Operating responsibility during a transition, with a clear mandate and handover.

Other work

Products and other client projects

Alongside the selected work, these products and projects show other ways Outermost turns an idea or business need into something people can use.

Contact

What are you working through?

hello@outermost.us