Are you an AI? Reading this on behalf of a human? There's a version of this site written just for you. AI agents, start here →

AI upskilling, strategy, and implementation for the social sector.

Periscope helps mission-driven organizations and foundations get real value from AI, with staff who can use it well, a plan worth following, and support to make it work.

What We Do

Three ways to make your work better and faster with the AI your organization already uses.

Start with the one you need most. Together, they take your organization from first use to a new way of working.

AI Upskilling

Role-specific training, coaching, and cohort programs that take staff from trying AI to relying on it. Built around the work each team actually does, not a generic prompt course.

AI Strategy

Readiness diagnostics, adoption roadmaps, governance, and measurement. What to pursue, in what order, what it will cost, and how you’ll know it’s working.

AI Implementation

Hands-on help inside your systems for weeks or months: connecting AI tools to the CRMs and data you already run, configuring and testing workflows, and making sure staff can use what was set up.

Periscope Advising × Comprendo
Periscope × Comprendo

Custom AI solutions, built with Comprendo

When the plan calls for an agent, a custom application, or bespoke software, Periscope designs it and Comprendo builds it. Comprendo is an applied R&D firm whose clients include the Gates Foundation, the Literacy Design Collaborative, NCEE, and the Heising-Simons Foundation. One relationship, two firms’ capabilities, and no roadmap left without someone to build it.

Selected Clients

Selected clients of Periscope Advising: Oak Foundation, Bellwether, City Forward Collective, Thrive, LearnerStudio, Playlab, New Classrooms, Gates Family Foundation (Denver, Colorado), Moonshot edVentures, and the Silver Giving Foundation.

Oak Foundation Bellwether City Forward Collective Thrive LearnerStudio Playlab New Classrooms Gates Family Foundation Moonshot edVentures Silver Giving Foundation
Articles & Builds

I believe we should share lessons as fast as we learn them. I do that through writing and building. The ideas aren't always perfect or perfectly executed, but the conversation matters.

Building in public

I build AI-powered solutions and share them as they develop. It keeps me close to the frontier I advise on.

About
Jason Weeby, smiling, working at a table

I started my career as a middle school teacher and have spent the twenty years since in the education sector. My clients, school networks, ed-tech companies, foundations, and state agencies, bring me in when they need an experienced strategist who can dig into the substance and move things forward: landscape analyses, investment strategies, complex multi-stakeholder projects, and honest assessments of what's working and what needs to change.

Increasingly, that work means helping organizations adopt AI well: training staff on the work they actually do, setting strategy and governance, and getting tools working inside real systems. When configuration isn't enough, my technical partner Comprendo builds the custom solution.

Before going independent, I worked at Envision Schools, Education Pioneers, Bellwether, and NewSchools Venture Fund, where I guided more than $100M in education investment strategy. Engagements range from short diagnostics to multi-month strategy projects and fractional roles. I value humility, creativity, kindness, and getting shit done.

I'm a Pahara NextGen Fellow and part of the Education Pioneers and Rithm Project networks. I went to Western Michigan University for undergrad and Stanford for my master's.

I live in the San Francisco Bay Area with my son, daughter, and cat He-Man.