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I help social sector leaders make high-stakes decisions and answer complex questions.

Independent strategy consulting, with a focus on AI adoption.

What I Do
Make High-Stakes Decisions

Strategic Planning

Setting direction is hardest when the ground keeps moving. I help organizations map the landscape, pressure-test their options, and build plans that survive contact with reality.

Answer Complex Questions

Research & Discovery

Some questions can't be answered from a desk. I run design groups, interviews, and original research that turn open questions into evidence leaders can act on.

Right now, AI requires both.

The decision is too important to get wrong. The questions have no settled answers.

Adopt AI Strategically

Strategic AI Adoption

Most organizations are stuck between scattered experimentation and paralysis. I help teams figure out where AI actually fits their mission and workflows, then build the strategy, governance, and capacity to use it well.

Build Custom Solutions

AI Solution Design

Sometimes the answer is a working solution, not a plan. I design and build AI-powered solutions with my technical partner Comprendo, an applied R&D firm that turns organizational questions into working software.

Periscope Advising × Comprendo
Periscope × Comprendo How the AI services are delivered

I deliver the AI services in partnership with Comprendo, an applied R&D firm that turns complex organizational questions into working software. They've built AI-powered solutions for the Gates Foundation, the Literacy Design Collaborative, NCEE, and the Heising-Simons Foundation. The partnership means strategy and technical execution live in one engagement: you don't end up with a roadmap and no one to build it.

Selected Clients

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

LearnerStudio Playlab New Classrooms Gates Family Foundation Bellwether 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 think clearly about AI. Not just the technology, but the strategy, governance, and capacity needed to adopt it well, and, with my technical partner Comprendo, the working solutions when advice alone isn't enough.

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.