AI Strategy Cohort
A 6-month cohort where nonprofit leaders build their organization's AI strategy, with AI doing the heavy lifting between meetings.
- Applications close
- Sun, Nov 29
- Program
- 6 months, 6 meetings
- Format
- A small, selective cohort
- Founding rate
- $15,000 per organization
AI can do far more for your organization than you've seen so far.
The capability is already remarkable. What leaders need is a clear line of sight to where it fits their mission, and a way to put it to work across the whole organization.
Since ChatGPT arrived, AI has moved from a novelty to something far more capable. The technology has grown rapidly in popularity, sophistication, and scope, and agentic workflows now carry out complex, multi-step organizational work. The tools are usable and powerful enough. What most nonprofits are missing is a way to integrate them strategically into their work.
If you run a small or midsize nonprofit, you don't have a chief technology officer or a strategy team to hand this to. The question of what AI means for your organization lands on your desk, alongside everything else. And it raises questions that trainings can't answer on their own. How do we drive consistent use across a lean team? How do we extend our capacity without adding headcount? Where can AI meaningfully increase efficiency? How do we minimize the liabilities that come with it?
Most nonprofits are already using AI in pockets. Staff are experimenting with tools, and some teams have done training. Training matters because it raises individual fluency, but it addresses what people can do and leaves the organizational questions above unanswered. Most organizations don't yet have a coherent strategy, a charter, a governance policy, or an implementation plan grounded in their mission and operations.
The result is scattered experimentation, with pockets of value, pockets of risk, and not yet the organizational capacity to make AI adoption deliberate and durable. Meaningful value is still sitting on the table, including fewer hours absorbed by administrative work, better-informed decisions, and more capacity for mission delivery.
This cohort is built to show you what AI can really do, by having it do the heavy lifting alongside you, on your own strategy, in full view. You leave with the judgment to direct it and the assets to sustain it.
A full set of working assets that do two jobs.
Each organization comes away with documents that chart its course, and a Context Pack that feeds its AI.
Chart your course · Foundational documentsAI Readiness Scan
A benchmarked read on where your organization stands today across key organizational domains. It gives your team a shared starting point and a baseline for measuring progress.
AI Charter
A values-based statement, written for your whole organization, that defines your relationship to AI. It guides everyday decisions about when and how your team uses it.
AI Adoption Strategy
Your priorities for where AI fits your mission, with an integrated change-management plan. It tells staff, board, and funders what you're doing with AI and how you'll bring people along.
Implementation Roadmap
A 90-day capacity plan with named owners that turns the strategy into specific work. It keeps momentum going after the last cohort meeting.
Staff Training Plan
A plan for building the skills each role needs to use AI well in its own work. It ties learning to your priorities so it sticks.
AI Governance Policy
Clear rules for data, privacy, tool use, and accountability. It lets staff use AI with confidence and gives your board a policy it can stand behind.
A Context Pack
The Context Pack is what turns the documents from shelfware into working infrastructure.
A structured library of your organization's essential context: mission, strategy, programs, operating model, voice, policies, and the documents above, formatted to load directly into whatever AI your team uses.
Instead of every staff member starting from a blank prompt, your AI starts every task already knowing your organization.
For the optimal cohort experience, we recommend having a paid team or enterprise account on an AI platform your organization already uses, such as Claude, ChatGPT, Gemini, or Copilot. Free and individual versions don't offer the data protections or features this work depends on. If your current tool is holding you back, we'll address it in your strategy.
Six working meetings. The AI does the drafting in between.
The meetings are the program. Cohort meetings run 90 minutes to 2 hours on Wednesdays, at times set with the cohort. Between them, an AI harness turns your organization's context into draft artifacts, so every minute in the room goes to judgment and decisions, not document production.
Select a meeting to see how it comes together.
Jason spent eight weeks helping us build tools that improved the efficiency and quality of the real work in front of us, rather than running us through a series of hypothetical training sessions. We came out with a new vocabulary, shared tools our team actually uses, and customized workflows and skills that shave significant time off tasks we do repeatedly.
Forming now, as a pilot.
- A small, selective cohort of peer organizations
- Six months, six meetings
- Full deliverables for each participating organization
- Application-based enrollment, screening for decision-making authority, ED/CEO sponsorship, and organizational readiness
- A team of 1 to 3, including your ED or CEO
- Every meeting attended: the December one-on-one and all five cohort meetings
- 1 to 5 hours a week from your team between meetings
- Staff interviews of 30 to 90 minutes per participant
- Feedback from your board, at your organization's discretion
Standard price for future cohorts is $20,000 per organization. Pilot partners get the founding rate in exchange for helping shape the program: candid feedback at the close, a short case study, and permission to share anonymized samples of their deliverables.
A cohort just for your grantees.
We can run a custom cohort for a group of organizations in your portfolio, timed to your grant cycle and tuned to what your grantees share.
Let's talk about a grantee cohortIf the timing isn't right, there's still a path.
This cohort works best for organizations ready to commit now. If one of these describes you today, a later cohort or a different kind of support may serve you better.
- Funding isn't in place yet. We're glad to help you make the case to a funder.
- Your team can't make every meeting this round. Tell us when timing works, and we'll reach out about the next cohort.
- Your organization is just getting started with AI. We can point you to introductory supports we believe in.
- You're a school district, government agency, or for-profit company. This cohort is built for nonprofits, and we're developing other offerings.
- You'd rather have a dedicated engagement. Periscope also does upskilling, strategy, and implementation work, on its own or in combination.
Whatever your situation, reach out. Part of every conversation is finding what fits.
Who's behind it.
Jason Weeby
Founder · designs and leads every engagement
Periscope Advising helps social sector organizations close the gap between the AI frontier and their current practices, through strategy, upskilling, and implementation. Jason brings 20+ years in education and nonprofit strategy, including roles at NewSchools Venture Fund, Bellwether Education Partners, and Education Pioneers.
Brandon Malmberg
Cohort lead · participant experience
Brandon has spent more than 20 years building talent, partnership, and revenue pipelines for leadership development organizations, including about seven years each as an early staff member at the Pahara Institute and Education Pioneers. He created Prologue: Into AI, a program of applied coaching and training for leaders building their AI fluency. He holds an MBA from UCLA.
Advisory and technical partner
Comprendo is 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 Comprendo team will provide advice for complex technical questions.
Common questions.
What AI tools do we need?
For the optimal cohort experience, we recommend a paid team or enterprise account on an AI platform your organization already uses, such as Claude, ChatGPT, Gemini, or Copilot. Free and individual versions don't offer the data protections or features this work depends on. The drafting between meetings happens on our side, so you don't need any special setup to get started.
How much time does it take?
A December one-on-one, then five cohort meetings of 90 minutes to 2 hours each, all on Wednesdays from January to May. Between meetings, your team spends 1 to 5 hours a week reviewing drafts and making decisions, and participating staff give 30 to 90 minutes each for interviews.
Who should take part from our organization?
A team of 1 to 3, always including your ED or CEO. The work sets organizational direction, so it needs the person who can make those calls in the room.
What if we can't make a meeting?
The program depends on every organization being at every meeting, because each one builds on the last. If you already know about a conflict, tell us on the form and we'll talk it through. If the timing doesn't work this round, a later cohort may be a better fit.
Who else will be in the cohort?
A small group of peer nonprofits of similar size. We build each cohort with care, and we avoid placing direct competitors or funder and grantee pairs in the same group.
Can a funder pay for our participation?
Yes. Many organizations fund this from their own budget or a funder. Foundations can sponsor a grantee for this cohort, or ask us about a custom cohort just for their grantees.
How to join.
- Fill out the short form. It takes about five minutes.
- We review it and email you a link to book a 30-minute conversation with your ED or CEO about your organization, the calendar, funding, and your questions.
- You leave with a recommendation: an invitation to join this cohort, or a suggestion that fits better.
Want to talk before filling out the form? Email us at jason@periscopeadvising.com.
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We read every response and will email you within a few days with next steps. If you'd rather not wait, write us at jason@periscopeadvising.com.