PROPOSED Sequel to the workshop · Prepared for the Urban Arts leadership team

Five AI initiatives — and a fractional AI Co-Leader to help land them.

Pulled directly from the post-workshop debrief: five organization-wide initiatives the leadership team named as priorities, plus an embedded support layer that builds AI fluency across the org while operational wins happen in the background. Sequenced so the team keeps moving on EOS rocks without adding a sixth one.

For Urban Arts leadership team
From Daniel Townsend, Co-Pilot Innovations
Horizon 6-month engagement, 90-day momentum gates
Source Post-workshop debrief · Opportunity Report · Workshop output
What this proposal covers
A portfolio, not a project.
Five org-wide initiatives + a fractional AI Co-Leader for adoption and operational lift. Three engagement tiers let you pick the right pace for the next six months.
Revenue · Dev
Grants + Donors
Programs · Scale
Data + Studio
Brand · Ecosystem
UA 100
The premise

Five priorities. A team already in motion. A pragmatic next step.

On the post-workshop debrief, leadership named five org-wide AI initiatives that should sit above the individual 90-day projects already underway. They span the three muscles Urban Arts is trying to build: revenue velocity (grant writing, major donors), program scale & insight (Game Academy data, lighter-weight studio model), and brand & ecosystem (Urban Arts 100).

The team also flagged a real constraint — capacity. Coming out of EOS planning with a deck of 90-day rocks, there isn't headroom to stand all five up at once. So this proposal isn't five projects starting at the same time. It's a portfolio framework, sequenced into 90-day waves, with a fractional AI Co-Leader running alongside to handle the smaller operational ideas and lift the whole org's fluency in parallel.

"Three to five ideas that kind of represent a little portfolio of your AI program — a couple of quick wins, one moonshot, two that are a little more challenging with P&L impact." From the workshop framing · echoed back by leadership on the debrief
At a glance

The five initiatives the team named.

Each tile is one of the five priorities. Color indicates the org muscle it builds; tag indicates the lift profile. Detail panels follow below. The Fractional AI Co-Leader (next section) is the support layer that runs underneath whichever tier of engagement leadership picks.

INITIATIVE · 01
Revenue · Development
Grant Writing Acceleration

Shrink time-per-grant. Distinguish foundation vs. government workflows. Free hours for relationship work.

Owner: Director of GrantsQuick win
INITIATIVE · 02
Revenue · Development
Major Donor Prospect Engine

A weekly qualified-leads brief on the CDO's desk. Tied directly to the 50 new major donors goal.

Owner: Chief Development OfficerP&L impact
INITIATIVE · 03
Programs · Data Layer
Game Academy Data → Insight Engine

Airtable as the system of record. Claude as the analyst. Dashboards that ship themselves — and surface trends proactively.

Owner: Programs + DataFoundational
INITIATIVE · 04
Programs · Reach
Lightweight Game Studio Model

Scale the spirit of Game Academy without the cost of the full curriculum. Studio clubs in high schools, AI-augmented delivery.

Owner: Programs LeadershipMoonshot
INITIATIVE · 05
Brand · Ecosystem
Urban Arts 100 & Brand System

Cement Urban Arts's place in the AI-native creative-tech ecosystem. Design system + program design + ecosystem messaging.

Owner: CEO + ProgramsStrategic
RUNS UNDERNEATH
Adoption · Operational
Fractional AI Co-Leader

Base support layer. Handles operational side-projects (recruiting, policy, admin-assistant Claude) + 3 structured trainings + office hours.

Included in every tierBase layer
The five initiatives

Each one, with the business case in one panel.

The structure is the same every time: what's happening today, what AI does about it, why Urban Arts is well-positioned to ship it, and a short outcomes scoreboard. Specific KPI targets get baselined per initiative during scoping — the scoreboards below name the metrics we'd track, with directional language for the direction of travel. The realistic ambition across any initiative leadership picks: MVP-level delivery inside the 6-month engagement window.

INITIATIVE · 01 Revenue · Development Quick win

Grant Writing Acceleration — fewer hours wordsmithing, more hours with funders.

Two distinct workflows under one roof. Foundation grants — relationship-driven, where AI accelerates research and first drafts but the human handshake still wins. Government grants — blind and quality-driven, where better-written grants directly raise the win rate.

Grant writing sits mostly with one person, supported part-time by senior leadership. Quality is strong; capacity is the constraint. There's a clear tension on the dev team: more grants out the door is good — but only if hit-rate doesn't collapse. "Just putting out more grants into the world that you end up not getting is not a strategy either."

An AI-assisted grant workflow that splits foundation vs. government tracks. For both: a project workspace pre-loaded with prior winning grants, program statistics, current outcomes data, and a structured prompt library. For government: a stronger emphasis on quality scoring against the funder's published rubric. For foundation: research and personalization on the relationship side. Realistic objective: meaningfully reduce drafting time on grants the team is already writing — then decide whether to write more or reinvest hours into donor cultivation.

The data and the institutional knowledge already exist — they just aren't structured for reuse. A Claude Project with the right corpus loaded is a 1-week build, not a 3-month one. And the avoided rehire of the associate operations role is a tangible offset against any retainer math.

INITIATIVE · 02 Revenue · Development P&L impact

Major Donor Prospect Engine — a weekly qualified-leads brief on the CDO's desk.

Urban Arts is robust on corporate, government, foundation, and gala revenue — and underweight on individual major donors. The CDO has a stated goal of identifying 50 new majors. This initiative builds the engine that puts a curated prospect list, with personalized approach strategy, on her desk every Monday.

Prospect research is ad hoc and reactive. The CDO is tasked with a 50-donor target but doesn't have a systematic pipeline feeding qualified individuals in. Leadership named this on the debrief as a known weakness: "that's not happening."

A prospect-research agent that runs continuously: ingests publicly available donor data, philanthropy databases, board affiliations, and giving history; matches against Urban Arts's giving criteria and the AI-native programmatic direction (Founders Lab, creative tech); and outputs a weekly digest with personalized approach strategy — talking points, mutual connections, and a recommended next action per prospect. Reviewed and triaged in 15 minutes a week instead of researched from scratch.

Direct line to a named target (50 new majors), a named owner (CDO), and a workflow that scales without adding headcount. The AI-native programmatic pivot makes Urban Arts more attractive to a specific donor profile — surfacing that match systematically is exactly where AI earns its keep.

INITIATIVE · 03 Programs · Data Layer Foundational

Game Academy Data → Insight Engine — Airtable as the source, Claude as the analyst.

Step one: commit Game Academy data to Airtable as the system of record (the leadership team is already leaning this way). Step two: connect Claude to that data so annual dashboards build themselves and trends surface proactively, not on request. This is the foundational play — every other program-side initiative gets easier once this is in place.

Program data lives in a mix of Airtable and Google Docs. The annual dashboard is built manually by programs leadership, pulling figures together by hand. There's no proactive insight layer — useful trends only surface when someone goes looking for them. "It would be so much cooler to not have to do any of that work and it just all…"

Three-phase build. (1) Data architecture — finalize Airtable as the source of truth, migrate what's in Google Docs, define the schema for student/cohort/outcome tracking. (2) Claude integration — connect Claude to the Airtable layer so anyone on the team can ask English-language questions of the data. (3) Proactive insight agent — a scheduled job that scans the data weekly and surfaces noteworthy trends: "Hey, retention in Cohort 14 is tracking 12 points below last year's Cohort 11 — want to dig in?"

Unlocks capability for initiatives 2 (donor reporting), 4 (knowing what's actually working in the program before scaling it), and 5 (data points for the brand story). This is the leverage play — relatively contained scope, but it makes the other four easier.

INITIATIVE · 04 Programs · Reach Moonshot

Lightweight Game Studio Model — scale the spirit, not the cost structure.

The existing Game Academy is rigorous, robust, and expensive to deliver at fidelity. The opportunity is a lighter-weight delivery model — Game Studio clubs in high schools, AI-augmented teaching support, curated student outputs — that preserves the spirit of "diverse teams creating together" without the full unit-economics drag.

Scaling Game Academy as it exists today would either lose money or dilute quality. Programs leadership has been thinking about a club model but hasn't had the time or the tooling to design what AI could do inside it: "is there like a lighter thing we can do… we can get little game studios in high schools around the country?"

An AI Canvas exercise first — this initiative is deliberately the least defined of the five, because the model itself needs design before the AI scope makes sense. The likely shape: AI-assisted teaching artist support (lesson prep, student feedback, project critique), AI as a creative collaborator inside the student workflow, and a lightweight reporting layer that feeds initiative 3's data engine. Decision gate at the end of the design phase: pilot or pass.

This is the moonshot in the portfolio — the play with the highest upside if it works. It also threads directly through the brand initiative (#5): a national lightweight footprint feeds the "Urban Arts in the ecosystem" story in a way no single flagship program can.

INITIATIVE · 05 Brand · Ecosystem Strategic

Urban Arts 100 & Brand System — cement Urban Arts's place in the AI-native creative-tech ecosystem.

A flagship program ("Urban Arts 100" or similar naming) that curates the top student creative technologists, XR / game designers, and entrepreneurs that companies want to hire. Revenue-generating and brand-building — not scale-for-scale's-sake. Backed by a Claude-designed brand system so the whole org can produce on-brand collateral fast.

Urban Arts is pivoting AI-native: Founders Lab launches imminently, game design is shifting in the same direction, and leadership has made the strategic call. What's missing is the ecosystem-facing flagship that telegraphs that pivot externally — to donors, partners, employers, and the press. "If we don't build the urban arts brand, you're scaling a negative."

Two threads. Program design — concept the flagship (naming, format, judging, prizes, partner roster); the AI accelerates research and prototyping, the team makes the strategic calls. Brand & design system — use Claude design to build a true atomic design system so anyone in the org can produce on-brand decks, social, web, and donor collateral in hours instead of weeks. Together these turn the AI-native pivot into a story the ecosystem can see.

This is the strategic spine of the portfolio. It threads directly through the major-donor work (initiative 2 — a strong ecosystem story attracts the donors who write the bigger checks) and the lightweight studio model (initiative 4 — a national footprint plus a flagship is a more compelling ecosystem narrative than either on its own).

Base support layer

The Fractional AI Co-Leader — runs underneath every tier.

The five initiatives are the visible work. The Fractional AI Co-Leader is the support layer that lifts the whole org's AI fluency in parallel — and absorbs the smaller operational ideas that came up on the debrief without needing their own project line. Think of it as having a senior AI partner on call, embedded in the leadership cadence, for a fraction of what a full-time AI hire would cost.

01

Structured trainings (up to 3)

Designed and delivered against where the team actually is — not generic AI 101 content. Sample topics:

  • Claude as a personal admin / chief of staff
  • The "when to use AI / how to prompt / how to verify" framework
  • Claude Projects as a shared team workspace
  • Building lightweight workflows without code
02

Office hours

Pre-arranged recurring slots where the team can bring real work, real prompts, and real stuck-points to a senior partner. Cuts the time team members spend wrestling with Claude alone — and surfaces the next wave of opportunities organically.

  • 2x per month, scheduled in advance
  • Anyone on the team can book in
  • Open Q&A or pre-submitted topics
03

Operational side-projects

The smaller ideas surfaced on the debrief — the ones too tactical to warrant a project line but real enough to compound. Worked between the leadership team and the Co-Leader as they come up:

  • Recruiting / resume review workflow
  • Policy & document generation
  • Claude-as-admin for individual leaders
  • Operational productivity ideas as they emerge

Why this matters in framing: Leadership repeatedly emphasized on the debrief that they want the team playing with Claude, not waiting for formal training. The Co-Leader layer respects that — it doesn't replace play; it gives the play structure and a senior partner the team can lean on when the playing gets serious.

Engagement options

Three ways to start. Pick the pace.

Every option includes the Fractional AI Co-Leader. The tiers differ in how many of the five initiatives we tackle in parallel — and how deep we go on each. All tiers can be cancelled with 30 days' notice, so the commitment is real but not rigid.

OPTION · 01 · Foundation

Co-Leader + AI Activation

The activation layer every other option is built on
$2,497/ month
3-month minimum commitment · month-to-month after
  • 1:1 executive AI Co-Leader access — a senior AI partner for each of your four leadership-team executives.
  • Foundational Claude setup across the org — shared Projects, context, skills, and a Claude Design–powered design system.
  • Quarterly AI Exec Program — strategic review aligned to your EOS rocks, plus AI policy & governance scaffolding.
  • Training & office hours — up to 3 structured trainings, plus 2× monthly open office hours.
  • Operational side-projects — recruiting, policy, Claude-as-admin, and other productivity wins as they emerge.
  • AI tool stack guidance — vetted recommendations + partner discount negotiation across major AI platforms.
  • Initiative delivery sits in Options 02 & 03
Best fit when: Leadership wants to build the org's AI capability from the ground up. Many orgs start here and graduate to Options 02 or 03 once the foundation is in place.
Recommended starting point
OPTION · 02 · Active

Co-Leader + 2 initiatives

For: prove the model on two initiatives, then expand
$4,997/ month
6-month engagement · cancel anytime with 30 days' notice
  • Everything in Option 01 — full Co-Leader + AI Activation layer
  • 2 of the 5 initiatives picked at kickoff, delivered to MVP
  • Hands-on design, build, and launch support on the two picked
  • Weekly working session per active initiative
  • Per-initiative scoreboard with monthly progress readouts
  • Quarterly portfolio review to assess what to add or change
Best fit when: Leadership wants real outside lift on the priorities — but doesn't want to take on more EOS rocks than the team can absorb. Recommended picks vary, but the typical starter pair is the highest-ROI quick win (Grant Writing) + the highest-leverage foundational play (Game Academy Data).
OPTION · 03 · Accelerated

Co-Leader + 4 initiatives

For: compress the timeline and run the portfolio in parallel
$7,497/ month
6-month engagement · cancel anytime with 30 days' notice
  • Everything in Option 02 — full Co-Leader + AI Activation layer
  • 4 of the 5 initiatives running in parallel, each to MVP
  • Hands-on delivery across the portfolio
  • Weekly working session per active initiative
  • Cross-initiative integration work (e.g. data engine feeding donor brief)
  • Monthly portfolio readout to leadership + quarterly board-ready summary
  • 5th initiative held for the next 6-month cycle by design
Best fit when: Leadership wants the AI program to land as a coherent portfolio, not a sequence of single-threaded projects. The compounding gains land faster — initiative 3 feeds 2, initiative 5 feeds 4, and the Co-Leader keeps the team's fluency curve ahead of the build.

All three options include: access to the Co-Pilot Innovations leadership team, the Workshop Hub artifacts (this proposal, the AI Opportunity Report, the workshop output), and a 30-day notice cancellation window on Options 02 and 03. Initiative scope, deliverables, and the specific picks within each tier are fixed in a 60-minute kickoff conversation once an option is chosen.

What's next

Three decisions for leadership, in the next two weeks.

This proposal is designed to be actionable inside the leadership team's existing cadence — no committee, no long evaluation cycle. The decisions are small in number, but real in commitment.

DECISION · 01

Pick a starting option.

Option 01 if the team wants to lead with internal muscle-building. Option 02 if leadership wants outside lift on two priorities while preserving EOS rock capacity. Option 03 if the goal is to land the portfolio as a coherent program inside six months. All three include the same Co-Leader base layer.

DECISION · 02

For Options 02 & 03 — name the initiatives.

Pick the 2 (or 4) initiatives to tackle in the first six-month wave. Recommended starter pair if Option 02: Grant Writing Acceleration + Game Academy Data → Insight Engine. Recommended starter set if Option 03: those two plus Major Donor Prospect Engine + Urban Arts 100 / Brand System.

DECISION · 03

Schedule the 60-minute kickoff.

That's where initiative scope, owners, the training calendar, and the office-hours cadence get fixed. From kickoff, the team is operational inside two weeks. The longer the gap between picking an option and the kickoff, the more momentum from the workshop fades — getting this on the calendar is the single most important next step.

Urban Arts · AI Roadmap & Engagement Proposal · Prepared by Daniel Townsend, Co-Pilot Innovations · May 2026
Sourced from the post-workshop debrief and the AI Opportunity Report.