What the board is converging on, what we're not yet talking about

All eight deep dives complete. Each section below summarizes the headline finding, then links to the full document on this issue.

I. CEO synthesis: what we're converging on, and what we're NOT talking about

What the board is converging on

• AI is the unlock. Infra-first, then everything else. Sunny's capacity is the binding constraint until AI absorbs the manual layer.
• Grow/Keep/Kill: Grow = First 50K, Rim to Rim, Calendar, Summit Scholarship. Keep = Trailblazers, See Her Outside, Grit Lit. Kill = nothing.
• Comp follows revenue, not the other way around. Hold the ~$50K surplus as a buffer.
• LOWA is the apex sponsor; Title IX is the next strategic anchor.
• The funnel matters more than reach. Film festival visibility will flood Summit Scholarship; the bridge to GEA Alliance donations is the work.

Ten things we're NOT talking about (and should be)

1. Sunny is the single point of failure — and that's a governance failure, not a scheduling problem. Every brand relationship, the Summit Scholarship reputation, the LOWA boot launch, the Matterhorn film, and the AI buildout sit on one neck. If Sunny is unavailable for 90 days, every program stops. The board has not named this risk, has not authorized a succession plan, and has not funded a deputy. "Content strategist + program manager" is too tactical to fix this. The staffing deep dive adds a harder fact: Sunny's personal income runway ends September 11, 2026 when her OR Leadership Village contract concludes. The board has not been told the founder underwriting this org is herself running out of personal runway.

2. The "$50K surplus" is partly fictional. It exists because Sunny is donating ~$80–110K/yr of executive labor at market value, and because Rachel (content strategist) is on Sunny's personal payroll rather than the org's. Booking a notional ED salary turns the surplus into a structural deficit. The board has been making financial decisions against a reported number that doesn't reflect the true all-in cost.

3. We're stacking a major brand year on unsigned LOWA contracts. TransAlpine, Chamonix/Cosmex, and the Cervino boot launch are all publicly committed at the LOWA sales meeting but none are under contract. LOWA's new US marketing director starts in ~10 days with unknown priorities. If the partnership pivots, a meaningful share of the FY revenue plan disappears. Concentration risk is acknowledged in the notes; no mitigation is on the agenda.

4. We made a "Grow" decision on First 50K without a year-2 ops model. Year 1 stood up by Angie in 2 weeks over the holidays. Year 2 = "expand and potentially festivalize" — and the lead is off-grid during the event. The board said "grow it" without naming who runs it operationally during the founder's absence.

5. Trailblazers "keep" is passive, not decided. The retreat notes themselves say rolling enrollment killed community and deadline-driven marketing. "Keep as-is" + "AI will help" is hopeful, not strategic. Either re-cohortize or shrink the time cost — both are choices, "keep" pretends there's no decision.

6. The board has not been asked to do anything. Marcia floated as a fundraiser host, LOWA-attending board members hinted at, TEW grant is a board connection — but no board member has a written quarterly commitment (relationship, dollars, hours). Boards that aren't asked drift.

7. We don't have a defensible IP/asset position. We rely on Sunny's relationships, sponsor goodwill, and one filmmaker. Photos, footage, interview transcripts — we keep producing high-quality assets we don't archive, license, or compound into a moat. AI buildout could solve this cheaply if scoped now.

8. The Cairn→Summit funnel is a product problem, not a comms problem. The board keeps describing the bridge in terms of messaging (thermometer, "outdoor education" framing, newsletter). The bridge is actually a product: who is the recurring GEA-level giver, what do they get monthly, what's the rung between $5 newsletter signup and $1K Trailblazer? That rung doesn't exist. That's why visitors bounce off the ask.

9. DOI insurance is buried in action items — it belongs at the top. We're running group fundraisers and a Matterhorn expedition with no directors & officers insurance. Growing group events without this is a fiduciary failure, not a chore.

10. No one is staffed for Q1 2027. Everyone is sprinting to October (Matterhorn film, EOFT, year-end giving). The film's success in Q4 means Q1 is when the org breaks under volume — applications, press, sponsor inquiries, donor cultivation. We should be hiring/contracting for January now, while Sunny is still available.

Five more blind spots that warrant a follow-up: - Tax-deductibility limits on adventure experiences (affects what we sell vs. donate) - International donor compliance — 82 countries, no stated position - Board self-assessment cadence — flagged at retreat, never scheduled - Climate/wildfire risk to the event calendar (Grand Canyon, PNW, Alps) - Unfinished legal transition: no binding asset-transfer agreement between TCP and SSF/GEA, fiscal sponsorship under SEE (EIN 95-4116679) never formally terminated, bylaws corrections pending. No one is owning this.

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II. Deep dives

1. SheJumps / Alpine Finishing School partnership

Full doc: Read the deep dive →

Headline: Accept with one structural term, or decline cleanly. Don't accept on the terms as offered.

The default offer is lopsided: a ~$3–4K in-kind slot from SheJumps (FY25 revenue $1.18M, operating at a $173K deficit) in exchange for GEA Alliance's brand association on a marquee program SheJumps owns. That's charity for them, not partnership for us.

The fix: require a warm introduction to Arc'teryx, Nordica, or Ikon Pass as a condition of acceptance. If SheJumps will put that in writing, accept. If not, decline with goodwill. SheJumps is presenting Arc'teryx as their marquee sponsor on the Alpine Finishing School — they can make this intro.

Red flag in the data: SheJumps is running its first operating deficit ($173K in FY25) after three years of surpluses. Their net assets dropped from $422K to $249K in one year. They're in a contraction posture; GEA is in a growth posture. The power dynamics of "they can help us" are murkier than they appear.

More durable deliverable: the doc also includes a reusable 5-criteria GEA Partnership Decision Framework for scoring the next 5+ partnership asks (LOWA pull-throughs, Gore-Tex, Swiss retailer, Deuter expansion) in under 20 minutes each.

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2. Staffing & resourcing

Full doc: Read the deep dive →

Headline: This is a staffing architecture problem, not a headcount problem. And the architecture is held up by Sunny's personal subsidy.

Five things the board hasn't said out loud:

1. Sunny is a functional volunteer at $10–12/hr. MASTER CONTEXT: ~$1,000/mo for 20–30 hrs/week. The "$50K surplus" is only real if Sunny's labor donation and Rachel's personal payroll stay invisible.
2. Sunny's personal income runway ends September 11, 2026. Her OR Leadership Village contract concludes then. No visible replacement income. The board has not been told.
3. GEA has an unfinished legal transition nobody owns. No binding asset-transfer from TCP to GEA; fiscal sponsorship under SEE never terminated in writing; 990 filed under former name; bylaws need correction in a 90-day window. Any new operations hire spends their first 90 days doing archaeology, not building.
4. The 90-day stress test fails across all programs. Angie and Roxy both escalate to Sunny; Alison's TEW Foundation relationship has already moved to Sunny's lap. One unavailability and everything stops.
5. The hire the master context names — and the retreat didn't — is a development lead. Not a content strategist, not a program manager. A fractional or full development lead who frees Sunny for relationship-building is the single highest-ROI hire at this revenue tier.

12-month hire sequence (from the doc): - Month 1–3: Rachel onto org payroll (from Sunny's personal payroll) — highest urgency - Month 3–6: Fractional development lead ($2–3K/mo) - Month 6–9: Summit Scholarship program coordinator (PT) - Month 9–12: Re-scope Angie role with title/comp clarity; evaluate COO/Deputy need against April 2027 deadline

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3. Long-term AI integration risks

Full doc: Read the deep dive →

Headline: "AI makes the cheap, fast, frequent path easier than the careful path. The careful path then stops happening." That's the assessment in one sentence.

The doc argues that PII breach is the least important risk on the list. Three losses compound faster and are harder to reverse:

1. The ED's reversibility instincts. The AI runs faster than Sunny can sanity-check, and the binding-capacity constraint gets worse, not better, the moment AI absorbs her donor voice.
2. Recipient trust that a human cared enough to write. Every nonprofit pitching LOWA and Fjällräven this fall sounds the same. GEA's differentiation has always been the quirk.
3. Discoverability of decisions. The AI's reasoning lives in vendor logs, not board minutes or a 990 narrative GEA controls. That exposure expands silently with every new integration.

Top risks not on the board's radar (beyond PII): - Tool-call privilege creep: connected AI accumulates write scopes (Kit broadcasts, Classy refunds, Drive deletions) faster than humans audit them. Worst single action today: a Kit broadcast to the full donor list — seconds to execute, months to recover trust. - Brand voice homogenization: all outbound eventually sounds identical; differentiation collapses. - Hallucinated facts published under GEA name and sent to LOWA's team. - Vendor lock-in and model deprecation: prompts tuned to Claude 4.7 break on 5.0. - Compounding errors: AI outputs feed AI inputs (newsletter quote → social post → donor email). - Loss of institutional memory: humans stop doing the work AI now does, and the org loses the knowledge of how to do it.

Three guardrails to ship inside 30 days (from the doc): (1) kill-switch protocol for all connected write surfaces; (2) dry-run mode for all bulk communications before send; (3) weekly reversibility audit — one human, 15 min, checking what the AI changed in the last 7 days across all connected surfaces.

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4. Compensation benchmarks (Angie, Sunny ED, Roxy)

Full doc: Read the deep dive →

Headline: The most important number in this analysis is not a salary — it's that the "$50K surplus" is a mirage built on Sunny's labor donation and Rachel's off-books payroll.

Three things the board should do, in order: 1. Move Rachel to org payroll in 90 days. Currently paid by Sunny personally. This is an undisclosed related-party subsidy — a governance problem before it's a comp problem. 2. Establish a "shadow ED salary" now (board-approved, documented in minutes) reflecting Sunny's market rate, even if not paid. This creates a real baseline for future comp conversations and proves comparability data for IRS purposes. 3. Give Angie the first real cash raise when the next revenue milestone lands (suggest $300K threshold). She is the single highest-retention risk by board's own notes.

On Roxy: long-form content writer and growth marketer are different professions. Don't retrain or replace Roxy — augment with a fractional growth marketer (or formalize Rachel's role) and let Roxy own her lane. Spending to convert Roxy into something she's not is a worse bet than paying a specialist.

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5. Sales targets: Calendar + Grit Lit

Full doc: Read the deep dive →

Headline: The board's 500-calendar target is wrong without LOWA. Free international shipping must die. Grit Lit "keep as-is" is structurally the worst choice.

Calendar — three scenarios:

Recommendation: Print 400–450 for standalone. Don't print 500 to chase a vanity number — it costs ~$600 of paper with no structural lever. But aggressively pursue the LOWA co-commission conversation now, while the new US marketing director is still in onboarding. If LOWA bites, reprint at 1,500–2,500.

Kill free international shipping. Switch to shipping-at-cost. Single easiest margin improvement on any product in the portfolio.

Grit Lit — growth math: - 100 subs in 90 days: achievable on existing capacity - 250–300 subs ceiling: realistic on current model (DTC) - 500 subs: only achievable as a B2B2C gift product through sponsor employer programs (LOWA, Fjällräven, Title IX, Deuter HQ) — entirely different motion and staffing - Per the Grit Lit numbers deep dive: once Roxy's labor is properly counted, Grit Lit runs at approximately -$6K/yr, not the "small but net-positive" framing from the retreat. "Keep as-is" is the worst option. Binary choice: grow to 3–5x scale to clear the labor line, OR shrink to a no-recurring-billing donor-thank-you format.

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6. EOFT October visibility prep

Full doc: Read the deep dive →

Headline: Design for email converts, not donors. The biggest lever is the end-credit URL the film sends people to — not the landing page we build.

Four things the board should hear before spending anything on web work:

1. Film viewers are primarily email converts, not donors. A 15-minute festival film realistically yields $3–8K in direct donations. The actual prize is email list growth + brand inbound + scholar candidates. Design for those three first.
2. The audience won't land on a page you control. They'll Google "Summit Scholarship" or "LOWA Cervino" and land on your homepage, LOWA's page, or YouTube. The biggest lever is what the film itself sends them to — an end-credit URL coordinated with the producer — followed by Google Knowledge Panel cleanup. Build that first.
3. "Donations flow up to GEA" is half-baked technically. Today, every donation routes through Summit Scholarship's Donorbox campaign (branded "Summit Scholarship Foundation"). Re-routing to a GEA-branded surface in October requires a platform migration in the worst possible window. And Classy + Kit aren't live yet. Trying to do an EOFT push and a payments/ESP migration in the same window is the most likely way to blow this moment.
4. The STOP-doing list is more valuable than a build list. Pick a surface freeze date (August 15), ship the key moment-capturing changes, then don't touch anything else until December.

Webmaster punch list (top-priority items only): - Coordinate /film landing page URL with producer before Matterhorn departure (July) - Add end-credit URL to contract discussions with film director - Clean up schema.org/Organization legalName (still reads "Summit Scholarship Foundation") - Build /film redirect landing in Squarespace with: film embed or trailer, email capture, single donate CTA, link to application — before September 1 - Install UTM attribution on all film-sourced traffic - Freeze site changes August 15 — nothing else lands until after December

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7. Classy +$50K segmentation plan (by Dec 31)

Full doc: Read the deep dive →

Headline: GEA's year-end giving chronically underperforms. This isn't an acquisition problem. It's a second-ask + closing-rituals problem. The $50K is there.

Key data points from 2,579 transactions (2022–2026): - Lifetime donor base: 1,425 unique donors, $154,821 gross, $144,721 net - Top 10% of donors = 53% of all revenue ($82K) - Year-end (Nov–Dec) has never cleared $6.2K across four full years - GEA pulls 14% of annual revenue in the final 6 weeks — peers pull 25–35% - 2026 H1 already raised $33,987 — almost all of FY2025 — but $21.6K came from one campaign (First 50K Sisterhood) - Tribute/"in honor of" gifts: 73 transactions all-time, 3% of total — deeply underused

The $50K plan (six campaigns, total ~$52K forecast):

Lowest-hanging fruit in order: (1) Recurring payment recovery — automated, fast; (2) Major donor personal re-ask to top 20 lapsed (Sunny has the relationships); (3) LYBUNT sequence — 180 warm donors who gave in 2024 or prior but not 2025.

Compound play: October film festival → November cultivation → December year-end. If the film hits, the sequence already running will capture the conversion. Don't run them as separate campaigns.

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8. Grit Lit numbers

Full doc: Read the deep dive →

Headline: The retreat called Grit Lit "small but net-positive." Once labor is properly counted, it's -$6K/yr. "Keep as-is" is the worst option.

Validated numbers (from retreat + Notion; primary subscriber data unavailable — Roxy's spreadsheet needed for v2):

The decision the retreat avoided: The retreat's "keep as-is" decision was made against a fake P&L (labor as free). The real decision is binary: - Grow to ~180–250 subscribers (3–4x): Grit Lit breaks even on a fully-loaded basis; at 300+ it becomes genuinely profitable. This requires a marketing push and likely a price increase from ~$33 to $38–42. - Shrink to a donor-thank-you format: No subscriptions, no recurring billing. Quarterly curated box sent to top donors as stewardship. Roxy stays, labor cost disappears from the program budget. Side benefit: Grit Lit boxes going to board members is already happening — this formalizes it.

What's missing for a definitive analysis: Roxy's subscriber spreadsheet (cohort by acquisition quarter), Squarespace/Shopify order history, cancel rate. Request this before the next board meeting.

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III. Immediate actions (aggregated from all deep dives)

This week (before Sunny's 10 business days run out)

1. Move Rachel to org payroll. Currently on Sunny's personal payroll. This is a governance issue. (From: staffing, comp)
2. Confirm film end-credit URL with Matterhorn producer — before departure. (From: EOFT)
3. Start major donor re-ask outreach (top 20 lapsed) — doesn't need systems, just Sunny's relationship. (From: Classy)
4. Board vote: shadow ED salary — document Sunny's market-rate comp even if not paid. (From: comp)
5. Get LOA contract in writing — the verbal commitment at the sales meeting is not a contract. (From: meta-synthesis)

Before August 15 (website freeze date)

6. /film landing page live on Summit Scholarship Squarespace. (From: EOFT)
7. schema.org/Organization legalName corrected. (From: EOFT)
8. Grit Lit decision made: grow OR shrink. Pull Roxy's spreadsheet first. (From: Grit Lit numbers)
9. LOWA co-commission calendar conversation — new US marketing director onboards in ~10 days. (From: sales targets)
10. DOI insurance — get quotes, bring to board for vote. (From: meta-synthesis)

Before October (film festival go-live)

11. SheJumps: respond with terms or decline — either is fine; continued deferral is not. (From: SheJumps)
12. Three AI guardrails shipped: kill-switch protocol, dry-run mode on bulk comms, weekly reversibility audit. (From: AI risk)
13. Angie's role clarity and comp milestone documented. (From: staffing, comp)
14. Legal transition completed (TCP→GEA asset transfer, SEE fiscal sponsorship closure, bylaws correction). (From: staffing)
15. Kit + Classy live — critical for October film push; don't attempt EOFT campaign without these. (From: EOFT, Classy)

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All section documents available at . Jump to any deep dive via the links in Section II.