Staffing & resourcing — deep dive with blind spots

TL;DR (90 seconds)

1. The ED is functionally a volunteer at $10–12/hr (master context: ~$1,000/mo for 20–30 hrs/week = ~$10–12/hr effective). Founder underfunding is so deep that the "$50K surplus" the board references is partially fictional — it depends on Sunny's personal labor donation continuing and on Rachel still being paid out of Sunny's pocket rather than the org's. Sunny's own personal income runway ends September 11, 2026 when her OR Leadership Village contract concludes (no visible post-September pipeline). The board has not been told that the founder underwriting the org is herself running out of personal runway.
2. GEA is operating with an unfinished legal transition that nobody is owning. Per the master context: there is no binding asset-transfer agreement between TCP and SSF/GEA; TCP's fiscal sponsorship under SEE (EIN 95-4116679) was never formally terminated in writing; the most recent 990 was filed under the former legal name; bylaws still need correction within a 90-day window; cumulative historical funding figures are unreconciled ($225K vs $185K). This is a binding staffing question because no operations, development, or finance hire will be effective until the legal entity story is clean. The first 90 days of any new hire will be archaeology, not building.
3. GEA does not have a staffing problem. It has a staffing architecture problem. One sub-market founder-ED, two part-time contractors (Angie unsalaried-as-named, Roxy at $1,500/mo restored from a $1,000/mo cut earlier in 2026), one off-books contractor on the founder's personal payroll (Rachel) who also splits time with AWE's for-profit side, and a volunteer board with reduced bandwidth on the chair. That is not a $170K-revenue, $120K-operating nonprofit org chart — it is a personal project with a 501(c)(3) wrapper. The growth plan to $900K requires us to admit that and rebuild from the org-chart up.
4. The 90-day stress test fails on every program if Sunny is gone — including Angie's and Roxy's because both still escalate to Sunny. The 2027 May–August off-grid window is not a scheduling problem; it is the fiduciary deadline. By April 30, 2027 we need a Deputy/COO with signing authority. Separately: Alison's 2026 reduced bandwidth has already moved the TEW Foundation grant relationship onto Sunny's lap (Alison "delegated TEW renewal to Sunny") — so the marquee $30K grant is now subject to the same single-point-of-failure that everything else is.
5. The hire the master context already names — and the retreat did not — is a development lead. "GEA scaling unlock = development hire. Fractional or full. Frees Sunny for storytelling + relationship cultivation. LOWA $40K proves money is there." We are sitting on 2,100 warm Summit Scholarship leads across 82 countries with no CRM owner; the EOFT visibility wave hits in October into the same void. This hire is higher-ROI than any program hire on the table.
6. Angie is the highest-leverage retention risk in the org, ahead of Sunny. Sunny's retention is a question of pace and burnout; Angie's is a question of recognition and ceiling. We can lose Angie to a peer org in 12 months if we don't act this quarter. Retention is not a comp problem in isolation — it's title + autonomy + visibility + comp, in that order. Roxy's retention dynamic is different and the cut-then-restore precedent earlier in 2026 makes it more delicate, not less — see Section 6.
7. The AWE → Shea sale (Jan 1, 2027) creates a permanent conflict-of-interest surface the board has not formally addressed: AWE is core to several GEA programs (logistics, expedition planning), and "if AWE remains core to GEA programming, structural conflict moves from 'Sunny owns both' to 'Sunny's successor profits from Sunny's nonprofit'" — quoted from the master context. This is a governance hire (legal/policy work, not a person) but it belongs on the same list. The rest of this document shows the work behind each of these.

§1Current human + contracted map

This maps who actually does the work, not what the org chart says. Hours are estimates from the retreat materials and observed scope.

Sunny Ströer — Executive Director / Founder

• Compensation (per master context): ~$1,000/mo at 20–30 hrs/week → ~$10–12/hr effective. Title is "Founder & volunteer ED." This is "subsidized through personal labor."
• Personal income runway flag (per master context): Sunny's external income from OR Leadership Village ends September 11, 2026 with no visible post-September pipeline. Sunny is co-owner of Dreamland and has an AWE sale to Shea structured as "$5K + profit share." None of those bridge to a stable founder-ED draw in the near term. The board has not been formally briefed on this constraint.
• Functional scope (estimated, in any given week she is "on"):
• ED governance, board management, fundraising strategy: ~25%
• Brand relationship ownership (LOWA, Fjällräven, Title Nine, Deuter, Gore-Tex routing, Adidas/Terrex, EOFT director): ~25%
• Program oversight + Summit Scholarship final calls: ~15%
• Calendar curation + production: ~10% (this cycle)
• AI infra rollout (personal build): ~10%
• Speaking, content, expedition (Matterhorn): ~10%
• Bookkeeping / finance ops / admin (likely): ~5%
• Capacity reality: ~10 focused biz days near-term then largely off until first week of August; meaningful resumption in fall; late-May through mid-August 2027 off-grid (Strategy session, ED Update). Plus AWE ownership close target Jan 1, 2027 (master context).
• Single-point-of-failure footprint: Every revenue dollar above $50K passes through her. Every named sponsor relationship (LOWA: Ulf Michels SVP Marketing, Kathrin PM, Lesley Christoph outgoing US MD, Christian Bischler likely CEO) is held by her; no internal backup is named.

Angie Lake — Trailblazer Community Manager (functionally Director of Programs)

• Owns: First 50K Sisterhood (stood up end-to-end in 2 weeks); See Her Outside podcast (6+ month episode backlog, ~200 listeners, 0.5–2% conversion); Trailblazers oversight; co-RD of Wild Woman Trail Runs; Outdoor Retailer presence (Aug 19–21, no plan beyond her attending); growing Title Nine touchpoint (separate from Sunny's track, flagged as tension); published author.
• Compensation: Part-time contractor; specific terms not surfaced in master context (gap worth closing).
• Capacity reality: Booked. The retreat noted concern about "retaining Angie long-term as workload and impact grow" (Strategy session). She delivered a year-1 program at a fraction of its potential (could have had 300–400 applicants with proper marketing) — that is a high-output worker being capacity-constrained, not a low-output worker who needs more work.
• Career signal: Builder. Built First 50K from zero. Builders are the most flight-prone class of employee in nonprofits because their work product is recruitable.

Roxanne "Roxy" Dawson — TCP contractor (Content + Operations generalist)

• Owns: Grit Lit logistics (60 subscribers, ~$8K/yr, 20–30% margin); blog writing; website copy; newsletter writing (twice monthly, 400–600 words).
• Compensation (per master context): $1,500/mo, restored March 2026 after an earlier cut to $1,000. Newsletter writing was added to her scope on restoration. The master context flags two retention signals worth weight: "precedent set for transparent restoration if cuts recur" and "direct, human acknowledgment of prior cut preferred over silent restoration."
• Capacity reality: Fully booked given the surface area. The work product is invisible in a way that makes scope inflation easy to miss until she breaks.
• Career signal: Generalist. Generalists in nonprofits become indispensable but unpromoteable — the work expands faster than her title can grow. This is the source of "Roxy becomes the bottleneck" risk, not "Roxy quits."

Rachel Fagiano — Part-time Content & Community Strategist

• Owns: Regular social posting across both brands; bi-weekly AWE newsletters; monthly SSF newsletters; strategic reporting; alumni mentor coordinator (per board roster reference); Summit Scholarship content; Fjällräven Classic videographer ($5K Fjällräven contribution covers this trip); plausible Cervino/Matterhorn film support.
• Reporting (per master context): Split between Shea (AWE GM — for-profit) and Sunny (SSF — nonprofit). This split-reporting itself is a compliance and IP surface not on the board's agenda. The master context also flags an open question Sunny is tracking: "Are Rachel's performance gaps driven by capacity/overwhelm vs. attention/prioritization?" Recently surfaced operational gaps during Sunny's absence: missed IG/FB posts, misconfigured Later auto-post, unaddressed Title Nine newsletter request.
• Compensation status — flag: "Currently paid personally by Sunny" (GEA-74 brief). This is the single most important governance fact in this document. It means:
• Work product IP may not legally belong to GEA.
• Compensation is invisible to the IRS / Form 990 and to the board.
• If Sunny disappears, Rachel's contract disappears with her — and so does the Summit Scholarship storytelling pipeline.
• It implicitly understates GEA's true personnel spend, which means the $50K surplus is partially fictitious.
• Compounded by the split AWE/SSF reporting, this is plausibly a private-inurement question for the IRS if Rachel performs nonprofit work paid through a personal channel that also benefits a for-profit (AWE).

Alison Wright — TCP co-founder / Board Chair / operational volunteer

• Owns: Grit Lit box packing and shipping; legacy face for grantor relationships (especially TEW Foundation, the $30K/yr repeat grant).
• Bandwidth flag (per master context): Reduced 2026 bandwidth (family). Has "delegated TEW renewal to Sunny." Master context: "Identity continuity with legacy funders: TEW's relationship is to 'The Cairn Project' and Alison personally; merger framing risks confusion."
• Single-point-of-failure footprint: TEW grant ($30K). With Alison stepping back and the org renamed, the relationship is now load-bearing on Sunny precisely when Sunny is most over-committed and the founder identity is changing.

Sarah Castle — TCP co-founder (board)

• No operational role surfaced. Status (per master context): a co-founder figure, recorded but quiet in the retreat material we have.

Other board / advisory roles (Lisa, Justine, Noelle Sadler, others)

• Noelle Sadler — board member; "Title Nine ally" per master context.
• Lisa Gilliland — Title Nine ally; offered to attend Fjällräven Classic.
• Other board members visible from retreat materials as engaged participants in strategy and program prioritization. No written quarterly commitments (relationship, dollars, hours) are surfaced. The CEO synthesis already named this; we will not repeat it.
• Possible Stewardship Board exists separately — master context flags "Faye Norby … Possibly same Faye on the Stewardship Board per userMemories — worth confirming." There may be a second governance body not mapped at the retreat.
• One specific gap: nobody on the board is named as the chair of a committee. There is no Finance Committee, Governance Committee, or Development Committee surfaced. For a nonprofit at our revenue tier, that is a structural omission, not a stylistic one.

Operating partners (Wild Women Trail Marathons, All Expeditions, Upwards Transitions, She Moves Mountains, Mahua Collective)

• Treated as: mission multipliers, story partners.
• Actually functioning as: unsupervised vendors holding the program-delivery surface area. No contracts, no SLAs, no documented insurance verification, no quality control on what their guides do with our scholarship recipients in the field.
• Founder-conflict layer: Sunny is transitioning out of All Expeditions by January 2027 to Shea ($5K + profit share). After that close, if AWE remains core to GEA programming — and several Summit Scholarship expedition logistics depend on it — the structural conflict moves from "Sunny owns both" to "Sunny's successor profits from Sunny's nonprofit." This needs an arm's-length structure in writing before the close, not after.
• Ines Papert — 4× Ice Climbing World Champion, LOWA athlete — is named in the master context as Matterhorn co-leader/mentor. She is the only named ground leader in the entire material. With the Matterhorn program being replaced by Cosmiques (Chamonix) in 2027 per master context, no successor leader has been identified for the replacement program. That is a hire / partnership decision the board needs to make before LOWA's commercial calendar drives it for us.

Volunteer ground leaders (Rim to Rim, Grand Canyon, future Cactus to Clouds, Timberline Trail)

• Owns: Live participant safety on multi-day backcountry events.
• Compensation: Unpaid (and must be unpaid — Grand Canyon will not permit commercial guiding, only unpaid leaders for groups under 11, per ED Update).
• Training, screening, waivers, insurance verification: Not surfaced in retreat materials. Assume not formalized.
• Liability reality: The combination of (a) unpaid amateur leaders, (b) strangers grouped together, (c) high-consequence terrain, (d) no DOI insurance, and (e) no documented training program is the single highest-magnitude liability vector in the org. This deserves equal treatment with DOI in the board's risk register.

The "unowned" column (no human in any role)

This is the most important part of the map. The following functions have no owner today:

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§2The 90-day stress test

For each person, what stops if they are unavailable for 90 days?

Sunny gone 90 days (the May–Aug 2027 expedition)

Catastrophic absent intervention. Specifically: - All sponsor account relationships freeze. LOWA's new US marketing director (starts 10 days from the retreat) will have no consistent counterpart. The Cervino boot launch and TransAlpine trek (June–July 2027 — overlap is exact) will need a delegated decision-maker with sign-off authority on financial terms. - The Cairn → Summit Scholarship → GEA donor funnel goes dark right when EOFT amplification is still fresh. - Sunny is the named Summit Scholarship representative for the TransAlpine trek — by definition she cannot be that representative. "Ambassador or expedition partner" was floated (Strategy session); that is a person we have not yet identified. - Bookkeeping/finance close stops unless explicitly delegated. - AI tooling rollout halts. - Board decisions requiring ED input stall — and there is no Deputy ED to receive the delegation.

Mitigation must be in place by April 30, 2027. That is the binding date for the Deputy/COO hire.

Angie gone 90 days

• First 50K year-2 stops. There is no other person who knows the application pipeline, the selection criteria, or the sponsor relationships specific to the program.
• See Her Outside podcast stops releasing (mitigated only by the 6-month episode backlog, which is a real cushion — the only one in the org).
• Title IX relationship goes cold; the "separate conversations" tension flagged at the retreat becomes an unmanaged risk.
• Outdoor Retailer presence collapses.

Roxy gone 90 days

• Newsletter stops (this is the bridge for the EOFT visibility wave).
• Blog stops.
• Grit Lit fulfillment stops; subscribers churn.
• Website maintenance lapses.
• Roxy's absence is the most quietly catastrophic, because the work product is least visible to the board until it stops.

Rachel gone 90 days

• Summit Scholarship content pipeline stops.
• Fjällräven videography ($5K commitment) at risk of non-delivery.
• Cervino/Matterhorn film support undermined.
• The IP question of "what content already exists, who owns it, where is it stored" becomes urgent rather than theoretical.

Alison gone 90 days

• Grit Lit packing falls to whoever is available — Roxy presumably, expanding her scope further (and Roxy just had a comp cut/restore cycle, so unilaterally adding scope here is exactly the wrong move).
• Board chair / governance functions she carries out become uncovered.
• The TEW $30K relationship is at risk specifically because TEW knows "The Cairn Project" and "Alison personally." Alison's reduced 2026 bandwidth has already partially triggered this stress test — Alison delegated the TEW renewal to Sunny. A 90-day absence would compound the identity-transition risk and the founder-bandwidth risk simultaneously.

Any single other board member gone 90 days

• The TEW grant relationship showed how concentrated those relationships are. The org has no documented "who else can warm-introduce to TEW" backup.
• No succession pipeline for board roles means a single resignation is unrecoverable in the 90-day window.

What this stress test is really telling us

Every person on this list shows up as a single point of failure. That is the diagnostic. A healthy nonprofit at our revenue tier should have 2-deep coverage on at least the top three critical workflows (program delivery, donor management, financial close). We currently have 1-deep on all three, plus 0-deep on most everything else.

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§3Resourcing vs the FY26 → FY30 growth plan

The growth plan is $170K → $900K over 4 years. What follows assumes a roughly linear ramp ($170K → ~$300K → ~$500K → ~$700K → $900K).

Industry benchmark grounding

• Well-run small US nonprofits typically spend 55–70% of revenue on personnel (salaries + benefits + payroll taxes + contractor fees). Outdoor/youth-services nonprofits cluster on the higher end.
• Nonprofits that try to ramp revenue without proportional personnel investment hit a ceiling around 1.5× their last "comfortable" revenue level and then stall — the literature on this is consistent across the BoardSource and CEP studies.
• GEA today (per master context): Operating budget ~$120K. Recorded personnel cost in the visible categories: Sunny ~$12K/yr at the $1,000/mo "volunteer ED" rate; Roxy $1,500/mo = $18K/yr; Angie undisclosed; Rachel paid through Sunny personally so $0 on GEA's books. Recorded personnel ≈ $30–45K against $120K operating budget (25–38%). Add Rachel and a market-rate adjustment for Sunny and the real personnel cost is closer to $90–120K (75–100%) — but most of that is hidden because the founder is donating labor. The implication: GEA is under-paying by industry standard, but the financial picture the board sees is artificially favorable because the founder underwrites the gap from personal income. That subsidy is now constrained by Sunny's own September 11, 2026 income cliff.

Tiered staffing model

FY26 — $170K (today)

• 1 FT founder (under-comped), 2 PT contractors (Angie, Roxy), 1 off-books contractor (Rachel), volunteer board, volunteer ground leaders, unmanaged operating partners.
• This works exactly for $170K. It does not work for $300K.

FY27 — ~$300K (next year, partial revenue lift from EOFT visibility, LOWA contracted programs)

Required additions (must, not nice): - Operations Manager / Chief of Staff — the role that holds Sunny's absence together and that runs the back office (contracts, payroll, calendars, vendor management). - Rachel formalized onto GEA payroll as Content Strategist or Storytelling Lead. (This is a governance fix, not a comp question.) - Bookkeeper / monthly close. Outsource (Bench/Pilot/local CPA) before in-house. - Insurance broker engaged; DOI + event GL + international medical bound. - Angie's role formalized as Director of Programs; same scope, real title. - Roxy's role decided as Content lead or Operations generalist (see Section 6); cannot remain both past ~$400K.

FY28 — ~$500K

Required additions: - Director of Programs if Angie has stepped up into a senior role and we now need a deputy under her (or, if we keep Angie at her current scope, hire a separate Summit Scholarship program manager — Sunny named this as a priority). - Development / CRM Director owning donor cultivation, grant writing, sponsor renewals. This person pays for themselves at this tier — every dollar spent here should return $4–6. - Marketing / Comms coordinator (likely PT or contractor). - AI tooling owner / part-time technologist — can be contracted, ~$15–25K/yr.

FY29 — ~$700K

Required additions: - Deputy ED / COO as a permanent role (not just absence-coverage). - Finance Manager (in-house, replacing or augmenting bookkeeping). - Second program manager if First 50K + Rim to Rim + Calendar all scaled. - International ops contractor (Europe-based, focused on TransAlpine / LOA / Chamonix / Title IX EU activations).

FY30 — $900K

• Communications Director (FT).
• Sunny transitions to outward-facing role (sponsors, board, vision); Deputy ED runs internal ops.
• Founder-succession plan should be in writing by this point.

What this implies for FY26 budget

If we want to hit $300K in FY27, we need to authorize the FY27 additions during FY26. Even at modest part-time/contractor terms:

FY27 new annual cost ≈ $70K–$135K depending on how we sequence and how heavy we go on the Operations role. Against expected revenue of ~$300K, that puts us at a healthier 50–55% personnel ratio when combined with current spend. We have the $50K cash surplus to absorb the front-loaded portion in Q3–Q4 FY26 before FY27 revenue lifts.

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§4Blind spots the board has not named

The CEO synthesis on GEA-71 named several big-picture blind spots (Sunny as SPOF, LOWA contract risk, First 50K year-2 ops, Trailblazers passive vote, no board commitment matrix, no IP moat, Cairn→Summit as a product problem, no partnership framework, DOI buried, no Q1 2027 plan). Those are correct and we do not repeat them.

The following are staffing-specific blind spots that did not come up at the retreat:

B1. Rachel is on Sunny's personal payroll. That is a governance and IP failure, not a comp question.

Three problems live inside this fact: - IP ownership — Without a written contractor agreement to GEA, the work-for-hire doctrine does not automatically transfer. Rachel may legally own her content; GEA may not be able to license it for the EOFT film, for Cervino, or for any future use. - Reported financials are inaccurate. The $50K surplus we keep referencing assumes Rachel costs $0 on GEA's books. Whatever Rachel actually costs is the "true" surplus — and the board has never seen that number. - Sunny carries personal financial risk for a worker performing GEA functions. If something goes sideways (Rachel claims employee status, gets injured on a shoot, mis-files taxes), Sunny is the legally responsible party, not the org.

Fix: Move Rachel to a GEA contractor agreement by August 31, 2026 with IP assignment language and a defined scope. Sunny stops the personal payments same day.

B2. Operating partners are mission multipliers in pitch, vendors in practice. We control neither.

The retreat lists Wild Women Trail Marathons, All Expeditions, Upwards Transitions, She Moves Mountains, Mahua Collective as critical partners. The board has never seen the contracts for any of these relationships — because in most cases there isn't one. We have no quality standards for what happens to a Summit Scholarship recipient on a partner trip; no insurance verification; no incident reporting obligation. And Sunny is transitioning out of All Expeditions in January, dissolving the implicit warranty that flowed through her personal involvement.

Fix: Adopt a one-page Operating Partner Agreement template; require it of every partner running a program with a GEA-funded participant. Build it in Q4 2026 and roll out before the spring 2027 season.

B3. Volunteer ground leaders are unmanaged labor with the highest single liability vector in the org.

DOI insurance covers officers and directors. It does not cover what happens when a volunteer leader takes 10 strangers into the canyon and someone falls. The retreat treated this as Grand Canyon permitting trivia. It is not — it is a "one incident and we are sued out of existence" risk. There is no documented: - training program for volunteer leaders - screening / background check process - waiver and assumption-of-risk language reviewed by counsel - incident reporting / debrief protocol - general liability insurance with volunteer-act coverage

Fix: Treat this as a tier-1 risk in the same workstream as DOI. The Operations Manager hire should own it as a first 90-day deliverable. Estimated cost: $3–8K for legal review + training program; $4–8K/yr GL premium with volunteer-act endorsement.

B4. We have no grants function.

TEW Foundation gave $30K. That came from a board relationship, not a process. As we scale, foundation revenue is the most leverage-able revenue category we have — well-suited to a part-time grants writer working on commission or retainer. We could plausibly add $50–150K/yr in foundation revenue within 18 months with one good hire here, and we are not even surfacing the role.

Fix: Hire a grants contractor by Q1 2027. Commission-only structure to start (5–10% of awarded grants) limits downside.

B5. We have 2,100 warm leads and no one to cultivate them.

This is the highest-ROI staffing omission in the document. 2,100 self-identified Summit Scholarship applicants across 82 countries is a list any peer org would invest a full-time development hire to nurture. We have no segmentation, no email nurture sequence, no annual giving funnel, no major gifts pipeline. The film festival surge in October will hit the same void.

Fix: Development/CRM Director is the second hire after Operations Manager. PT to start, $25–40K. Pays for itself in <12 months if the org takes donor cultivation seriously.

B6. Founder-brand tax: sponsors are buying Sunny, not GEA.

LOWA's Matterhorn film is built around Sunny. The German-language keynote was Sunny. The Marco-and-EOFT-director conversation was Sunny. The Adventure of the Year nomination was Sunny. A successor with the right title and salary will not inherit any of these relationships unless that successor is also a recognizable public figure in the women's outdoor space — and growing that successor takes 2–3 years. The board has not started this work and there is no candidate. This is a different succession problem from "who runs ops if Sunny is on Matterhorn" — it is "who closes a six-figure sponsorship deal if Sunny steps back in 2030."

Fix: This is a 3-year project. It starts with a Deputy ED hire whose job description explicitly includes external visibility — speaking, writing, attending sponsor events alongside Sunny. Budget for that visibility (travel, conferences, content production) is part of the comp package.

B7. Contractor classification risk.

Angie, Roxy, and Rachel are likely all 1099 contractors. As we direct their hours more, set their schedules more, and integrate them more into core operations, we move closer to the IRS's "common-law employee" test. The risk isn't an audit in year 1 — it's that we hit a milestone in FY28 or FY29 and discover we owe back payroll taxes on three years of compensation. This is also the kind of thing a future foundation funder or an insurance underwriter asks about during due diligence and we don't have a story.

Fix: Adopt a written contractor policy by Q3 2026. Either commit to keeping them 1099 (with the constraints that implies) or move them to W-2. Don't drift.

B8. There is no internal AI tooling owner — and "Sunny rolls it out personally" is a year-1 plan, not a 4-year plan.

The retreat correctly framed AI as the unlock. It then assigned the rollout to the binding capacity constraint in the org. By 2027 when Sunny is off-grid, the AI infrastructure either works without her or it doesn't. The internal AI owner role (could be a contracted technologist, could be a hire) is what carries the AI plan past month 6. It is also the role that trains Angie and Roxy so AI literacy becomes organizational, not personal.

Fix: $15–25K/yr contractor by Q4 2026. Scope: own integrations, train staff, document workflows.

B9. Operational knowledge lives in Sunny's head and inbox.

There is no documented sponsor history, brand contact list, program runbook library, or vendor list. A new Operations Manager joining in Q4 2026 will spend their first 60 days excavating institutional knowledge from email threads. The cost of this is invisible — every onboarding day spent on excavation is a day not spent shipping.

Fix: First deliverable for the Operations Manager: a single internal wiki with sponsor history, contacts, runbooks, vendor list, contract repository. Budget: included in the role.

B10. No HR / employment agreement function.

No written agreements with Angie/Roxy/Rachel have been surfaced. If any of them leave under bad circumstances — non-compete, non-solicit, return of materials, IP — we have no documents to lean on. This is also a foundation/sponsor due-diligence question.

Fix: Adopt boilerplate contractor agreements (~$1–2K with counsel) by end of Q3 2026. Re-paper existing relationships in Q4 2026.

B11. International operations have no owner.

Summit Scholarship is 82-country reach. LOWA wants a TransAlpine trek and a Chamonix/Cosmex climbing component. Fjällräven's brand sits in Sweden. The Matterhorn film is Swiss/German. Today this is all Sunny operating across timezones with no localized support. By FY29 this needs a Europe-based contractor or a small EU entity. By FY28 it needs a defined owner.

Fix: Note this in the 12-month plan as a Q4 2027 hire, not Q4 2026 — but flag it now so the board makes the legal/tax-entity decision (US-only vs EU presence) by mid-2027.

B12. Storytelling IP rights have no rights owner.

The film, the photo archive, the calendar imagery, the interview transcripts — they are not catalogued, the rights are not centralized, and there is no licensing strategy. This is plausibly a 6-figure asset class earning $0 today. Even modest catalog discipline (a Dropbox structure, a release-form template, a usage log) unlocks future revenue.

Fix: Operations Manager owns the catalog discipline. Licensing strategy waits for FY28.

B13. Insurance is a function, not a chore.

DOI is the bare minimum. We also need: general liability with volunteer-act coverage; event insurance for group fundraisers; international medical/evacuation for Summit Scholarship trips; cyber liability when we centralize donor data; potentially professional liability if guides or therapists are involved. A broker relationship — not a one-time quote — is the right structure.

Fix: Hire a broker by August 31, 2026. Annual review thereafter. Budget: $1.5–4K in fees, $8–15K/yr premiums depending on coverage.

B14. Board recruitment pipeline does not exist.

Small board, no committees, no nominating function, no pipeline. One resignation and we are scrambling. The retreat materials surface this only obliquely (Alison's "board self-assessment" note in the CEO synthesis).

Fix: Stand up a Governance Committee in Q3 2026 with explicit responsibility for recruitment pipeline, annual self-assessment, and committee structure.

B15. Founder self-undercompensation is a future hiring constraint, not just a personal sacrifice.

Sunny pays Rachel out of pocket and takes ~$1,000/mo (effectively $10–12/hr) for an ED role. This feels noble and prudent. It is also setting the future salary for her successor — every grant application, every Form 990, every comp benchmarking exercise will reference her current compensation. When the org needs to hire a $90–130K market-rate ED in three years, that will look like a 700%+ raise to the board and to funders. Sunny should normalize her own compensation to market for the role she actually performs, now, even if she elects to donate the delta back to the org. This preserves future flexibility and improves financial transparency.

Fix: Set a market-rate ED salary at the FY27 budget review ($75–110K for a $300K-revenue founder-ED is defensible; see Section 5). If Sunny wants to take less, frame it as a board-approved discount that can be removed in the future without a "raise" event.

B16. The TCP → GEA legal transition is unfinished and nobody owns closing it.

Per the master context, four open legal items: - No binding asset transfer agreement exists between TCP and SSF/GEA — described in source as "the most significant outstanding gap." - TCP's fiscal sponsorship under SEE (EIN 95-4116679) was never formally terminated in writing. - The most recent 990 was filed under the former legal name. - Bylaws still need correction within a 90-day window.

This is a staffing question because no Operations Manager or Development Director can effectively operate (sign contracts, run grant applications, file 990s, take payments under the right entity) until those four items close. Any hire's first 90 days will be archaeology rather than building unless legal cleanup precedes them.

Fix: Engage nonprofit counsel by August 15, 2026 to scope a closing project; target completion of all four items by November 30, 2026 before the Operations Manager + Development Director hires ramp into FY27. Budget: $5–12K legal fees.

B17. Historical cumulative funding figures are unreconciled ($225K vs $185K).

The master context surfaces an unresolved discrepancy in cumulative funding figures, flagged "must reconcile before external use" (e.g., for the .ORG Impact Awards 2026 entry). Any sponsor or foundation due-diligence in 2027 hits this gap. A finance / bookkeeping function — even outsourced — is what fixes it. This is part of why the bookkeeper hire is a must, not a nice.

B18. AWE's January 2027 sale to Shea creates a permanent conflict-of-interest surface.

AWE is the operational backbone for several Summit Scholarship trips. After the January 2027 close, every dollar of program logistics flowing through AWE is potentially Sunny's family receiving payment from the nonprofit Sunny leads — and after a successor ED, Sunny's successor paying a former founder's family business. The board has not addressed this in writing. The cleanest answer is a written arm's-length structure (procurement policy, conflict-of-interest disclosures, board approval for any AWE contract over $X) before the close, not after.

Fix: Conflict-of-interest policy + arm's-length procurement policy adopted by December 31, 2026. Any AWE engagement after Jan 1, 2027 follows the policy.

B19. There may be a separate Stewardship Board that is not mapped.

The master context flags "Faye Norby … Possibly same Faye on the Stewardship Board per userMemories — worth confirming." If there is a second governance body (advisory board, stewardship board, donor board), the staffing analysis needs to factor it in. If there isn't, this is a useful name to disambiguate. Either way: before any board-recruitment work begins, clarify how many governance bodies the org has and who sits on each.

B20. Ines Papert is the only named ground-leader, and the program she anchors is being sunset.

LOWA's 2027 plan replaces the Matterhorn flagship with a Cosmiques scholarship (Chamonix-based). Ines Papert anchored Matterhorn. No successor leader is named for Cosmiques. This is also true of the Cactus to Clouds and Timberline Trail events the retreat floated — the conversation discussed whether to run them, not who runs them on the mountain. Ground-leader sourcing is its own function and needs a named owner (Director of Programs is the right fit, post-promotion).

B21. Sunny's own income runway ends September 11, 2026.

Per the master context, the OR Leadership Village contract ends September 11, 2026 with no visible post-September pipeline. Combined with the AWE sale closing on Jan 1, 2027 (one-time $5K + profit share) and Sunny's Dreamland co-ownership, the founder's ability to keep underwriting the org through unpaid labor will be materially constrained from Q4 2026 onward. The board needs this fact on the table — it changes both the urgency of the development hire (revenue must lift) and the urgency of normalizing Sunny's comp (she cannot continue the subsidy). This is the connective tissue between every other blind spot in this list.

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§512-month hire / contract sequence with cost bands

Sequenced by tightest binding constraint, not by org-chart ideal. Must-hire items are listed with no fallback; nice-to-hire items are listed but can slip.

Q3 FY26 (Jul–Sep 2026) — close out unfinished governance first

Q3 must-hire/must-do total: ~$80–135K annualized + $10–25K one-time legal/reconciliation. Most are formalize/governance actions with low recurring cash impact; only the Operations Manager and Rachel formalization carry real new payroll cost.

Q4 FY26 (Oct–Dec 2026)

Q1 FY27 (Jan–Mar 2027)

Q2 FY27 (Apr–Jun 2027) — the binding period before Sunny goes off-grid

12-month summary

Plotted against expected revenue: at the must-hire ceiling (~$235K added on top of current ~$30–50K personnel base), total personnel runs ~$265–285K. Against $300K FY27 revenue that is 88–95% — too hot. Sequence the must-hires against revenue events: Operations Manager + Rachel + bookkeeper + insurance in Q3 (tightest binding); Development Director after the EOFT amplification shows real fundraising lift (target Q4 confirmation, hire Q1); Deputy ED only after FY27 Q1–Q2 revenue confirms ~$300K trajectory.

Practical framing for the board: commit dollars to Q3 must-hires now; gate Q4 / Q1 / Q2 hires to revenue milestones. This is risk-adjusted scaling, not a wishlist.

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§6Retention strategy for Angie and Roxy

Angie — highest-leverage retention move in the org

Angie built a program from zero in 2 weeks and delivered it under-marketed. She is the most poachable person in the org because her work product is recruitable. Comp is necessary but not sufficient. The order of operations matters:

1. Title — by Aug 31, 2026. Promote to Director of Programs before another org puts a Director title in front of her. Title is cheap; titles you don't give become reasons to leave.
2. Autonomy — by Oct 31, 2026. Authorize her to make First 50K year-2 hire decisions and contract decisions up to a defined budget ceiling (e.g., $10K per decision). Builders need ownership; clipping it is the fastest way to lose them.
3. Visibility — across FY27. Sponsor one major speaking slot per year (Outdoor Retailer panel, a podcast appearance on a peer-org show, a keynote at a sponsor event). Pay for travel and prep time. Visibility builds her career with GEA, not in spite of it.
4. Compensation — at the FY27 budget review. Annual base + revenue-linked bonus tied to First 50K participation count and total fundraising raised. Floor that's defensible to her network; ceiling that scales with the program. Order: title first, autonomy second, then dollars — flip the order and the dollars feel transactional.
5. Development budget — $1.5–3K/yr. Allows a nonprofit management cert (a tangible career artifact), a conference, or AI literacy training. This is small money that signals long-term investment.
6. 3-year commitment ask — paired with all of the above. The conversation should be: "We're investing in your career as a 3-year horizon, here's the package, are you in?" That conversation is owed to her by Sept 30, 2026.

What we explicitly do not do: treat retention as a comp question alone. The retreat materials lean toward "compensation should follow revenue growth." That's correct as policy, but Angie will not wait for revenue to compound. Title and autonomy can move now without breaking the budget — and they are what builders actually leave for.

Roxy — the bottleneck risk, with a fresh comp-trust scar

Roxy is unlikely to quit. She is likely to silently absorb scope until something breaks. The retention problem is a role-clarity problem layered on top of a comp-trust problem. The master context flags two specifics worth weight: - Earlier in 2026 her comp was cut from $1,500/mo to $1,000/mo, then restored in March 2026 — with newsletter writing added to her scope on restoration. The cut and the scope add happened within months of each other. - Retention learnings from that cycle, per master context: "precedent set for transparent restoration if cuts recur" and "direct, human acknowledgment of prior cut preferred over silent restoration."

What this means for retention strategy:

1. Acknowledge the 2026 cut explicitly in the next 1:1. Not as an apology, as a context-setting. Roxy already lived through one comp move; the next conversation about scope or comp needs to land with her knowing it is not the same dynamic.
2. Decide her role by Sept 30, 2026. Two options: - Path A — Content Lead. Owns blog + newsletter + long-form storytelling. Grit Lit fulfillment moves under the Operations Manager. Roxy reports up through a future Marketing Director (or interim through Sunny / Deputy ED). - Path B — Operations generalist → Operations Manager track. Owns the back office. Content gets handed to Rachel + a new Marketing/Comms coordinator. Roxy reports up through Deputy ED. - Either is fine. Both is not — that path leads to a burnout exit in 12–18 months.
3. If we add scope, add comp. The 2026 precedent — restored to $1,500/mo with new newsletter scope — implicitly told her that scope additions ride along with comp restorations rather than triggering new comp. We should not repeat that pattern. If Path A or Path B adds scope materially, comp moves with it as a separate, named event.
4. Title to match the path. "Content Lead" or "Operations Manager" — written, formal, in the next board pack.
5. Comp at the FY27 budget review. Tied to revenue similar to Angie's structure. Floor + scope bonus. Realistic band: $24K → $36K/yr depending on path and scope clarity.
6. Same development budget structure. Same visibility opportunity (a guest essay, podcast appearance, conference attendance).
7. Off-ramp Grit Lit fulfillment from her plate if Path A. Alison's box-packing role plus paid help during peak seasons is a defensible model — but mind Alison's reduced 2026 bandwidth (B above); cannot lean on her for additional ops.

A reminder about retention math

The cost to replace a contractor-level program lead at a peer org is conservatively 30–50% of their annual comp in lost time, hiring fees, and onboarding drag. For Angie, that is plausibly $15–30K in soft cost plus 4–6 months of program decay. A $5K title + $8K comp lift + $1.5K development budget is cheap insurance. The board should approve all three for both Angie and Roxy as a package, not as separate line items.

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§7What the board should commit to (this quarter)

Each item below is binary — yes or no — with a date. The point is to convert open conversations from the retreat into decisions on the record.

1. Close the TCP → GEA legal transition project by Nov 30, 2026 — asset transfer agreement; SEE fiscal sponsorship formally terminated in writing; 990 amendment filed under correct legal name; bylaws correction within the 90-day window. Owner: Board chair + ED + nonprofit counsel.
2. Reconcile cumulative funding figures ($225K vs $185K) by Oct 31, 2026 before any external use including the .ORG Impact Awards 2026 entry. Owner: ED + new bookkeeper.
3. Authorize a Deputy / COO budget envelope of $80–135K annual (FT equivalent; PT can scale) by Sep 30, 2026, with the hire to be made no later than April 30, 2027. Owner: ED + Governance Committee.
4. Move Rachel to GEA payroll by Aug 31, 2026, with a signed contractor agreement and IP-assignment language. Disambiguate her AWE vs SSF reporting at the same time (separate engagement letters; private-inurement exposure addressed). Owner: ED + bookkeeper + counsel.
5. Adopt a contractor → employee classification policy by Sep 30, 2026. Decide for each of Angie / Roxy / Rachel: stay 1099, with what guardrails, or move to W-2 in FY27. Owner: ED + Treasurer.
6. Bind DOI insurance by Aug 31, 2026. Pair it with a general liability + volunteer-act endorsement quote by Oct 31, 2026. Owner: Board chair + new insurance broker.
7. Adopt a conflict-of-interest + arm's-length procurement policy by Dec 31, 2026 ahead of the AWE → Shea Jan 1, 2027 close. Owner: Board chair + ED + counsel.
8. Approve a 3-year retention package for Angie by Sep 30, 2026 — title, comp ladder, autonomy budget, development budget. Owner: ED + Compensation discussion at the board.
9. Decide Roxy's role (Content lead vs Operations) by Sep 30, 2026 with a 90-day transition plan; pair any scope add with a comp event named separately. Owner: ED.
10. Approve an Operating Partner Agreement template and rollout by Oct 31, 2026, covering at minimum: insurance verification, incident reporting, brand standards, IP sharing, termination terms. Owner: Operations Manager (once hired) + ED.
11. Stand up a Governance Committee in Q3 2026 with responsibility for: board recruitment pipeline, annual self-assessment, committee structure, succession planning. First task: confirm whether a separate Stewardship Board exists and map it. Owner: Board chair to name.
12. Adopt a personnel budget ceiling (e.g., 55–65% of revenue) at the FY27 budget review, replacing the current ad hoc framing. Owner: Treasurer + ED.
13. Add a written quarterly commitment for each board member — one relationship cultivated, one $ ask made, one volume of hours committed — by Sep 30, 2026. Owner: Board chair (the CEO synthesis on GEA-71 flagged the same gap; this is the operational form of that commitment).
14. Normalize Sunny's ED compensation to market at the FY27 budget review (target: $75–110K salary equivalent for the role; recorded with a board-approved discount if Sunny elects to take less). Acknowledge the September 11, 2026 personal-income runway constraint in that conversation. Owner: Compensation discussion.
15. Approve a volunteer ground leader liability program (waivers, training, insurance endorsement) by Dec 31, 2026, plus a named successor leader for the LOWA Cosmiques scholarship before LOWA's commercial calendar drives the decision. Owner: Operations Manager + insurance broker + ED.

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SourcesSources

• ED Update — GIA Alliance Board Retreat / Executive Director Update Notion meeting note (the page titled "Meeting [date 2026-06-19 12:37 PM PDT]").
• Strategy session — "Where we're going" Notion page.
• Vision session — "GEA vision session" Notion page.
• CEO synthesis — GEA-71 (board retreat meta-analysis hub document).
• Task brief — GEA-74.