The Leadership Experience · Working Session
Two things to move now: harvest the endowment commitments to reach our $3M goal by next summer, and settle how membership actually gets charged so no one falls through the cracks. Below is the recommendation on each, the plan behind it, and the calls we need to make together.
The bottom line, twice
Endowment: we finished the quiet phase at $2M and announced in April. Now we harvest. The ask is a five-year commitment, so this is about converting verbal interest into documented commitments and closing the last ~$1M to reach $3M by next summer. Year-end is a milestone inside that push, not the finish line.
Membership: stop relying on people to remember the $2,400. Put payment on autopilot with card-on-file, then wrap relationship around it. The open question has been which system runs the autocharge; there's a recommendation below.
They don't compete: membership renews in summer on the July–June cycle; the endowment is an over-and-above, multi-year commitment. One calendar, two clean asks.
Part 1 · Endowment Harvest
From $2M announced to $3M committed by next summer.
The quiet phase did its job: $2M in verbal, five-year commitments, and a public announcement in April. The work now is harvest — turning the momentum and the warm-but-unclosed conversations into documented five-year commitments, and closing the remaining ~$1M to hit the $3M initial goal by next summer. This is a relationship close, not a broadcast. Because the ask is a multi-year commitment rather than a one-time gift, the calendar year-end matters mainly for timing the first annual installment (tax-deductible before December 31) and as a natural milestone to show progress, not as the deadline. The deadline is summer.
The one move that matters most: a board-led ask sprint
Closing the last third of a campaign is personal. Assign every warm prospect to the right person — Bryce, Brian, or a board member with the relationship — and run a focused round of 1:1 asks that convert verbal interest into a signed commitment (a simple five-year intention form). A verbal "yes" isn't in the campaign until it's documented.
Give the room something to rally around: a visible progress marker toward $3M, updated as commitments land. An optional challenge — one lead donor matching new commitments through a date — can accelerate the close, but it's the accelerator, not the engine.
Name every prospect from the quiet phase and since April. Assign each to an owner. Finalize a one-page case and a simple five-year commitment form.
Bryce, Brian, and board make the 1:1 asks. Convert verbal to documented commitments. Line up any December first installments.
Book commitments before year-end; time first-year gifts for the tax deadline. Publish progress toward $3M. GivingTuesday (Dec 1) as a visible checkpoint.
Work the remaining list steadily, monthly progress updates, and steward those who committed so they feel the momentum they're part of.
Close to the $3M goal, celebrate publicly, and set the runway toward the $5M stretch.
The core structure. A five-year commitment with annual installments, documented on a simple intention form.
For annual installments, giving stock avoids capital gains and is often a larger gift than cash. Send transfer instructions early.
Many of our leaders already have donor-advised funds. Make recurring annual grants a one-click ask.
Our donors are builders. A business sale or bonus is a natural time to accelerate or add to a commitment.
For discussion & decisions
Part 2 · Membership Follow-Up
The fix for "people forget" is to remove memory from the equation.
If members are forgetting the $2,400 base, the answer isn't more reminders, it's making payment automatic by default and wrapping relationship around it. Automate the transaction so every human touch can be relational. Here is the system, strongest lever first.
Automate the transaction so every human touch can be relational.
The open question · which system runs the autocharge
We have two jobs to run: recurring membership billing and tracking five-year endowment commitments and their installments. A standalone payment button handles the first but not the second, so the durable answer is one system that does both, keyed to each person.
Alternative — Neon CRM, if a self-serve member portal and native membership auto-renewal are the top priority; it leans more "membership org" out of the box.
Fast interim — Givebutter or Donorbox, if we want autocharge live before choosing a CRM. Both do card-on-file recurring with auto-retry today, cheaply; we'd migrate the records into the CRM later.
Decision criteria to hold any option against: recurring card-on-file with automatic failed-card recovery (non-negotiable), multi-year pledge tracking, ease for a small team, and total cost including processing fees.
For discussion & decisions
How they fit together
One calendar, two engines, no competing asks.
Membership is the accessible, ongoing base, renewed on the July–June cycle in summer. The endowment is the durable anchor, built through five-year commitments toward $3M now and $5M over time. Both roll into the three-leg model we've been building: membership as the growing base, the endowment as the anchor, and sponsorship as the shrinking delta.
The rhythm across the year
Now → next summer: the endowment harvest — personal asks converting verbal interest into documented five-year commitments toward $3M.
December: a milestone within the harvest — book commitments and time first-year installments to the tax deadline.
Summer (July–June renewal): membership renews automatically; one clean renewal-and-upgrade campaign.
All year: automated payment and relational stewardship keep members current and known.
Sources: Givebutter — Recurring Donations · Bloomerang — Membership Software for Nonprofits · SelectHub — Bloomerang vs Neon CRM · GivingTuesday — December 1, 2026