alongsideAI
alongsideAI
alongsideAI
You shared where things get stuck. We read everything carefully. What follows is a plan written for you — not a template — and yours to keep whether you decide to continue or not.
We don't sell software, and we don't make anything on the side from any of the tools we recommend. That means we only suggest things we'd use ourselves, and only when the math clearly works for you. If a recommendation below doesn't feel right, say so — we'll happily rework it.
Everything here is a suggestion, not a commitment. You can do all of it, some of it, or none of it.
Not problems — just observations. If we got anything wrong, tell us and we'll fix it before going further.
You're the director of development at a Pasadena arts nonprofit with a team of three. Fundraising, events, the board, donor stewardship — it all flows through you. Your husband jokes that you work two full-time jobs and call it one.
Your inbox is the boss. On a good morning there are 180 unread; on a bad one, over 400. You triage by guilt. Important donor replies sit next to calendar invites next to vendor quotes.
Board decks get built the night before. The annual report took forty hours of evenings last spring. Thank-you letters to donors are personal — which is why they keep falling behind.
You're on Google Workspace (nonprofit discount), pay for ChatGPT but "don't really use it," keep files in Dropbox, and sign everything in DocuSign. Calendar is a scheduling nightmare — you spend a meaningful chunk of each week arranging donor meetings.
You're good at this job. The donors love you. The board trusts you. The question isn't whether you can keep doing it — it's whether there's a version where the job stops bleeding into your evenings.
Everything below passed three tests: the company is well-funded and unlikely to disappear in the next year; the security posture is enterprise-grade (SOC 2, encryption, clear data handling); and the capability genuinely fits what you told us — not a generic "AI for work" pitch.
We looked at twenty-plus products in your space. What's here is the short list that survived. You'll see a few we considered and cut in the footnote at the end.
Two groups. Foundation tools are the plumbing — email, calendar, files. AI tools are where the biggest time savings come from. Each has a plain-English explanation of what it is and why we're suggesting it for you specifically.
What it is: A faster email app that uses your existing Gmail underneath. It writes replies in your voice, summarizes long threads in one line, and sorts your inbox so the ten things that matter rise to the top and the rest goes quiet.
Why it helps you: You said the inbox is the boss, that you triage by guilt, that 400 unread by Friday is normal. Superhuman replaces that grind with a 15-minute morning pass. It drafts responses in your tone so the donor thank-yous and board follow-ups stop sitting in "I'll write that tomorrow." SOC II compliant — safe for donor communications.
What it is: A calendar assistant that shares a booking link with donors (they pick a time, the meeting appears on both calendars), defends your focus blocks for writing, and reshuffles your week when a board chair reschedules.
Why it helps you: The 5–8 emails per donor coffee collapse to one link. And those hour-and-a-half writing blocks for the annual report? Reclaim puts them on the calendar on purpose, so they stop getting eaten by drop-in meetings. We'd set up two booking links: one for donors (flexible), one for vendors (15-minute slots only).
What it is: The file storage you already use — but reorganized so finding a past grant narrative or donor profile takes seconds, not minutes.
Why it helps you: The content is all there. It's the structure that's working against you. Sort by program, donor, and year. Add saved searches for the questions you ask every quarter. No new software — just an afternoon of housekeeping that pays back every week.
What it is: A writing partner (from Anthropic) that you talk to in plain English. Drop in a donor's last five years of giving history plus the new ask and it drafts a thank-you that sounds like you. Drop in three pages of scribbled board notes and get a clean one-page summary in 30 seconds.
Why it helps you: The forty evenings on the annual report were mostly staring at the cursor. Claude drafts section one from last year's version plus this year's numbers — you edit, not write from scratch. It's also meaningfully better than ChatGPT for long-form writing in a consistent voice, which is why we're moving you over and canceling the ChatGPT sub you said you don't use.
What it is: A meeting transcription app. Hit record on your phone or laptop — during a donor coffee, a board call, a strategy session — and afterwards you get a clean transcript, a one-paragraph summary, and a list of who said they'd do what.
Why it helps you: Instead of scribbling notes while trying to have a real conversation with a donor, you listen properly. Afterwards Otter hands you the followup-ready summary, which you paste into Claude to draft the thank-you email in your voice. SOC 2, GDPR, and EU AI Act compliant — the only transcription tool we recommend for donor content. (Always ask for consent before recording.)
What it is: AI grant-writing software. You load it up with your nonprofit's past applications and org voice. When a new grant comes up, it drafts the answers from your organization's own language — not a generic template.
Why it helps you: Only worth it if you're writing four or more grants a year. At that volume, it pays for itself in the first application. If you write one or two, skip this and lean harder on Claude. We'd ask about your grant pipeline before recommending a yes or no.
Some of these are big weekly chunks. Some are small daily savings that compound. We'd rather understate than overpromise.
| Task | Today | With the plan | Weekly saved |
|---|---|---|---|
| Email triage & drafting | Constant background tax; 400 unread by Friday | 15-minute morning pass; Superhuman drafts replies in your tone | ~3 hrs |
| Scheduling donor coffees | 5–8 emails per meeting | One Reclaim booking link | ~2 hrs |
| Thank-you letters | Drafted from scratch, always behind | Claude drafts from donor history; you edit and send | ~1.5 hrs |
| Board deck prep | Night before, from scratch | Claude drafts from notes + last deck; you refine | ~1.5 hrs |
| Donor-coffee follow-ups | Scribbled notes, remembered partially | Otter records; Claude turns it into a draft email | ~1 hr |
| Estimated weekly savings | 8–10 hrs | ||
The hours are real, but the bigger shift most people describe a month in is different: "evenings back." The annual report no longer eats March. Sunday-night email dread stops. That's harder to put on a spreadsheet.
This plan gives you enough to do the setup yourself — each tool has a short setup guide and we've flagged the decisions. If you'd rather we handle it alongside you (for a fee — see section 7), that's optional. Either way, here's the order we'd suggest.
Put the plumbing right before introducing AI. This is the week that gives you Sunday evenings back.
With the foundation working, you layer in AI. Start with real tasks, not demos.
Whether you did this yourself or hired us to help, give it 30 days and look back honestly: what stuck, what didn't, what feels awkward. If you want a 30-minute session to tune things up, it's included in the optional implementation package (see next section). If you're DIY, just reply to the email with what's not working — we'll help troubleshoot.
The plan you're reading is free. The only costs are the software subscriptions below. If you'd like us to set things up alongside you instead of going DIY, the implementation package is optional.
Every plan starts with your actual answers — seven short sections of plain-English questions, around 20 to 25 minutes at your own pace. You can skip anything that doesn't feel right.
Not a template. We read every answer and recommend the tools that actually fit your work, your budget, and what's driving you up the wall. The plan is yours to keep, whether you do it yourself or decide to have us help set things up.
Start your plan