Jen CherniskeLet's Talk →

My Process

A few of my systems and tools.

These are the actual checklists, prompts, and frameworks I use doing development work. All free — no form, no sign-up, no catch.

Next

See some of my grant writing.

VIEW SAMPLES →

Work with me

I do this work for my clients' nonprofits.

Book a free call →

Free resource

The High-Capacity Donor Discovery Checklist

18 signals that reveal who's actually ready for a bigger ask, hiding in the CRM you already have.

Most nonprofits don't have a donor discovery problem. They have a donor attention problem. The next major gift on your list is rarely a stranger. It's someone already in your database whose giving pattern, capacity, and engagement never got connected into one picture.

This checklist is the same lens I use in a full CRM audit, just aimed at your own donor list. Run through it section by section. Anyone who checks 5 or more boxes belongs on your priority discovery list.

01

Giving history signals

What their pattern already tells you, if you look at more than the last gift

  • Donor has increased gift size in at least 2 of the last 3 years
  • Donor has given consistently for 3+ years, even at a modest level
  • Donor's cumulative giving is meaningfully higher than any single gift suggests
  • Donor has made an unsolicited gift outside a campaign or appeal
  • Donor has given to more than one fund, program, or event

02

Lapsed donor red flags worth a second look

The donors everyone assumes are gone, but usually aren't

  • Donor gave $500 or more at some point but hasn't given in 12–24 months
  • Donor stopped giving right after a life event (move, retirement, career change) noted in their file
  • Donor was a recurring or sustaining donor who canceled without explanation
  • Donor's last gift was notably larger than their prior pattern, then they went quiet

03

Capacity indicators

Often sitting in the file, rarely connected to the ask

  • Donor's employer or job title suggests income beyond what their giving reflects
  • Donor has real estate, business ownership, or a professional license you can find on file or through public record
  • Donor's giving to other organizations is visible (donor walls, board bios, event programs)
  • Donor sits on, or has sat on, another nonprofit board

04

Engagement & relationship signals

Capacity tells you who can give. This tells you who's actually leaning in.

  • Donor attends events consistently, even if their gift size is modest
  • Donor opens or clicks email at a noticeably higher rate than your average
  • Donor has a personal connection to staff, a board member, or a program participant
  • Donor has volunteered, toured a program, or asked questions that show real interest
  • Donor has referred another donor or brought a guest to an event

How to use your results

Tally each donor's total checks across all four sections. 5+ checks means they belong on a priority discovery list this quarter. 8+ checks means they're likely ready for a direct conversation, not another appeal letter. The goal isn't a longer list. It's a shorter, better one.

Want this run across your entire database?

This is a slice of the full CRM audit inside the Development Audit & Activation Sprint — a 30-day engagement that ranks your entire donor list, flags your best lapsed and under-realized donors, and puts me on the phone closing the best of them.

jencherniske.com · Fractional Development Director

Free resource

5 Steps to Land Your First (or Next) Corporate Sponsor

A quick-start guide for nonprofits who've never pitched a company before, and the ones who pitch the same three every year.

Corporate partnerships get treated like a mystery box in most nonprofits. It isn't one. It's a sales process — the same one companies use to close each other every day. You just haven't been taught to run it that way.

Here's the five-step version I use to help nonprofits identify, pitch, and close corporate partners, borrowed directly from 20 years of enterprise sales.

01

Find companies with a reason to say yes

Skip the "who's big and local" list. Look for companies with an actual connection point: a new office opening near you, a stated CSR focus that matches your mission, leadership with a personal tie to your cause, or a competitor who already sponsors someone in your space. A weak lead with a generic ask converts far worse than a strong lead with a specific reason.

02

Find your actual decision maker

Marketing, community relations, or the CSR/foundation team almost always owns this budget — not the CEO's inbox. LinkedIn Sales Navigator, or even a plain LinkedIn search for "community relations" or "corporate giving" at the company, will get you closer than a general info@ email ever will.

03

Lead with their outcome, not your need

"We need funding" is not a pitch. "Here's the audience and visibility you get, and here's the impact data you can put in your own ESG report" is a pitch. Build one page that shows what's in it for them — reach, employee engagement opportunities, brand alignment, and a measurable outcome — before you ever mention a dollar amount.

04

Offer a tiered ask, not a single number

A single price invites a single answer: yes or no. Three tiers — for example, a presenting sponsorship, a program sponsorship, and an in-kind or event-level partnership — invite a conversation about fit instead. Let them self-select into the tier that matches their budget and priorities.

05

Treat the first year as a pilot, not a proposal

Companies rarely commit to a multi-year partnership on a cold pitch. Frame year one as a trial: a defined scope, a clear report-back on results, and an explicit conversation about renewal or expansion once they've seen it work. This lowers the risk of saying yes and sets up the renewal conversation before you've even signed the first agreement.

Quick gut check before you hit send

If your pitch could be copy-pasted to any company in any industry, it's not ready yet. The strongest corporate partnerships come from a specific, researched reason why this company, this year.

Want this run across your entire database?

This is a slice of the full CRM audit inside the Development Audit & Activation Sprint — a 30-day engagement that ranks your entire donor list, flags your best lapsed and under-realized donors, and puts me on the phone closing the best of them.

jencherniske.com · Fractional Development Director

Free resource

The AI Prompt Library for Nonprofit Development Teams

9 ready-to-use prompts for research, prospecting, and reporting — never for donor-facing writing.

AI is genuinely useful in a development office, but only in the back office. It should never write to a donor, draft a thank-you note, or touch anything with your organization's voice on it. What it's excellent at is the research and synthesis work that eats hours every week.

These are the same categories of prompts I build into every CRM audit and activation sprint. Copy them into your AI tool of choice and swap in your own details wherever you see brackets.

01

Prospect research

Finding out who a donor or company really is before you ask

Prompt 1

Individual donor background scan

Summarize publicly available professional background for [donor name], including current employer, job title, board memberships, and any public philanthropic activity. Cite only what you can verify and flag anything uncertain rather than guessing.

▸ Use for: building a capacity picture before a discovery call. Always verify before including anything in a donor file.

Prompt 2

Corporate prospect fit check

Based on this company's public CSR page and recent press [paste link or text], identify their stated giving priorities and suggest whether our mission around [your mission in one sentence] is a strong, moderate, or weak fit. Explain your reasoning.

▸ Use for: qualifying a corporate lead before spending time on a custom pitch.

Prompt 3

Peer organization scan

List organizations similar in size and mission to [your org] that this company or foundation has publicly supported in the last 2 years, based on the text or links provided. Note the approximate gift size where stated.

▸ Use for: benchmarking before you set an ask amount.

02

CRM & data synthesis

Making sense of what's already sitting in your database

Prompt 4

Lapsed donor pattern summary

Here is a giving history export for [donor name] [paste data]. Summarize the giving pattern in 3 sentences: frequency, trend direction, and the most likely reason engagement dropped, based only on what's in the data.

▸ Use for: prioritizing your lapsed donor discovery list.

Prompt 5

Segment-level trend analysis

Using this export of donors segmented by [gift range/program/acquisition source], identify which segment has the strongest year-over-year retention and which has the steepest drop-off. Summarize in a short paragraph a board member could read in 30 seconds.

▸ Use for: board and committee reporting.

Prompt 6

Data hygiene scan

Review this list of donor records [paste sample] and flag likely duplicates, missing key fields, and inconsistent formatting (names, addresses, employer fields) that would interfere with a wealth screening or mail merge.

▸ Use for: cleaning a CRM export before an audit or an appeal.

03

Internal reporting & prep

The behind-the-scenes writing that isn't donor-facing

Prompt 7

Board report first draft

Turn these raw fundraising numbers [paste data] into a 3-bullet board summary: where we are against goal, the single biggest win this period, and the single biggest risk. Plain language, no jargon.

▸ Use for: a starting draft only. Always review and add context before it goes to your board.

Prompt 8

Donor meeting prep brief

Using this donor's giving history and notes [paste CRM notes], build a 1-page prep brief for my meeting: their giving pattern, what they've been engaged with, and 2-3 open questions I should ask to understand what they care about most right now.

▸ Use for: prepping yourself before a call, never for scripting the conversation itself word for word.

Prompt 9

Grant requirements checklist

Read this grant RFP [paste text] and produce a checklist of every required document, word/character limit, and deadline mentioned, organized in the order they appear.

▸ Use for: making sure nothing in a lengthy RFP gets missed under deadline pressure.

The one rule that matters most

AI drafts the research. A human writes anything a donor actually reads. That line is what keeps your donor relationships genuine and your organization's voice intact.

Want this run across your entire database?

This is a slice of the full CRM audit inside the Development Audit & Activation Sprint — a 30-day engagement that ranks your entire donor list, flags your best lapsed and under-realized donors, and puts me on the phone closing the best of them.

jencherniske.com · Fractional Development Director