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For leaders and ops at midsize nonprofits to get guidance, uplifting, and resources for philanthropy data, database, and operations.

Ops Insights #096 - Executive Leaders: Add Equality to the Backline
Jenny Kleintop Jenny Kleintop

Ops Insights #096 - Executive Leaders: Add Equality to the Backline

Add equality to the backline to see philanthropy efforts grow faster. 3 ways I’ve seen successful (and unsuccessful leaders do it: 1, have the lead of the backline report directly to you, the leader. 2, give them a seat at the table. 3, allow them room to fail. 1, 2, 3: Do all 3 for fundraising efforts to grow better and higher. For the love of fundraising, add equality to the backline.

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Ops Insights #095 - How I Used AI for a Board Deck
Jenny Kleintop Jenny Kleintop

Ops Insights #095 - How I Used AI for a Board Deck

The CEO asked me to present at the board meeting on our progress toward our $25M campaign goal. I’m doing fractional support, so I say “our” as I’m integrated into the team leading their philanthropy services. We have one other person in philanthropy services who focuses on gift processing and basic requests. The CEO looks to me to run the more complex requests, and the board meeting warranted more complex reporting. Since I wanted stronger analysis and turnaround time was tight, I turned to AI for help. I’m going to walk you through an example so you can see how to do it.

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Ops Insights #094 - Data Trust, Have a Merge-a-Palooza
Jenny Kleintop Jenny Kleintop

Ops Insights #094 - Data Trust, Have a Merge-a-Palooza

When we do outreach to our donors and prospective donors, the details matter. The details and inclusivity matter, especially when multiple household members have a connection to you. If we send two mailings to the same household addressed to the same person, it’s wasteful. If we send two mailings to the same household addressed to the same couple, it’s wasteful. Let’s fix this. Start with those duplicates.

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Ops Insights #093 - That is Not Going to Raise You More Money
Jenny Kleintop Jenny Kleintop

Ops Insights #093 - That is Not Going to Raise You More Money

That is not going to raise you more money. We can fix your posting processes to finance and your cash and revenue reports format, but that is not going to raise you more money.

Those are the exact words I said to the Chief Philanthropy Officer as we were talking about how I could help her and the team. We talked through how to get her to where she needed to go. Yes, the finance and revenue reporting were important and necessary. We’d start there but at the same time we would start to build the foundational work that would bring in the results - a major gifts program from the ground up.

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Ops Insights #092 - How to Thrive When Working Remotely
Jenny Kleintop Jenny Kleintop

Ops Insights #092 - How to Thrive When Working Remotely

For today’s Insight I thought I’d change pace a bit and share a presentation I did last month for WIT, the Women in Tech Conference. I recorded my practice runs to make sure I could watch, adjust, and be ready to present at the conference. Session: How to Thrive When Working Remotely.

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Ops Insights #091 - How to Enter DAF Gifts
Jenny Kleintop Jenny Kleintop

Ops Insights #091 - How to Enter DAF Gifts

Donor Advised Fund (DAF) gifts are quickly gaining in popularity. According to a Chronicle of Philanthropy, as of December 2025, there was $326 billion currently tied up in donor-advised funds (DAFs) across the United States. So much so that fundraising leaders are developing targeted strategies and hiring consulting advisors to help guide their teams. It makes sense, as we want donors to recommend that the money be directed to charities rather than have it sit in their DAFs.

Then, as we secure more DAF gifts, the question of how to enter them into our fundraising database has become increasingly important. From all the nonprofits I’ve advised and observed over the years, the following is how I guide leaders and teams.

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Ops Insights #090 - Check That Email Before You Click It
Jenny Kleintop Jenny Kleintop

Ops Insights #090 - Check That Email Before You Click It

Doesn’t that slogan have a ring to it? Check it before you click it? One of my clients has a fabulous cybersecurity team. They send newsletters that you actually want to read. The one sent yesterday grabbed my attention immediately because it’s timely, and it’s relevant to my day-to-day work. It’s about email safety so sharing 10 tips with you.

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Ops Insights Ops Insights #089 - Split Gifts
Jenny Kleintop Jenny Kleintop

Ops Insights Ops Insights #089 - Split Gifts

A donor signs a pledge agreement for $100,000 to support two different funds. As we enter that pledge into the database, should we use the split gift feature to keep it as a single gift line, or enter two separate gift lines? This is a question that comes up often in my work with philanthropy teams. I’ll walk you through the response I give when working with RENXT clients.

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Ops Insights #088 - Data Trust, Start with Duplicates
Jenny Kleintop Jenny Kleintop

Ops Insights #088 - Data Trust, Start with Duplicates

Fundraising leaders often say to me, "Our data is a mess." They are really saying something deeper. They do not trust the data. Which means they do not trust the decisions coming from it. I see this pattern across teams raising $2M to $25M. Reports are pulled but questioned. Lists are built but triple checked. Metrics are shared but not fully believed. So teams create workarounds. Spreadsheets, side systems, manual tracking. Over time, the database becomes a system of record but not a system of truth.

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Ops Insights #087 It’s Not Above Your Pay Grade
Jenny Kleintop Jenny Kleintop

Ops Insights #087 It’s Not Above Your Pay Grade

It’s my birthday today. I’m going to celebrate it by giving you some tough love to reach the next level that your leader relies on as a value-add to the team. You need an important skill.

Ownership. You need to take ownership of the 8 buckets of philanthropy operations. Part of taking ownership is to stop saying “That’s above my pay grade.” Let’s give you 14 examples that I’ve mentored on recently.

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Ops Insights #086 Optimize Processes Before your Processes Outpace You
Jenny Kleintop Jenny Kleintop

Ops Insights #086 Optimize Processes Before your Processes Outpace You

Process optimization is one of the eight buckets of philanthropy operations. This bucket ensures you have the workflows and processes in place to succeed. It’s building flowcharts and SOP documentation, such as how you will handle the various data streams coming into your organization and optimize them for efficiency and effectiveness. 

As we think about process optimization in this way, it’s helpful to consider how fundraising strategies change over time and how technology, especially these days, advances rapidly. In November 2022, we saw a huge shift in what’s available in terms of modern tech advances, and we continue to see the pace accelerate every year.  If you are running processes the same way you were 5 years ago, it’s time to take a step back and ask yourself, is there a better way we can do this today?

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Ops Insights #085 Trust Nothing, Question Everything
Jenny Kleintop Jenny Kleintop

Ops Insights #085 Trust Nothing, Question Everything

I’m working as a system lead to bring 8 foundations into one fundraising database. We’ve been at it for a year and are close to the finish line. Bringing together 8 separate databases into one is not just about the database. You know me, I say this all the time, Philanthropy Operations is not just about the database.

When you are bringing together 8 different databases, you are bringing together 8 different teams, 8 different philosophies, 8 different ways of doing business. It goes well beyond the database - people, processes, and change management. I say trust nothing, question everything, as someone nudging you to say just because we’ve always done it that way doesn’t mean we have to keep doing it that way.

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Ops Insights #084 - Do you have the 8 buckets of philanthropy operations covered?
Jenny Kleintop Jenny Kleintop

Ops Insights #084 - Do you have the 8 buckets of philanthropy operations covered?

Philanthropy Operations is not just about CRM data and database management. It goes well beyond the database. There are 8 buckets essential for effective philanthropy operations, also known as development or advancement services.

When you have effective, efficient, streamlined, and maximized donor-centric Philanthropy Operations, your fundraising results increase by 3x and can even reach 10x with the right resources. Let’s walk through the 8 buckets of philanthropy operations.

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Ops Insights #083 - Respond Like a Leader: Recurring Donors Report
Jenny Kleintop Jenny Kleintop

Ops Insights #083 - Respond Like a Leader: Recurring Donors Report

When you want to be invited to the leadership table, you don’t want to respond like most when a data request. You want to respond like a leader, meaning think a step or two ahead. Figure out what they are trying to solve for, enhance, build, or grow, and look to answer that question. For example, let’s talk through a data request for monthly donors.

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Ops Insights #082 - 4 Steps to Assess Online Fundraising Platforms
Jenny Kleintop Jenny Kleintop

Ops Insights #082 - 4 Steps to Assess Online Fundraising Platforms

Online fundraising platforms, just like the World Wide Web and your tech stack, have exploded over the last five years.  It feels like it’s now over-saturated with options, and it’s hard to know what direction to go in. Spoiler alert: I have not yet found the perfect “one” platform. Instead, I encourage you to take the time to find the one or couple that work for your team’s needs today and as you move into the future.

Having just gone through this with a nonprofit I’m working with, I’d like to lay out the steps for you to take as you lean into this endeavor. After you go through this, if you have realized staying with the one you have is the right choice, then that’s a worthwhile endeavor as well. As such, it will satisfy “the grass is greener on the other side” conversations.

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Ops Insights #081 AI Objectives for Lapsed and Lost Donors
Jenny Kleintop Jenny Kleintop

Ops Insights #081 AI Objectives for Lapsed and Lost Donors

When Mike was looking into AI tools that vendors offered, he asked me, “Do you have any thoughts about who would be the best targets for our AI, event donors, lapsed donors, etc.? Here’s how I responded: It depends on the goal of the AI. Is it to steward and thank donors to retain them?  Is it to re-engage lapsed or lost donors? Is it to try to convert more donors into sustaining donors? Is it to upgrade donors whom we can’t get a fundraiser linked to? AI should not be a catch-all to try to do too many things. There should be various journeys with one goal/purpose/thing to solve for.

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Ops Insights #080 Gift Officer Using CRM Performance Measures
Jenny Kleintop Jenny Kleintop

Ops Insights #080 Gift Officer Using CRM Performance Measures

When the CDO asks how can we incorporate CRM performance measures for gift officers, you know that it is a CDO who values the CRM Database. And that is a good thing. Here is a real-life example of a performance measures I helped set for gift officers at one nonprofit.

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Ops Insights #079 Goal Setting for Development Ops
Jenny Kleintop Jenny Kleintop

Ops Insights #079 Goal Setting for Development Ops

As our current year comes to a close and goals for the new year are set, it’s important to participate in goal-setting actively. Often, many think it’s hard or even impossible to set goals because we are not frontline fundraisers with a dollar goal. However, that’s not the case.

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Ops Insights #078 Why I Hired a Gift Processor with Zero Experience
Jenny Kleintop Jenny Kleintop

Ops Insights #078 Why I Hired a Gift Processor with Zero Experience

The best gift processor I ever hired had zero gift entry skills. Lisa was her name. When I heard Lisa was getting laid off because a spreadsheet said she was "non-essential," I called her and told her we had an opening. I worked with her at my prior employer and knew how good she was with people.  She was our front desk administrative assistant and colleagues and donors loved her.  There were candidates with stronger resumes on paper. We hired her anyway.

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Ops Insights #077 - Why I Decided to Treat AI as a Partner
Jenny Kleintop Jenny Kleintop

Ops Insights #077 - Why I Decided to Treat AI as a Partner

Lately I have been getting a lot of questions about AI. Where do I even start? Do I have to be technical? Am I already behind? If you have wondered about any of those, I want to share a bit of my own AI story.

I started learning about AI in 2017, when it still felt like a black box that required engineers, data scientists, and technical trainers just to ship one model. When tools like ChatGPT arrived in 2022, non-coders finally had a way in, but the noise grew. New tools every week, experts to follow, prompts to perfect, “custom” everything. I often felt the same thing my clients feel now. Overwhelmed, behind, and burnt out before really getting started.

In 2025, AI shifted from “nice to have” to “must know.” That is when I decided to treat AI as a partner instead of just another tool.

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