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

Ops Insights #073 - It’s Not Worth Compromising as Your Donors Expect Better
Jenny Kleintop Jenny Kleintop

Ops Insights #073 - It’s Not Worth Compromising as Your Donors Expect Better

Goals are getting bigger, you are being asked to raise more with less, and your team is stretched far too thin. So what do you do? You compromise. You tell yourself: We manage with sub-par data because our team is busy. We hobble along with a database that is burdensome because we don’t have the expertise to fix it. We go slower than we’d like because many of our data requests or processes take a long time.

It’s not always immediate when this happens. It’s often slow, sometimes over the course of years, and sometimes with the same people in the roles for many years. It’s been this way for so long that it’s become the norm, and you keep saying there’s got to be a better way. Many times, it’s a feeling where something’s off, but you can’t quite put your finger on it or explain it.

Think of it this way: It’s not worth compromising as your donors expect better.

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Ops Insights #072 - 3 Leading Questions to Ask Your Leader Today
Jenny Kleintop Jenny Kleintop

Ops Insights #072 - 3 Leading Questions to Ask Your Leader Today

One of the two main reasons I went to work for my second nonprofit was to report directly to the head of development. This way, I could learn how to report to and interact directly with the leader. As I’m naturally an introvert, at the time, I didn’t have the skills I knew I needed to acquire this skill. So, this gave me the opportunity to learn.

I read books, listened to podcasts, watched webinars, and observed others. I was eager to learn anything I could about leadership and how to report to a C-suite executive.  Between this approach and interacting directly with the leader, I grew tremendously in my skill set. Now I’m super comfortable interacting with, understanding, and supporting CEOs, CDOs, EVPs, VPs, and others. Over the years, I have learned to ask three leading questions to leaders.

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Ops Insights #071 - Simple Board Reports
Jenny Kleintop Jenny Kleintop

Ops Insights #071 - Simple Board Reports

You want to balance between showing the data and telling the story. If you present too much data, the board members may become disengaged, and if you tell too much of a story, the board may not trust the narrative. It’s a delicate balance between the two. To keep it simple, engaging, and trustworthy, align the board reports to answer three questions. Where are you in terms of progress toward the goal? What is in the pipeline to help fill the gaps? Where do the gaps still exist, and where can the board help with those gaps?

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Ops Insights #070 - 2 Lists to Find Planned Gift Prospects
Jenny Kleintop Jenny Kleintop

Ops Insights #070 - 2 Lists to Find Planned Gift Prospects

Whether you have one or 5 people focusing on bringing in major gift donors. One pipeline is ensuring you have Planned Gift donors and I’ve seen it work best when it’s integrated in major gift prospecting efforts as some donors want to give blended gifts as the moves efforts are aligned. To get started, there are two lists you can request to find planned gift prospects to cultivate. Let’s show you how to make the request for these lists.

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Ops Insights #069 - Grants in Moves Tracking
Jenny Kleintop Jenny Kleintop

Ops Insights #069 - Grants in Moves Tracking

When I get asked: How do grants fit into moves tracking? I respond: A similar way you track your major gifts. There is uniqueness such as in the stages, but keep it simple and follow your overall moves tracking processes for clarity. Moves tracking is made of of 4 things: Assigned relationship managers, such as Primary and Secondary; Prospect coding, such as Classification and Prospect Stage; Actions to track all interactions with prospects and report movement; and opportunities to track future asks and view projections. Let’s get into the details.

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Ops Insights #068 - 7 Data Flows to Retain Donors
Jenny Kleintop Jenny Kleintop

Ops Insights #068 - 7 Data Flows to Retain Donors

It’s a long-standing statement that retained donors are easier and less costly to retain than it is to acquire new donors. And there are a lot of complex tools in the market and lots of talk about AI, but if you’re not doing the basics, then the more complex processes will feel impossible. Here to give you 7 data flows that are simple and basic for you to implement today.

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Ops Insights #067 - 6 Strategies to Navigate Disagreements Between Operations and Fundraisers
Jenny Kleintop Jenny Kleintop

Ops Insights #067 - 6 Strategies to Navigate Disagreements Between Operations and Fundraisers

I co-wrote this edition with my husband Doug.  He’s a frontline fundraiser, always has been, and I’m in philanthropy operations, always have been. Can you imagine the many conversations we have at the dinner table? Why can’t you get your contact reports into the database?  Why can’t you make it easier for us to get our contact reports in?  On and on.

Even though we often “duke” it out in conversations, it has really balanced each of us. I’ve gained a better understanding of his perspective, and he’s gained a better understanding of mine.  Together, we navigate to common ground to ultimately figure out what the best route or solution is. Sometimes we figure out it's best to go my way, other times his way, and many times somewhere in the middle.

Disagreements between development operations and frontline fundraisers are inevitable. Let’s talk through 6 strategies to navigate these disagreements.

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Ops Insights #065 - Learn and Gain Confidence 3x Faster
Jenny Kleintop Jenny Kleintop

Ops Insights #065 - Learn and Gain Confidence 3x Faster

I believe confidence comes with practice and it’s the type of practice you get that allows you to get confident faster. For example, early on in my career I took the long route. I dove into online documentation, courses, and tutorials all on my own for days before I attempted to do something. I read, studied, and then read and studied more before attempting to do database set-up, configuration, imports, or list pulls. For some reason I thought I had to know every little detail before diving in.

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Ops Insights #064 - Always Become Very Curious
Jenny Kleintop Jenny Kleintop

Ops Insights #064 - Always Become Very Curious

Become very curious as this is how you'll learn, grow, and evolve. If you need encouragement, take a look back at how far we've come or talk with those who have been in the profession for a long time. You'll hear all about paper files and those Rolodexes that kept contact information. And don't get me started on the evolution of online donations. Keep on learning as we need you to keep the profession thriving. Learn by taking action.

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Ops Insights #063 - Save 3x Hours by Finding Unique Identifiers
Jenny Kleintop Jenny Kleintop

Ops Insights #063 - Save 3x Hours by Finding Unique Identifiers

This edition is for my operations peeps. I’m going to walk you through an example of how I took a process that was taking 18 hours down to 6 hours. Why? Because I want you to think of ways to save yourself hours of manual work and redirect that time to that long list of to-dos you have piling up on you. I’ll give you the background, the pause moment, how we did it and why we did it.  Let’s dive in.

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Ops Insights #061 - If Your Nonprofit Was an Album
Jenny Kleintop Jenny Kleintop

Ops Insights #061 - If Your Nonprofit Was an Album

A great way to become more comfortable with all the chatter around ChatGPT is to start using it yourself. Pay attention to how others are using it and the prompts they share. The best part of this AI  era is that those of us embracing it are learning openly, sharing our experiences, and helping others who may not feel as confident yet.

Here’s a quick idea you can run with: Go to ChatGPT and enter this prompt “if my nonprofit were an existing album, what would it be and why.” Let me walk you through the details.

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Ops Insights #060 - CEO & CDO’s Strategy for Dev Services Leader
Jenny Kleintop Jenny Kleintop

Ops Insights #060 - CEO & CDO’s Strategy for Dev Services Leader

As a CEO or CDO, you don’t want your 3 am thoughts to be about your concerns with the quality of your data or database. Nor do you have to stress about your staff not getting what they need to be effective or broken operational processes slowing things down. The data, database, and operational processes should not be a pain point. You want data that is right. You want a database that is clean. You want operational processes that allows you to be a proactive leader.

You want a smooth, well-run area where you and your team can have trust and confidence in what you are investing in, seeing, and using every day. To get here, the key is understanding the area and making sure you have the right person in place to lead the area. This area is called Development Services, also known as Philanthropy Operations or Advancement Services. Let’s dive in.

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Ops Insights #059 - Fundraiser Fast Start Initiative (Part 3 of 3)
Jenny Kleintop Jenny Kleintop

Ops Insights #059 - Fundraiser Fast Start Initiative (Part 3 of 3)

Building off our prior two editions we were ready. It was time to launch and get moving. We ran team check-ins to look at progress and I offered additional opportunities to support with 1:1 sessions. We would have liked to run bi-weekly check-ins, but in reality we could only fit in monthly team check-ins. Which we were okay with as the CDO has her check-ins with the fundraisers on strategy and I did 1:1s to help with tracking activity in the database. You see, I was invested. I wanted them to hit the 100% goal and it’s not always intuitive to a fundraiser to make sure to mark all the details on the action to ensure it’s pulling in as completed on the report. Let’s dive in.

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Ops Insights #058 - Fundraiser Fast Start Initiative (Part 2 of 2)
Jenny Kleintop Jenny Kleintop

Ops Insights #058 - Fundraiser Fast Start Initiative (Part 2 of 2)

Building off our prior edition, we are going to walk through how we cleansed portfolios and filled gaps in portfolios to lock and load them. We held three 1.5-hour sessions over a 4-week period. The objective of the first prospect review session was to go through all the existing prospects and portfolios and ask the questions: Are these viable prospects that you currently carry? So viable that you will be able to have a meaningful interaction with them in the next 90 days? Let’s dive in on the details.

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Ops Insights #057 - Fundraiser Fast Start Initiative (Part 1 of 3)
Jenny Kleintop Jenny Kleintop

Ops Insights #057 - Fundraiser Fast Start Initiative (Part 1 of 3)

The CDO came to me and said the board and her created a Fast Start initiative and we need reports to hold the team accountable and show progress. I thought this was really cool and immediately my brain went into action mode – how can I set up the tracking and reporting for her to be able to report out, but also how can I support the fundraisers to hit 100% of the goal? Let’s dive in.

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Ops Insights #056 - Let’s Move You Forward
Jenny Kleintop Jenny Kleintop

Ops Insights #056 - Let’s Move You Forward

Sharing some of my comments on LinkedIn from 2024 in hopes these words will guide, motivate, or move you forward in 2025. Plus my one big recommendation for you to take action is Community - Find Your Community. You’ve Got This!

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Ops Insights #055 - From AI Headshots to AI Agents
Jenny Kleintop Jenny Kleintop

Ops Insights #055 - From AI Headshots to AI Agents

It’s hard to believe a year ago I was presenting  at the AASP conference and the latest and coolest thing to share was Ai headshots. I showed 18 headshots and asked the audience to pick the one photo that was not created using Ai. Only a handful guessed it correctly.  

Fast forward to today and the latest mind blowing thing in artificial intelligence is Ai agents.  We went from automation to Ai Automated to Ai Agents. 2025 is the year of Ai Agents. Live dive in to learn more.

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Ops Insights #054 - Thankful, Grateful
Jenny Kleintop Jenny Kleintop

Ops Insights #054 - Thankful, Grateful

I was making my morning Chai Tea Latte and grabbed a cup that said Thankful, Grateful. It made me smile as my daughter gave it to me, and she knows I love sappy sayings.

Then I thought, "What's the difference?" 

According to dictionary.com, thankful is “feeling or expressing gratitude,” and grateful is “expressing or actuated by gratitude.” Both revolve around gratitude, and I for one, feel this every day. Let’s dive into why.

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Ops Insights #053 - Ambassadors Refer Potential Donors
Jenny Kleintop Jenny Kleintop

Ops Insights #053 - Ambassadors Refer Potential Donors

An Ambassador Program is a way to drive referrals of potential donors. Ambassadors have existing relationships and serve as connectors to potential donors they know who care about your nonprofit, such as individuals you serve, friends, or organizations. You can partner with various Ambassadors who pass referrals to your Philanthropy team. Let’s walk through the reasons you want ambassadors, the stages, and ways to track them.

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