#391- What Happens When You Stop Fundraising on Hope with Amy Lester

Summary

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Nonprofit Lowdown #391 – What Happens When You Stop Fundraising on Hope

Host: Rhea Wong
Guest: Amy Lester, Major Gifts Officer, Polar Bears International
Date: June 1, 2026

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Overview

In this insightful episode, Rhea Wong sits down with Amy Lester of Polar Bears International to explore what truly happens when nonprofits move away from "hope-based" fundraising and implement a strategic, consent-based major gifts program. Amy shares a candid case study on transforming an ad hoc, “hopeful” system into a structured, results-driven approach—highlighting powerful lessons learned, specific strategies implemented, and remarkable outcomes achieved.

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Key Discussion Points & Insights

Amy’s Background & Initial Challenges

• Amy’s experience: Over 15 years in nonprofit work, transitioning from programs to a Certified Fundraising Executive focused on major gifts.
  [01:22]
• Major gifts at Polar Bears International: Before Amy’s arrival, the "program" was little more than a list of high-level donors, with no real system for engagement or stewardship—just "hoping" donors would give again.
  [02:07]

“It was really hoping that the major donors would donate again. But no real strategy around how we were going to get those donors to reengage at that major gift level again.”
— Amy Lester [02:35]

Overwhelm & The Desire for a System

• Inherited chaos: Amy began with a spreadsheet of 400 “good prospects” and a portfolio of ~80–90 donors, which she found overwhelming without a clear structure.
  [03:50]
• Seeking support: Amy valued learning from outside experts and needed external guidance to avoid reinventing the wheel or being “the system” herself.
  [05:00]

The Shift: Key Strategies Implemented

• Donor Pipeline Audit:
  By auditing the donor pipeline, Amy identified gaps and "leaky" spots where potential revenue was lost.
  [06:07]

“This was really eye-opening for me...lots of areas in red, things that needed attention.”
— Amy Lester [06:30]

• Consent-Based Fundraising:
  Amy learned to explicitly seek donor consent upfront, creating clear, mutual expectations for engagement, and saving time by not pursuing unresponsive donors.
  [07:00]

“I had people in my portfolio...but I doubt they even knew it.”
— Amy Lester [07:19]

• Operate the System, Don’t Be the System:
  Amy developed a replicable process, enabling her to run the system instead of being solely responsible for its success.

“Previous to you, I was the system. And going through [your program], you helped me put this system into place at my organization. Now I run the system, and it’s much more empowering.”
— Amy Lester [08:15]

Concrete Donor Success Stories

• Donor Upgrade Example:
  By co-creating an engagement roadmap with a donor, Amy doubled his annual donation from $20k to $40k and secured a 3-year pledge; the donor felt more involved and valued.
  [08:15–09:40]

“He doubled his donation...and he also made a pledge for the next three years...$120,000 gift, where he was typically given at $20,000.”
— Amy Lester [09:06]

• Strategic Board & Team Involvement:
  Amy incorporated her executive director and engaged board members tactically—especially for stewardship and cultivation—by giving them a clear role in the well-defined process.
  [10:29]

“Our board was worried about handing over any names...and so really putting some trust in me and trust in the system...”
— Amy Lester [11:23]

Results Achieved

Dramatic Improvements in Key Metrics

• Revenue:
  Surpassed an aggressive fundraising goal:

  • Goal: $1.2 million
  • Actual: Over $1.6 million
  • Increase even with a late start in the year [14:30–15:05]

• Conversion Rates:

  • Pre-program: ~40%
  • Post-program: 84% conversion
    [13:43]

• New Major Donors:

  • Prior years: 3–4 per year
  • This year: 19 new major donors
    [13:41]

“My conversion rate pre-Rhea was around 40%. And post-Rhea, I'm up at 84%...getting the right ask to the right person at the right time for the right amount.”
— Amy Lester [13:34]

• Portfolio Quality:
  Portfolio narrowed to 75 actively-engaged prospects, with a goal to refine further, now that the system is operational.
  [13:52]

• Notable Upgrades:
  One donor increased their commitment from $200,000 to $300,000 after Amy was encouraged to make a bolder ask.
  [13:41]

• Winning Back Lapsed Donors:
  Amy used new strategies from a workshop on re-engaging lapsed donors to recover a $100k gift with a single targeted email.
  [18:49]

Organizational Buy-In & Takeaways

• Proving ROI and Changing Minds:
  Amy initially paid for program participation out-of-pocket, but her organization later reimbursed her after seeing the clear ROI in results. [17:53–18:39]

• Replication and Sustainability:
  The system now makes major gift work less overwhelming and more manageable, with templates and processes that can extend to others on the team. [15:14; 20:22]

• The Human Element and Accountability:
  Continual coaching, peer accountability, and immediate, actionable feedback were named as central to Amy’s rapid success. [16:06]

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Notable Quotes & Memorable Moments

• “I am not the system. I run the system.”
  — Amy Lester [08:15]

• “We are leaking money. We are leaving money on the table. This was really eye opening for me.”
  — Amy Lester [06:22]

• “If you create a process where they feel like they're bought in, we're all on the same page, they understand what's happening, that they're in control. It just changes the whole dynamic.”
  — Rhea Wong [09:40]

• “They reimbursed me for the months that I paid on my own and they're paying for it now. So they started to see the results and we're like, oh yeah, this is pretty phenomenal.”
  — Amy Lester [18:04]

• “The accountability piece...you put in the work and then you see the return pretty quickly and you can tell what's working, what's not working.”
  — Amy Lester [17:19, 19:37]

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Timestamps for Key Segments

• Amy’s background & initial approach: [01:22–03:50]
• Inherited portfolio & overwhelm: [03:50–05:00]
• Joining Rhea’s program and first steps: [05:00–07:00]
• Consent-based fundraising details: [07:00–08:15]
• Major donor upgrade case study: [08:15–09:40]
• Board engagement and systemization: [10:29–12:33]
• Results: Upgrades, new donors, pipeline: [13:41–13:52]
• Blowout fundraising year: [14:29–15:05]
• Ongoing improvements and next steps: [15:14–15:38]
• Personal investment and organizational support: [17:53–18:39]
• Re-engaging a lapsed $100k donor: [18:49]
• Reflections on the program and sustainability: [19:37–20:22]

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Final Thoughts

• Strategic, consent-based major gifts fundraising is transformative: it replaces guesswork and wishful thinking with clear systems, donor empowerment, and bold (but respectful) asks.
• Support, accountability, and immediate feedback accelerate growth and professionalization.
• Even experienced fundraisers benefit from external structure, expert coaching, and systems that spread beyond one person’s desk.
• The power of investing in yourself—and then building organizational buy-in through clear, measurable success—cannot be overstated.

For more details or to connect with Amy, check out the show notes for her LinkedIn.

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Transcript

[A]

Hey, you. It's Rhea Wong.

[B]

If you're listening to nonprofit Load On, I'm pretty sure that you'd love my weekly newsletter. Every Tuesday morning, you get updates on the newest podcast episodes. And then interspersed, we have fun special invitations for newsletter subscribers only and fundraising inspo, because I know what it feels like to be in the trenches alone. On top of that, you get cute dog photos. Best of all, it is free. So what are you waiting for? Head over to riawong.com now to sign up. Welcome to nonprofit Lowdown. I'm your host, Rhea Wong.

[A]

Hey, podcast listeners, it's Rhea Wong with you once again with nonprofit Lowdown. Today I am super excited because we are going to walk through a case study with my friend and client, Amy Lester. So Amy currently is the major gifts officer at Polar Bears International, and she's going to share with us some of the things that she has done to make this a banner year for her and her portfolio. So, Amy, welcome to the show.

[C]

Thank you, Rhea. It's so great to be here.

[A]

We appreciate you being here. So before we jump into your current situation, walk us through a little bit of your background because you are. You're very experienced with fundraising. This is not your first rodeo. So tell us a little bit about your background before you got to Polar Bears International.

[C]

Yeah, sure. So I've spent most of my career in the nonprofit world. I spent probably the first 15 years in programs, and then of course, being in programs, you help out a little bit with fundraising. And I really connected with fundraising, and I loved being able to set goals and hit goals and work with donors and really have a much larger impact on the organization with fundraising. So I've been in fundraising for the past 15 years. I'm a certified fundraising executive. I think I've held every job in the development department and really love working with major donors. So when I saw this position open up at Polar Bears International, I started last March, was really excited to build a robust major gift program for them.

[A]

That is so awesome. So walk me through this. When you first started, what did the major give program actually look like? So when we spoke before, you called it the HOPE strategy. So walk me through, like what? Paint me a picture. What did your major gift program look like or did it actually exist?

[C]

Yeah, I. It depends on who you talk to. You know, they felt like a major gift program did exist. It was based on level of giving, but there wasn't any true engagement, any real personalized stewardship, things like that. It was really hoping that the major donors would Donate again. But no real strategy around how we were going to get those donors to reengage at that major gift level again. And it was pretty hands off with how much we were engaging with them. And we'd send out the E blasts with our quarterly reports and things like that. But there wasn't any real strategy behind the program. It was they give at this level, so they're a major donor.

[A]

Got it. And I feel like that's very common for a lot of shops. It's like you have major gifts, but you don't necessarily have a program or a system. So does that feel like what's happening with you?

[C]

Yeah, absolutely. I'm glad you brought that up. It's very, very common. And I realized through this process that even in the past, but at Polar Bears International, I was the system. And that's creates a lot of pressure and a lot of stress.

[A]

Yeah. And so we should also just say that your organization is a $6 million organization, which I think a lot of people might be shocked to hear. Wait, at a $6 million org, there was no system? So tell me a little bit about when you walked in. Why did you decide that you needed something different?

[C]

Yeah, so when I walked in, I had about. I think it was about 80 or 90 people in my. They had built a major gift portfolio just based on giving. And then they gave me a spreadsheet with like 400 names on it that they felt were good prospects or needed to be people that needed to be re engaged. And I'll be honest, I felt really overwhelmed. I wanted to do a really good job. I wanted to build a robust major gift program. We obviously had a lot of potential, but I wasn't quite sure how to kind of take it and run with it. And I'm one of those that is totally fine saying, hey, I probably don't have all the skills that I need. I want to look externally to see who's out there, who's doing what, and really thought about who do I know that that's doing major gift work. And I had done some of the trainings that you had done, like the one hour kind of webinars and things like that. So I was like, I need to look up Ria Wong and see what she's doing now. Is there webinars or programs that are coming up to really bring in some external support to help me build this robust major gift program?

[A]

So when you decided to start working with me and sign up for what we're calling the Big Ask Gift program, was there a Specific problem that you were looking for or was it more just, I'm overwhelmed and I need some structure? Like, what was the problem that you were looking to solve?

[C]

I really wanted to build a robust major gift program. And I knew on my own I probably could have done it, but it would have taken me a lot longer. And there's some things that I learned in bag that really changed how I was doing it, which made things more efficient for me. And so I knew that if I brought in some external support for me, I would also have this team that I could brainstorm with. And what do you think? And this is what I'm seeing. So just wanted to help build this external team to help me with the major gift program.

[A]

That's great. And can you talk us through what were some of the things that we tackled together that you felt like were a huge value add out of the gate? Because you've had a. You had a tremendous year. We'll get to the numbers in a second. But I'm just curious, like, if someone's listening, they're like, okay, Amy, what did you work on? Like, what was the project that really kind of got you started?

[C]

There was two things that come to mind. So the first one is I attended one of your one hour webinars where you do the donor pipeline audit. And I thought that was really great because. And the reason I was signed up for it is because I wanted to see, where are we starting from? What's our starting point? And so to do that audit really showed me where some of the gaps were. And so again, it was like, okay, yes, we do need to be part of Big Ask Gifts. But that was the first thing that was like, yes, we are leaking money. We are leaving money on the table. This was really eye opening for me to walk through it with you with my own numbers and see lots of areas in red, things that needed attention. And then the other kind of pivotal moment was you talk about consent based fundraising. And that really resonated with me because I had people in my portfolio, and not just at pbi, but in my past, that were in the major gift portfolio, but I doubt they even knew it. And so, yeah, I really love this. Consent based fundraising for major gifts and getting the donor's consent up front, doing some of the things the survey and some things like that. So, you know, pretty early on whether they want to engage or not. And that was really pivotal for me because I can look back onto last year and see some time, see some significant time that I spent trying to engage People. And it was really clear that they weren't at a point that they wanted to engage with me.

[A]

Yeah. I think that's so powerful. And I think for a lot of fundraisers, because they haven't operated or been taught how to operate within consent, they end up chasing people who frankly don't want to talk to them.

[C]

Yeah. And that's a hundred percent me.

[A]

So talk to me about a specific donor, because I think we're all nosy out here. But you mentioned that you upgraded someone using what you had learned in bag. And so can you walk me through the path from where they were, what you did, and where they are now?

[C]

Yeah, absolutely. Instituting your system of creating the roadmap with them. Right, Creating the system. So I operate the system. I am not the system.

[A]

Say that again, because that's just such a beautiful thing to say.

[C]

Yeah. So previous to you, I was the system. And going through bag, you helped me put this system into place at my organization. And now I run the system, and it's much more empowering. It doesn't feel as overwhelming. It's very strategic. So going through all the steps of we had a relationship with this donor, but not at the level I do now. Creating the roadmap, really understanding with him what inspires him to give, and then creating this roadmap together. And again, it's always consent based, where he can always opt out. He's really in control over the process. And then designing some really great options for him to support our work using the BAG system. And he doubled his donation. So he went from 20,000 a year to 40,000 a year. And then he also made a pledge for the next three years, 26, 27, and 28. So that turned out to be $120,000 gift, where he was typically given it at 20,000. And he gave me feedback about how this was so wonderful. He felt so engaged. He really understands the work that we're doing. And I and the rest of the fundraising team really know him better and what resonates with him through this process.

[A]

Oh, my gosh. That makes me feel so good for you and for the team and the donor. Right. Because I think if you create a process where they feel like they're bought in, we're all on the same page, they understand what's happening, that they're in control. It just changes the whole dynamic.

[C]

Yeah. And he was really excited about the work. And then he also left the door open. He said, if you get in a bind later in the year, please feel free to reach out again. So, so it was like, it wasn't even, it was like 40,000 and we'll talk next year or anything like that. So. Yeah, yeah. Much, much better engagement after I instituted at my org and let's talk about

[A]

this because I'm a big proponent of the system. Like it, it shouldn't be all just you. And now that you've put in the system, do you feel like, do you have other people who are working on major gifts with you?

[C]

So definitely the executive director. And then we do have board members that are engaged to help with either meetings. Oh. And obviously the team. So I have been able to get a number of people engaged. So as we're putting proposals together, whether it's for stewardship or cultivation, getting some meetings with the, the donor and some of those key staff and then having a board member also involved thanking those donors has been really pivotal as well for the organization.

[A]

Yeah. Because I think this is the biggest issue I hear from folks, which is my board isn't doing anything. And I think when you have a system and you're very clear with them about specifically what they can do, it changes a little bit. Because I think before, and I'm not saying this is your board, but I think boards have this idea of, oh, you just want me to go ask my friends for money and so. No, no, we actually want you to be part of a process.

[C]

Yeah, absolutely. And I really had to, I was new and build the relationship with them and do some board training. And you're exactly right. Our board was worried about handing over any names and then are we going to hound them? What does it look like? And so really putting some trust in me and trust in the system and seeing, being part of the process to see, no, this is really up to the people in their network. We can create an opportunity and then if they would like to walk through the door, that's wonderful. And if it's not the right time, they know how to get ahold of me.

[A]

Yeah, for sure. And I think when you take the pressure off, when it's really consent based and respectful. Because the other thing is everyone is protective of their personal relationships because our reputation is everything. And I understand that completely.

[C]

Right.

[A]

And so I want to know as a board member, Amy's going to treat my people right.

[C]

And our donors have also said they really appreciated knowing ahead of time what the call was going to be about because they would say, I always felt like if, if you guys wanted to talk to me, it was, you were going to ask me for a Gift. And this has been a whole different process and really appreciate it. And so we've gotten really good feedback from the donors, too.

[A]

Oh, that's so awesome. So let's talk numbers here.

[B]

What changed in the revenue and the

[A]

conversion rate in the nine months since you joined bag?

[C]

Yeah, you definitely had some really wonderful upgrades. Some examples. I had a $200,000 donor, and through my work, through bag and with you guys and your team, you guys really encouraged me. You felt like a $300,000 ask was really doable. And I would have never asked that on my own, but I really trusted in the process and made the ask and we got $300,000. So it was a beautiful upgrade. Lots of upgrades, lots of new major donors. I think I ended the year with 19 new major donors. And the previous years, we were right around the three to four new major donors. So that was great. And my conversion rate, I love my conversion rate. My conversion rate pre rhea was around 40%. And host RIA, I'm up at 84%. And it really, really shows. You guys really helped me narrow down. Getting the right ask to the right person at the right time for the right amount and especially getting that consent at the front end has really impacted my conversion rates.

[A]

Amazing. And you've had some really big wins. So you talked about some of them increasing the number of major donors. What does your pipeline look like now?

[C]

So my pipeline, Now I have 75 people in there. I would like to try and get that a little bit lower. It's still really hard to manage, so I'm still working out some of those kinks and things like that, but for the most part, it's a much more engaged, robust portfolio than we had a year ago. Absolutely.

[A]

And let's talk about your year, because I've heard you talk about that a lot, which is you started your job in March and you were given a goal. You and I started working together in August, I believe. Right. So walk me through what you were told in March and what ended up happening nine months later.

[B]

Yeah.

[C]

So my fundraising goal for the year was set at 1.2 million. It was a significant increase over the year before. The leadership also said, hey, we know you're starting in March and didn't fundraise in January. February. And you are also new. You had to learn the organization. So if you don't hit 1.2, that's okay. Let's just keep it as at the goal and see how we end up. And I ended my year over 1.6, which was so Incredible. So I exceeded the goal even though I didn't fundraise the beginning of the year and just had a phenomenal first year.

[A]

That's incredible. So what's next for you? I really. You've started to implement this system. You seem like you have a really robust pipeline. What's the next step for you?

[C]

Yeah, I really want to get the system down and really, really start working the system now that I have it, now that I've tested it and have gone through, I feel like it can really ramp up now. And I have some great resources, I have some great templates, all these resources that you brought. I really feel like now it's time to really ramp it up to that next level.

[A]

Yeah. And I would love if you hired another MGO to bring in more money of the recommendation.

[C]

Yeah, I would do.

[A]

We'll leave that one aside. Okay, so if someone is listening to this and they are in a similar situation, maybe they have some major gifts, but they don't really have a system and they're wondering what changed for you? What does joining Bag or working with Ria offer that I couldn't find on ChatGPT or something like that? What would you say to them about whether or not it was worth it?

[C]

I would say the things that I love is that when we go through the trainings and the trainings are weekly, there are things that we can walk away with that we can implement that day and we see the results. The other part I love about it is the accountability piece and it's sometimes easy to get a little bit pulled in all different directions. But I know that on Monday Soraya is going to be asking what I got done over the last week. And some things like that, or even amongst the group where we say we're going to make these calls and do these things and then you guys put in the Slack channel that you did it and stuff like that. So I do love the accountability piece. I love all the resources, the things that you can implement right away. I also love the immediate feedback. I can send you a template and have you look through and you give me immediate feedback on what you liked about it, what I missed. Let's tweak this, let's polish this. And so it's not like I send it in and then two weeks later I get it back and I can't even remember what I was working on two weeks ago. So that and the team, I love the one on one coaching, the support and the resources and the timeliness is where you can't find that anywhere else.

[A]

Yeah, yeah. And Amy, what I will say that I really appreciate about you is you are a doer. Right. And I think when I think about the people who've been most successful working with me, it's the people who are taking action and even little action which compounds over time. And so I think that is a testament to you and the fact that you're just, you're a doer. You're willing to put things in a place and keep it going. So kudos to you.

[C]

Thank you. Yeah. I think you do have to be for this program. You have to be somebody who wants to get after it. And if you are willing to do the work with the resources that you're given, it will be phenomenal.

[A]

The other thing I'd say, I will say, which is quite unique to you, is you decided to pay out of your own pocket, which was a tremendous commitment. And then what ended up happening with your organization?

[C]

When I pitched it to them at the beginning, I was also new. And then obviously this program is new and it made them really uneasy. But I knew me and I know your training and so I knew that this is exactly what I needed to do. So I was paying for it out of my pocket. And then they started seeing the results and I tied it back directly to you and the program. And so now they reimbursed me for the months that I paid on my own and they're paying for it now. So they started to see the results and we're like, oh yeah, this is pretty phenomenal.

[A]

Yeah. Because based on what you're telling me, it was. Let me do some math, like 100x ROI, right? Oh, yeah. Everything into account.

[C]

Absolutely. And we didn't even talk about. You did a training the end of April about re engaging laps donors and how to do that. And I drafted the email and sent it off and re engaged a hundred thousand dollar donor. I should probably go through and look at all my donors and which ones have been impact by bag and look at that. But it's been huge. It's really helped me step out of my comfort zone and push a little bit more than I would have just on my own.

[A]

Oh, I'm so happy to hear that, Amy. And I'm so happy that we're able to support the polar bears and you particularly. Is there anything else that you feel like folks should know about your time in the program? Any. Any negative things about the program? Because I do think people, let's be honest, everything's not perfect. Right. So anything that you'd flag is like an improvement maybe.

[C]

Honestly, I can't. It's just everything's been so great and it's a lot of work. But the thing that I love is that you put in the work and then you see the return pretty quickly and you can tell what's working, what's not working. It's all been great. The team, the resources. Yeah, I honestly, I wish I could. Believe me, I'm one that can usually be like, oh, it'd be great if you could improve your X, Y and Z. I can't.

[A]

Amy, thank you so much for sharing this. And I just want to be clear, y'. All, I did not pay Amy to say any of this. This is not at all her true testimonial, her representation. So, Amy, thank you so much for sharing your thoughts on this and for walking us through this case study because I think it's really interesting from where you started to where it is now. And that's been less than a year.

[C]

Oh, it's been a little over a year now. Yep. So March. Yeah, I've been 14, 15 months. But yeah, it also feels, it feels so much more manageable. I feel so much more empowered and like I know what I'm doing and it feels so much better too. It doesn't feel so overwhelming. And how in the world am I even gonna do this?

[A]

Yeah. And I will say too, I think one of the things that we really help folks like you to do is to just get a little bit of perspective. Because I think when you're in the work, it's so hard to see it. You're just in the trenches and you're going. And so the value add for us is helping you to kind of just get up to the balcony to kind of see what's happening.

[C]

Yeah, absolutely.

[A]

Yeah. All right, friend, thank you so much. And I'm going to put your LinkedIn in the show notes if folks want to get in touch with you.

[C]

Great. Sounds wonderful. Thanks.

[A]

Thanks, Amy.

[B]

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