Rethink your email strategy for donor engagement & retention

Shannon Gendreau: Okay. Hello, everybody coming in. Welcome. Welcome. We are a couple minutes early, so I’ll let everyone drop in the comments your name and where you’re from, and Vanessa has a fun question for y’all while we’re waiting.

Vanessa Chase Lockshin: Yeah. We were talking about icebreaker questions. We would love to know what your coffee order is, and I will put it here in the chat as well. Oh, that just sent to just us. Let’s see if we can send it to everybody. There we go.

Shannon Gendreau: Wilmington. Oh, I’ve always wanted to visit Wilmington because I was a big One Tree Hill fan, and I know that’s where they filmed it. Oh, Palestine. Fort Lauderdale. Welcome, everyone. Vanessa, what is your coffee order?

Vanessa Chase Lockshin: Almost always a decaf vanilla latte.

Shannon Gendreau: Decaf. Okay. Nice. It depends on the time of year, but typically I do the brown sugar shaken espresso. So I love my caffeine. The stronger, the better.

Vanessa Chase Lockshin: Unfortunately, I don’t drink caffeine anymore. Otherwise, I feel like there’d be a whole other world of coffee drinks out there for me. Like cold brew. I have never had a cold brew, because they don’t make me cold brew.

Shannon Gendreau: So strong. So strong.

Vanessa Chase Lockshin: You all have some super fun coffee orders. I love this. A white chocolate latte. I have never tried that. I have to add that to try sometime.

Shannon Gendreau: Delicious. And we’re getting everyone from all over the place. So welcome. For those who are joining, our icebreaker question is, what is your go-to coffee order? And feel free to share your name and where you’re from as well if you’d like. Oh, we got a comment that you’re kinda hard to hear, Vanessa.

Vanessa Chase Lockshin: That’s okay. Is this better? I’ll scoot forward a little bit closer to my mic. Hopefully it’s better. But if not, let me know. I can also speak louder. Oh, you can’t hear me. Okay. Alright. Let me see if I can try that. Is that better for everybody?

Shannon Gendreau: Perfect. Sounds good on my end but feel free in the comments to let us know if her audio is a little better.

Vanessa Chase Lockshin: Oh can't hear me OK. All right, let's see if I can try that. Is that better for everybody?

Shannon Gendreau: Yeah. Yep.

Vanessa Chase Lockshin: Okay. Great. We’ll go with that then.

Shannon Gendreau: Better. Okay. We are at the two o’clock hour, and I know we still have some more people rolling in. This webinar will be recorded, so we will be sharing that out. But thank you all for joining us on this lovely Thursday morning or afternoon or evening, wherever it is or whatever time it is for you. My name is Shannon Gendreau. I’m on the product marketing team here at Bloomerang. I’m here to introduce Vanessa as she walks us through how to rethink your email strategy for better donor engagement and retention, which is such an important topic, especially as we’re getting into the more active giving season.

Just a couple of housekeeping items. Like I did mention, this webinar is being recorded. We will email the recording and speaker resources later today from the webinars@reply.bloomerang.com address. So make sure to keep an eye out for that. It might also end up in your spam, depending on what your filters are. We do have a comment section and a Q and A section. So if you have any questions, feel free to drop them in the Q and A portion. We will answer those at the end of the presentation, or if Vanessa is paying attention, she will answer during her presentation as well. Vanessa, if you have any additional resources, feel free to drop them in the comments near the end. But you’re also welcome to connect with either our team here at Bloomerang or Vanessa for a copy of the slides.

And if you are new to Bloomerang, welcome. We are a fundraising and donor management software that is built for purpose. We provide a giving platform to help you build strong relationships with volunteers, fundraisers, and donors. We have tools like donor and volunteer management, online fundraising, peer to peer campaigns, and custom donation forms, and we’re designed to help organizations of all sizes and types thrive. We find it really important to provide resources like these webinars to allow you to focus on what really matters and really increase your retention and donor engagement. So I’m gonna pass it over to Vanessa. Feel free to introduce yourself.

Vanessa Chase Lockshin: Hey, everyone. My name is Vanessa Chase Lockshin. I’m a consultant. I do fundraising, email fundraising, copywriting, and email fundraising programs are basically all that I do these days. I always tell people it’s a great day for me when I get to talk about email fundraising with other nonprofit professionals. I’m really excited to be here. I have been a fundraiser for fifteen years now, almost sixteen, and have worked in consulting for twelve of those years. I have worked on a number of fantastic email fundraising programs over the years.

I think probably one of my career highlights has been working with Variety BC, which is a children’s charity here in British Columbia. I helped them go from an email program that was pretty much not doing anything, where they had an email list, to raising 1.5 million dollars in about a year and a half, which was really, really exciting for them, and really helped establish a digital direct response program and harness the power of a second annual giving channel for their fundraising program. But in addition to them, I’ve also worked with organizations like Win Without War, Black Appalachian Coalition, BC Women’s Hospital Foundation, Burnaby Hospital Foundation, and also Girl Scouts of America, just to name a couple.

Shannon Gendreau: Right. Thank you.

Vanessa Chase Lockshin: Okay. Well, I am just gonna go ahead and share my screen here with all of you. Alright. There we go. So let’s talk about this. As I said, I’ve been in email for a long time, and I’m very passionate about what email can do for nonprofits. A lot of times when I talk with clients, or even with folks on webinars like this, one of the things we often talk about is the broad purpose of email, but also what it is and what it’s not. I think for a lot of organizations, they see it as the e-newsletter, which is how many of us have seen it for many years. This is our digital newsletter. We’re sending out the email newsletter to people. It is so much more than that. I’m here to tell you that if that’s the only way you think about it, I hope that one of your takeaways from today can be broadening your view of what’s possible for email, what you can send to your email list, and really thinking about it as a much more holistic strategy than just your e-newsletter.

The thing that I often say to people about email that’s different from direct mail, for instance, is that we have some added, I wouldn’t say complications, but other fun problems to solve. We have the issue of wanting people to make a donation, but we also have the challenge of making sure people stay engaged with our email list. Both of those things are things that we have to think about when we’re talking about email fundraising. So I hope that by rethinking our strategy a little bit, we can solve both those problems and hopefully have high email list engagement and also good donor retention.

Alright. So I feel like most of us are familiar with some facts about fundraising, but I’ll just mention these real quick. I think we all know that a lot of the success in fundraising is in our relationships with people: having regular contact, conversations, informing donors about their impact, and keeping in touch with them. And yet, we know donor retention is still not potentially where it could be. Donor retention last year, according to the Fundraising Effectiveness Project in the last quarter of 2024, was 43 percent, and first-time donor retention averaged about 19 percent. I feel like my heart breaks for all of us, because 19 percent for new donors, first-time donors, is so low. And I know from my own work experience how hard it is to acquire new donors. It is the hardest and most expensive work that we do a lot of times in fundraising programs, and the fact that we can’t retain more of those people over time is really, really sad. So I hope that we can change that in the coming years, because I do think there’s so much potential for our fundraising programs if we work on increasing retention, and in email, increasing engagement on our email list.

So let’s talk about this a little bit more. I always tell people that the foundation of donor retention requires communication. We have to be building relationships actively with donors. And you might think, well, Vanessa’s here to talk about email. Is it possible to do that on email? Yes, it is. Email is still a really great relationship-building tool. One of the things I often point to as proof of that was when I was working with Variety BC, I had a conversation with one of their major gift officers. I think they had a team of three major gift officers at the time. We were talking about what else we could do to help support their major gift efforts with the email program. And she was like, “You know, I’ve worked at a lot of organizations over the years, and never have I had so many conversations with donors where I’ve asked them, ‘Is there anything else I can share with you, any stories you’d like to hear about the work?’ Nine times out of ten, people tell me, ‘I feel so well informed because of your emails. I don’t feel like I need to know more.’” Which I think speaks really highly of what email can do in lots of donor relationships, even major gifts. Sometimes I think we think major donors only need personal touch points. We’re only calling them, visiting them, that sort of thing. But email can also play a role in that. And if it’s doing that sort of thing for major donors, just imagine what it could do for your annual-level donors as well.

Alright. So let’s talk about acquisition versus retention really quickly, and just make the case for all of this. Retention really is such a game changer for fundraising programs. I’ve seen this for clients in the last couple of years where we’ve had digital fundraising programs where we’ve increased retention from somewhere in the mid-forties to somewhere in the mid-fifties over the course of a year or two, and that’s resulted in higher lifetime donor value for the organizations. Also, more people upgrading their gifts over time, and more money coming in the door for the organization, which has been really fantastic. But we also know that acquiring new donors costs, you know, five to ten times more sometimes than retaining an existing one. And when we’re talking about email and digital donors, we have to think about the ever-increasing cost of digital ads and digital ad buys, which can be really, really expensive.

All right. So let’s talk about some common pitfalls with digital fundraising. Oh, I’m sorry, everybody, that my volume is so low. Let me see if I can fix that real quick. Please hold on just a second. Let’s see. If I turn my headphones, maybe this will be better. Give me just a minute here and see if I can get this better for all of us. Okay. Maybe that’s better. Let me know in the chat. Okay. Fantastic. So glad to hear that. Great.

So let’s talk about some of the common pitfalls with digital fundraising that are contributing to us having challenges with a less engaged email list and also lower donor retention, because these are problems that we have to solve through our email programs. One of the top ones that I see a lot is the one-and-done automated thank you emails. I think we all send these. Hopefully we do, because they do need to go out. This is the transaction email. When somebody goes through your CRM or a payment processor, they have made their gift, and automatically, usually, hopefully, there’s an email that goes out to people right away thanking them for that gift, and often it also has the tax receipt attached.

I think the problem is a lot of organizations see this as the sufficient stewardship that needs to happen for that digital gift, and then go quiet until the next email that goes out, or maybe even the next fundraising campaign that they send by email. I think this creates a lot of transactional expectations and a transactional relationship with email donors, that donors are only gonna hear from us regarding transactions, regarding giving us money, and then us giving them a tax receipt. And we want to be more than that. I think we all want people to be more invested in our cause and to stick around a lot more than that.

Feeding into that, long silences in between emails are a big one. As I said earlier, I think one of the unique challenges about email is that we both want to retain somebody as a donor, but we also need to retain them as an engaged email subscriber. When I think about engaged email subscribers, I usually look at our most engaged segment of the email list as anybody who has taken an action, meaning made a donation, opened an email, or clicked on an email, in the last zero to thirty days. They’re highly engaged. People who are still pretty engaged, I would say, are anywhere from zero to ninety days, people who’ve been engaged in the last three months. But the further we go out from that thirty-day mark is where we start to lose people.

And I think this might surprise some of you. When somebody has not taken an action in at least ninety days, so they haven’t opened an email, they haven’t clicked on an email or done something related to one of the emails that we sent them, I consider that person inactive. Now you might think, well, it’s only been ninety days. But I would encourage you to think about your own inbox. You probably still get emails from people you haven’t unsubscribed from, and it’s been longer than ninety days since you opened one. It’s probably gonna be incredibly difficult to get you to open that email again, just like it’s going to be for your own email subscribers. So some of what we have to do in email is think about the frequency at which we communicate, which can help get people used to opening emails from us and engaging with those emails. The other part of the equation, of course, is the content and the quality of the content in the emails, and we’ll talk about that a little bit later.

The last thing here I’ll just say is that the email content isn’t relevant. That is a huge pitfall sometimes in fundraising. Just imagine, for instance, you are a first-time donor to a local food pantry in your neighborhood or your community. Part of what has prompted you to give to the organization is that inflation is high, and you feel like it is really challenging right now, with food costs for low-income families or families living in poverty, and you had an extra twenty bucks and you wanted to donate it to this organization. So you made this gift to support their food pantry. And you get your automated thank you email. That’s great. And then the next day or the day after, you receive an email that’s sent to their entire list, presumably, about an upcoming community event that has nothing to do with the food pantry or food insecurity in the community. I could just imagine. That doesn’t always lead to the smoothest transition to being a part of an email list, or the smoothest donor journey either. So think about how segmentation and the types of content that we want to send people can enhance their relationship with our organization and hopefully keep them more engaged as a donor.

I would also say, when we think about how to send good emails and what to put in emails, we know a lot about what donors want from the research that Penelope Burk has done over the years in her work with donors and fundraising. We know on a very basic level the four things donors are after are consistency, relevance, impact, and connection. And good news, we can deliver all of those things through email, which is really great for us.

Donors want to know that they are making a difference. That’s really important for them at some very basic level. They want to know, no matter whether they give five dollars or five thousand dollars, that they have been a part of something and that they are contributing to something meaningful and good. If you think about us as humans, all of us, we have confirmation bias. We want to know that we were a good person doing something. We want to feel validated, to have our values reflected back to us. And that is part of the role that we can fulfill as nonprofits in our communication and in our stewardship with donors.

We know that our donors also value consistency. Reliable communication does build trust, and there’s also been some research on this from the Lilly School of Philanthropy at the University of Indiana, that one of the reasons donors don’t give again is because they just never heard from the organization again. So being a reliable communicator to our donors is one of the things that can increase our retention, and it also builds trust in that relationship over time. Relevance is a big piece: content that speaks to their values and their giving journey. And I always say relevance is so much more than just the personalization of the email, of somebody saying, “Dear Vanessa.” It’s like, “Vanessa, thank you so much for making your donation to the food pantry last week. This week, we’re able to help a hundred families thanks to you and other donors.” That level of relevance and personalization can really make a difference. But also human connection. I think sometimes we doubt this is possible in email because we think, well, they’re going to hundreds or thousands of people, and how can that feel personalized? But it can, in the way that you write the emails, in the tone that you take, in the style of writing you have. Emails can and should feel like they’re coming from a real person and not a faceless organization. So hopefully, when we can combine all of these things in our communications to donors, we can help them feel more invested in what we’re doing, so that they will give again the next time they have the opportunity.

Okay. So let’s talk a little bit about going beyond the first thank you in the digital donor experience. As I said earlier, we all know that automated thank you emails go out. That’s one part of the process. But there is quite a bit more that we can talk about, and this is also where we can talk about the ability to leverage tech tools that we have in our stack, like automation journeys or other automation tools inside an email tool.

Okay. So the first forty-eight hours after somebody makes a gift, let’s talk about that. I always tell people that when somebody on an email list takes an action, whether that’s making a gift, signing a petition, or doing some other high-value action where they had to click out of the email and complete some kind of transaction, that is a peak moment in their relationship with our organization, because they have actually done the thing we wanted them to do. They followed through and did that, which is really great. Usually at those moments where they have made a gift or signed a petition, people are feeling highly excited about what they’ve done. They feel like they’ve done something good, and that is a really great time to capitalize on some momentum in the relationship with that donor. That is a time to reinforce that they did something great and that we want to appreciate them for what they did.

So, obviously, as a first step, we can send them an immediate auto-generated email, that receipt, and the heartfelt thank you, which is really great. But the thing I always encourage organizations to think about is, within the next twenty-four to forty-eight hours, following up with some sort of warm personal touch. This can be an email. It does not have to be you getting on the phone. But if you want to think about multichannel pieces here, you absolutely can. I think sending people a separate thank you email that feels warm and personal, and has that level of acknowledgment of what they’ve donated to, why they might have donated to that specific thing, can really enhance that relationship and the sense that your organization values this gift. I personally love a thank you email that brings in a staff member story, the story itself, which can be quite powerful. And I have a really good example of this kind of email to show you in a couple of slides.

Then, also in this process, the other thing we want to do is set some expectations for what people can hear from us, especially if they are also a new subscriber to our email list. What are they gonna hear from us? Are we gonna email them once a quarter, once a month? Every so often, we’re gonna send them things like updates about our programs, maybe stories, impact reports so they can see the gift in action. I think giving people some idea of what is to come in that early communication can hopefully shape the relationship so that the donor sees themselves both as a partner in the mission, but also knows what to expect. For instance, that you’re not gonna be emailing them every day unless you had a really good reason. Maybe you’re running a rapid response petition program. Who knows? But give them the opportunity to understand what they can expect to receive from your organization. And we do that with offline donors as well. This is just about figuring out how to do this digitally.

Alright. So let’s talk about a sample post-donation journey. This is the kind of thing that you can automate through tools like Bloomerang or Mailchimp or other email tools that you might be using. Most of these days have donor journeys or automation tools that allow you to set up a series of emails that can go out to people who meet certain criteria. When you have a simple framework for what kind of emails you want to send out and what that flow looks like, you can then start to leverage tools like this that will make your life a lot easier. It’s not like you’re having to sit down and send these emails every single time someone makes a donation. That would be exhausting. I don’t want you to do that.

We already talked about the first two pieces in the framework, which are the thank you email and the personalized follow-up. But once we get past that point, we want to have a welcome series. Or if it’s not for a new person or a new subscriber, you could think of it as the post-gift series, where we continue to give people some update or orientation to our work, sharing stories, inviting them to connect beyond giving. As I said earlier, people who’ve donated are highly engaged, so getting people to self-select to that next rung on the ladder of engagement can be a really valuable thing for our organizations. That can be two to three emails over two weeks. You can use your own judgment on the number of emails you send in that kind of series and what kind of spacing you want to give it. But usually I do two to three emails over about two weeks.

And then, typically after that, sending some sort of specific impact update thirty to sixty days post-gift, where we hopefully can share more in-depth information about how their gift made a difference, whether that’s some facts and figures, a story, or photos. Chances are your donors are giving to a couple of different funds within your organization, so I would be unsurprised if you had content for some of that that you could draw on to create some standard thank you letters or update emails for people. Just follow up with them to say, “Since your gift two months ago, our team has continued to deliver these kinds of programs,” or “These are the kinds of stories we’re hearing from people because we’re able to offer this service in the community.” There’s lots that you can do with that. Again, it’s just about providing people with that kind of meaningful update.

And then, hopefully, we get to a next ask at some point. But the idea here is that after we’ve had several positive, trust-building touch points along with other communication, we’ve hopefully earned the ability to ask people again and have that be successful. I always hope that progressions like this build trust and loyalty before the next fundraising opportunity. For many of my clients, they’re not running concurrent, evergreen fundraising opportunities that are always going. A lot of them have anywhere from three to five branded campaigns that they run a year, like Giving Tuesday. I’ll use BC Women’s Hospital as an example. Giving Tuesday, International Women’s Day is another one, and they run a campaign around Mother’s Day. Those are all really specific branded campaigns that they run every single year, and have for a while now. In between those opportunities, we’re earning the ability to ask again. Hopefully, we are sending people highly valuable, engaging content that continues to prove that we are doing great things with their money and also keeping them engaged as a subscriber.

I will also add that once people get out of your welcome series, in that space between the welcome series and the impact update, you are probably sending them other emails. If you are sending things to your list, you’re probably not suppressing them at that point from those emails. So, hopefully, they’re receiving other useful, engaging content from your organization.

So let’s talk about some examples of thank you emails and what this follow-up can look like. This is an example from 350.org, an organization that I made a donation to, as a part of my ever-ongoing experiments, to see what happened. I’m always curious, for organizations that run primarily digital fundraising programs, what they are doing in terms of stewardship and follow-up after they get a gift from somebody. A couple of things I liked about this first thank you letter, which is more the transaction email that I got. I really appreciated the brevity of it, because we all know people have short attention spans. It was easy and quick to read. It was highly readable and skimmable in terms of the formatting. But I also really liked the four bullet points. When I write fundraising emails, I love being able to distill down to some key points what donor support is going to do. Usually that comes back to the areas of focus the organization has and where they’re putting time and resources for their work. Being able to say, “These are the things we’re doing, and with your support, this is what we’re gonna continue to work on,” is a really great level of preliminary accountability for an organization. These are the things we say we’re gonna do, and guess what? We’re gonna report back to you on that hopefully afterwards, and they did. But I won’t show you that email.

What I want to show you next is the second follow-up email I got from them, which came from their development director. I think it was a day or two after I made that gift. I was really pleasantly surprised that I got this email. I wasn’t expecting anything like it. And it’s something I now do in my practice with digital fundraising. What I like about this email is specifically the second-to-last paragraph. It says, “Now that you’ve donated to build the climate movement, I want to make sure you’re plugged into all of our campaigns and local groups. Click here to check out our featured campaigns and find a local climate action group.” This is fantastic. They spent a lot of time in this email telling me a little bit more about what they do and how the money is used, and that they’re an organization that isn’t just about asking people for money. It’s also about engaging activists in climate justice work. So giving people something really specific and concrete, that one call to action of ways I can be plugged in, is great as a donor. I probably wanted to do that, or other donors probably want to do that.

I will also tell you, from a fundraising and prospecting perspective, this is really useful information. Getting people to self-select into other opportunities, whether it’s volunteering or learning about something, will tell you more about who the most highly engaged people are in your donor base and also on your email list. So if you don’t have something like this in a follow-up email, think about what you could do to help people raise their hand and indicate more excitement in your fundraising or in your organization, because this will also help you with other types of prospecting, whether it’s trying to find volunteers or people who are super supporters who can really help you during key campaigns. It’s all really good information that you can then use for your organization, and it also shows how email can support all the other areas of fundraising.

Alright. So let’s talk about some other non ask emails that you can send to build trust and loyalty and that are stewardship-aligned. I’m gonna go through this pretty quickly. I feel like we probably all know why non-ask emails matter. To me, it’s all about prioritizing the relationship over the transaction and making sure donors feel that in their relationship with us. They want to feel seen and valued, not used. I can still tell you there’s one organization that sticks out to me, that my husband and I made a gift to that, at the time, was a pretty big gift for us. It felt personally significant. We made this gift to the organization. We got a text receipt back and a thank you, but after that, we never got any communication except for postal lock-drop acquisition direct mail pieces, which I always thought was really odd. From a donor experience perspective, it was just weird not to get personalized mail after we had made a gift to this organization that we were really excited about. And you can think about that with email too. Where might you be dropping the ball in that relationship, so that if somebody had donated recently, this would land well with them? That’s where you can start to use tools like inclusions or exclusions in emails, where people are either receiving the email or they’re not, so you make sure the right people are getting the right emails.

Ultimately, communication does build trust. I really believe that, and I really believe email can be something that builds trust with our audiences. I know tools like email and SMS texting do get a bad rap these days, mostly from political campaigns who horribly abuse them and become spammers, and also lots of other bad actors in this space. But I think there is a role for all of us to step into and be good, reputable email senders, and to build trust that can really drive giving. And we have to have some balance. If you sent every single email to your list as a fundraising email, you’d probably figure out pretty quickly you’re gonna burn that list to the ground, and then you won’t have an email list, which would not be awesome for lots of reasons.

Alright. So these are the four types of emails that I tend to send to lists that I work on. Impact stories and testimonial emails, where we’re really showing donor impact in action. Behind-the-scenes, insider updates, where we can pull the curtain back on some work that we’re doing. A good example of that was BC Women’s Hospital Foundation. We sent some updates about capital improvements that were happening as a result of their capital campaign. That was a really great opportunity for us to show people the dust and the dirt sometimes: here’s the new thing that’s being built, it’s in progress, but hopefully a month from now, we can send you new pictures. It was a really good opportunity for donors who didn’t come down to the hospital very often to feel like they were a part of the project.

Then we can also send education and values-based content. I think this is really important, and something a lot of organizations underestimate is their expertise. You have things to offer. There are things you know about, issues that you’re an expert in. Chances are you have some perspectives and opinions that can be valuable or educational to people, that you can send to reinforce the shared values you have with your donors. There’s a role for that in email. I think about them as the op-ed pieces that we might send to our email list, and they’re a really good piece to use if you need to respond to something in the moment, if something has happened in your community or in the world that ties into what’s going on with your cause and the issues you work on. And gratitude and recognition messages. I think we all know those. We thank, we celebrate, and we recognize our online donors who have helped us.

Alright. A couple of examples here that I’ll just give you. This is from Variety BC. This is an email that I worked on as a part of their World Autism Acceptance Day campaign. This was just them using an awareness day, which we all can do. We can all find awareness days for our causes and send thank-you and stewardship content around those days. The subject line for this email was “Four amazing kids you’ve helped.” We wrote the body of the email, which is on the left side here (I couldn’t get it all in one line), to tell people one story, and then give them some other links, which are the ones here on the right side, where people can click in and see some more stories about kids they’ve helped. The idea was to remind donors that today was an important day for many of the families that Variety helps, and also the impact that having support for a child with autism has had on those families, whether it was getting an autism diagnosis because they received an autism assessment, or getting help through tuition for extra tutoring support or speech therapy. All of those things are ways they were helping kids in their community, and things they could highlight in the impact email.

And this is another one that was a little bit different. This was a one-off email that we sent after a campaign they ran called Show of Hearts, which was their big fundraiser that they do every year. This specifically spotlighted one child, an eleven-year-old named Sophie. I remember the subject line of this. It’s really cute: “Nothing Stops Sophie,” which was just a way to get people excited about what they were gonna read. We gave people a little bit of a teaser of the story at the top of the email, but what we really wanted people to click through to see was the video that we had of this little girl and her family. It was all about how she received some mobility equipment after having been diagnosed with spina bifida at birth, which meant that she would often get tired and be in pain very easily. We wanted to show how having the right mobility equipment, which her family couldn’t afford out of pocket but Variety could pay for, really changed her life and theirs as well. So lots of warm fuzzies.

And I know this is a children’s charity, so some of you might be thinking, “We don’t work with kids. We don’t work with puppies. We don’t have warm fuzzy content.” It doesn’t always have to be this type of tone and style in your content and your stewardship. For instance, as a big contrast, one of the other organizations I work with is the Center for Family Equity out of Vancouver, and they are an organization dedicated to eliminating family poverty through government policy. They do a lot of lobbying, a lot of organizing, and a lot of activism. The warm fuzzies are not their brand of stewardship, and that’s okay. They are more focused on the wins they get through legal action and the number of people they can bring together to come to the legislature for a lobbying day, things like that. And given the nature of their work, a lot of families don’t necessarily want to come forward and talk about their experiences in poverty. So it’s about finding the right angle and framing for the content that donors do want to hear about. For them, donors want to hear about the policy wins that they have, which probably sounds a little wonky, but they know that’s what their audience cares about.

Alright. So let’s talk a little bit about donor segment strategies, and then we’ll talk about how we bring this all together. One size doesn’t always fit all, which is always important to remember. With email, some of the magic we’re trying to capture in the bottle is the right message for the right donor at the right time. I want to say, though, the caveat: you’re not gonna hit that nail on the head every single time. I certainly don’t, and I do this all day, every day, for lots of organizations. The danger of segmentation is also that we can over-segment. We can have so many segments that the juice is no longer worth the squeeze for the amount of work we’re pushing into it. So some of this is just a balance. I don’t want to tell you that you need to go aggressively into segmentation on your email list. What I will say, though, is that personalized communication and segmentation generally has higher engagement. There is a benefit to it. And we can also acknowledge that donors are at different stages in their relationship, and so sometimes that requires different types of communications.

I would say at the simplest level, if you want to dig your toes into segmentation with your donors, dividing up new donors versus repeat, returning donors is a great way to start looking at your list. Also non-donors, because I’m sure you have some people on your list who have not yet donated. Those three categories are really great ones to consider. You might also want to consider these categories. Recurring monthly donors. These are our steady supporters who still need appreciation and impact updates, but it probably looks a little different. They’re giving all the time. We also have major donors, who are high-level investors and maybe need personalized stewardship sometimes, maybe not. Who knows? And then also in our email list and in our databases, we have lost and re-engagement donors who haven’t given recently, and maybe they just need a little different perspective to hopefully nudge them back into our active donor file.

To give you some examples of what this could look like in stewardship communication, I created a little table here for all of us. It shows how small tweaks in language can make a difference in terms of the tone, style, and approach that we have with each of these segments. You can imagine, for instance, if you were a monthly donor or a repeat donor and somebody sent you a message that says, “Your first gift has already helped so-and-so,” you might think, “That’s not my first gift.” That might be confusing. It would certainly be confusing for me. But to send a monthly donor a message that says, “Because of you, every month families are...” again, that small nuance in language makes the difference. As you think about how to segment your email list and engage people based on where they are in their donor journey, these are all little things we can do that can add up to really effective communication and really effective fundraising down the road.

Alright. Let’s talk about bringing this together in an email strategy. We talked about segments. We talked about the different types of communication that we can do after a gift. We talked about the post-donation journey and what that can look like. But what does this look like on a day-to-day basis in your email program? I think it all starts with having an email calendar. This is the thing that saves my sanity regularly. I’m in email calendars all day, multiple times a day, for my clients. It helps me avoid feast or famine, being like, “Oh, we have so many emails to send,” but also, “I don’t know what we’re gonna send this week,” or “We have nothing to send for a month, and what are we gonna say to the email list?” The other thing it helps me do, which I think is really valuable for being in a proactive position of managing an email list, is have medium-term vision and short-term execution.

What I mean by that is, having a medium-term vision for what you’re gonna send to your email list is super, super valuable. It will help you build narrative arcs. It will help you build momentum going into a fundraising campaign like Giving Tuesday. It will help you be more organized in what needs to happen in that medium term, which I would say is about three to eight weeks out on your email list. And in the short term, in terms of execution, it can help you project-manage what has to get done, which is definitely part of email. Somebody has to have an eye on the ball, and somebody has to be kicking the ball down the field. Maybe that’s you, or maybe that’s a group of you at your organization. That’s part of what an email calendar can help with.

This is separate from donor automations or journeys that you might set up through automation tools in your CRM. These are the emails that go out when they need to go out, and they’re often a mix of asks and non-ask emails. Ideally, there are regular touch points. I know at least one of you is probably thinking, “Well, how often should we email?” It’s a great question. I always tell people it really depends on your capacity, the size of your list, and some of your goals. To give you concrete examples: with Variety BC, they had a fifty-thousand-person email list, which is pretty large for a regional nonprofit like them. We aimed for one email every one to two weeks. I would say it was more like every two weeks sometimes. There were times definitely where we sent an email a week. During campaign periods we sometimes sent more frequently than that, but we waited until those key times when we could really capitalize on some multichannel momentum to send people multiple emails in a week. But the idea was we just wanted to keep people engaged. We wanted to send them warm fuzzy content. We wanted to remind them about the organization and the brand and keep them invested in the work as a donor.

If you are struggling to think about how to map out an email calendar, the best thing I would say is start by aligning it with your campaigns or the seasons of work that you’re in. A good example of this is that we have Giving Tuesday coming up. If that is your next fundraising campaign day, I would start by putting that on your email calendar first. Then think about all the time between now and Giving Tuesday and what you would put on the calendar between that. What kind of conversation do you want to have with your email list leading into the messaging and ask that you plan to make on Giving Tuesday? You don’t want it to be the situation where you’re just flipping the switch and suddenly talking about something you haven’t talked about before. You can be strategic, and this is the great thing about email: you can really have this level of strategy in the messaging and content that you bring to your emails. If it were me, I would focus on donor impact content between now and Giving Tuesday, really giving people lots of proof that making a donation makes a difference. And I would also think about content that helps people see what the problem is, the current landscape of the problem, and why the problem is a problem, because those are the things that ultimately motivate people to donate to your cause when you put an ask in front of them.

Alright. Let’s see what else I want to tell you. A couple more things, and then I’m gonna answer some questions. With the email calendar, it really is about balancing our asks with stewardship. I personally try to prioritize stewardship over solicitation. For a lot of our clients, I aim to run three to six fundraising campaigns a year, which are branded, specific campaigns where we go out over multiple days asking for donations. To me, that’s about building enough trust and enough engagement with people in between those asks so that we aren’t getting list and donor fatigue. If you’re thinking, “Oh, maybe we need to run six campaigns,” you don’t have to run six campaigns a year. But also have a strong campaign idea. This is a separate thing about email that I can tell you all: don’t just ask to ask. I know lots of you are probably on nonprofit email lists where you get fundraising emails and you’re like, “Oh, we should be sending more asks to our list.” Maybe. But I think you want to make sure that what you do send in terms of fundraising packs a punch. Sending a fundraising email usually has higher unsubscribe rates and usually has lower engagement, because it’s fundraising, and that’s just the nature of the beast. So you want to make it worthwhile for you and for your list when you send it out. Make sure you have a campaign idea that’s strong and compelling, with a really good theory of change behind how donating makes a difference. All of those things can add up to a motion.

Alright. A couple of quick ideas for you. I would really encourage you to leverage the power of automation in your email tool. Bloomerang has a great donor journey tool. I use Bloomerang with several of my clients, and I really enjoy using the automation tools that they have. At the end of the day, they save time and scale stewardship. And no matter what email tool you’re in, you probably have access to that in some way. Again, just remember personalization. I know we talked about this with segmentation. It really is about feeling seen and feeling valued, and that’s a gift we can give back to donors. And in our content, storytelling is a really powerful tool for us to build and foster emotional connection, which can lead people to feel excited about the work and excited about what they are investing in.

Alright. Before we go to questions, I would love to know, what is one tip from today’s webinar that you think you might implement, something you’re excited to try with your list? I’m always curious to hear that, and then we’ll go to some questions as well.

Segmenting. Great. I love it. It’s a good bunch of stuff. Email calendar. Oh, awesome. I love that so many of you are saying email calendars. In case you need a template for an email calendar, I’ll put this in chat for all of you. I do have a template for an email calendar. You can download it for free on my website, thestorytellingnonprofit.com/toolkit. There are two tools in that toolkit. One is an email campaign planner. The other is the email calendar, and that’s the calendar that I use in my agency. So if you want one with all the fancy Excel formulas and everything already in there, it’s there. You can grab it for free, and hopefully it’ll help you. Alright, friends, go send me some emails. I’m excited to answer some questions, Shannon.

Shannon Gendreau: Yes. Thank you. Before we get into questions, Vanessa, this was fantastic. I was taking notes myself, because I think all of this is valuable. Before we get into questions I’m just gonna pop up a poll. Feel free to answer it or not for those who are attending. But we do have some good questions in the Q and A, two of which are about whether you are able to share these slides after the webinar is over, Vanessa?

Vanessa Chase Lockshin: Yeah. I think I sent them to you all yesterday to send out, so you should have a link to those to include in the follow-up email.

Shannon Gendreau: Okay. Perfect. So we will include those with this recording for those who are asking. Another good one, from Julie, is how often is too often to email? I’ve heard from older adults that they don’t like how often they’re getting them.

Vanessa Chase Lockshin: That’s fair. The thing I always tell people about email frequency is that, as the sender of the email, we are hyper-aware of how many emails we’re sending. I always know how many emails I’m sending on behalf of the organizations I work with as a consultant. But I would encourage you to think about yourself as a consumer of emails. Do you remember what was in your inbox this morning? Your personal inbox? I do not. I definitely don’t remember what was in there yesterday either. And I’m not saying that’s your permission slip to email people daily. That’s not the takeaway here. But I will say that one year, two or three years ago, there was finally an organization in December where I was like, “I feel like they’ve emailed me a lot.” I went back in my inbox and searched their sender name and their email address just to see how many emails I’d gotten from them in those last few weeks. And over the course of three weeks, which was twenty-one days, I had gotten something like twenty-five emails from them. I use that example not to say that was good email practice, but just to say that the line of “too many emails” is much further over than we think. I think the problem for most organizations is we actually understand, and then we end up having [inaudible] problems because of it. That said, I usually encourage people to think about a weekly email or every other week. I find it’s a good cadence. But I think the amount of emails you send often comes down to your capacity in some cases.

Shannon Gendreau: Fantastic. That was a great question. Great answer. We have one from Hayden. How can we share stories like this when we have to protect our audience? I’m assuming they’re talking about case studies.

Vanessa Chase Lockshin: Yeah. Absolutely. I think that’s a really valuable question to ask. I know some of you might work in health care settings in the US where you have HIPAA compliance issues, or you work with a vulnerable population where sharing stories and identifying details just isn’t appropriate. I can think of clients I’ve worked with in the past where that is the case. The thing I often do and think about is sharing staff member stories instead. Staff members are there on the frontline. They see the work in action. They can opt to speak to the power that donations have for an organization.

I remember years ago, I worked with a sexual assault support center. At the time, they had a six-month wait list for crisis counseling services, one-to-one crisis counseling. For obvious reasons, we could not really share a lot of their clients’ stories. It just wasn’t appropriate. Some of them were in legal cases and some just didn’t want to be identified. Just totally fair. I remember we had a staff member who told us that she’d had somebody come in for their first appointment, and her story was basically about how grateful this person was. They were finally in and finally getting some support. It was a really lovely, moving story about the power that counseling support can have and how important it was for people to be seen quickly. So we were able to tell that kind of story without actually telling a specific client story. Sometimes you just have to get a little creative about the angle you come at things from.

Shannon Gendreau: Perfect. Thank you. And what are your thoughts on sending an email ask along with a USPS or snail mail ask? Same message, same look, but trying to cover both channels.

Vanessa Chase Lockshin: Yeah. You should do it. That is the basis of multichannel marketing, multichannel fundraising. It works. It is highly effective. I’ve worked with lots of clients over the years who have pretty robust direct mail programs, and I usually just work on email for them. Normally what I see is people will send direct mail and then, usually four to seven days later, we send the first email. Sometimes they drop the email on the same day they drop the direct mail. It really just depends on personal preference. But it’s a good idea, and you probably will see a lift in giving because you’re doing follow-up with people.

Shannon Gendreau: Perfect. Do you have any tips for coming up with a catchy or attention-getting subject line?

Vanessa Chase Lockshin: Yeah. What a great question. I don’t wanna say formula, but my guideline for writing good subject lines is be just vague enough to be interesting. The best example I can give you of that kind of subject line was when I wrote for Variety BC. This was probably three or four years ago now. It was one of their best-performing subject lines and best-performing fundraising emails. The subject line was “Parents can’t keep up with these costs.” That subject line did a couple of things. It told us who the email was gonna be about, a subject, a character, if you will, in the story: parents. It told us about a problem, so they can’t keep up with something. And then what that something was: costs. And the keyword in there that made that whole thing vague but interesting was the word “these.” People wanted to know, what are these costs parents can’t keep up with? What’s happening here? It naturally piques some questions in your mind. That is a really great way to write subject lines, I find. Obviously, you can veer into spammy territory with that, so use your judgment, and don’t write spammy subject lines.

But especially on giving days like Giving Tuesday, if you look at your own inboxes, lots of those subject lines will be like “It’s Giving Tuesday, make your donation” or “Double your impact on Giving Tuesday.” Your donors, in a lot of ways, and I say this not with any disrespect, don’t care as much that it’s Giving Tuesday. They are ultimately more moved and motivated by the impact and the difference that they can make. So I have historically found, on giving days like Giving Tuesday, that writing subject lines that speak more to the impact, to what’s going on at the organization, is a little bit more effective in terms of getting people’s attention and getting the rates higher.

Shannon Gendreau: Oh, perfect. We are getting a lot of great questions in, so I’m gonna try and get through the next few in the minutes we have. Can you share your insight on segmenting donors in other ways other than gift amount or frequency?

Vanessa Chase Lockshin: Yeah. That’s a great question. Gift amount and frequency are probably the big ones that you want to focus on. It’s really gonna depend on how big your email list is and how big your donor file is, to direct the level of complexity that you want to have. I have worked with a client before who segmented by what donors gave to. They had a couple of pretty distinct programmatic areas that people could give directly to, and so they had donors segmented into two, maybe three different groups based on what they gave to. And there was a while with Variety BC where we had a stewardship follow-up strategy that we ran where we followed up with people based on the areas that they gave to at the organization, like mobility equipment, speech and language therapy, private assessments, things like that. We gave people really specific content. We ran that test twice. I didn’t see a lift in giving on that. That doesn’t mean you won’t with yours.

The other segmented test that we ran with Variety BC that did actually do pretty well was based on geographic location. We didn’t do every city, obviously, in British Columbia, because that would be quite a few places, but we picked six or seven of the densest places where donors lived, so we had big enough segments of people. This was probably for Giving Tuesday, I think. On Giving Tuesday, we sent an email saying “Help a child in Vancouver” to people who lived in Vancouver, and then we told them a story about a child who lived in Vancouver and who Variety helped. For that test and that follow-up, I found people were highly motivated by the idea of local giving, helping kids in their neighborhood, in their backyard. That was a message that worked really well for that audience. So depending on how big your service area is and your donor base, geography can also be an interesting one to play around with too.

Shannon Gendreau: Those are all really good suggestions. Gracie wants to know what are your thoughts on having donation asks in newsletters?

Vanessa Chase Lockshin: I think you can do it. I have lots of clients who want to send a soft donation ask at the bottom of their emails, and it’s fine. For most of them, they rarely, if ever, see a lot of donations come in that way. Most of their donations come in through direct fundraising emails where we are making a very specific, clear ask to people, and that is the only thing the email is about. My personal feeling is that I would rather have pure stewardship and cultivation be just that, and not tack on an ask at the end. That might be an unpopular opinion. But I think it’s good to give people some breathing space sometimes from those donation appeals, and to make that email about something that’s not just about asking for money. But you can test this. That’s always my advice with email. You can test it and see what works.

Shannon Gendreau: Awesome. And do you have any suggestions on how to navigate email consent? This person is asking because their email newsletter is currently opt-in only.

Vanessa Chase Lockshin: Yeah. That’s a good question. I feel like I might need more details on that. Your email list shouldn’t be opt-in only, friends. Nobody should be just adding people to their email list. This is 2025. Email consent is important. The gold standard for email opt-in is a double opt-in, where people have signed up on your website or somewhere, and then they also get a confirmation email to their inbox that they have to click. Those are the best type of subscribers, because they have actually consented to wanting these emails.

There are lots of ways, though, to acquire people for your email list. If you have a big direct mail base, for instance, and you want more people on your email list, I found for a long time, and still do, that one of the ways we collect email addresses pretty quickly is by making sure we have an email sign-up option on the reply device and also on the donation form on the website. Those are low-hanging fruit opportunities where you can get those email addresses. But I feel like there are more details on that one. If you want to email me, I have my email address here on the slide. I’m happy to answer more specific questions about consent on email lists.

Shannon Gendreau: Okay. I think we have time for one more. How many people in an email list is too much for true cultivation?

Vanessa Chase Lockshin: I’m sorry. Can you repeat that one for me?

Shannon Gendreau: Yes. How many people in an email list is too much for true cultivation?

Vanessa Chase Lockshin: How many people on an email list? I’m not sure if we understand that question. Maybe you can tell me what your interpretation is, Shannon. Can an email list be too big to be effective? Is that the question you think?

Shannon Gendreau: Yeah. I think also, is there, in your mind, too few as well?

Vanessa Chase Lockshin: Oh, too few. Yeah. That’s a really good question. I don’t think there can be too many. I have a client who has an email list of over a million people, and they do very well with it. Email is a lot of times a numbers game, and so the more people you have, the more successful it is gonna be. But too few, I never think there’s too few people. The challenge with few people on an email list is that you can’t really test things. If you have fewer than five or ten thousand people on an email list, it’s probably not gonna be useful to test subject lines, because it’s not gonna be statistically significant. And A/B testing the bodies of emails, the content inside the email, you’re not gonna get a lot of information from that either, because your sample sizes are too small. You could do broad-based message testing over time if you wanted to. The other thing about smaller email lists is they often tend to be more engaged. As you add more people to your email list over time, you will see your open rate drop. You will see your click-through rates drop somewhat, not dramatically. That’s just what happens when you have more people, because you then have more people who are disengaged on your list. So I’m sorry. I feel like I’m not answering that question super well, but there are pros and cons to both.

Shannon Gendreau: Yes. Well, we are out of time, and thank you to everyone for asking these amazing questions. A very engaged group of attendees. We appreciate you both. You both. There’s more than two of us. We appreciate all of you attending. Vanessa, is there anything else you want to say before we conclude, or any resources you want to drop in the chat?

Vanessa Chase Lockshin: No. I just wanna thank everybody for being here today. It was great to spend this hour with you. I hope it was really helpful. And I always tell people, if you have questions, feel free to email me anytime. Consider my email address yours if you want to reach out and ask email-related questions, even it's like a month from now. I’d be happy to hear from you.

Shannon Gendreau: Well, yes. On behalf of Bloomerang, we’d like to thank you, Vanessa, and all who took the time to attend, for spending this hour with us. The recording will be sent out later this afternoon along with Vanessa’s resources. That concludes our session today. Thank you so much. We hope to see you again soon.

Vanessa Chase Lockshin: Bye, everyone.