092: How to increase customer retention for your membership – with Jeremy Redleaf

Jeremy Redleaf is the Co-founder at Caveday, a global community of makers that come together to do focused work built with MemberSpace. In this episode, he joins Ward to discuss early-stage customer retention strategies that work.

✍️ Show Notes

📄 Show Transcript

This transcript is computer generated, please excuse any errors 🙂

Ward Sandler: Welcome, everyone. Today, I’ll be talking to Jeremy Redleaf, the co-founder at Caveday, a global community of makers that come together to do deep-focused work built with MemberSpace. Jeremy, welcome to the Membership Maker podcast. We’re excited to have you here!

Jeremy Redleaf: Thanks for having me. I’m team MemberSpace; I’m here!

Ward Sandler: Awesome. One of the best things any membership business owner can do is provide value to their members from the beginning, so they’ll stick around for a long time. Those initial days are extremely important, and it will be what can later on scale things for any business, Right? So what is Caveday approach on how to delight users in the early days?

Jeremy Redleaf: Yeah. Well, you know, it’s, it’s what we did was just sort of allow ourselves to be in the community and just constantly keep the conversation open. People will give you feedback if you ask for it, for sure. And especially if you make them feel like you’re listening. So when people canceled, we, you know, instead of saying like, Hey man, well forget it, you would ask them like why are you canceling? And, you know, two out of 10 times it was actually some something we could address. And of course, eight out of 10 times it wasn’t. But we learned from those experiences. A story that comes to mind early on is that we, we used to use didn’t have, standing reservations and people were coming all the time and decided to do one reservation at a time. And it was so annoying for them, but we didn’t have the, we didn’t own the code base, so we couldn’t just add that feature. So what could we do? So we created a Typeform and we were able to do another backend for them. So we created a Typeform place where they could submit their standing reservations. And then we had to hustle on the back end to make it happen. But it was a way that we could delight them that, you know, wouldn’t have scaled at every customer did that. It would have been a nightmare, but we were able to speak to that complaint.

Ward Sandler: Do you have any examples from like onboarding or how do you kind of welcomed members that was a focus of delighting them in any way?

Jeremy Redleaf: Yeah. So we’ve played and with different drips and try to figure out what, you know, what, how do we engage members early in that first week or two and frankly, we just let other companies inspire us. They’re like a lot of companies that do drips really well. Obviously superhuman is really famous for their drip and you know, there are some other, other ones that we’ve found along the way that we thought were really interesting. I think you have to assume that nobody reads anything, whatever you think is clear to your customers is probably not clear to 30% of them, or maybe even more, who knows. So, just requires you to allow yourself to be a little more repetitive. Basically we, we offered any new customer a one on one on with us for 10, 15 minutes. If you’re stuck, click this link; you know, here’s how we use this service. Here’s how, you know, here’s how we think you should use it here. Things that come up all the time that you probably didn’t read in our FAQ that you’ve, you know, you should probably still know. And, uh, You know, we’ve every time we get more feedback from things that aren’t clear, we add that to the drip. But it really, we just sort of like over, over deliver, like we’re a small company, we’re bootstrapped. We’re approachable, you know, you can’t figure something out, we’ll get in there. You know, that’s just sort of our ethos and our approach. And so that bleeds into all our choices here.

Ward Sandler: And for folks who aren’t quite clear what grit means, probably most people do, but it’s like an email sequence that goes out over time, right? So like maybe as soon as someone signs up, they get a welcome email. Maybe a day later, they get another email, and it be three days later, they get another email. So on and so on. And the point of that usually is to make people feel welcome, um, to kind of point out how to get set up and whatever your, your tool or your software, your community is, um, how to, how to get the most out of it. And then over time you can kind of branch the drip out to like, okay, these are the people that are set up. These are people that are not set up, send them different emails, so you can get kind of crazy with it, but it’s generally a welcoming onboarding.

Jeremy Redleaf: Yeah. And thanks for clarifying that. And another thing that I’d add to that is that you need to be, uh, you need to remember that most people sign up for things and then don’t immediately use them. It’s not like I’ll do that all the time. I’ll sign up for a thing, and I’d be like, cool. And then I got to go. And then those drip emails remind me like, oh right. I’m paying for that thing now. I didn’t set it up yet, you know, but if I don’t get those, you know, pings, I might go three weeks, and then I might be a lot more likely to cancel, you know? So it really is important to make sure that people get won’t build a habit of using your thing but to like actually fully set up. Because cause just because they created an account doesn’t mean they’re in.

Ward Sandler: And I think it’s an important point, right? Like if after I signed up for X, if the first thing I have to do as a, as a user, as a customer is like, oh boy, here’s a checklist of work that I need to now go do. You’re giving me a good chance to be like, cool. I’ll procrastinate that and do that later or something. So yeah, I think it is important to use the welcome emails, the dripping emails to kind of remind people and also to help them get back into the tool. And then it’s also an opportunity to think about, Hey, How can I take work off their plate, Right? Like how do I make this easy or easier for them? And to kind of constantly be striving, how do I make this easier? How do I make this easier? And it’s challenging. It’s not simple. It’s one of those things that everyone wants to be easy, but most software is not, and everyone can, can improve in this way, but it’s just something to kind of always be in the back of your mind, right?

Jeremy Redleaf: Totally. And I’ve noticed that I don’t know if this is for all sorts of businesses, but I’ve noticed in our business that people really just have this question of like, I must not be doing this right. Or I must, how did, how did the best people use this thing? And so, you know, they’re always asking the question and the answer isn’t very satisfying. You know, there’s no one way to use it, but I, but in the times we’ve been able to say like the, you know, people that use it this way, you know, tend to get the most value out of it. Uh, people really appreciate that and want to try that way first. So if you can speak to that any way, I think it can be really, uh, really helpful cause people, you know, just sort of naturally assume that they’re, you know, not totally understanding the tool yet.

Ward Sandler: Yeah. And, talk a little bit more about the delight concept. Like for example, at MemberSpace in our early days, I would literally text every single person that signed up. And I’ve shared this story before on the podcast. Sorry for folks who’ve heard it, but it’s like, literally, I would text them, and people would think I was like a robot or like, not real. They assumed it was some sort of automated text, I’m like, and they’d like send weird messages back, and I’ll be like, no, this is really me. And that would delight people. It would surprise them. It would be, they’d be like, wow, that’s crazy, what a good customer support, blah, blah, blah. And like that kind of thing that we don’t do it anymore for obvious reasons. But when you’re first starting, you know, those are unfair advantages. Those are things that you can do, do to stand out. And that will buy you goodwill. Because there will be some rough edges, for whatever you’re offering when you’re first starting. And there’ll be some things that are not simple, that are broken, that could be better, etcetera. So by building up that goodwill where you can, delight, either texting, sending up one-to-one calls, just being generally available and responsive, that goes a long way towards trying to build a relationship and kind of laying the groundwork up. Here’s a foundation of members and customers using us that are willing to talk about us and be evangelical about us. And then that’s where we can start to grow and spread through word of mouth, right?

Jeremy Redleaf: Yeah. And I think I saw somewhere on your documents an idea around using Zapier to ping it, a video app to send video messages to new customers.

Ward Sandler: Yeah. Bonjoro. Is the one I keep bringing up here, I swear we’re not paid by them. I keep talking about them. Basically it’s a way to send like an individual video message to folks, as soon as they sign up for whatever your thing is. It doesn’t need to be long, you know, 10 seconds, 15 seconds just welcome, but you use their names, so they know it’s not automated and they know it’s not just a recycled video and. We’ve been experimenting at personally at MemberSpace last, uh, last week or so. And yeah, it’s been very interesting. We get some really good positive responses. So it’s something to something to consider again, especially when you’re first starting, and you have, maybe time is an asset you can use here and to do something that other companies are just not doing, you know?

Jeremy Redleaf: Yeah. And do they respond with video? With text? How do they respond?

Ward Sandler: They can just respond with text, but yeah, generally, it’s not generally just start like a support conversation or just to start a conversation in general, just to kinda kick things off, like in a, in a nice way to be like, wow, like this is the kind of company I’m dealing with. Like the founder sends a video to each customer, it was just a cool thing to start with, right? It gets a good way to start a relationship.

Jeremy Redleaf: Yeah. Well, I think what you’re getting at is that in the bootstrap space, right? What, what, how can you use the bootstrap penis to your advantage? How can you, uh, how can, you know, not only delight your customers but also make them feel seen. And like you’re approachable and, you know, with what you’re going to lack in features or, uh, you know, A, B and Z you’re going to make up for and being human.

Ward Sandler: Yeah. A hundred percent. Thanks for taking the time to talk with us, Jeremy, we really appreciate it. Would you like to share any resources or recommendations for folks trying to learn more about Caveday?

Jeremy Redleaf: Yeah, sure. Come, come check us out. We’re at caveday.org. And if you use the code Memberspace, you can get a three sprint cave for free. Come check it out!

Ward Sandler: Awesome. Thanks, Jeremy.