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Classroom to CX: How Kendra is building onboarding and customer support with empathy

Updated July 18, 2025

Kendra’s career journey has been anything but conventional. Before she joined the raisin team, she taught English abroad and learned how to connect with people through creativity and empathy. Whether explaining complex software or troubleshooting technical issues, Kendra’s approach is all about translating the “why” in ways that make sense for each client.

She’s there every step of the way, ensuring clients feel supported, heard, and empowered. From ensuring that fundraising campaigns launch smoothly to building systems that enable teams to solve problems independently, Kendra’s focus is always on making clients feel confident, informed, and in control.

Kendra Irwin has spent five years carving out a path from Account Coordinator to Client Experience Manager, and now to her new role as Manager of Onboarding and Support. This conversation follows her journey, the work she’s doing to support raisin’s clients, and her plan to keep that support going.

You joined raisin in September 2020. What did those early days teach you about building genuine connections? 

So the early days, when I first came on, it was in the peak of COVID, and I found it was really easy to humanize each other because you were getting this peek behind the curtains. You know, there’s a cat walking across your board, or your child is running around in the background. And I think it just helped make things feel more genuine. And that genuineness is what I try to carry through the day-to-day.

I think that really helped to humanize everybody, and it just made it feel like you got to know people a little bit better in this weirdly intimate way.

Totally agree with you. COVID was terrible, but it helped build connections. Now, before that, you taught English abroad for a number of years. How did that shape your approach to supporting nonprofits? 

Yeah. So, there’s actually so much overlap between teaching somebody another language and teaching them how to use new software. I think one of the biggest similarities between both of them is that if you can’t explain something right the first time, you have to find a new way to explain it.

Kendra and a few of her former students smiling at the camera
Kendra and a few of her former students

Same thing with a word you could use in a sentence. If the word isn’t clicking, you need to find a new example, a new definition. It’s the same thing with explaining a concept with software.

You just need to get a little bit more creative and be able to translate it in a way that makes sense for that person, because everybody’s going to be different.

That makes a lot of sense. 

You recently celebrated your anniversary. Congratulations again 🎉

Thank you!

Now, you’ve evolved into what Star [raisin’s COO] calls the true raisin product whisperer, and I’ve seen it in action. It’s impressive. Were there specific moments or projects that helped you gain that depth of experience? 

I think I’m just very inquisitive. I want to know the “how,” and I want to know the “why”. And that has been a big thing ever since I started with raisin. I also have to commend my team for feeding into me and answering my 8 million questions.

When you know why something works the way it does, it’s a lot easier to train others on it. And it’s a lot easier to investigate if something isn’t working as it should.

So I think that inquisitiveness and the need to know a little bit deeper have paid off immensely. That’s been the biggest strength and has really helped along the way in both roles.

What’s a campaign or project you are most proud of being involved in?

There are so many to choose from, which I think is the best part, because all organizations are different, and their causes are different. I think the most fun was with Janeway Children’s Hospital Foundation, out on the East Coast, and onboarding was really hands-on. 

They had a commercial spot, and we were going live 10 minutes before that. So, we hit the switch, went live, tested the gateway, and everything was good. Then, the commercial aired, and I was still on the phone when they got their first organic donation. We all celebrated together.

It’s just really nice to be a part of that moment and really feel like you’re an extension of the team. And, yeah, there are many to choose from, but that was a really fun experience.

The registration page for the "Race For The Kids" event by Janeway Children's Hospital Foundation. Created using raisin software's campaign website builder.
The “Race For The Kids” event by Janeway Children’s Hospital Foundation

That sounds very exciting. I can’t even imagine how it felt.

It was stressful because we weren’t sure if we were gonna make it on time. But when we did, it was that much more of a celebration.

What does seamless onboarding look like? How does that experience feel for non-profit clients, especially those running their first fundraising events with raisin?

For me, a seamless onboarding experience is simply feeling supported. I’m incredibly hands-on, to the point where I might be annoying to you and your team. But I’m going to be involved every step of the way.

I always say there are no stupid questions. When I first started raisin, I had a really stupid question I needed to ask, and I didn’t. That made my work unnecessarily difficult for a week.

So I want people to feel supported. I want them to feel confident. And to know that they always have somebody to go to. With raisin, you’re not just getting sent out to the wolves once you’ve gone through your training.

To be able to feel supported, heard, seen, and to have somebody to actually work with, instead of just throwing some training at you. That’s my definition of seamless onboarding, and I’m glad that raisin clients get to enjoy that with me.

That sounds a lot like empathy. So, how do you balance technical troubleshooting with genuine care for the people you’re supporting? 

In support roles, people are coming to you with problems. That’s never the happiest version of them you’re going to get.

I want people to feel heard more than anything, and to be honest with them. If there’s a mistake on either end, I’m not going to fluff things up just to spare feelings. I want the people raisin supports to feel like they are a part of the journey to success, even if it’s not always positive.

So, transparency is really, really important here. And again, just treating people like humans.

What’s one key outcome you’d like every client to feel after onboarding?

raisin Software has so much flexibility and a great front-facing website builder. We’re not all web designers or developers, but raisin makes you feel as if you were.

So, after onboarding, I want clients to feel good about their sites. I want to make you feel like you’ve made something beautiful and really professional. I want everyone to walk away and feel proud of what they put together. To know that you did that. It might not be specifically your role, but I want you to feel really proud of your work.

If onboarding and support had a mission statement under your leadership, what three words would sum that mission statement up? 

Confident. Informed. In control. 

I want you to feel like you have a say. I want you to feel like you’re part of this, whether that’s feedback, learning, or helping us build out the product.

What’s one tip or word of wisdom that you can share on how nonprofits can get the best from support teams?

If someone wants to get the best value out of support, come to us with more information than you think we need. Screenshots, your participant IDs, your event IDs, every single piece of information, if you can throw it in there, even if you don’t think it’s relevant.

It eliminates a lot of back and forth, and helps point us in the right direction. We can troubleshoot and eliminate issues just based on that information. So when you’re coming, give us everything you’ve got, all the information you possibly can to help us work along the way.


Hello! I’m Kendra, and I’ve just stepped into the Manager of Onboarding and Support role here at raisin – a journey that feels pretty meaningful to me.

Over the past five years, I’ve had the chance to grow within our company, starting as an Accounts Coordinator, then Onboarding Manager, and now into Support. It’s been one of those career paths where each role built on the last, giving me a pretty comprehensive view of how everything connects.

What I love most about this new role is that I get to be there for people during those crucial first moments. Helping them navigate their first campaigns, making sure they feel confident and supported, watching them flourish with their dedicated Client Experience Managers – and then seeing them again in our support channels.

It’s like being part of their story from the very beginning, and watching it unfold in the best ways. There’s something pretty special in that.