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Ep 569: Culture and Connection In Distributed Teams


Three and a half years on from the first pandemic lockdowns, the debate about returning to the office still rages on. However, despite all the noise this year, as some large well-known companies tried yet again to force their employees back to the office, many employers have embraced the reality of remote and hybrid and are working hard to adjust and deal with the challenges of having a distributed workforce.

Culture and connection are often cited as reasons companies want to bring people back to their offices, particularly when supporting the new generation entering the workforce. So, what are remote and hybrid organisations doing to address these challenges without invoking a mandatory return to the office?

My guest this week is Dena Singleton, Chief People Officer at Kajabi. Kajabi strongly focuses on developing its culture and building connections within its organisation, and Dina has some excellent advice to share.

In the interview, we discuss:

• The unique market that Kajabi serves

• TA challenges

• Job vs Opportunities

• Building culture and connection

• Foster community

• Supporting the new generation in the workforce

• Onboarding

• The impact of AI on the talent function

• The future of work

Listen to this podcast on Apple Podcasts.


Matt Alder: Support for this podcast comes from Greenhouse. In today’s competitive hiring landscape, taking a people first approach is business first. That’s why Greenhouse helps companies adopt a flexible, fair, and efficient approach to hiring. Greenhouse empowers everyone from recruiters to hiring managers to make confident decisions that help strengthen your business, so you can get measurably better at hiring. Discover how Greenhouse can help you hire for the kind of business you want to build. Learn more at That’s Greenhouse dotcom slash hire.

[Recruiting Future Theme]

Matt Alder: Hi there. This is Matt Alder. Welcome to Episode 569 of the Recruiting Future Podcast. Three and a half years on from the first pandemic lockdowns, the debate about returning to the office still rages on. However, despite all the noise this year, as some large well-known companies tried yet again to force their employees back to the office, many employers have embraced the reality of remote and hybrid and are working hard to adjust and deal with the challenges of having a distributed workforce.

Culture and connection are often cited as reasons companies want to bring people back to their offices, particularly when supporting the new generation entering the workforce. So what are remote and hybrid organizations doing to address these challenges without invoking a mandatory return to the office?

My guest this week is Dena Singleton, Chief People Officer at Kajabi. Kajabi strongly focuses on developing its culture and building connections within its organization, and Dena has some excellent advice to share.

Hi, Dena, and welcome to the podcast.

Dena: I’m super excited to be here with you today.

Matt Alder: An absolute pleasure to have you on the show. Please could you introduce yourself and tell us what you do?

Dena: Sure. My name is Dena Singleton, and I am a career HR generalist. I like to say that modestly. I’ve been doing HR for about 20 years now. I specialize in doing human resources in high tech environments and supporting engineers. I started my career a while ago. I came out of Cornell University, which is one of the top schools in the US for industrial and labor relations, where we specialize in human resources. If you can believe it, people actually go to school at 18 thinking that “I want to grow up and be an HR person.”


Dena: So I’m one of those people. I went there from grad school. But the only jobs I’ve ever had was working at Wendy’s in high school and then doing human resources. So I started my early career in plant. I like to call myself plant life. I used to work for Allied Signal, where we produced industrial fiber and we turned that fiber into carpets. And then I went through Y2K and the big tech boom there where we were so afraid that going to two-zero-zero-zero would crash computer systems everywhere.

I worked for one of the first all online banks. I then went and did more industrial work. And then I spent 10 years of my career at Microsoft, which was phenomenal because working at Microsoft is like getting an MBA every day. I was 1 of 1,000 people in their HR organization and it was phenomenal. When I left Microsoft, I decided to take a bet on team Dena and go into the startup world, which has been super exciting. I’ve spent the last six to eight years of my career working in the startup environment.

Matt Alder: Fantastic. And tell us a little bit about what you do now.

Dena: Now, I am fortunate enough to work for a company called Kajabi. I’m their chief people officer. We’re 350 people. We’re globally based. The majority of our people are here in North America between Canada and the US. But then we also have about a third of our people in the Philippines. And as Chief People Officer, my primary job is to think about the wellbeing of our 350 employees and their families, and think about how do we create a great environment where people can thrive at work every day and be excited about not only their job, but how do they make life great and awesome for our external heroes, our customers that we have at Kajabi.

Matt Alder: Fantastic stuff. Now I want to dive into that and find out a lot more. But before we do, tell us a little bit about the unique market that Kajabi serves, because I’m well aware of it, but I’m also aware that people listening might not be.

Dena: I like to explain my work in a way that my mom would understand. And so the way I talk about Kajabi is that we are a platform that helps people turn their passions, their knowledge into digital products that you can monetize. And so what that means is that, if you’ve got a passion, if you love gardening, if you love playing the piano, if you want to tell people how to do personal finance, we can help you turn that into courses, newsletters, memberships, coaching, podcasts. Kajabi is the platform that allows you to take that. And instead of just telling one person or two people in your small Facebook group, we can help you take that out worldwide and globally.

So over our lifespan of the company, we’ve helped our creators who sit on our platform make over $6 billion in revenue, and we’ve touched over 85 million people have learned something from the creators who sit on our platform.

Matt Alder: Wow, that’s amazing. I would say it is a great product. Switching back to HR and talent acquisition, what are the main talent acquisition challenges that you have at the moment?

Dena: I’m so glad you asked that. I’m going to give you a really personal answer and then I’ll talk more globally. Personally, when I think about the main issue that we have, the main issue that I think any company has is really convincing people. I tell this to every single person who interviews with us. Anyone can get a job. We are all capable. There’s a job out there for every single person. The true challenge is finding the right job for you at the right moment in your life. And so I don’t want people to come and work at Kajabi or work anywhere where it’s just about, “Can I get a job? Can I get a paycheck?” I want people who come to work here because it’s aligned with their passion, it’s aligned with what is appropriate for their career and how they want to have career growth. We are a place where we can serve them as much as they can serve our heroes and our customers.

So finding that right alignment where at this place in your career, this is the place where you can have growth and we can be of service to you as a company. So that is the biggest challenge that we have is getting people to understand that it’s not about the job, it’s not the prize, the right opportunity for you is the prize.

Matt Alder: How do you do that, and what are the ways that you get that across to people?

Dena: We are super careful in our interview process. So one of the things that we spend a lot of time talking about our interviews, we have six values, and we have all of our interviewers talk about what our values at the company, and then we also have people talk about what is it like to work here at Kajabi. So when we talk to people about our values, we make sure that if you come and you work for us that it’s important that you are into fostering belonging.

So you have to be in a company not only where you want to feel like there’s a sense of belonging, but where you actively work to create a sense of belonging for others, where you believe in controlling your destiny, where you think about how do you simplify work for yourself, and what you think would simplify work for others, what you think about creating heroes. And so our values are absolutely critical for every hire that we have, because that is what really makes the difference between whether or not you’ll be successful here or whether or not some other place is a great place for you.

Matt Alder: So it’s been an incredibly disruptive few years for work as a whole. How are you making sense as an organization of the post-pandemic world of work? Are you remote, are you hybrid, are you something in between, are you returning to the office? What’s your strategy in that area?

Dena: I love how people always say it’s been disruptive since the pandemic as if we were perfect prior to the pandemic.


Dena: So we’re a combination of most of the above. And so we’re based in Orange County, primarily based in Orange County. So for the people who are in Orange County, California, we come to work on three days a week. And so if you come into our office on Mondays, Tuesdays, and Thursdays, you’ll see a percentage of our population is in the office on those days. However, like I said, we have 350 people. So for all of our people that are in the Philippines, they’re remote. For people who are not in Orange County, they are primarily remote. And then for the people that are in Orange County, they come to work.

Now there are some commuters too. So I live in Seattle, and I commute to Orange County on Mondays and Tuesdays. So I get on a plane, I fly to Orange County. Quite honestly, my total commuting time through the week is about what it was before when I drove to work and I got stuck in traffic every day crossing the bridge.

Matt Alder: That makes sense. I suppose building on what you were saying about the importance of the values that you have, how do you build culture in a team like that where some of them distributed, some of them in the office, some of the time. How do you build culture in that kind of environment?

Dena: That is my favorite question, and it’s a question that I ask my managers, I ask ICs. Every week, I think I have three to five conversations about that very specific question, because I know that that is the answer to figuring out how we’re going to, not only be a great place for our employees but do great things for our customers and our external heroes. And so the question that I specifically ask people is, “Who’s your community?” And the answers that I get range from people will tell me, “Oh, it’s the people who are on my team.” And then my follow up question is, “Why? Why are they your community?” And then what they start to talk about, “Well, these are the people who I work with most closely, or the people that I saw the last time we had an onsite event, or the people that I’ve known the longest.”

And so then my third follow up question is, “What are you doing to build community for people who are outside of that immediate circle, so that new people who come into the organization or so the people that you don’t encounter on a regular basis feel like they have a community as well?” And so the way that we’re building culture is, one, we have some on site events where we bring our entire company together so that we can see each other.

Two, we call ourselves, we call Slack, one of our virtual communities. So we spend a lot of time in Slack and chatting with each other. We have informal channels in Slack. Three, this year we’re actually downsizing our physical office space and all the money that we used to spend on rent with our physical office spaces, we’re channeling the majority of that money into making sure that we can have meetups with people that are in our organization, because we want to make sure that we have an opportunity to see each other and connect with each other.

Three, we spun up a number of culture teams for the very specific purpose of understanding how do we continue to build culture. So this, I know, is the secret sauce to success is figuring out how do we make people love us in the good times and the bad times, and that’s all about us understanding how do we connect with each other when we don’t see each other on a regular basis.

Matt Alder: What about the new generation that’s coming into the workforce? People who were high school or college during the pandemic and have had a very different introduction to working life than perhaps we did, what do they need to thrive and how are you helping them?

Dena: Yeah, those are some of the people, Matt, that I worry about the most because they missed some pivotal developmental moments that we had. So if you think about it, this generation that’s coming to the workforce right now, they miss graduation. So as high school seniors, they miss that moment, and that year, when they all came together as seniors and they went to work together and they learned what was it like to work together in an environment.

They may have missed their freshman year, or their senior year of graduation, or they missed those first two years when they come to work and they learn, what is it like to have a really great manager or a not so great manager, and then sitting around in the cafeteria and talking about what is it like for you? What is your manager like? What time do you come to work and having those conversations where they level set with each other. And so we’ve got to figure out– I think it’s the company’s responsibility and our manager’s responsibilities to figure out how do you bring that generation of employees into a work environment successfully. So for us, it’s a little bit of an extra lift, but it’s an extra lift that we’re glad to take on. So it means giving them onboarding partners.

Whenever you do an onboarding partner, it may or may not work when it’s formal, and so we have a formal onboarding partner and that’s someone who you walk through your first 30, 60, 90 days with. But then maybe that onboarding partner doesn’t stick. And so we also have employee resource groups, and so you may find your tribe or your community within your employee resource group.

We also make sure that when your team has some kind of onboarding connection with you and your team, and we’re just about to roll out something that we’re calling freaky Fridays, which is twice a month, we are going to have mandatory team meetings that are designed to get people to connect with each other on their own teams, and then we’re going to switch it up where on some of these Fridays, you actually meet and switch off and meet with other teams. So the whole goal is to create connections with people who you may not ordinarily see at work.

Matt Alder: One of the other things that we’ve seen, certainly this year, has been this huge acceleration with technology, and in particular with AI, what impact do you see AI having on the talent function moving forward?

Dena: I am excited about AI and talent. The reason I’m excited about it is because what I think it will allow us to do is brush through some of the administrative items and think about the kind of company that I work for. So in Kajabi, the way that we use AI is our creators generate a ton of content. And so we use AI, we just started rolling this out. So we use AI to help them sort through their content and then create little snippets, so that they can have commercials, so that they have better ways of connecting with their customers. And so I would like to use our AI technology, so that I can take the content that we create in HR instead of asking my employees to say, “Oh, my gosh, read through all of this stuff. I can use AI to generate snippets of information, so that it’s easier to digest.”

So the same technology that we use with our heroes that make our heroes connect better with their customers, we can use AI, so we can connect better with the people that we’re recruiting and our internal customers as well. So AI is a tool that we can use in order to accelerate our ability to connect with people. I’m going to pause there, and also say the first name in my team’s function is people. And so this does not mean that we are letting go of our responsibilities to connect with people one on one, that will always be part of our people function.

Matt Alder: I suppose that leads nicely on to my final question, which is, we’ve talked a lot about work and culture and community and things that have changed. What do you think the future looks like? What’s work going to look like in five years’ time? I know it’s an impossible question to answer, but just interested in terms of your perspective, your view, or what you hope might happen.

Dena: The number one thing that I think will happen in five years’ time is that we’re going to have to get even better at how managers lead organizations. What this reminds me of is– I spent a long time in technology, and it used to be that you could be in technology. And the fact that stock prices for our companies were rising so fast, it erased a lot of the sins of bad management because stock prices were rising fast, and that was a great thing for everyone who worked in technology. And then when stock prices slowed down, we found out that we had to get really good at being great managers in order to retain our people.

Now that people don’t come to work as much and we live in a more distributed workforce, we’re going to have to get really good at managing people and creating connections, which means that we don’t have the luxury of not being great managers anymore. And so I think that work in five years for good companies means that the life of individual contributors is going to be a lot better because that is the thing that is going to make good companies thrive.

Matt Alder: Dena, thank you very much for talking to me.

Dena: It has been so much fun. I hope we do this again. And I love talking about people and I love talking to you, Matt.

Matt Alder: Thank you very much.

My thanks to Dena. If you’re a fan of the Recruiting Future Podcast, then you will absolutely love our monthly newsletter, Recruiting Future Feast. Not only does it give you the inside track on what’s coming up on the show, you can also find everything from book recommendations to insightful episodes from the archives and get first access to new content that will help you understand where our industry is heading. For a limited time, subscribe to the Recruiting Future Feast newsletter and get instant access to the video recording of the recent remixed webinar on AI and talent acquisition, featuring some of the smartest thinkers in the industry. Just go to to sign up. That’s Matt Alder dotme slash webinar.

You can subscribe to this podcast on Apple Podcasts, on Spotify, or via your podcasting app of choice. You can also find and search all the past episodes at, and don’t forget to sign up for the newsletter, Recruiting Future Feast. Thanks very much for listening. I’ll be back next time and I hope you’ll join me.

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