HR Happy Hour 497 – Meeting HR Challenges as a Chief People Officer

Hosted by

Steve Boese

Co-Founder of H3 HR Advisors and Program Chair, HR Technology Conference

Trish Steed

CEO and Principal Analyst, H3 HR Advisors

About this episode

HR Happy Hour Episode 497 – Meeting HR Challenges as a Chief People Officer

Hosts: Steve Boese, Trish McFarlane

Guest: Jenny Dearborn, Chief People Officer, Klaviyo

This episode of the HR Happy Hour is brought to you by Paychex, one of the leading providers of HR, payroll, retirement, and insurance solutions for businesses of all sizes. 

 Paychex just released its 2021 Pulse of HR Report, which sheds light on what businesses need to do right now to meet the new expectations of a workforce no longer satisfied by the status quo. The fifth annual report provides an in-depth look at how HR professionals are contributing to the success of the companies they serve during this transformative time. To learn how your peers are navigating the start of a new workplace era, download the report at

This week we talked with Jenny Dearborn from Klaviyo about current issues and trends facing HR leaders today; return to work, inclusion, mental health, and more.

– How organizations are finding new ways to connect and engage with their customers

– The shift in how candidates speak about mental health with potential employers

– Training leadership on how to interview candidates during a time of continual change

– How the pandemic has provided new opportunities for organizations to improve DE&I


Thank you Jenny, for joining us!  Remember to subscribe to the HR Happy Hour wherever you get your podcasts.

Klaviyo Website:

Careers at Klaviyo: here


Transcript follows:

Steve 0:21
Welcome to the HR Happy Hour Show with Steve and Trish, sponsored by our friends at Paychex. Today we are going to be talking about some really current issues and trends facing HR leaders: return to work, inclusion mental health, and more. A great guest is waiting in the wings but Trish before we welcome her, I have a question for you. Soup or salad?

Trish 0:44
Soup or salad? I will say typically salad although last night I had that choice and I chose soup. So I don’t know, what about you? A salad for me is like more refreshing. I think feels healthier, I don’t know.

Steve 0:57
Salad every time.

Trish 1:00
Salad every time okay? I don’t want olives involved in the salad. So as long as there’s no olives then salad it is.

Steve 1:07
Alright, we’ll ask our guest. I knew the question would be a simple one not noncontroversial. I’m staying away from controversy Trish, with the question of the day today. We are super excited to welcome our special guest Jenny Dearborn. She’s the Chief People Officer at Klaviyo. Previously she was Chief Talent Officer and VP of Human Resources at SAP, who we know very well Trish. She was responsible for the training strategy and education programs for 95,000 employees worldwide. She came to SAP through its acquisition of SuccessFactors, another company we know well, where she was VP of Sales. She’s a mother of four and obsessed with military history. That’s pretty cool. We might have some Civil War questions coming up, Jenny. And she wrote a book called “Data Driven” about using data analytics to improve performance. And one of her favorite quotes is from Madeleine Albright, ‘there’s a special place in hell for women who don’t help each other.’

Trish 1:56
You know what? I like the part about helping women because as he’s reading this thing, like I really want to use your bio as my new bio.

Steve 2:03
Yeah, well, awesome. Welcome to the show. Jenny, how are you? Well, do you want to weigh in on soup or salad before we ask you about what you’re doing?

Jenny Dearborn 2:09
A salad every time, unless it is roasted red pepper tomato. 100% of the time when I see that on the menu, I switch over to soup.

Steve 2:21
Nice. Yeah, Jenny it’s awesome for us to have a an HR leader on the show, such as yourself. It’s great to see you. Great to talk to you. First off before we get into some of the topics, we want to talk about some of the challenges facing HR leaders today and even maybe even your own organization. Maybe you could give us like 60-90 seconds on Klaviyo and tell us what Klaviyo is and what’s it all about? Maybe some of the footprint of Klaviyo?

Jenny Dearborn 2:44
Yeah, for sure. So, Klaviyo is a database company. Our first application on that database is email marketing. We were founded in 2012. We have just under 1000 employees. We’ve had our series D and we are on the road to IPO and doubling year over year. We are based in Boston, MA, but have a global footprint.

Steve 3:13
Nice. That’s pretty cool. Yeah, Boston’s a great town. It’s a good, interesting kind of market to be in, right? Because organizations of all kinds are trying to find ways to meet their customers, engage with their customers, right? And I guess that’s what you guys do, right? Help organizations kind of connect with their own customers?

Jenny Dearborn 3:30
Absolutely. So we are a one to many communication platform at scale. And so we allow entrepreneurs to connect with their customers in a highly personalized way.

Steve 3:46
So Jenny, let’s talk about some of what’s been happening, you know, as an HR leader, God, I can’t think of the last year and a half or so right? Has it ever been more difficult, challenging for HR leaders like yourself, maybe tell us a little bit about how things have been going at Klaviyo, and some of the big challenges you guys have seen and how you’re managing to kind of navigate through everything that’s been going on and continues to go on?

Jenny Dearborn 4:11
Yeah, I think the short answer is it’s never been harder. Probably the most significant issues for us as HR leaders is growth and scale and times like this, managing workplace mental health, managing the distributed workforce, especially those companies that had a strong face to face or in office presence. Going to a distributed or remote or hybrid model has been very challenging for lots of my peers at other companies. But I’d say probably the most consistent across all companies has been workplace mental health.

Trish 4:51
Yeah, you know what, I’m glad you mentioned that Jenny because we’ve been doing a series of shows over about the last almost two years on just different ways to think about mental health in the workplace, to have people feel more comfortable to disclose if they’re having issues. I just love to hear your perspective. I mean, you’ve obviously worked in the HR tech arena, as well as your current role. Could you maybe just talk a little bit about over the years that you’ve been involved? You know, working with both large organizations and smaller ones? Are you seeing a shift in people’s willingness to maybe disclose that they need a little help and assistance? Or is that still kind of a stigmatized conversation? What are you seeing?

Jenny Dearborn 5:34
Yeah, I’m absolutely seeing a shift towards employees feeling comfortable talking about that, raising their hand, and employers needing to adjust and accommodate. So I would absolutely encourage everyone to speak up, raise your hand, say that you need help push the organization that you work for, to say we need more time off, we need more PTO, we need more services. We need more HR business partner support for you know, sort of being a sounding board and and being somebody that you can go to and talk to, employees should be pushing their employers for more support and more services. And employers need to know that that’s what the best talent out there is looking for. The best talent expects a high touch high service environment when it comes to being sensitive to workplace mental health issues. And you know, it’s a candidate’s market out there right now. You know, it is hard to find top talent, we are absolutely in a war for talent. And every candidate should know that they need to be asking about this in their interview process, right. I mean, I talk to candidates all day long, for all of the openings that that we have. And really savvy candidates will say to me in the first interview, you know, tell me about your workplace mental health initiatives. People don’t ask me about comp, right? Because they just they assume that that’s going to be good. And they’re looking for what are those differentiators? Right? What really sets apart one company from another company. If everybody has a level playing field with the same comp, what really sets your company apart? And it’s Tell me about your commitment to corporate social responsibility? Tell me about your commitment to diversity? And how are you holding yourself accountable to achieve your diversity goals? And tell me about your workplace mental health? Those are the three things I hear the most of from candidates asking us questions as an as an employer, like, think about 15-20 years ago, a candidate wouldn’t ask those questions, right?

Trish 8:01
No, they would not.

Jenny Dearborn 8:02
They do now, which I think is awesome. So candidates are so empowered to speak their truth and say what they need and demand more from their employers? And they know that it’s a candidate’s market? I think it’s awesome.

Trish 8:18
Are you doing anything to train your leaders who are also interviewing? Because I mean, I was in HR for almost 20 years, and I can’t recall anyone ever asking that. Right, but I’ve been out for about seven years. So for perspective, are you training and specifically telling people have that conversation about what you offer? Is that a thing?

Jenny Dearborn 8:41
Yeah, I mean, we are now. We track internally, you know, what are the most frequent candidate questions? So we keep a running list that is always being sort of reprioritized at the top 10 most frequent candidate questions that are given to interviewers, whether it’s a hiring manager, or anybody on the interview team, or coming into talent, you know, the talent acquisition team, the recruiters, and so the recruiting team keeps track of this, and they keep track of those top 10. And we are always going back out to managers, so or anybody who is an interviewer, they are required to be certified, right, you can’t talk to a candidate until you’ve gone through interviewer certification, and you have to keep that fresh, right. And so part of that is knowing how to answer the top 10 most frequently asked questions and it’s dei workplace mental health, you know, it’s these things.

Steve 9:43
Jenny, have you adapted or added to your sort of outbound maybe content on the website, the way the messaging you’re doing out to the community about, you know, how Klaviyo emphasizes some of those things? Have you had to make some effort to put that more in the forefront?

Jenny Dearborn 10:00
I would love to say that I am. Our website, to be totally honest, is a complete mess right now. It has a lot, I have all that stuff documented. And when candidates reach out to us, we send them a PDF of you know, here’s our employer value proposition, all that stuff. So I have it all documented, it’s not outwardly facing right now, because our website needs to clean up.

Steve 10:24
I llived through many years of when you go to the IT team, if you will, and there’s website updates that need to be made. The HR/recruiting team was always at the bottom of that list for IT project prioritization. At least in my experience.

Jenny Dearborn 10:40
Oh, yeah we’re victims of our own success. We’re hiring so fast and so I have roles open right now for marketing engineering, which are the people who keep the website updated.

Steve 10:55
Maybe one of those folks will hear this show.

Jenny Dearborn 10:57
I hope so! I have a hundred roles open right now, please apply.

Steve 11:03
Wow, that’s pretty cool. We’ll make sure we share the link to that page where those roles can be found. And people can learn more about them at the end of the show. Jenny, you mentioned diversity a couple of times, I’d love for you to share some thoughts on kind of crisis that all organizations have gone through and really still continuing to navigate with, you know, ongoing issues here in the US, return to work plans, starting stopping starting again, etc, etc. I’d love your thoughts on maybe the opportunity for HR leaders to use this crisis, if you will, is an opportunity to improve specifically around diversity, equity inclusion, which is that’s been important for a long time, but maybe it’s even more important. Now. I wonder if you have any thoughts on? How to take advantage of the situation, if that makes sense?

Jenny Dearborn 11:51
Yeah, no, it absolutely does. I don’t know who said the quote, and I might get it wrong, but it was something like, never let a good crisis go to waste, right. So use social, you know, the the issues that are going on in society as a forcing function for driving change. So we stay true to the change that we want to see. And we seize these opportunities that happen in society in the world to make big jumps forward, it’s a perfect time to be in HR. It’s a great time to be in HR to be able to harness, you know, the issues that are going on in the world to drive more equity and inclusion and belonging in our companies. Right? So we’ve got social unrest in the world, let’s use this as an opportunity to demand that all companies publish, externally, their diversity and inclusion metrics, right? You’re the breakdown of you know, at a minimum, let’s start with race and gender, by function by level, right? So imagine a matrix. And the columns across the top are sales services engineering, GMA, and the rows horizontally are entry level, first level manager, second level manager, director, VP, executive, whatever, however you want to structure it. And you know, every company should be, you know, standing up every publicly traded company, you know, it would be great if everybody followed suit, but shouldn’t be saying to the world, congratulations to us. 20% of our employees are diverse, but Gosh, isn’t it a shame that 100% of those diverse candidates are in the bottom tier of your company? Come on, guys, seriously, you know, you need to, you need to be a lot more transparent about what you were congratulating yourself on before, or, you know, congratulations to us. 40% of our employees are women. But if 100% of those women work in human resources, and there’s zero in the in sales, or in these other functions, come on, you know, you can be better than that.

Steve 14:03
How do you figure out how to kind of return to work right is some companies and maybe it’s really kind of a broader discussion of our, you know, you talked about earlier, Jenny, about the culture of the organization. Was it really an in person kind of collaborative, we’re all gonna sit around the same table or, or sit on a long table of people and write code together all day long, but versus like, because we see the hybrid, the remote work, certainly that maybe the ongoing hybrid strategies is an opportunity for companies to expand the net, right and say, well, we don’t necessarily have to hire candidates who live 30 minutes from this office. It can open up more in theory that can open up more opportunities to improve DE&I, right?

Jenny Dearborn 14:41
For sure, opportunities to improve DE&I but also just get greater diversity. We have seen time and time again, and the data shows up that the flexible work schedule is an absolutely critical need for women. Yeah, women have school aged kids. And that if we were to be more generous and accommodating to a flexible schedule, you would have a significant population have very motivated employees that would did not feel like they need to drop out, or take a completely different job and then come back in later, you know, after a 10 year gap when everybody else has gone way ahead. Because they didn’t have those same at home demands. And if companies can say my recruiting bubble is not just people who are willing to drive into Boston, but it’s really we’re going to go find the best talent regardless of where they live. And if we can rely more on collaboration tools and technology, and a more structured way of tracking and measuring goals and performance instead of I see you with my eyes, therefore, I know your finger, your finger, I can see your fingers moving on the keyboard, therefore I know you’re working. If we can move our mentality from that, then we know we don’t just need to, to see you to know that you’re working. So I think the pandemic has also been a forcing function, you know, never let a good crisis go to waste, to really challenge ourselves in terms of our flexible working schedules.

Trish 15:16
Yeah, I think you’re right about that the pandemic has sort of forced it on us, right. So we had no choice but to be flexible. It was interesting, I was just watching on Netflix the other day, there was like a special about Dolly Parton that recently came out. And one of the things of course, that went over her role in the movie nine to five. And I haven’t watched that in probably I don’t even how many years, right? 30 years, 25 years, something like that. But it’s interesting, because you’re sitting here and you’re talking about all these examples of what we need to be doing, especially for women, in order to keep them engaged in the workplace. And we don’t want to lose good workers like this, this problem goes back so far, like that was a major part of that movie, I thought, we probably need to go back and rewatch that if you remember, it was like job sharing where they had like, Oh, this woman comes in the morning and does this right, in the in the afternoon. It’s this woman and, and but what does that say about us as a as a culture, that we haven’t fixed that, since the 80s, when it was starting to be really, really talked about? It almost makes me a little sad. So I’d be interested in your thoughts on like, do you really think like, I feel sort of like the pandemic is going to be enough of a change factor to hopefully make this happen? Or do you feel that way? Are you still skeptical?

Jenny Dearborn 17:51
No, I’m very optimistic that this moment in time, especially, you know, right now with Delta variant, like where we’re getting ready to go back? Oh, no. So we were like, it’s going to be August, it’s going to be September. Now we’re saying January. So you know, it’s working from home, and it’s okay. And now we don’t need to go back to how it was before. We do need to say that leaders are responsible for, you know, knowing what their folks are doing setting clear goals and objectives, managing performance against those objectives. And one of your performance measures should be engagement, culture, connection, fun friendships, all of that. And you use to just say, Oh, no big deal, that stuff was going to happen automatically when everybody was in the office. And we’ll you know, we’ll have a beer bash on Fridays, you know, and it would just happen. Well, now you need to be more purposeful about it. As a leader, you have to be deliberate. You have to plan. You have to think what can I do remotely? That’s fun. What can I do remotely that creates connection and friendships? What can I do remotely, that’s going to drive people to have a higher level of engagement, it’s harder, it’s much harder. It makes the job of the leader so much harder.

Jenny Dearborn 19:13
I mean, I had two exit interviews at my company in the last quarter that I conducted, and both of these folks said to me in the exit process, I’m going to, you know, these are both high performers and very regrettable attrition. And they both said to me, I’m going to a company where I have friends and where I feel a connection. Now, I was hurt because I thought well, I’m your friend, but hold on a minute they on boarded remotely. Our entire professional relationship has been over zoom. I’ve never met this person in person. You know, they worked here for a year. They did great work, but something was missing. And it was an emotional thing, right? Their career was progressing great. They were paid great, all of this great stuff working for a great company, all this wonderful thing. But it wasn’t the engagement and the emotional connection that they need it. And I was like, Oh, my God, that is the that is going to be the hardest part of managing remotely and leading remotely is that emotional engagement?

Steve 20:31
Yeah, Jenny, that’s such an interesting story. Because we’ve been obviously doing the show every week for a while I’ve been doing the show every week for a decade plus, but obviously, in the last 18 months, we’ve done so much, you know, pandemic related content. And so we’ve had seven conversations probably about remote hiring and remote onboarding, right? At least, that’s the first conversation that we’ve had on the show about, hey, what’s happened with some of these folks, or at least a couple of examples you’ve given about folks who were hired completely remotely, probably it sounds like on boarded remotely, and their whole relationship with the organization and their and their colleagues and peers, and probably their manager has been through screen like we’re talking about now. And what may be some of the negative effects. It’s really interesting. Thank you for sharing that.

Jenny Dearborn 21:17
Yeah. I mean, we’ve been doing this for what, 18 months now. So we’ve got enough time to start to see some trends. People come and go all remote, you know, and so we’re starting to now be able to measure what is consistent about people that have come and gone when it’s all been remote and why. And and it’s been the softer part, the traditionally softer part of the role. It’s not about, you know, did the company have a clear purpose? Yes. It was like, were they working on challenging work? Absolutely. Were they paid? Great. Yes. All the stuff that we have wonderful benefits? Yes, we did. Where did we fall short. It’s creating community. It’s creating a sense of friendship. And that’s it’s challenging. I think it’s not it’s not just my company. I think it’s challenging for everybody.

Steve 22:06
Jenny, let me just take a quick pause, we must thank our show sponsor. Of course, our friends at Paychex. This episode of the HR Happy Hour is brought to you by Paychex, one of the leading providers of HR payroll retirement and Insurance Solutions for businesses of all sizes. Paychex has released the 2021 pulse of HR report, which sheds light on what businesses need to do right now to meet the new expectations of a workforce no longer satisfied by the status quo, what we’ve been talking about for the last 40 minutes or so. The Fifth Annual Report provides an in depth look at how HR professionals are contributing to the success of the companies they serve during this transformative time to learn how your peers are navigating the start of a new workplace era, download the report at And thank you all as always, to our friends at Paychex.

Steve 22:54
Jenny, you know you mentioned when you gave us kind of the overview of Klaviyo we’ve talked about all these difficulties, all the other workplace disruptions and the challenges the mental health crisis, etc, etc. But many companies and it sounds like yours is one of them. As it’s actually growing still, despite all this numbers, you know, numbers are up funding rounds, etc, etc. and growth and employees. And I guess my question is like, how do we balance that? How do we balance kind of like, Hey, we’re doing great with Oh my god, there’s so much things going on in the world, which are not so great. It’s tough. Like we’ve talked to so many tech companies on this show HR tech companies, especially who’ve done really well they’ve told us 2020 was our best year ever. And it’s it’s weird to reconcile that right with, with all the all the challenges that have happened with in society and organizations that for people but yet, some organizations are thriving. I don’t know. Do you ever think about that? Like, like, how are we still doing so well, despite all this?

Jenny Dearborn 23:55
Yeah, I mean, for our individual company, we have a great product market fit for something that is needed. Right now and and moving forward. And we are growing. So when I started 13 months ago, we had just over 300 employees and we have just under 1000 today. And you know, we’re doing our 2022 planning and looking to double again to end the year at about 2000. You know, it’s a significant strain on the people function, right to put all the processes in place to be able to handle that growth. And you know, how are companies still growing and surviving it, about being able to adjust to the needs of the market and being able to flex to, you know, yeah, where things are growing right now.

Steve 25:00
Yeah, so you’re putting a lot of pressure right now, I don’t mean you personally, I’m not calling you out. But there is a lot of pressure on the HR and talent teams and the recruiting teams and that and that type of environment, right to support the growth to find the talent you mentioned, it’s a war for talent, talent has the upper hand, etc, etc. Yeah, have you had to do anything, I don’t know, just different or special. Just make sure your own team is hanging in there and doing okay, and getting food because they have though, they have all the same problems at home that we all have with caregiving and disease in schools maybe not being open and all those things, right?

Jenny Dearborn 25:33
Absolutely, absolutely. And, so when I came, you know, 13 months ago, I think there were 14 folks in the people operations function, and I have about 85 now. So in that time, I’ve, you know, built out my HRIS team, and, you know, I more than tripled my recruiting organization and in my recruiting organizations, like 40 people now, and yeah, built out a Benefits Program, and a comp program, and a learning development program and talent management, and all of this stuff, and a whole hrbp organization. So thankfully, we’ve got a great board of directors that understands that in hyper growth, which is anything that’s more than 100%, during phases of hyper growth, your GMA function needs to be out ahead as a percentage of the total company out ahead of the total organization, to be able to lay the tracks and that groundwork to be able to absorb the growth in the organization. So yeah, so you know, my people function is probably 8%, right now of the total employee population.

Jenny Dearborn 26:51
Where if you were a large, super stable organization that had a minimal turnover, and, you know, all of the processes and programs were already built, and you were just maintaining and sort of monitoring the dials, you know, you might have an HR organization of 2%, or 1%, right, for a big, big one.

Steve 27:09
One per 100. Right, that’s the number they always use. Right?

Jenny Dearborn 27:12
And that assumes, you know, minimal growth, and a lot of stability and your business model and things like that. But given that where Klaviyo right now is, you know, we’re talking about new geographies, new products all of this really, really, exciting stuff. And in order to do that, you know, you need to have a pretty significant HR organization that can, you know, accommodate what the business needs moving forward.

Steve 27:47
Jenny, awesome, this has been a really fascinating conversation. It’s great to hear from a Chief People Officer kind of leading through everything that’s gone on in the last 18 months or so especially as a new one. And in your organization you’re at, you’re new to your organization, and specifically, and just sharing really some interesting insights and stories about how you guys are doing and what you’re doing and what organizations should be doing. I’ve one last question that before if you’ll indulge me, before we let you go, Jenny, do you miss HR tech? Do you miss it? You were there for a long time.

Jenny Dearborn 28:22
No, I do miss it. I love I love HR technology. You know it is so important to be that technology foundation for any organization. There’s only there’s only so much work that humans can do before humans go crazy, right? I mean, as humans need to understand. I think this is the challenge for HR leaders moving forward is understanding for all of the work that needs to get done what what can and should be done by humans and what can and should be done by technology. And that really is the one of the key problems or challenges that HR leaders need to address moving forward. You can’t just throw people at the problem over and over and over, especially as you scale you need to really look at the outcomes you’re trying to achieve. And say where do we need critical thinking creativity, innovation, problem solving, empathy, you know, cross cultural awareness that is work for humans. And what is something that a problem that is going to be reoccurring? You know, I keep telling people, if you’ve seen a problem more than twice, automate it right? If the same problem comes up, over and over, figure out a way to automate that away to create space in your life in your day and your calendar, to do the work that only humans can do to do the work that that requires a high touch, very empathetic human, to interact with an employee to do that stuff and automate away anything that happens over and over and over. You should never have humans doing that stuff. So you have to have HR tech as a foundation for any great people strategy.

Steve 30:13
All right, love it. Thank you Jenny. I had to throw it out there just because of my connection to HR tech, Trish does as well and since we talked about that so much on the show, this has been super fun. Thanks again, Jenny for taking some time and spending some time with us today.

Jenny Dearborn 30:26
Absolutely. My pleasure. Thanks.

Steve 30:28
Awesome. Trish great stuff we will make sure we get the link out to the Klaviyo opportunities help Jenny out. She’s got hire hundreds and hundreds of people it sounds like maybe 1000.

Trish 30:37
Sounds like it.

Steve 30:38
We’ll have to try to help her out with that, so. Awesome, Trish good stuff.

Trish 30:41
No, great show. Thank you Jenny for coming on. I feel like I learned so much just in this conversation. And I look forward to just following you in the future. So hopefully all of our listeners will as well.

Steve 30:52
Alright, great. So thanks to our friends at Paychex, of course. Check them out at Check out all the show archives at For our guest, Jenny Dearborn, for Trish McFarlane, my name is Steve Boese. We will see you next time on the HR Happy Hour Show.

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