DEI for the Startup Community 4: Pendo Head of DEI Jessica Jolley

Pendo is what startups aspire to be. Launched in October of 2013 with 4 founders, it has now raised over $200M, has over 500 employees, and is valued at over $1B. In many ways, Pendo is the poster child for startup success. But with that growth comes challenges. Today, Jessica Jolley, Head of Diversity, Equity, and Inclusion at Pendo, talks initiatives she’s excited about and gives tips for startups to set the groundwork for a DEI-friendly culture.

JOIN THE DEI FOR STARTUPS WEBINAR, presented by The Diversity Movement, with Donald Thompson, Shelley Willingham, and Lister Delgado.  And please donate any amount to the Thurgood Marshall College Scholarship Fund.



Shelley Willingham:  Welcome to Winning with Diversity, a podcast to help you be the diversity champion in your business. This is episode four of our series of DEI for the startup community, where we’re talking about how founders and investors can think about DEI when they’re just starting out, why it’s so important and actionable steps leaders can take right away to align DEI initiatives to overall business goals. I’m your host, Shelley Willingham, vice president of business strategy at The Diversity Movement and with me today is Jess Jolley, head of diversity, equity and inclusion at Pendo. Thanks so much for coming on the show, Jess.

Jess Jolley:  Thanks, Shelly. I’m really excited to talk with you today.

Shelley Willingham:  So for those of you that don’t know Pendo is what startups aspire to be. It was launched in October of 2013, with four founders.

It’s now raised over $200 million has over 500 employees and is valued at over $1 billion. It was in 2019. So Pendo is definitely the poster child for startup success in the Southeast. So Jess, as the head of diversity, equity and inclusion at a company that is hiring hundreds of employees this year, you have a lot on your plate.

Jess Jolley:  Yes. Yes. We are a lot on my plate, a lot of initiatives going on right now.

Shelley Willingham:  So let me ask you this. When was the need recognized for a head of diversity, equity and inclusion at Pendo?

Jess Jolley:  Yeah. So Shelly, prior to my role, we have a lot of employees at Pendo that were really engaged and passionate and started affinity groups at Pendo.

And so our affinity groups, those are, you know, communities for employees that might be you know, identify in spaces that are underrepresented in technology. So we have an affinity group for a BIPOC community for women at Pendo for neuro-diversity. So our affinity groups you know, Or doing a lot of work, doing a lot of effort to really, you know, lead our DEI efforts. And I think last summer, after the death of George Floyd, You know, kinda like many companies had to have a lot of hard conversations around what race looked like in our country and also in, you know, day-to-day interactions in a workplace. And so our affinity groups and our leadership team did a series of town hall conversations. And something that came out of that, you know, it was a lot of conversation around what Pendo was doing a good job, you know, where Pendo was doing a good job, but something that came out of that was the need for an investment and a DEI team and a DEI leader. And I think, you know, when really expanding out the why there people were doing the work of diversity inclusion, but it was split between our people team, between our communications team, between our affinity groups.

And there wasn’t one person really, you know, driving the charge, making sure we had a process to be accountable and to kind of organize cross-functionally so that DEI was embedded in all the aspects of our work at Pendo.

Shelley Willingham:  Got it. Got it makes perfect sense. So you’re obviously been very successful with growth and you know, Pendo is consistently on the list for the best places to work. What are some of the challenges you’re facing around DEI right now?

Jess Jolley:  Socially, one challenge we’re facing, you know, we’re growing so quickly, we’re over 500 employees. Now we’re going to hire 400 to 500 people in the next year. And that’s not only in our Raleigh office. We are growing globally. And as we’re growing globally, I think that’s been an aspect we’re having to think about and really make sure we’re being not only aware of the differences we talk about DNI, but also just having cultural competency.

You know, we have an office in Israel and, and with everything happening right now, how do we make sure that our employees feel like the culture is, is inclusive, that they feel, you know, safe coming into the office and having conversations that we can celebrate differences. And even tactically, you know how, when we’re talking about diversity and inclusion, you know, that that’s measured differently, you know, and, and there’s different implications when you think about, you know, the global scale.

And so that’s something, you know, as women scaling and growing, we really want to make sure, sure we’re thinking about how does D E and I  you know, show up across the world and not just in our Us offices.

Shelley Willingham:  Yeah, that’s so important because definitely the DEI conversations are not one size fits all right. So it’s really making sure that you understand the different dimensions and then there are going to be different issues in different parts of the world. And so that’s great that you’re doing that.

Jess Jolley:  You know, and I think that’s also, we’re being really intentional to think about does our workforce represent the communities we’re in? So does our work force in Raleigh represent the Raleigh community, does our workforce in Sheffield in the UK represent that community. So those, those dimensions really play out when we’re really thinking about that.

Shelley Willingham:  Absolutely. And I think he would agree that, you know, when you are rolling out these DEI initiatives, again, going back to the one size doesn’t fit, all, it really goes back to understanding the nuances within an organization. So you have your Pendo DNA, but then in your different locations, they have their own DNA as well. And you have to be sensitive to those, those issues as you’re rolling out. So you’ve got a big job ma’am so let me ask you about kind of just being in the startup world. Right? So with this series we’re doing about DEI for startup community. We want leaders to think of DEI at the ground level when they’re just starting out with a few employees or even when it’s just them. So what tips can you give that set the foundation for success with DEI, no matter what kind of where you are when you’re just getting started?

Jess Jolley:  So I love this question because prior to joining Pendo I was, you know, founded a company. We were really small. I joke with our founder, Todd, you know, nowhere as near successful as Pendo,  we had about five employees, but I know what it’s like to be at that ground level where you’re balancing so many aspects of your company. You’re trying to think about product market fit. You’re trying to think about growth. You’re trying to think about marketing, you know, how do you manage payroll and with all of that, you know, I’m sure if you, like, how can I think about diversity, equity and inclusion when I’m already thinking about all these other pieces?

I think a piece of advice. I would share it with founders in that early stage is to recognize that DEI efforts. They’re not just something that larger public companies do to check a box. This isn’t, you know, PR, but,  it really is about having diverse teams. So you’re driving innovation in your company and even in early stages that’s still so critical. I think tactically, you know, as you’re thinking about growing your teams, how are you sharing job descriptions? How are you, you know, networking, you know, how are you using tools. And the reason I say that is because as you’re building a team it’s so easy and it’s natural to want to bring in people that you trust people that you know, and if you’re not intentional thinking about you know, diversity in those hiring efforts, you could look up in three or four years, you know, everyone looks like, you know, everyone has gone to the same school has had the same lived experience might look like you might be the same gender.  And there’s nothing wrong with that, but then you’re missing out on so many other aspects of, of people’s lived experience. So many other skill sets that you might be able to bring in, and that could really push the innovation of your company. And I think I talk a lot, you know, and we talk a lot at Pendo. We strive to be a product led company. And that means we’re building products for everyone. And so we have to think about that and we need teams  that can do that and have that lived experience in that perspective.

Shelley Willingham:  I love that. And the innovation piece is so huge, but you know, to your point,

I’ve started a few companies myself and yeah. I’m like DEI. I’m just trying to make sure I can make payroll. So it is so intentional in the beginning, but when you do think about it in terms of, okay, this is really laying the foundation for future growth and innovation, those things that we need to be successful, it just makes sense.

So I’m so glad that you said that because I totally agree with you on that.

Jess Jolley:  Another thing that I also think is important to think about you know, you hear the saying culture eats strategy for breakfast, but starting those conversations around culture early, like day one and then asking yourself, your founders, your company, you know, is our culture inclusive?

Do people feel like they belong here? Do we celebrate differences? And so I think just as you’re building culture, those are things you can just ask, you know, really in day one, you know, as you’re thinking about your company grow.

Shelley Willingham:  Absolutely. And step outside of your comfort zone, because to your point, you know, we attract and deal with people that are we’re comfortable being with that are like us. And so our boards may look like us in our early employees may look like us, but you know, if you intentionally say, okay, I’m going to be very deliberate about making sure that I’m widening my reach here, that definitely makes a difference. So, yeah. Great tips. So let’s talk about hiring, since you said you’re hiring so many people right now, and I know that as with your role, you’re definitely wanting to use a DEI lens as you’re making those hires. How do you recommend interviewing with that lens? But at the same time, not filling a position with a certain group in mind.

Jess Jolley:  Yeah, no, this is a great question. And it’s something we are talking a lot about at Pendo.  And as, as we’re doing so much hiring, so our goal is to make sure we are as objective as possible in our interview process that we are fair. We are objective and that the process is the same for everyone. No matter how they identify. And so I think a big piece that we have worked on over the past six months with our recruiting team is standardizing our interview process. And this sounds simple.  But when you really think about it, when you’re going through an interview process for candidate, do you have the same questions?

Do you have the same interview panel throughout? Do you have the same criteria that everyone is using to evaluate and to measure if a candidate fits, you know, the role and has the skills.. So just from beginning to end, you know, standardization throughout. And I think that kind of adds a layer of being more objective and an interview process. So that’s one aspect, you know, we’re really working on.

The second you know, everyone in our company does unconscious bias training, but we’re trying to go beyond that. We’re really trying to have real time conversations based on what’s happening in the business. And we’re spending a lot of time talking about breaking bias and thinking about how that shows up in the interview process.

We all have bias, but when you’re interviewing, making sure you’re checking that, and you’re not just saying, I like this person because maybe, you know, we liked that you went to the same school or we, you know, there’s something in common. You know, we talk a lot about affinity bias in our company and, and how that shows up that you sometimes, you know, you value someone who has an affinity or share thing that, that you might have.

And so really being intentional and aware there. I think the last thing we’re really trying to, and I’m really excited about this work going forward. It will start early on when we post a job description, really checking our assumptions to, to think about what, what we need in the role and what someone needs to be successful.

And examples of that, you know, we’ve looked at some of our job descriptions where we said we need four year. You know, college degree, we need XYZ years of experience. And we started to shift that because, you know, in our engineering roles, there could be candidates from boot camps who didn’t go to a traditional four year school, you know, maybe colleges. And I think being able to really expand and kind of really look and say, okay, we’ve set a bar here, but is this bar measuring what we need it to measure? And are we missing out on amazing talent? And is this just an arbitrary, you know, thing that that we’ve set. So I think that’s something I really am excited that we’re working on as we continue to scale over the next year.

Shelley Willingham:  I love that, you know, at the Diversity Movement, we work with a lot of clients that of course want to diversify their employee base. And we have a TDM talent management division where we work with our clients on just what you said, because there’s no need to put for a huge diversity recruiting strategy if internally, you’re not prepared to welcome this inclusive talent that will be coming on board. And then it’s the entire process, like you said, looking at the applications, looking at the wording, looking at where you’re posting. I mean, all of those things are so important, so you all are doing so many of the right things. So that’s really great.

All right. So Jess, we’ve talked a lot about all the hiring that Pendo is doing. So can you tell us about how you’re ensuring that there’s also an equitable slate at the mid-level and executive levels?

Jess Jolley:  No, it’s a great question, because I often think when people talk about diversity and talk about recruiting, they think about the early career aspects and those early career partnerships, but we’re trying to be just as intentional at our manager level and our executive team.

We recently have hired chief revenue officer, general counsel and chief people officer, and all of those leaders are women. And so that’s changing the, the gender representation of our leadership team. And we’re seeing people you know, who are now saying, oh, I want to learn more, you know, external candidates seeing that and seeing people that represent them in leadership.

I think the same thing across, you know, race and ethnicity, as we’re really thinking about how are we finding manager, how are we finding talent at the manager level and doing intentional searches? And I think the manager level is a focus area for me, because those are the leaders that are investing in your early talent that are managing coaching and developing, you know, almost all the employees that are at an early stage, but they’re also the leaders that, that are eventually going to be the VPs and the C team of your company. And so that succession planning. So I think managers are really critical and doing no intentional searches, bringing in external partners that might have networks and might be able to have, you know, helps expand your searches. I think that’s, those are some aspects to, to make here that we’re not just focusing solely on the early career phase.

Shelley Willingham:  I love it. And that’s just how, you know, people kind of maybe start with diversity recruiting as part of their diversity strategy. But you mentioned earlier about needing to filter through all parts of your organization. So Pendo is product first, right? Everybody uses the product. So your consumer base needs to be reflective of your employee base. So taking the time to ensure that you have that equity, there just makes good business sense and it makes good business sense from a sales perspective and a marketing perspective. So that’s great.

What are you excited, really super excited about besides the hiring, but what other type of DEI initiatives are happening at Pendo that you would like to share with us?

Jess Jolley:  Yeah. I mean, we’re knowing so much internally, you know, I think we talked a lot about the, the, the talent side, but also thinking about the equity and inclusion pieces and, and what does that look like for our employees once they joined Pendo and I just want to, you know, have to shout out our affinity groups again, they’ve done so much work even over the past year, but I am really excited  about the work they’re planning on going forth.. And when I talk about some of that work, we’ve had sessions where we’ve had leaders from fortune five hundreds, come in and talk to our employee base around what it looks like to be neurodiverse and, and how that’s different than being neuro-typical how that shows up in, in day to day workplaces and really talking in tactical ways around how to make sure that if someone is not neuro-typical, they’re set up for success. We had a great speaker in conversation series. We had Jim Seals, who’s the CEO of MNF bank and he came in and he talked about the history of black banks in Durham and black banks across the U S and just thinking about the opportunity gap and the wealth gap, and, you know, and finally, you know, there’s so many, really, really good conversations around product inclusion. And I’m excited about that because that’s what, and our employees, you know, that education building starts to happen. People are educated on something they might not have been exposed to. But then I think the next level is that empathy building where we’re employees are saying, hmm, I’ve never thought about, you know, what it might look like for someone who’s not who’s neuro-typical now I can understand that I have the empathy and I think that’s really, when you start to build a culture that that’s more inclusive and so excited about that work, that’s going to continue. And then also just thinking about, you know, how are we making sure our employees are set up to succeed no matter, you know, their demographics, but, you know, as we grow and promote and succession plan, how are we really developing our talent and, and making sure that we’re continuing to support people throughout all the levels within our company.

Shelley Willingham:  Awesome. That’s great. So when you think about some advice you could give to a startup leader about the importance of having someone leading the DEI effort, what would you tell them?

Jess Jolley:  Yeah, I mean, I would just say that the work takes time and you have to be intentional from the start.  You know, diversity equity inclusion should be embedded in all aspects of what you do.

So not just hiring, you know, we’re talking about culture building, we’re talking about values. It should be embedded when you’re thinking about marketing and communications and branding. So I think just making sure that this is not an afterthought that you are thinking about equity from the beginning

I also think really. Trying to remember that again, this is this leads to innovation within your companies. And, and I think, you know, we spend a lot of time at Pendo talking about being a product, you know, product inclusion. And if you’re building products for everyone, you have to have representation internally. So I think having that aspect.. And finally, I think just taking the time to really educate yourself and your employees on the structural barriers that have led to the under-representation in tech, across, you know, across communities. So thinking about, you know, black and Latin X communities thinking about, you know, women in tech, thinking about the LGBTQ community, but like not understanding that history, I think is just as important as doing the, you know, tactical efforts to build a more diverse and inclusive workforce.

Shelley Willingham:  Awesome. And that’s great. So, and we need to listen to you. Everybody needs to listen to you, to Jess. Look what Pendo has done in terms of growth and as a startup. And in diversity, you just have some, some amazing things. So, again, thank you so much for being on today. Loved talking to you. And this is exciting to see companies that are doing the DEI work the right way, but are also experiencing exponential growth.

And so it just underscores that this is important work to do, and it does overall support the business case and their success metrics attached to the work. So. Thanks again for coming on. And I look forward to talking more about diversity with you at some other time.

Jess Jolley:  No, thanks Shelley. This has been a great conversation and look forward to more like this.

Shelley Willingham:  Absolutely. Thanks Jess.

Shelley Willingham: Before we get going, I want everyone listening to know that we will be holding a special webinar, DEI for the startup community on Thursday June 3rd at 12:00 Eastern Time, and we want YOU to attend. The signup link is in the show notes, and here’s the deal: you can sign up to attend this webinar by donating any amount to the Thurgood Marshall College Fund. And if you want to sponsor this event, contact us at (email?). I’m so excited for this, and I hope to see you there.

Alright, thanks for listening, everyone. We’ll be back again soon but until then, be sure to visit for more podcasts, articles, and educational content.

Full Episode Transcript

Winning with Diversity is brought to you by The Diversity Movement, hosted by VP of Business Strategy Shelley Willingham, and is a production of Earfluence.

Amplify Your Expertise
About the Author
At Earfluence, we are proud to produce this podcast. We believe in sharing amazing stories, providing knowledge to the world, and celebrating diverse voices. Through podcasting, our clients are amplifying their expertise, expanding their networks, building a content engine, and growing their influence. If you're interested in podcasting, we'd love to hear from you! Schedule your free 15 minute podcast consult today.