How People Leaders Nurture Culture as a Business Scales

Growing a business? Don't miss the wisdom of Jane Jaxon, VP of People at Wistia! Jane has served as a people leader at three scaling businesses and took Ben and Grace to scale-up school. Come join us!



We're ecstatic to welcome our new friend Jane Jaxon from Wistia to Start with Who! Jane is a serial people leader at scale-up companies—and she in this episode, she'll share:

  • A few stories of culture-building from her VP of People playbook
  • How to navigate changes as the business evolves
  • The tactics Wistia is using to revamp their hiring and encourage DE&I
  • The importance of hard work upfront to recruit a great team—and the long-term impact on the business

P.S. Thanks to Wistia for hosting this podcast!

Thanks for listening to Start with Who: The Interview Intelligence Podcast! This podcast is presented by —where we're on a mission to make hiring and interviewing more efficient and equitable. Come check out what we're building, or connect with Grace and Ben on LinkedIn! See you next time!


(Transcribed by robots...sorry for the errors!)

Jane: My take is, yes, there's a lot of work involved in interviewing, but the impact is huge. And I think folks don't realize that or take a step back to be like, how will this impact us over the long term? Well, it's like a three year, four year investment. So, like, pretty markedly.

Hosts: Welcome to Start with Who, the interview intelligence podcast, I'm your host, Grace Tyson, and I'm Ben Battaglia join us on our journey as we learn about talent acquisition, hiring and tackle the challenge of building an amazing team. One interview at a time. We've invited ceos, innovative people, leaders, talent acquisition experts and DIY movers and shakers as our guides would love to have you join us. Welcome to Start with Who.

Ben: Oh welcome back to the start with who podcast, so excited to have you all here for another episode and excited to welcome today's guest. Jane, Thanks so much for joining us.

Jane: Yeah, I'm super excited to be here today,

Ben: Jane, for those who don't know you. Will you tell us a little bit about you and who you are?

Jane: Yeah, absolutely. I am, Jane. I'm the VP of people at Wistia. This is my third go round with a startup in the HR people world, and I caught the bug with the first one and just really enjoy digging into how to scale cultures and support businesses as they grow because it's really just like super energetic and is my sweet spot.

Grace: I love that. And that is a perfect segue into exactly what we want to pick your brain on today, Jane, which is the fact that you have helped a number of companies to scale up. And so we really want to dive into how you think about maintaining culture as you scale. So just curious if you could debrief us a little more on. What are your experiences with that. And your past companies and now at Wistia?

Jane: So the first company. I joined in the tech world was called Buildium. It's a Boston based company and they've been super successful. And I joined at 20 people without a whole lot of experience in the real world. So I learned a lot. And continue to learn. But it was really interesting coming in to bootstrapped business and putting all these systems in place that you continuously needed to tweak as the business got bigger, and the culture kind of shifted to support a different and a growing business. So it was really awesome to think about ways to bring people together. We used to make sure that we were able to bring in fantastic talent consistently, even as that number of recs increased and increased. And, you know, one of the things I'm still friendly with a number of folks at podium. And one of the things that's really exciting is some of those core things that we put in place at 20 people or 80 people still are fundamental to that culture. And bring people together. And then there are things that were really great at 20 people or 80 people that we had to kind of leave behind as we welcomed new people, had different size demands. And it was just really interesting learning and figuring out the things that worked and didn't. And sometimes I think back at some of the things that probably needed to go away and how attached to those I was. And look back now. And I'm like, oh, but such great things came after it. And the Segway into what I'm doing now. I think Wistia is very similar. We were 80 when I joined. Was it like 125 right now, expecting to grow anywhere from 40 to 50 people this year. So we're in that fun stage where you're figuring out the things that should come along for the journey and the things that either need to be left behind or tweaked as we think about keeping people connected to each other, feeling purpose in their work, and also dealing with the curveball of being remote for quite a bit of time. We see is such a strong in person culture. It's our bread and butter. It's a differentiator. People come in and they feel it, whether they're working there or not. And to just lose that suddenly last year was tough. And it's been interesting seeing the things that we have, you know, moved to the remote only worlds. And that are very similar in terms of the feelings that people get. It's just really exciting to think about how we get to the next stage from here and how we channel all that energy effectively.

Grace: I love that. And I have a million questions, but I'll start with one, which is you mentioned that at Buildium when you were 20 employees, there were a number of things that you put in place from a culture perspective that are still around and continue to be relevant. I'm curious, digging into your VP people playbook, like what are some examples of the types of things that maybe you see as evergreen, regardless of whether your 20 employees are 80 or 120 five, that you think every people leader should be thinking about?

Jane: Yeah, I think each company, how they do this is going to be different. But starting at that early stage, one of the things that was really important to our culture is every Tuesday, we would book lunch at a local four point restaurant where we could just sit together as a team and eat and you'd sit next to New people and you'd get to know them. And I think informally, a lot of our communication and collaboration happened there. And You were able to build up trust, so when we went through the tough things, you know, there was trust there and everyone knew that we were aimed in the same direction. That became a little bit harder as we were bigger and bigger. And we had to think of different ways to create that experience where folks could comingle, share a meal. And at first, it was just kind of a shared lunch once a week in the office. And then it was a more specific event on, I think, the third Thursday of every month where we would try to design different ways of pulling people together. I remember, we did like office Olympics once. So I think different companies, some companies may have video game tournaments or may do a whole lot of volunteering together. I think there's something to really digging deep to what's important to the founders and feels organic with the team you have and thinking how you can use that as a way to pull people together and get people able to build relationships across the company. That's certainly super hard as you get bigger. And it's really going to look different company to company. But it's super important, I think, given how much you have to get done, given how fast a lot of startups move to have that foundation in place where people know each other. And obviously, it's much harder remote as well right now.

Ben: Yeah, I think that's a phenomenal idea. And the reason we started this podcast is because grace and I are currently working on trying to build the company. And we wanted to learn as much as we could from people like you. And you mentioned Wistia strong in person culture. And the company that grace has started is a remote company, like we have teammates in our small team. In five different four or five different states. And so you really do have to be creative about how do you coordinate and do cultural moments like that where you can build trust when you can't go to the restaurant down the street together. Does that resonate with you?

Jane: It does. This was a very great memory. I have. But the first time you go to either an all hands meeting or what we call, show and tell at Wistia, they'd be in the office. Everyone would be sitting in the bleachers and the energy in that room was phenomenal. So with all hands, it was a bunch of stuff that we need to communicate out. Different teams, talking about their goals or things that they're learning from. Customers, show and tell, is focused on work that's ongoing. So it's never a surprise when stuff comes out. And it's really cool to see behind the curtains of different departments. But one of our values is presentation. So the amount of effort people put into their slides, how they present the jokes or punch lines that are in there, the videos, it just makes it such an enjoyable experience. There's a lot of clapping, a lot of laughter. I've never been to a meeting like this where I actually really enjoy going. And it's exciting to come together and going remote. You know, you don't have the clapping. You have one person who's mic is live and you can hear that one person clapping. So Chris and Brendan are founders. I think spontaneously we're going through and we recognize people's anniversaries and started doing this thing where they share someone's anniversary. And pause. And we go to the Zoom chat and people are sending emojis to the person getting recognized. So let's say I was into baseball, traveling dogs. All of my coworkers will be sending these random emojis to recognize. And it just like the chat goes super fast and it replicates some level of that interactivity and that energy. And that's been super cool to have stuff like that. And then some of the folks who've hosted show and tell, we did one where it was. Where in the world is Lenny, who's basically our office dog, and you see him in some of our logos and whatnot. And it was based on where in the world is Carmen, San Diego. So he took us on this whole journey around the world, interspersed with people's updates. And it was just really spectacular. I think it was our first or second show until after we went remote. And it just felt like, OK, we can do this. We can still have some culture. It's going to look different. But we can figure this out. If we lean into our values and just figure out new ways of applying them.

Grace:I love that. That's, first of all, adorable.

Ben: I love that idea of sticking to values. I'd love to hear like how do you continue to encourage values in a remote world? So I feel like oftentimes those get reiterated or talked about or lived out really naturally in. Office setting, but are you guys doing anything intentional that Wistia in a remote world to try to continue to nurture values in your culture?

Jane: Yeah, I think there are a couple of things. First is we certainly interview in alignment with our values. And I think that sends some strong signals to candidates that this is important to us. It's also involved in onboarding, which is just helpful in understanding how we think about them, how we apply them. But I think the only other thing that we've done, we use a tool called fifteen five to do kind of 1:1 to ones with our manager and to do our reviews. But one of the tools that it has is the ability to give other folks high fives. And in our profession, I've talked to a million different salespeople who are like, oh, recognition is great. It'll definitely work in this tool, but it never actually delivers. And Wistia has such a great culture of recognition. This tool certainly helps. And people will call out folks for their thinking or performing through the lens of values, which I think reinforces it. But I don't think we've done anything overt. I imagine that past companies, this probably would have been more of a challenge. I don't think values is something we're dropping lower in as a remote workplace right now, and I'm not totally sure. I can't put my finger on why, other than I think it's just so deeply ingrained in people and they're very genuine and we hire people for whom those things are important. So we have been able to luckily, not worry too much about that in the remote world. And that's one thing that's been relatively easy to navigate for us.

Grace: I love that. And it sounds like you incorporate the values into the way that you interview the way that you hire. And then, of course, that then trickles into everything else, which is definitely a best practice. That's amazing. Jane, I have another question for you about scaling up. And it's a very broad one. So very whatever pops to mind. But for you, in your experience, scaling up three companies, what has been the most invigorating thing? And then maybe what has been the hardest aspects of scaling up?

Jane: I think one of the most invigorating things, I think is twofold. One is the people that I've gotten to work with. I've been privileged to work with some really exceptional humans who are exceptional at what they do. And I think that brings out a level in performance overall as a team that just feels really energetic and good. And I think has pushed me to grow faster and in different ways than if I hadn't gotten to work with. So many really exceptional people across the business. In problems that are not people focused, it's just really great to get to work with my peers that way. I think the other thing is just the energy as you start to grow and you feel the product market fit and you're like, wow, we need more people to take care of our customers and to bring more value to them. There's just an energy that makes years go by very quickly. And that's for better and worse. Sometimes, you know, you don't realize how many hours you're putting in. But I think that energy is something that I, I feed off of. And I find is where I want to be in startups for the near future in terms of, like, the hard things. I've learned this as I've spent a little bit more time. I probably wouldn't have said this at building, but I think, you know, navigating cultural change is hard. There are things you're attached to that you need to let go. I think in the people role, there's also an element of sometimes you as a business need to shut down a unit or a project that people are really attached to and disappointed to let go. I think in some circumstances, if you need to shut something down, sometimes that means laying folks off, which is certainly not a fun thing, but is a requirement of the job for businesses to meet the needs and be successful over the long term. And both of those things can be emotionally draining to navigate and make the decisions. And then help other people navigate. Because if you love this project or this element of the culture, it's really hard to let it go and feel like. What will come in its place is also super valuable and exciting when you don't know what that is. And it's sometimes sad to say goodbye to things. And it's really hard to help people navigate. But having been through the growth cycle a couple of times, it is really exciting. Two years later to look back and see all that you've changed and all the things that you feel are actually better in this new world. So that's one of the hard things, is knowing when it's time to say goodbye to some beloved traditions like that lunch or when you need to shut down a project that everyone loves and it's just not working. And it's distracting from what you need to do.

Ben: Yeah, that makes sense. I think what I'm hearing on both sides of that answer is like this year, excitement of building something great. And also just the classic Spider Man with great power comes great responsibility of making hard decisions. You know, I'd like to hear also about the element of DGR in your culture. And I know that's important to Wistia and I would love to hear how do you ingrain that in a culture? And then also specifically, how do you ingrain that in hiring and interviewing?

Jane: I will preface this with we are still learning and figuring out what works. We're learning from consultants and speakers in the space and trying a bunch of things. One of the things that was already in existence at Wistia when I started that was really helpful is Chris and Brendan have built a company with consistently hiring good, empathetic, humble people who are willing to learn and adapt. And I think that's one of those values that has helped us on the front, is people genuinely care about one another. They're willing to admit when they're wrong, whether it's in a project or whether it's missteps interpersonally. And so I think that's really been helpful. Just as having a learning culture. I think some of the other things that we're trying right now with some of our processes are leaning into with hiring specifically. We basically revamped our process totally to focus on really sussing out the things we need to assess and the things that don't matter. And we put in. So much work up front before a job, even goes live down to what are the questions different interviewers are going to be asking and what is a good answer versus a bad answer. So that once we start seeing folks, we're able to use the same rubric, the same experience, and it makes it harder to accidentally lean into likability or affinity bias because you've quantified what your look. Four and I think the other thing, we didn't have this till later at building, but I think one of the other things that's really helpful with Wistia is, you know, we've invested in talent acquisition. So if you feel like you have the culture where folks are inclusive and feel a sense of belonging and you feel like the process mitigates out as much bias as you can, and you're educating people about how to recognize it in themselves and others. To have a talent acquisition arm that is going out bounds and has control over the funnel. Is leap year or leagues different from what we had at building, where it was very much dependent for a long period of time on your inbound volume? And I look back at some of the job descriptions that I wrote in building, and I think about how gendered the language is and how we were probably diluting our pool with some of the things that, you know. Now I know that's really not great. We didn't need 50 things on a job description. We just needed the things that people need to do. So I think those three things, the culture being very sound and inclusive and reflective, looking at your process and making it as fair as possible. And then for companies that have the ability to invest in talent acquisition, to really get somebody who's passionate about this. So that you can control your pipeline in a way that's very different. Like right now, Taylor, who's our manager of talent acquisition, he will spend a couple weeks building the pipeline based on what our inbound is and what we need, in addition to make a more representative pipeline. And we won't start interviewing people until we feel good about the diversity of that pipeline, because once you get started. And you get that one person who's great. And qualified for the job, but you haven't seen a diverse pipeline, it's really tough to say. Hold on, hold on a little bit. We need to get some other folks through here. So he's done a great job managing our roles. So that we're not starting until we feel like we've done the diligence to get diversity of all different types in the pipeline. And we have seen some changes in our 2019 and then our 2020 hiring class that are really promising and seem to indicate that we're on the right track with some of the changes we've made.

Grace: There were so many great Nuggets in what you just said, Jane. First of all, just to call out what you said about your reflection on some of the job descriptions you wrote in past roles at the podium and your learnings, essentially, I love that you were willing to acknowledge that because we're all on this journey. And we all do that. We've all done that. We've all well, I don't know about everyone, but I've definitely done it. I've definitely been guilty of, you know, maybe not writing the most inclusive sounding job description and not really thinking about it, not realizing it in the past. So I love that, first of all. And then second of all, what you said about Taylor going ahead and building the pipeline and cultivating it before even starting interviews is so amazing, because what I've experienced is that once you start interviewing, you're trying to move fast, you're scaling up and you're going really quickly once you get candidates to the final stages. But you don't end up having a diverse candidate pool at that stage. It's really hard to force yourself to go back and build a more diverse pipeline when you have a promising candidate. So I love that you're doing that. I just want to call it out. I think that's amazing.

Jane: Yeah and certainly, like, there needs to be room for collaboration, whether it's doing some phone screens and just the hiring manager interview to make sure he's got the right profile. But we try not to start in earnest until we feel like we've got a whole range of folks that we think are capable of not just making it to round one or two, but are capable of making it to the final rounds. And he's really done a fantastic job on that front. And it's made an impact. And I think it's given folks a little bit more confidence in our process and what we're trying to do on the talent acquisition side.

Grace: That's great. I mean, you mentioned a lot of best practices as you were talking through the interviewing process and the recruiting process in general at Wistia. Is there anything else you think is just really important, like any hot takes on interviewing or things you're especially passionate about being part of the interview process?

Jane: Yeah, we ask a lot of our hiring managers and our interview team. There's a lot more upfront work, then I think most companies ask. And the reason for that is as a manager, there's generally a million things that you are trying to do. But how you build your team and the people that you hire, there's very little that you can do in a given quarter. That's going to have a higher impact over the long term. You may have this to do the. You want to get out or you want to write a PR release or something like that, and yes, it needs to get done. And certainly will have an impact. But if you are cutting corners on finding the right set of skills that fits with your existing team members and has the right growth trajectory for how you see the company growing in the future, if you cut corners on that, you are doing a disservice to your selfish ability, totally self-centered ability to impact the business. You have a strong team around you. Yes, there's a whole lot of pain in interviewing. It's not the most phenomenal thing when you have a million things going on. But those teams that are exceptionally strong accomplished so much more. And so much more seamlessly than those for hiring managers who don't pay as much mind or are willing to settle for good enough or are not putting in the effort to do their own sourcing as well. My take is, yes, there's a lot of work involved in interviewing, but the impact is huge. And I think folks don't realize that or take a step back to be like, how will this impact us over the long term? Well, it's like a three year, four year investment. So like pretty markedly.

Grace :I totally agree.

Ben: You're like the Ted laso of people. Opps, it's amazing. Just so quotable. Have you seen Ted laso. It's really one day I will take a look. It's really great. He's amazing. And so are you. Thank you.

Grace: Jane might be spending her time not binge watching as much Netflix and Amazon Prime videos as we are Ben

Jane: hard Disagree, hard disagree?

Grace: I do realize that Jane added to the list. I just want to underline and highlight everything you just said, because that is exactly what happens. And I, again, have been guilty of that as a hiring manager on the sales side of Oh my gosh, I have to have an interview. I'm so busy. I don't want to do this interview. Like, what if it's a waste of my time. And it's like, wait, hold up. This is the single biggest thing that will allow you to sleep better at night. Grace, this is the single biggest thing that will make an impact on your team's ability to perform and to thrive and to bring joy to work. So give it its time basically

Jane: I have done the same thing. It's like when everything's on fire, it's really hard to be forward thinking. And I think interviewing and hiring is one of those forward thinking things. And it's really easy to put on the back burner. But the flip side of that is if you hire wrong, you're going to have another fire in like six to 12 months. So, yes, try to, like, keep that from happening. Yeah, ideally, it makes all the difference, truly so.

Grace: OK, Jane, thank you so much. That a very wise words. Really appreciate all of your perspective on interviewing and scaling up culture. We love to close each episode with a little speed around. So that our listeners, and we can get to know you outside of work. So we have a few questions for you. Are you ready?

Jane: I am ready.

Grace: All right, fabulous. I will kick it off. What brings you joy outside of work?

Jane: I am a big fan of spontaneous day trips to go hiking or find a brewery or both of those things with my dogs and my wife.

Grace: Oh, I love it. I love it. That's how I spent my yesterday. So that's my favorite thing too. That's great.

Jane: What's one thing you've watched or read recently that you've loved? You know, I absolutely loved the flight attendant on HBO, max. I wasn't expecting anything. I didn't follow any of the actors or actresses and put it on. And all of a sudden, we were watching however many hours of that in like two, 2 and 1/2 days. It was great.

Ben: Oh, great. I saw I scrolled by that yesterday. And I was like, I wonder what that is. So thank you. That's what I needed.

Grace: Yeah it's on my list not to have a go either way. Too many episodes of TV shows lately. So perfect.

Ben: you can add Ted laso from me to your list.

Jane: Done.

Grace: it's great. Fair trade. Oh wonderful. Do you have a go to favorite food or favorite meal.

Jane: It's kind of a split between probably pizza and tacos. I think tacos has been winning out the last couple of years.

Grace: Excellent choices.

Ben: I think everyone's favorite food, should it be either tacos or pizza, period. It's just like a golden rule.

Jane: Yeah, they're just fantastic.

Ben: What's your favorite place you've ever traveled?

Jane: I was fortunate enough to be able to go to New Zealand. And Australia for three weeks, several years ago. And I think New Zealand just blew my mind. And I can't wait to go back. It was beautiful. The people were really nice. The hiking was. But the air was fresh. That's my jam,

Grace: feel like I'm about to tear up just thinking about traveling. That's lovely. Oh, my goodness. That is on my bucket list. New Zealand. I heard great things. OK, Jane, final question. Something we ask everyone. We are dying to know your thoughts. Do you believe aliens exist? Why or why not?

Jane: You know, I feel like yes, just statistically, to think that we're the only things in this whole universe is a little bit ridiculous. So I believe that they exist. I try to stay away from, like, the deep dive into it because it may freak me out a little bit. But statistically, they're definitely out there.

Ben: There it is. That's the hot take we were looking for, Jane. I'm coming around slowly. That's what prompted this question is I'm not there yet, but grace is definitely there. So you're in the lady, Jane. You're in the same chameleon's. Get there eventually while. Jane, thank you so much for joining us. We really appreciate you taking the time today and for sharing with us.

Jane: Thanks for having me. It was really fun.

Grace: And if you don't know Wistia, you should check them out. Jane, where can we find out more about all of the roles you're hiring for and what you are up to at wistia?

Jane: Check out We've got all sorts of stuff on the product and plenty of linky goodness on the careers and our culture. So check us out.

Ben: Sounds great. Brand affinity marketing. See you there.

Hosts: Thanks for joining us for another episode of start with who, the interview intelligence podcast presented by Pillar. Find out more about Pillar and how to do the best interviewing of your life and build an amazing team, all starting at And if you like this episode, leave us a review or shoot us a note. We'd love to hear from you. Thanks for listening. We'll see you next time.