Using kindness and core values to scale a fully distributed team with Becca Van Nederynen of HelpScout

After experiencing a pain point in customer communication, HelpScout founders identified a need for a product that support small and medium-sized businesses. They’ve scaled their fully distributed team from 10 to 100+ in the last 5 years. Head of People Operations, Becca Van Nederynen joins us on the Talent+Tech podcast to discuss how they have fine-tuned everything from being flexible when it comes to customer needs, having a well thought out hiring process and People Ops team, setting new employees up for success in the onboarding phase to making terminations as clear and kind as possible.
A lot of information is shared via HelpScout’s blog where their CEO and other members of the company write transparently about what HelpScout is doing to support their customers.
Our biggest thing is about having options as a company and seeing where our customers need us to go.
While HelpScout is a fully distributed team, they do have two small hubs they use for new employee onboarding where they believe “It’s always nice as a new person to meet some friendly new coworkers” and in setting them up for success.
And since then we gather feedback, and we keep doing it because people tell us how impactful it is for them.
Becca shares how HelpScout’s hiring process has gone through many iterations, and she highlights mistakes they’ve made, lessons they’ve learned, challenges they face, as well as what works. She also describes HelpScout’s process when needing to offboard an employee on their fully distributed team. “Well, first and foremost, we try to be as kind as possible, because it’s an important transition. And it’s hard for everybody involved.” They also ensure that everyone from managers to the person being terminated have a lot of support and a clear idea of what is going to happen during the transition.
If you like this episode, check out our conversation Focusing on people ops from the start to grow a healthy organization with Eliza Blank of The Sill.
Be sure to check out Becca’s go-to book and podcast recommendations: Reboot: Leadership and the Art of Growing Up, The Reboot Podcast, and Powerful by Patti McCord.
Reboot: Leadership and the Art of Growing Up
Learn How to Negotiate with these 12 Tactics for Successful Negotiations

Maren Kate
Welcome to From Five to 50, the podcast dedicated to helping startups and founders survive and thrive through the early stages. I am your host, Maren Kate. And we are here with Becca Van Nederynen from HelpScout. Welcome to the show, Becca. And did I get your last name right?
Becca Van Nederynen
Hi, Maren. You sure did. Thanks so much.
Maren Kate
Awesome. So just to jump in when was HelpScout founded?
Becca Van Nederynen
HelpScout was founded in 2011 by three guys named Danny, Nick and Jarrett.
Maren Kate
Okay, and what was the why behind it? How did they come together?
Becca Van Nederynen
Great question. So they had actually been working together for many years, they had a business together where they helped other small businesses put together websites, and they had been really curious about developing a product of their own. But they were kind of waiting to see what that was, and how that could happen organically. And the opportunity came up when they were having a little bit of trouble managing their own customers, just keeping in touch with them and communicating with them back and forth. And they tried out a bunch of different tools like Zendesk and Freshdesk at the time, and neither one of them, or any of the tools that they tried, really met their needs. And so they're like, this is the product we should build. And so the idea was born from from that pain point of theirs.
Maren Kate
So kind of born from an agency shifting into a product. Awesome. I feel like so many amazing companies I talk to had started that way. I'm literally in the midst of doing that myself, building an agency, two years ago, to really figure out to do r&d, or what the next more scalable product is. So it's a great way to roll up your sleeves and really get in the weeds and figure out where the pain points are on both sides. So what is your role? And when did you join?
Becca Van Nederynen
I joined HelpScout in 2014. And I actually started as a UX researcher/product marketer combo, when the company was about 10 people. And I quickly shifted into a people ops role within probably nine months. And again, startup life, I was wearing a couple of hats on the marketing side and the people ops side for a while. But the last five years really have solidly been in a head of people ops role.
Maren Kate
That's a kind of awesome shift. How did you realize that you really loved the people side of the business? I guess UX and research, you're still doing it, you're doing the same thing. You're talking to people?
Becca Van Nederynen
Yeah, that's exactly it. When Nick first approached me about the shift. He was like, you can keep going on the marketing track if you want to backhoe but you seem to be doing all of these culture pieces just kind of on the side? And would you like to own that? And I was intrigued, but I was hesitant, because I didn't want to be the HR lady. And so I thought about it. And I realized that there were so many parallels between what I was doing as a UX researcher, and with product marketing, trying to figure out what it was about products that customers really love and what would meet their needs. And I realized it's the same thing for employees and employers. It's a relationship there that needs to be nurtured. There's an employee lifecycle, so many crossovers, and I got really excited about the opportunity to work with Nick and for him to be my support in that. And it was really the remote piece, too that kind of pushed me over the edge because I was like, this is something new that not a lot of people are doing. And I would be so stoked to be on the frontlines there.
Maren Kate
Had you worked remotely before?
Becca Van Nederynen
No. Well, there had been elements of remote work at my previous role in marketing at another tech company. But it was more I would say a flexible workplace and not a remote first workplace.
Maren Kate
Okay. So just kind of giving the audience an understanding of HelpScout’s size and especially being a remote first workplace. I think it's so interesting to see companies that are really succeeding in that space. So what's the business model? How do you guys make money and what's your current size?
Becca Van Nederynen
We are currently 105 people, which is so wild to me, still, because I remember joining back in 2014 when we were only 10 people. So we have grown to 105 folks over the last five years and and we are a, how do I want to put it, we're right in the middle of trying to define what our message is to our customers. So what HelpScout is, it's really a platform that helps small businesses convert, support, and delight their customers. We have a platform of different products that businesses, small businesses, medium sized businesses can use to support their customers, whether it's a help desk, a knowledge base, chat support, things like that. So we have, I think, well, I'm not going to get the exact number, right, but I'm going to look it up as we're talking. And we have tons of customers all over the world, mainly small businesses who are using our software to support their customers.
Maren Kate
Okay. And, obviously, the three founders came together and started this out of their own need. I'm assuming they began bootstrapped. But at any point, did you guys take on funding from outside investors? Or have you stayed bootstrapped?
Becca Van Nederynen
We started off bootstrapped and then HelpScout an then got involved with the TechStars program in Boston, so out of that they had a hefty seed round of funding. And we stayed in that mode until 2015, where we had our first round of VC funding. And we've had one other since then.
Maren Kate
What's the total raise 12 million?
Becca Van Nederynen
12 Mmillion
Maren Kate
Okay. Cool. I was reading through the site before this, especially the careers page, you mentioned that there's a culture of being financially transparent internally. How does the company approach that when it comes to sharing things externally? Like in terms of revenue, numbers, user numbers?
Becca Van Nederynen
Yeah, we share a lot of our information in our blog, Nick writes pretty transparently about where we're at as a company, we don't get into a lot of the specific numbers externally, like obviously, the amount of money we raised. But it's all through a lens of what we're doing to support our customers, it's customer driven. Our biggest thing is about having options as a company and seeing where our customers need us to go. Nick has written very publicly about how he never wanted to take on funding, and then we did end up taking on funding. So we've evolved, and that's largely been dictated by how our product needs to evolve to serve the needs of our customers. So when we did the initial raise, we put a lot of thought behind it in terms of, are we doing this for the right reasons, what does this mean to take on this funding? What are we accountable to, all of these kinds of questions? And so we really focused on finding and values aligned partner to work with us Foundry Group out of Boulder, Colorado.
Maren Kate
Yeah, they're great. They are excellent.
Becca Van Nederynen
They're so wonderful. So we don't get into the specifics externally other than how it relates to the customer.
Maren Kate
I think that's great. And it's awesome. As someone who's also blogged since my early 20s, and probably said a lot of stupid stuff back then. It's really cool to look at it from a lens of, instead of kind of that egocentric thing of I'm never taking capital, or I'm definitely taking capital or whatever, just say, Hey, we're approaching it from what serves our customers best. And if that changes, then we're open to it, versus being kind of stuck in one one way of thinking.
Becca Van Nederynen
Yeah, absolutely. And that's actually one of the things that's really inspiring about my experiences, and why I really love partnering with him because he will allow our customers and our employees to really drive decisions that we make as a company. And while we have a culture of accountability, we're not a democracy and not everybody gets a vote. We have different experts in areas where they are accountable for those things, but taking input all the while and really being driven by those needs. And yeah, I love how he will change his mind and talk about how and why he changed his mind. I think it's really important to see from a leader.
Maren Kate
Yeah, absolutely. I think the idea of the why behind everything can't be understated. You're a fully remote team, is that correct? Or are there maybe satellite offices or anything?
Becca Van Nederynen
We are a fully remote first team. We do have two small hubs. Sometimes we call them offices. Sometimes we call them hubs, but they're mostly co-working spaces and spaces we use for new employee onboarding. So there's one in Boulder and one in Boston.
Maren Kate
Interesting. So when you do onboarding, no matter where the person is in the world, do you always fly them to that onboarding location?
Becca Van Nederynen
Yeah, well almost all the time, we try to fly everybody to Boston, that's our biggest space that we have. And we also have a collection of about 10 people in the Boston area. So we can encourage people to come to the office. It's always nice as a new person to meet some friendly new coworkers. So we usually gather as many folks as we can during those onboarding weeks. Other times, we'll use the Boulder office, depending on people's schedules, or who's in town and who's around in Boulder, there's around four people in that area who can go into that hub. And then very occasionally, again, due to schedules or time constraints, or people's different personal circumstances, we will actually fly somebody to a new employee’s hometown and find some co-working space there and do some in person onboarding locally with them.
Maren Kate
How did you figure out this method? Because that’s interesting. I know another company that's fully remote. And they do something similar every quarter, they set up time for onboarding in New York, or I think it's Portland. And they run a group, and I only now has it kind of clicked. I mean, it makes a lot of sense. But I'm curious how you figured out that this was important.
Becca Van Nederynen
We kind of went back and forth at the beginning, around should we bring people in during the hiring process, we do also want to make sure we're being financially responsible and bringing people in during the hiring process was a lot more of a time investment, a lot more coordination. And ultimately, we discovered a process or evolved a process for our hiring, on the hiring side of things that made sense to us. And that worked, in one that didn't involve meeting people in person. So the next phase of the employee lifecycle orientation onboarding is so critical for setting folks up for success. Like already, you're joining a remote company where you've never met anybody in person, just having that in person face to face time, felt so important, in terms of getting them started off on the right foot, meeting people that they'd work with, meeting different leaders in the company, with onboarding presentations, and just having lunch and going out to dinner with people, just that social aspect that is really key in getting folks started off in a new company felt like a piece that I didn't want to lose, and colocated companies that happens because you go into an office. So it just felt we have so many programs in place for a remote first team to keep everybody connected. But really getting folks started and comfortable, meeting people in person felt important. And since then we gather feedback, and we keep doing it because people tell us how impactful it is for them.
Maren Kate
Do you do it in cohorts? Like once a quarter once a month? I mean, it's over 100 people, I'm assuming you're bringing on a decent amount of people every year.
Becca Van Nederynen
Yeah, it started off not in cohorts, just because really we weren't hiring a ton of people at a time. But recently, we have tried to organize people into cohorts, probably over the last year. We're really mindful of trying to get people in together, if we can.
Maren Kate
So outside of onboarding, are there any other, I call them IRL, type of meetups that as a company you do?
Becca Van Nederynen
Absolutely. We get together as a full company twice a year, for some in person time in the form of a team retreat. And we're actually meeting up together next week.
Maren Kate
Very cool. And now is your team spread out all over the world? Are they mostly in North America? How does that work logistically?
Becca Van Nederynen
We are spread out all over the world. I believe we're in about 75 different cities right now. So we have a number of different factors in choosing the location of the retreat. And we bounce between North America and Europe, and maybe someday we'll be able to get closer to Australia for five people who are there. They always have to travel so far.
Maren Kate
Exactly. Okay, so, walk me through your hiring process. It's outlined on your careers page, we'll link to it in the show notes. I loved the fact that in a beautiful visual presentation, really quickly, you were like, this is how our application process works. This is our hiring process. One of the things at my firm Avra, we tell companies all the time, like listen, you need to, just like sales or like a project or product management, you need to outline those steps before you go into it. And I think a lot of companies don't, or even if they do, they don't share it so publicly. So just in a few minutes, if you could walk us through your your hiring process, I think the audience would love that.
Becca Van Nederynen
Yeah, absolutely. It's something that we have had many iterations on and have learned a lot over the years. And, yeah, let's jump into it. So we we start off our hiring process by advertising a new role. We advertise on remote friendly and career sites like We Work Remotely. But before we advertise, there's already bit of legwork that our recruiters have done to start building up a pipeline of candidates, these are folks who have applied to our future openings role. There are folks that we've built relationships with over the years, if they've previously applied or reached out to connect, we start with those folks. And also reaching out to different affinity groups like Power To Fly, Women in Tech, People of Color in Tech, those kinds of places to really make sure that we're reaching everybody we can and build a diverse pipeline of folks. So we usually have a great pipeline. And then we advertise the role on our site. And We Work Remotely and a few other places. And the first step is, we usually try to get people to meet with the hiring manager right away for a first call. And that's usually 30 to 45 minutes. And we're looking in that phase for values alignment. And any remote work experience is not required to work at HelpScout. But we do want to get a sense of where you're at in that remote work journey. So values, alignment, career goals, things like that. If everything's looking good from there, then the next stage is a technical screen with someone else who's on the team that this candidate would be working on, if they are hired. And that's really another 30 to 45 minutes getting into the nitty gritty of different technical skills, depending.
Maren Kate
So like aspects of digital marketing, if you're hiring a marketer, understanding what their sell through has been if you're hiring a salesperson, things like that?
Becca Van Nederynen
Yes, absolutely. And on the engineering side, too, there's a ton.
Maren Kate
Yeah, a lot of tests. Jumping back to the very beginning, really quickly, you said the first screen is with the hiring manager, how are you vetting? Because as you and I both work at fully remote companies, you get a lot of applicants? How are you making the decision on who goes to the hiring manager and who doesn't?
Becca Van Nederynen
That is a great question. We have a set of application questions that we include in the process that we really look at. One of them is a Why do you want to work at HelpScout question that really helps us see what values alignment is. And a lot of times what people will do instead of answering that question, they'll answer why I want to work remotely.
Maren Kate
That’s not the same thing.
Becca Van Nederynen
Yeah, that's not the same thing. I'm assuming that you want to work at HelpScout already, because you want to work remotely. So I'm really interested in what about our values or product that you're curious about? So we pay really close attention to that question. And then on what the role is, there is some kind of technical aspect, like if you're applying for a customer support role, there's usually a question of like, how would you reply to a customer and we can already tell with people's writing style, how they would approach things, whether we're on the right track with that candidate or not.
Maren Kate
Got it. So after after the technical screen, then what's next?
Becca Van Nederynen
So just quickly before the next phase, we ask every everyone at that point to meet with somebody on our people ops team to get a sense of where they're at in terms of what kind of salary expectations they have and where they are in their process of looking for a new role. Just to get a sense of where the candidate is and what their time constraints are and if we are aligned in terms of timing, when they are ready to start a new role and also alignment, at least in general with with salary ranges. And we do that check in there. One because there might be a couple of follow up questions that someone needs to ask based on the first two interviews. And also the next phase of the process is to actually do a little bit of work with us, do a project with us. And so before people invest that amount of time, we want to make sure there's no deal breakers at that point. So the project phase is really another great data point for us to evaluate whether a candidate would be a good fit. And the project varies depending on what the role is. But it's usually no more than eight hours time investment, we also try to pay people for that time too, because we recognize it's an investment on top of their regular day to day, their job, their family, all that kind of thing. And that's the next phase. And then there's the project evaluation phase, where the hiring team is looking at what the candidate has worked on, sometimes it involves a presentation. And there is sometimes a little bit of back and forth too so we can ask follow up questions, because that mimics what would happen in real life anyway. And in our role, like you deliver something, you get feedback, you iterate kind of thing. So from there, it's really down to once we have that cohort of folks evaluated at the project stage, we usually have it narrowed down to about two, maybe three candidates. And we have a final interview at that point. And we ask folks for references too so we can ask a few questions about what it was like to work with that person. And then the most successful candidate gets an offer.
Maren Kate
That's amazing. I love how you've thought it through. Are there any roles that you find it hard to do a take home project?
Becca Van Nederynen
You know, there are roles that, at first I find hard, I'm like, Oh, we've never hired for this role. I don't know what kind of project to do, like for managers because managers are helping people grow. And sure we're aligned with our business needs. So there's not a project really involved there. But as you think through it, there's always something. We always manage to come up with something. For example, managers, instead of doing a full on project, in the past we've asked them to put together a readme or a what it's like to work with me document and actually meet with more members of the team. So instead of doing a project, they have a few more interviews just so we can get them in front of other folks who they would manage. But yeah for new roles that we haven't hired for I am sometimes like, Oh, what are we going to do, but something always comes together.
Maren Kate
Okay, what's been the biggest failure in building this? The hiring over the five years that you've been there? What was something you look back and you're like, we totally biffed it on that?
Becca Van Nederynen
Yeah, great question. This was definitely early on. When we look at our one year turnover rates there in the early years, 2015, where we just felt like we were making a ton of hiring mistakes. And one of the things that we realized we were doing is we were hiring folks who are a little bit too junior, for a remote team. And we weren't set up at that point. And I arguably, we're still not even at 105 people to be able to hire folks who are super junior, just remote requires so much autonomy, so it requires so much ownership and just experience working. And being able to own your own schedule and communicate really, really well. And so I think that has been one of our biggest learnings. And that happened definitely in 2015.
Maren Kate
Okay, that's great to know. I agree there's qualities, and then there there's personal qualities like over communication, extreme levels of autonomy, and then there's just experience, there's sometimes things that you really need to have done the work for a while or seen some ups and downs to get. So what are the hardest roles to hire throughout the history of the company? If you had to think of the ones that take the most time that give you the most pain as a remote company versus as a company in Houston or New York or San Francisco, what do you find?
Becca Van Nederynen
Hmm, this is a hard question to answer, because there are definitely roles that are hard to fill just because of supply and demand, just certain tech stacks that we don't have that many people who can do in the world, or who can handle in the world. But I think that's a problem everywhere. I would say that if I had to choose, marketing and sales have been kind of hard to hire for. And I'm not sure if that's because of a HelpScout thing. We've been trying to figure out what those roles are. For example, our engineering team is over half of our company. And we have several people doing a very similar role. So we know what we're looking for, we know who to hire. Whereas with the marketing, maybe less so sales, marketing, even people ops too these are always like new roles that we haven't hired for. So it's always something that we're learning new. So I guess scrap the sales part, I think it's really like marketing, where we're really hiring for the first time we're hiring this role. We don't have any historical like failures or successes to draw from.
Maren Kate
That makes sense. Firsts are always hard. Okay, so last question then I'm gonna run through the final three. How have you guys approached doing terminations in a remote environment? I always found that as a really tricky one.
Becca Van Nederynen
Yeah, that is really tricky. Well, first and foremost, we try to be as kind as possible, because it's an important transition. And it's hard for everybody involved, we make sure that managers have a ton of support, because it's really hard for them to go through that. We make sure that the person being terminated also, has a very clear idea of what's going to happen as well because that's the critical piece of a transition, like we we can make this hard thing that we have to do as easy as possible. So usually, we have a performance evaluation plan in place that's transparent to the whole company. And we have conversations, difficult conversations with folks along the way. And so when it comes down to actually parting ways with someone, it's always a conversation between their manager and with somebody on the people ops team, it's always a video call. It's always followed up with something in writing, because it's fine to get on a video call, but somebody might be in shock. They might not remember what was said. Video call following up with any important information in writing, and helping that person through the transition, wherever it may be, like offering generous severance, as generous as you can make it and making sure that that person knows who they can reach out to at the company for questions afterwards.
Maren Kate
I like that and it just can't be stated enough what you said the word kind, treating people like human beings and being more generous than necessary if you have the option to do that. If you have the resources available. You'll never regret that.
Becca Van Nederynen
Yes.
Maren Kate
So final three questions. What is your favorite book or podcast from the last year?
Becca Van Nederynen
Oh, my favorite book. Oh, ah. Right now I'm reading Jerry Colonna’s new book and I really liked that he's one of the Reboot Founders and a coach and that's been the title escaping me right now.
Maren Kate
I think it's Trillion Dollar Coach.
Becca Van Nederynen
Oh, is it?
Maren Kate
Nope, it's Reboot: Leadership and the Art of Growing Up nevermind either one.
Becca Van Nederynen
So I really love the Reboot Podcast as well. But another book in the past year I'm sorry I’m cheating and giving two, Powerful by Patti McCord has also been really impactful in terms of building a culture of transparency and honesty.
Maren Kate
I remember listening to a podcast with her. She's excellent.
Becca Van Nederynen
She's got a lot of really great stuff. I highly recommend it. You have to keep in mind that it's Netflix, and they've gone through major major transitions. And they're huge. But there are definitely some great nuggets to take out of that book and apply to your own culture.
Maren Kate
Okay, awesome. What business tool could you all not live without? Slack doesn't get to be included anymore because literally every person likes Slack, and not the Google stack. What else?
Becca Van Nederynen
Well, one that we've used from the beginning, that's really hard to give up is Trello. Even as we have moved to JIRA, on the engineering side, and Asana project management tool on the marketing and sales and support side, we still use Trello. It's so entangled and ingrained in everything from our employee onboarding Trello boards, our support training Trello boards, different projects that other teams are managing. So Trello, it's been with us and served us very well.
Maren Kate
I'm similar with that, I love Trello. Other people move past it, but it's so easy. Okay, so last question is for the founders in the early stage team listening who are somewhere between the five person and 50 person stage, what is the best piece of advice you either received as you were growing the people team, or that you can give from your experience with HelpScout, as they're thinking of specifically growing their people.
Becca Van Nederynen
One thing that I tell CEOs and founders that I talk to all the time is to actually hire a people team, hire a people ops team to own shaping your culture and to own some of these processes early on. There's so many times where I get questions from co-founders who have about 50 people already on their team. And they're like, I think that we need to hire people ops person now. And I’m like yeah definitely. Your culture is going to shape and evolve and form no matter what you do. And if you have someone paying attention to it, you can get ahead of some of the challenges that might come along. If you don't, for example, you know, defining what your team values are, from your team values. We did this very early on when we were only about 20 people. And from there, you can really define all of your processes based in values that you all care about. Having someone who's in charge of that and who really has their ear to the ground and is talking with your employees all the time. And it's just so so helpful. And I think so preventative in a lot of challenges that can arise on the people side, just in terms of employee turnover or retention rates. Things like that.
Maren Kate
Really good advice. So get someone in people ops before you think you need it.
Becca Van Nederynen
Yeah. It's a little self serving because I'm in People Ops. I don't have a background in people ops and and now that I've been through it and employee engagement score is always above 80 our employee NPS score and it's largely due to the fact that we have people paying attention.
Maren Kate
I love that you track your employee and NPS that's amazing, versus just the customer. Okay, so how can people find out more about you and find HelpScout online?
Becca Van Nederynen
Well, we have our website helpscout.com. And on that I would recommend our blog, we have a lot of great articles written by Nick Francis our CEO, and a lot of other leaders on our team. There's a great article about the art of negotiation from our Chief Financial Officer Shawna Fisher. And just a lot of information about how we've grown our culture and grown our team just in terms of what we do as a remote company a lot of our lot of our secrets we just share with everyone and same with our products and in how we help support support people, basically. We've got a another resource, in addition to our blog, called Help You and it's a lot of really great training resources for folks who are looking to develop a really awesome well supported support team, which is so key for folks having a good experience with your products. So definitely check out help you and our blog at helpscout.com And, and I'm on Twitter. I don't post very often, but usually it's stuff related to what we're doing at HelpScout.
Maren Kate
Well, Becca was so great having you on the show. Thanks a lot.
Becca Van Nederynen
Yeah, thanks so much for having me, Maren. It's been really fun.