Remote Work Interviews

Owl Labs (OL): You started at Help Scout a few years ago in UX research and marketing. How has your career at Help Scout evolved, what made you jump into People Ops?

Becca Van Nederynen (BVN): When our CEO, Nick Francis, asked if I wanted to shift into a people role, I was hesitant. In fact, I believe I said: "No, I don't want to be the HR Lady." I was happy doing marketing and UX work, and HR seemed outside of what I'd been doing throughout my career. Nick asked me to think about it so I took some time and did a ton of reading and found that there were actually lots of parallels between marketing and people ops.

Then, the deciding factor was really the opportunity to build a remote team culture. I noticed a few things that we were missing the mark on in terms of hiring, employee onboarding, and remote team connectedness and thought I could really make an impact there. Nick also promised to be my partner in building a culture we'd be proud of and nearly six years later, having grown the team from 10 people to 100, it's still true. We're still learning a lot, and I'm so glad I made the shift.

OL: Has Help Scout always been a remote-first company?

BVN: Remote culture has been in our bones from the beginning because Nick, Denny, and Jared, our three co-founders, often worked remotely. They had a small office space but they weren't always together. This made it easy for them to be open to remote work from the beginning, especially when they moved to Boston and found it hard to find talent in a competitive Boston market where no one had heard of Help Scout.

When I joined in 2014, there were 10 people on the team. Half of them were in the Boston office and half of them were remote. As we added more people to the team, it was important for us not to develop a "double" culture so we made a commitment to ensure only 25% of our team is in Boston, and 75% was remote, and to make sure all of our policies, procedures, systems, and guidelines are looked at through a remote lens. By 2017, less than 25% of the team was in Boston and then our co-founders also dispersed to Nashville and Boulder. Currently, we have employees in 75 cities around the world.

OL: So, you have the Boston office — do you have any other offices? 

BVN: We have two Help Scout "offices" that are used mainly for new employee orientations, team meetups, and board meetings. They act a bit like coworking spaces as well. I'm in the Boston area and I go into the office about one or two times a week. We look at everybody as a remote-first employee and don't have any groups regularly coming to an on-site location.

OL: What are some of the challenges remote workers face?

BVN: Two things are top of mind for me right now. One is imposter syndrome — it's something that comes up in our employee onboarding feedback. The normal thoughts of, 'Do I belong here?' and 'Am I doing a good job?', are heightened with remote work.

With co-located companies, you come into the office and someone smiles at you, or you have some watercooler talk with somebody. You have these organic moments that help you feel like you belong but with remote work, after the new employee orientation, you go home by yourself and nobody is smiling at you when you walk into your office in the morning. Those social interactions are missing. People Ops teams and managers need to work harder to make people feel a sense of belonging, give them feedback, and create opportunities for folks to make connections. That's not a Help Scout thing — it's a universal challenge with remote work.

The other challenge is managing remote teams. Managers can come in with a lot of experience and training which is really helpful and most of it translates well but remote managers do need to adjust their style quite a bit.

Remote managers need to consider things like imposter syndrome, communicating intentionally with their remote teams, finding ways to talk about productivity, and communicating in writing rather than face-to-face chats. All of those things turn the employee/manager relationship on its head a little with remote work. You have to be thoughtful about how you're managing your remote teams.

OL: How do you think differently about your perks and your benefits for your remote employees?

BVN: A lot of our perks end up being a lot more flexible than something you see for co-located companies. In-office lunches or meditation rooms or commuter passes don't work for remote teams. We have a remote office stipend and give everyone $1,000 to make their home office comfortable and a great place to work.

Another perk is our coworking space stipend. If you're more productive outside of your own home, we'll cover up to $350 per month for that. We also have a "learn something" stipend which is a set amount of $1,800 a year to spend on something to improve your craft and we're flexible with that. It can even be a language class or something that's not directly related to what you're doing. The other thing to keep in mind is if you have international folks and you're offering a U.S.-focused benefit, you have to make sure there's some kind of international equivalent.

One perk we introduced this year, which I, fortunately, took advantage of last month, is a sabbatical. Once you've been with the company for four years, no matter where you are in the world, you can take a one-month sabbatical. We even offer everyone a stipend to use towards that. I did a bunch of traveling in the national parks out west and had a chance to be in nature for a month. Another person is on sabbatical now at a cabin by the shore with their family and they're taking floral design classes. I'm fresh off and I feel so re-energized — it's a perfect benefit.

OL: I'm glad you had a good time and feel refreshed! How would you describe the ideal remote team member when you're hiring?

BVN: One of the big challenges of remote work is not being able to hire more junior-level folks. We need to hire people who are self-starters, super organized, and communicate well. Many of those things come with experience in the workforce. We tend to hire more senior-level folks to join the team.

OL: What are the biggest challenges managers face when they're managing people remotely, and how can they overcome those?

BVN: One thing that's somewhat counterintuitive with remote work is that remote work seems super flexible and that means your systems and processes should be too. When you're setting up systems and processes for your team, you think, "Oh, we don't need that because we're all senior enough here and everyone kind of gets it." But as your team scales, as you're growing, and as you're hiring managers who haven't grown up in the culture, you need more systems and processes for remote teams than you do for co-located teams. This ensures everyone is on the same page.

Going back to the impostor syndrome, our managers at Help Scout need to spend intentional time with their team members when they're coming up to speed. Not only to be their advocate but also to introduce them to other people they need to connect with. Our People Ops team and managers have an in-depth employee onboarding orientation process and managers in that process need to be open to a more rigorous structure than in a co-located space. It'd be easy to grab someone for a beer or have lunch with them. Some managers will even set reminders to ask someone how their weekend was. Those little things are important.

Another thing — and this is true for co-located companies too — with remote teams is you're forced to be transparent about what your performance processes are and how you evaluate performance. Celebrating wins is important too. It's easy in an office to get people together to celebrate a win, but you have to be more creative as a manager at Help Scout. We have something called Spot Bonuses where we can help celebrate those wins and we have a channel on Slack called 'Warm Fuzzy' where you can talk about how wonderful people are.

OL: Are there any tools, strategies, or events Help Scout uses to keep people connected?

BVN: We have a few things that help us foster connection at Help Scout: online, virtual things, and in-person. For our new employee orientation, we have people come to either Boston or Boulder. Sometimes we do remote onboarding because we're an employee-first organization. For example, one of our support managers flew to London because three of her people were within a short distance from London. Plus, it made more sense to send one person there than have three people here. We also have someone else on the support team who's in Florida right now, onboarding a new employee. Most of the time, however, we create space in our Boston or Boulder office to welcome people. There's lots of team building, dinners, lunches, meet-and-greets, one-on-ones, etc.

Then, twice a year we get together for whole-company retreats. They're one week, Monday-Friday, and they help us to create momentum and keep people together because nothing replaces face-to-face time. The retreats are opportunities for us to talk about our big-picture vision and then our individual teams have time to get together and have team bonding. We all have meals together too. It's a nice balance of social and business time, with a bit of downtime to make sure we don't overwhelm people too much.

We also have other programs and we use a tool called Know Your Team which provides an icebreaker and a weekly social question visible to the whole team. When new folks start, we ask everyone to answer five questions so we can take a look. Where did they go to college? What's a book they read? A lot of times people find things in common and they'll chat together in Slack.

We do a monthly troop talk — a facilitated conversation on a certain topic — it's totally optional and you can share something about yourself. Then we have something called FIKA. It's based on the Swedish concept of FIKA where you take a little time out of your day to have a conversation with friends or co-workers. Plus, we have a map that shows where everybody in the world lives and I really encourage IRL FIKA's. Folks can take their company card and buy coffee on Help Scout if they want to meet up with another employee visiting a different city. I always try to do that. It's always fun for someone to bring me to their favorite coffee shop!

OL: What are some of the tools your team uses for communication, collaboration, and working asynchronously? 

BVN: There's been a bit of a curve in terms of asynchronous and synchronous communication. When our team was small, we had a lot of synchronous communication. We moved to the other end of the spectrum to all asynchronous when we got a bit bigger and more spread out. Then, when we hit around 80 people, we needed some more synchronous communication because there were more dependencies and stakeholders. We're learning what the right balance is. It's still mostly asynchronous but we've seen the value of meeting with people in the same virtual room at the same time.

In terms of tools, Trello has been with us from the start and we continue to use it for all our teams. We use it for our onboarding schedules, project management, etc. Slack is used for most of our day-to-day communication. We also have an internal Wiki to make sure everyone has access to all of the same information. We were using Confluence but we recently switched to a product called Slab.

We also use Asana for project management. A big favorite of ours for collaboration is Dropbox Paper — it's beautifully designed and easy to leave comments and start discussions with folks in a document.

OL: How important is transparency and trust for building a remote-first company culture?

BVN: I love this question because it's important for all teams, but remote teams have a certain advantage here with transparency. For your remote team to operate, you have to write things down and document what decisions you've come to or what team guideline changes have been made, otherwise, people won't know how to get work done. If you're not transparent, then you're not going to have a successful remote company because people won't have the information they need to work independently or have the context they need to feel engaged.

Trust is important too. It's built on social interactions with each other, even social things, like knowing if someone's dog was sick last week. If you get to know people, and you know what's going on in their lives, then you have more empathy. With remote companies, it takes longer to build that trust with people so you have to be intentional about building relationships. If you don't trust your coworkers, you won't be able to work through problems effectively.

OL: How do you think remote work has contributed positively to your company's culture?

BVN: Remote work helps us stay true to our values. We have values of ownership, helpfulness, and excellence. To have any of those, you need to trust your coworkers and the intentionality behind relationship building at Help Scout has helped us build close connections with each other. I've heard feedback from people who say they have closer relationships with people at Help Scout than they had in co-located companies because of the intentionality behind communication. All of this benefits our company because we have people who work productively and efficiently with each other.

Hiring from around the world is another major benefit, not only for employee acquisition but also for retention. If someone's partner has to move somewhere, they don't have to quit at Help Scout; if they have to take care of a sick relative, they don't have to leave their job. The retention has been amazing and helps us to have longer, more in-depth relationships with each other. Plus, being able to hire from around the world means we've been able to hire super talented people that are values-aligned and not settle for talent that is close enough because we have a geographical limit.

OL: What's a myth about remote work or remote workers you'd like to dispel?

BVN: Every time I meet with a CEO and they're looking for people ops advice in building a remote team, their number one question is, "How do you know people are working?" and I reply, "How do you know the people in your office are working?"

It's so funny to me. People think if you have a remote team, no one is going to be doing work. From my experience, people who are working remotely are keen to prove that they are doing work and so they're often working more than the people in an office! You have to remind people that it's okay to take half an hour to have a FIKA with somebody on your team. No matter whether you're in-office or on a remote team, we all have systems and structures in place to evaluate productivity. Just because people are at home, it's not a free-for-all with everyone watching Netflix all day!

OL: When you talk to people about that particular challenge, how do you counter those myths with people?

BVN: I tell people they need a system, just as you would for a colocated team, and that depends on what your company culture is. At Help Scout, we have a couple of things. We have 'player roadmaps' where every six months you get together with your manager and you talk specifically about reflections over the last six months. What will you work on the next six months? How is that related to your career goals? Then, you have a document to check back in on the goals and say, "Hey, I said I was going to work on these things and I'm working on them." Or, "I said I was going to work on these things but I'm not, so how can we course correct?"

Our player roadmaps help with those measures and milestones as well as career goals. Then, in terms of communication guidelines, you need to show your work to other people so they can contribute their piece of the puzzle. Being clear on what the guidelines are for communication in terms of where things are documented is key. If you're handing off some designs to the engineering team, what format does it need to be in? What notes are important? We require our managers to have regular one-on-ones with their players as well. It's usually once a week or every two weeks, so you can check back in on all of those things. You need a system and success measures just as you do in a co-located company.

OL: What do you love most about working remotely?

BVN: Personally, early on it was the work-life flexibility. I have a six-year-old kiddo and it was nice to be able to transition into a style of work where I could move more fluidly between work and home life. I love that flexibility and don't take it for granted, but over the years, my answer to this question has changed. Now it's really about the deep connections I've been able to make with people that I would be less likely to meet in a co-located company. The intentional communication required of remote work helps make this possible.