A Look Into Help Scout’s Hiring Process: Megan Chinburg of Help Scout

What I believe is different at Help Scout and having a remote first company is that there’s a lot of energy that we put into being successful at doing asynchronous work. So there’s a lot of diligence around being clear and concise with your communication, loop closing and most importantly, trust.

Today on Outside The Valley we have Megan Chinburg, VP of Engineering at Help Scout!

We talked about Help Scout’s hiring and onboarding process from start to finish, with a discussion around the “value screening” stage, and how Help Scout makes sure to reduce biases in the interview process.

Megan also shared the one thing that Help Scout did in the early days that made them grow solidly, and her top two pieces of advice for engineering managers everywhere.

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Topics also covered on the podcast episode:

• 02:31 — How Megan started her engineering leadership career
• 08:40 — The differences between managing a remote vs co-located engineering team
• 18:06 — How Help Scout screens for value alignment and technical competence
• 35:38 — Help Scout’s onboarding process for new hire
• 40:10 — Why documentation is important when onboarding new engineer
• 41:00 — One of the best things Help Scout did early on to grow a solid remote team
• 43:35 — How Megan sees her responsibilities as a VP of Engineering
• 49:30 — Top two pieces of advice Megan would give to other engineering managers

Mentioned resources:

• Help Scout
• Nick Francis
• Denny Swindle
• Andreas Klinger: Normalizing Hiring Outside Silicon Valley
• AngelList
• Basecamp
• Help Scout’s 12 Step Remote Hiring Process
• Leah Knobler
• How to Knock Your Virtual Job Interview Out of the Park
• Help Scout “Fika”
• Mark Faggiano: Creating Remote Employee Culture
• Mark Faggiano
• I, Me, We, Us – Creating team ownership with better language
• Megan’s LinkedIn
• Help Scout Blog

Full transcript:

Jovian: Hello world, welcome to another episode of “Outside the Valley,” the podcast where we interview remote startup leaders, remote work advocates and CEOs of distributed teams who thrive outside of Silicon Valley. They share insight on what works and what doesn’t so you can learn to do it right. “Outside the Valley” is brought to you by Arc, the remote hiring platform that helps you to hire remote software engineers and teams easily. I’m your host Jovian Gautama.

Today on “Outside the Valley,” we have Megan Chinburg, the VP of engineering at Help Scout. We talked about Help Scout’s hiring and onboarding process from start to finish with a specific discussion around how Help Scout screens for value alignment and culture fit and also how Help Scout make sure to reduce biases in the interview process. Megan also shared the one thing that Help Scout did in the early days that made them grow solidly as a remote team and her top advice for engineering managers everywhere.

Now, we are 11 episodes strong and if you liked the show, we’d totally appreciate it if you can go to iTunes and leave us a review, hopefully, five-star. If you have any feedback about the content of the podcast or if you have any recommendation for guests, feel free to hit me up on email at jovian@arc.dev. It’s jovian@arc.dev. Without further ado, here’s Megan Chinburg of Help Scout. Here we go. Hello Megan, welcome to show.

Megan: Hi, Jovian, glad to be here.

Jovian: Awesome. So Megan, so let’s start off with yourself first and where are you based now and can you share a bit about your background and work experience?

Megan: Yeah, of course. Right now, I’m living in Turin, Italy. I am originally from Oregon. I was in Portland, Oregon for about 11 years. After getting the job with Help Scout, I decided to try international living. So I’m living here in Italy now and I love it. In terms of my background and work experience, I kind of got a late start in tech.

My first job in tech was as a junior in college, I worked for the tech support at my university. We supported students, staff, faculty with anything that they needed. I had recently switched my major from violin performance to randomly taking classes that sparked my interest. So I stumbled into a C++ class and instantly fell in love with programming. And from there I decided I needed to get a job in this realm, and so…

Jovian: What sparked like, I need to get a job, is what sparked in life.

Megan: Yeah, exactly. And so I tracked down the folks who ran the computing center and basically banged on their door in the dark basement and said like, “Hey, please give me a job.” They were like, “Who are you?” And I finally convinced them to give me an interview and it went terrible from the get-go. Like they were asking me questions I had no answers to and they asked me like, “Well, what Mac OS are you most familiar with?” And my answer was, “What does OS mean?”

But eventually, like I convinced them that I could learn anything and they gave me the job probably to get me to shut up and go away. And really like those, I do partially credit the folks who hired me there for a lot of the success in my career. I learned a ton about Linux and Unix system administration, networking. It kind of kickstarted everything.

And from there I got my degree in computer science. I moved on to a small startup and I was doing kind of like, you know, low level or I guess, you know, junior entry-level coding there. And after a couple of months, the CEO came and talked to me and was like, “Hey, I want you to start a new team here at the company. We need a white box QA team.” Like, okay.

At that point, like I just graduated college and my leadership background consisted of a three-month stint as a coach for a fifth-grade girl’s soccer team and I was currently the captain of the local rugby team, so it was definitely trial by fire. But I found that I really loved building teams and coaching and so this was a great start to my career in engineering leadership. I’ve realized that I have always enjoyed empowering a team of brilliant folks just to be the best that they can be. So it just sort of fits.

From there, I moved on to another startup this time in Portland, Oregon, a Jive software. I joined them when they were about 35 people and I moved from individual contributor pretty quickly to manager of the QA team and built out a pretty large organization there. After about four years, I moved on to another startup, even smaller. My previous boss had started a new company and he had tapped me to be the VP of engineering. It was a bit of a leap from QA manager to VPE. But the CEO believed in me and it’s kind of all I needed.

So there we grew the team from 6 to 17 engineers. I was there for about three years. That company eventually had a successful exit. And prior to that, I did leave after sort of I’d gotten them to a point where, you know, they could run on their own. I needed to take a break from tech and I decided to take a brief hiatus and pursue a career as a professional mountain biker.

Jovian: Oh wow.

Megan: So a slightly different twist, but I really enjoyed the break. And eventually, my desire to get back and work with engineers outweighed my desire to win bike races. And at that point, a long-term mentor of mine introduced me to Nick Francis and Denny Swindle, two of the cofounders at Help Scout. And it was seriously love at first video chat. I was enamored of the product and the company, the culture, it just really spoke directly to my heart. So I’ve now been at Help Scout for three and a half years and just recently in April stepped into the VPE role and I’ve really enjoyed the honor of working in this capacity with this great team.

Jovian: So Help Scout is your first remote role.

Megan: First remote-first role. In every company I’ve been at, there’s been some aspect of remoteness, you know, working with teams overseas, working with individual contributors in different countries. But this is the first remote-first company. Yes.

Jovian: Yeah. I just wanna say just before I forget. You mentioned that you’re super grateful to those first companies that give you the break because they’re crossing you. And I’ve found there’s some parallel in Help Scout when it comes to hiring remote workers. So from as far as I know, right, even though Help Scout prefer to hire someone that has remote experience, but it’s not really a deal-breaker because a lot of companies, a lot of remote companies, they actually put like heavy emphasis on you have to have an extensive experience in working remotely before, almost a deal-breaker for them if you don’t have that. So I just found that like, probably interesting.

You know, so Help Scout basically, yeah, if you don’t have a lot of remote experience is kind of fine, then we will help you do that. So yeah, I just want to say this out loud before I forgot. So in your previous companies, you already work with remote engineering teams, am I correct?

Megan: Yes.

Jovian: So at that time, was there any…did you encounter anything new in terms of, you know, managing engineer’s status on the same…not on the same location, or I’m not sure if there’s on the same time zone or not. Is there anything unique that, oh, it’s like this and then I need to learn something new?

Megan: Sure. I mean, working with remote teams, there’s always similarities and parallels. The biggest one being, there’s always a communication time lag, you know, between different time zones.

What I believe is different at Help Scout and having a remote first company is that there’s a lot of energy that we put into being successful at doing asynchronous work. So there’s a lot of diligence around being clear and concise with your communication, loop closing and most importantly, trust.

So this challenge of communication, time lag and asynchronicity definitely makes us all better communicators, but it also means that it takes longer to get things done or make large decisions. And I think that, you know, this isn’t a challenge that any remote company or any people with remote teams needs to overcome, but the fact that Help Scout was remote-first from the beginning, it’s just part of our DNA and it’s just infused in everything that we do. And I think that that is something that it gives us a unique leg up in surmounting this challenge.

Jovian: Yeah. Awesome. I’d love to get back to asynchronous communication topic a bit. So about yourself, so Help Scout is your remote first remote role. So personally, what positive impacts has working remotely brings to you?

Megan: Sure. I mean there’s the obvious positive benefits of having a lot of work-life flexibility, control over how I spend my hours significantly, reduce commute times. I have a five-minute walk to my co-working space. And you know, provided I can be online when my team needs me, I can really work from anywhere in the world. So it opens up a lot of travel that I wouldn’t necessarily have access to if I had to work in an office. There’s also like those are the obvious benefits that I think anyone would have. Like if you got to work from home.

But one thing that I find most delightful is that working remotely, like we work remotely but we still work with people. And it takes significantly more energy to cultivate and maintain positive, trusting, successful relationships, especially when we interact over Slack the majority of the time. So remote work has made me, and I think a lot of people that at Help Scout a better communicator and a better listener and definitely more thoughtful and empathetic. And so, I mean, how often do we get to say that, that like, my job makes me a better human?

Jovian: Not often. Yeah.

Megan: That seems pretty special.

Jovian: Yeah. That’s interesting. Because this is the first time I heard about this, like the fact that you have to be better communicator or a more empathetic person in your remote job actually makes you a better empathetic person as a whole. And okay, let’s get to the negative side of this. Like, I mean, remote work is not always, you know, butterflies and rainbows, right? Any challenges that you’ve found either when you first started and then you overcame it or even right now that you are still struggling with?

Megan: Beyond the communication challenge…and I mean, there’s like, just simple communication challenge of asynchronicity, but also like, as we’ve grown, you know, the number, the points of communication increase so, right.

So that means that it really requires a lot of intention around aligning people with goals, giving them the right information to make good decisions, and also just leaning so hard into transparency and trust.

I would say really communication ends up being the biggest challenge. And I could imagine that people who are not used to that sort of transparency and trust because you don’t need it as much in a co-located office. It could be a challenge to build those sort of relationships when a new person joins, but we do tend to hire for people who have high degree of empathy and humility. So generally, that doesn’t end up being a problem.

Jovian: Yeah. It’s funny that you mentioned about intention and being deliberate about stuff. So I had this chat with Andreas Klinger, the head of remote of AngelList, and he was also mentioning the same thing. It’s when it comes to engineering management in remote team, you have to very intentional when it comes to communication and you have to maximize or supporting every team members to be able to do great things by themselves, you know, like, but not isolate them, but it’s more like, like you mentioned, as the way the team grows, there’s a lot of different points of communication. And how to decrease dependencies, you know, so they can move forward.

So yeah, this is something that comes up a lot in this podcast, like being deliberate and in a way, you kind of see your company as a product, you know, and what is wrong and how I can improve and iterate or what can we test on this? I wanna move on about Help Scout as a company. You already touched this a little bit. How would you describe Help Scout culture?

Megan: Sure. Our culture from the beginning has been built on three values: helpfulness, ownership and excellence. And this hasn’t changed since the beginning of the company. These principles are woven to the fabric of every practice at Help Scout.

We hire people specifically for whom these values resonate and we hold each other accountable to practicing them in our day-to-day work.

I would say like beyond everything, this is what enables us to trust each other and have the transparency and vulnerability that is required in order to make remote work work.

Jovian: Exactly. And how many people is in Help Scout now?

Megan: Right now, and I’m sure as soon as I say this it’s gonna change, but last week we crossed over the 100-person threshold. We are now at 101. Yeah. Actually, didn’t know that until I looked this morning. I thought we were still under 100. And of that 101, roughly 65 are responsible for designing and building the products.

Jovian: So there might be a bit of overlap with my previous question about Help Scout’s culture, but I want to ask you about the culture within the engineering and product team itself. Maybe something that is pretty different from your previous jobs or what you see from other companies. But really specifically proc and that’s something that you can say, oh, only Help Scout engineering teams has this.

Megan: Sure. I mean I don’t wanna be pretentious and say that like we only do this because I’m sure lots of other companies are focused on these things as well. But I will say that one thing that I’ve noticed unique about Help Scout compared to other companies I’ve worked at is our team, what we do, everything is built on a culture of quality.

There’s a quote from Nick that I like to share with all of our new hires. I give a little presentation about the engineering and product team and it goes basically, “When prioritizing for quality, cost and speed, I want to put quality first, quality second and cost third.” So it’s a little bit tongue-in-cheek because obviously we do care about timely product releases for our customers, but speed is never the star of any conversation.

So quality comes first before everything. We simply just wanna build products that customers love, that delight them, and we have a very healthy test NPR culture across the engineering team in order to support this value.

Jovian: Right. Yeah, it’s interesting because this is just my hypothesis because I feel like remote companies has, I mean most remote companies, they actually optimize for the health of the team members, the health and or balance of the team member. It’s not about growing exponentially bigger. Like most of remote companies. I mean this might change a bit in the near future. But if you’re familiar with company like Basecamp, right, it’s about just building the best thing for the customers and not about growing 10X from year over year. So I personally think this is an approach that every company should have, not only remote companies.

Megan: Absolutely.

Jovian: So I wanted to hone in a bit on Help Scout’s hiring process and onboarding process for new hires. Can you share a bit about Help Scout’s hiring process?

Megan: Yeah, absolutely. As with everything that we do at Help Scout, we’re never satisfied with a current process. And so even though I think that our hiring process is probably the best I’ve ever seen, we’re always trying to make it better and higher so that we can make the process as good as possible for the people doing the hiring, but also for the candidates.

We tend to hire people with very high integrity. And so, we want them to come away from the process feeling like this met their expectations.

I would say that one place that listeners could go to, you read about our process is this wonderful blog post written by Leah Knobler. She is on our people ops team and is very involved with the engineering hiring process. So I recommend reading that to anyone who wants to better understand our process. And while you’re there, there’s another blog post written by a former team member about how to nail your first remote job interview. She leaves a lot of tips and tricks in there that would probably impress us if you practice them.

But generally, I do think our process is unique. I have the honor of doing the last interview for all of our engineers in the entire process. And so I always ask them, “What did you think about our hiring team and the interview process?” And without fail, every time people say something along the lines of, this is the best interview experience I’ve ever had. I recently had a candidate who’s now a Help Scout employee tell me, “This is the interview process against which all future interview processes will be judged.” I felt like that was a win.

But in summary, we spend a lot of energy sourcing.

So we care a lot about diversity and inclusion on the engineering team, but also across our organization. And so we put a lot of better energy into direct outreach for underrepresented folks in tech.

And then once we’ve done all of the sourcing that we feel good about, we post the job and we start letting the resumes come in. As you can imagine, Help Scout is a very popular place to wanna work. And so we tend to get hundreds of resumes for any application. I believe our customer support team, whenever we open a position there, we actually get on the multiple thousands of resumes for every position.

So it is hard to do the resume review and it is very competitive. But once we go through the resume review, you know, we pick the people that we wanna talk to. We move them through a multistep interview process.

First, we have a value-add screen where we’re really looking for the qualities I talked about before, helpfulness, ownership, empathy, humility, those sort of values.

Jovian: Yeah. How do you screen for that? Sorry.

Megan: It’s a good question. I’m always changing, you know, trying to make these questions better, but I’m looking for self-reflective folks, so I’ll ask questions that might seem very unrelated to a job. But what I’m trying to get at is how do you think, how do you see yourself in the world? How do you relate to other people? I want to hire people who think outside themselves and think about other people first who default to helpfulness. So most of the questions are focused on that.

Jovian: Okay. That is super interesting. Any particular answer that astonish you in a positive way? Of course, that, yeah, this was pretty good or something that just very memorable on that?

Megan: Oh, that’s a good question. I would say there are a lot.

One of my favorite things to answer or to ask is: when was the last time you had a positive effect on someone?

So if someone doesn’t have a good answer or if someone’s like, “Oh, I don’t know,” then I’m definitely raising eyebrows. But most people have a really good answer and it’s usually something along the lines of mentoring a teammate or, you know, some conversation that they had with a more junior person, ended up changing that person’s career and life path and they didn’t realize it.

So it’s that combination answer of like humility plus helpfulness, but also having a large impact. Those are the key qualities that I think are gonna make someone successful at Help Scout.

Jovian: All right. So that’s like this first screening process on the value screening. Sorry, any other questions that you previously asked that you think is pretty quirky in a way or pretty special?

Megan: I mean, I don’t wanna give away all the secrets to nailing an interview, but let’s see.

Jovian: I see, I can imagine like a lot of listeners that is like Help Scout career page in front of them and then just scribble down.

Megan: Yeah, exactly. I mean I’m trying to think of one that would’ve had like a really unique answer off the top of my head. But nothing’s really coming to me.

Jovian: That is not a problem. I really like the question about when was the last time you being helpful to someone. I think the best is, you’re not like, it’s not that we have low self-esteem, like, “Oh, I don’t know. I don’t think what I did was really helpful.” But you also don’t want people who, “Yeah, I did this and I do that,” like in a really arrogant manner, kind of one, the people that, “Yes, I did this and I am aware that it’s helpful,” but not really over the top about that.

So it’s kind of like you mentioned this, self-reflective, right? And I’m very aware of this and I don’t really think it’s a big deal for me, like genuine thing is not a deal. I just find it interesting because everyone is talking about hiring for culture fit, right? Whatever that means. I just founded that this value screening is basically just not a step forward when it comes to specific word is culture fit. And I think this question really embodies it. Okay. So yeah, we got value screening and then what’s next?

Megan: Right. So the next step is a tech screen. And this is an interview, like whether if it’s on the engineering team, then the interview is with an engineer. It is definitely technical. We’re asking questions like about their actual knowledge and decisions that they’ve made and real things that they’ve done and accomplished in their career. And trying to get at answering the question, could they do the job?

One piece of it, one thing that we’ve added to the interview process recently that I like is prior to this tech screen, we send out a piece of code. It’s not very long, it’s just a little snippet of code and we ask them to be prepared to do a live code review during the interview.

So one, we get to see like how well do they, you know, kind of pick apart a piece of code, which hats off to the people who created the snippet of code. It’s got a lot of things wrong with it. But we’re also looking to see like how thoughtful are they, how do they deliver feedback because I think being able to deliver a good feedback in a code review that is helpful, critical, but also not rude is definitely a skill. And then following that, then they just go through the regular technical screen with that engineer.

Jovian: Okay. Live code review, super interesting because I can definitely see that for every listener here. You probably need to, if we’re building a remote engineering team, probably wants to apply that because again, it’s doubled down on remote teams is all about communication angle. And if you’re in a live code review, you can feel, “Hey, this guy is, you know, not really good at communicating what he meant,” then he or she, it can be like disaster down the road. You mind me asking like for the next, so after the life code review thing, what was the technical screening looks like?

Megan: Sure. There’s a handful of questions directly related to the technology that we’re hiring for, you know, whether it’s Java, or PHP or JavaScript or, you know, operations. And then there’s a handful of questions around, I guess you could call them behaviors. You know, given an example of this problem that you would have to solve, how have you gone about this in the past? What sort of decisions, what brought you to that decision?

So kind of unpacking how someone addresses a large problem, how do they break it down? And how do they approach the development process for something large.

Jovian: Got it. What’s the timeline for the technical review, sorry, the technical screening itself? Is it like two weeks, three weeks?

Megan: Well, from start to finish, we do try to get the whole interview process done within two weeks. The value screen is, you know, 45 minutes to an hour. Tech screen is 45 minutes to an hour.

Following the tech screen, we do what we call a logistics call where the candidate gets on the phone with someone from our people ops team and we go through just a handful of logistics, you know, benefits package, discussions around salary. But it’s an interview as well. Our people ops team definitely has a say in who we bring on. And then following that call, we do send candidates project.

Jovian: Oh, sorry. So basically, the conversation about benefits and salary and whatnot is before the real project.

Megan: Yes.

Jovian: So that is quite unique. I need to do more…

Megan: Yeah, yeah. I’m not actually sure. I think we’d really care a lot about our candidate’s time. We do not want to waste it. And so, you know, if we have discussions with them around benefits and salaries and kind of like what it means to work remotely on this team and they’re like, “Nope, this is not gonna work for me,” fine. We save them the time of doing the project. So that’s why we put it before the project.

And then the project itself, we’ve iterated on it a lot over the years. The goal is to figure out, you know, what can the candidate actually do, what’s the code that they can write, the quality of it and avoid…we want to avoid them spending a lot of time on project setup. So we try to give them something that is, you know, foundationally set so that they can just start coding. And then we do ask them to limit their time. Like we don’t want someone to spend more than eight hours on the project. And so if they don’t complete it in eight hours, then we’d like them to write up a, you know, a description of like, okay, well, you’re gonna hand this off to a coworker or you’re gonna complete this later. Like what else would you do? Like what are the next steps.

Jovian: Oh, okay. That’s interesting. So this is like an eight hours project. Okay. I think yeah, I was going to ask like if there’s any, like on this project, was there any requirement that, you know, you need to communicate often with the team members, like to get the information, but I feel like based on what you said, like on this eight hours, I really like that approach. Like, if you don’t finish this and then what else would you do next. I think that’s a really smart way to kind of like condensate, make everything compact.

Megan: Exactly. Because we wanna be sensitive to people’s time. We know that not everybody has an entire day to spend on a project. We do offer, I mean it’s definitely not a full day’s worth of pay, but we do offer a gift. I believe it’s a gift card to Amazon for their time. I’m gonna have to check on that because we’ve changed like what we actually give and so it’s some monetary amount that we do give as a thank you for spending this time.

I realized that it definitely does not cover someone’s actual like billable hours, but it’s a gesture and we do try to be as sensitive as possible to, you know, people putting time into this application process.

Jovian: Okay. Awesome. So let’s say the project is finished, and how do you assess it? Is there any particular process?

Megan: Yes, there is. We have two people who will independently do the code review on the project. They have not been involved in the interview process so far, so they don’t know who the candidate is.

We anonymize the project, so we’ve got candidate one, two, three, etc. So they don’t know the name of the candidate, anything about the candidate. They’re just looking at the code and they’re assessing it on several different factors like, you know, following good standards and practices, documentation tests, solving the problem, that sort of thing. And then we compile all of their scores and we end up with a weighted score at the end of it.

And that’s the candidate score. It’s definitely not the, like, it’s just one piece of data that we use to make decisions. And so each piece of the process, you have value add, tech screen, project and then, you know, goes into the decision of whether we hire the candidate after the project.

Sometimes, people just submit like amazing projects and we don’t have any follow-up, but sometimes we wanna ask the candidate why they made certain decisions. What they would do better if they had more time. So we’ll schedule a call to do a follow-up walkthrough of the project, which is always really insightful, because we get to see how do they take feedback, you know, how is their thought process in decision making? So we find that part very valuable as well.

And I think the candidates appreciate it, too, because they likely feel that eight hours was not enough, you know, to deliver what they want to deliver. So it gives them a chance to talk through it. Following that if we move them forward, we just have one final interview usually it’s with the head of the department.

So I do the final interview for engineering. And the heads of each department typically do the final interview for the other candidates. And my interview is mostly to test the process. Like I wanna hear how they did and what they think of the process, etc. Like usually, by the time I talk to a candidate, you know, the team has mostly made a decision about whether they wanna hire them or not.

Jovian: Right. So just going back a little bit, so if we’re talking about the whole, from, you know, the first test to the offer, so you mentioned two weeks. Is it like from first contact to offer made or?

Megan: No. That’s usually a much longer. From the time someone submits their resume to the time they actually like get the offer can be several weeks. Our median, sorry, our average is pretty long, but that’s because we have a couple positions that are really hard to fill and so they kind of throw off our average. But we try to get people through, you know, in less than a month, you know, from end to end and sometimes that runs over just given the difficulty of some positions to fill.

Jovian: So less than a month. But is this something that you guys have been working on, like the duration of making a hire? Like since you first joined, because I remember probably, just imagining, because I remember Nick Francis, your CEO, just wrote about like a fantastic article about how to build a remote team. And I remember like this one part of them he’s basically saying, yeah, it can take like one or two months to hire and then they accept that just because it’s really not easy, you know, for remote to find the right fit. And now you mentioned that you aim to finish all of this within a month. So are you guys, oh, sorry, are you all working on that collectively?

Megan: I should clarify because sometimes, yes, it will take two months. Sometimes it takes three months to find the right hire and that’s okay. In terms of like two weeks to a month, that number is more of a commitment to the candidate. So if we want to get them, you know, a yes or a no as soon as possible. And if we think it’s gonna be a no, we wanna let them know sooner than later because we don’t want to waste their time.

So yes, it might take three months, two months, three months to find a candidate, but we like to get the candidate the information they need as soon as possible so that we don’t waste any of their time.

Jovian: Yeah, it makes sense because you’re also hiring for quality. Right. The same mindset when you’re hiring for product. And then was it ever happened that, because your hiring process takes a bit longer, you know, than the normal conventional company and then the candidates will just bounce off in the middle of the process?

Megan: It has happened for sure. It’s part of the process and we accept that there’s lots of wonderful humans out there that we can work with. So I don’t wring my hands too much about losing a great candidate.

Jovian: And just like you mentioned, optimize for quality, not for speed, same as people. Okay. Now, let’s say someone is hired and what’s next for the person? I guess it’s onboarding now. What does the Help Scout’s onboarding looks like?

Megan: Well, first we ask them what computer they would like so that they can have a choice over, you know, what machine they’re working on. Most of our engineers work on Macs, but we do have a handful who like to work on Linux. So that’s an option. We get their computer ordered. We get them a flight to Boston and they have their first week in-person in our Boston office, which has…

Jovian: You have a physical office.

Megan: We do have. We actually have two physical offices. One is in Boston and one is in Boulder. So the candidates come to Boston for the first week of onboarding. They spend a lot of time talking to people from our people ops team. We have three people on the people ops team that work there. And so they’re able to get a lot of in-face, in-person time with them to walk through culture, process, values, all the good things that they need to know and everything is very well organized into Trello cards. So every new hire has a handful of Trello cards they need to get through in order to complete the whole onboarding process.

Jovian: So this new hire now it’s in Boston now and then there’s just a list of tasks that he or she has to do. How long is this onboarding thing going on?

Megan: So the in-person onboarding is one week. Typically, on the second week, they are gonna be working with our support team.

So everybody at Help Scout does a week of in the queue support talking to our customers, learning our voice, learning how the application works, learning how we want to talk to customers. Everyone finds it one of the most valuable parts of the onboarding process.

Well, I was gonna say we also practice whole company support and so this sets people up to be able to participate in support as they go on with their time at Help Scout. Generally, everyone in the company spends roughly two hours a week working in the support queue, talking to our customers and answering questions about the product.

Jovian: Is there any, you know, some kind of buddy system or something?

Megan: Indeed, there is, we have what we call a work best friend for everybody. And so this is someone usually on their team, but sometimes, you know, if people are in the same town together, we might pair them up. But this is just someone that a new person can go to with any and every question. Like, I don’t understand where I should find this information, or is it okay if I post in the, you know, the big on-topic channel with everybody in it in Slack. So just kind of like help them feel comfortable moving through their onboarding process. And so that’s one piece of it.

We also have a very strong practice of holding fika. If you’re not familiar with fika, it is a Swedish word that means get coffee with a friend and talk. So we have a automated bot in Slack that pairs you up each month with a different person at the company. And so we encourage folks to set up a 30-minute chat with this person and talk about anything other than work.

So starting that from the beginning gives you a really good chance to meet a lot of your team members and feel comfortable joining the team. And of course, people are allowed to, you know, reach out and say, “Hey, can I fika?” At any time. You don’t have to wait for the bot to pair you. So this is also, I think a big part of onboarding that kind of keeps going throughout your time at Help Scout.

Jovian: Was there any like some particular vivid or memories about challenges or problems that you find during either the hiring process or the onboarding process or any other process that related to hiring new remote team members that you feel like, “Oh crap, this didn’t work,” and then either you or someone from the team saying that, “Hey, this gotta change?”

Megan: Because everyone is so thoughtful, and kind of this company, we don’t tend to run into like massive problems like that because we do try to think through our process pretty well and make sure that our practice is aligned with our values.

However, definitely, as we grew, if we had a lot of situations where we’re like, “Oh, crap, that’s not documented anywhere.” Or, “Ooh, we totally forgot to tell you about that.” You know, probably it comes up more often, you know, with new engineers stumbling through like old parts of the codebase. You know, things that are like entrenched institutional knowledge that maybe were never documented.

Jovian: Legacy code and whatnot.

Megan: Yeah, exactly. So, you know, we definitely run into things like that, but we do have very active support system. When new engineers joined the team, you know, they have someone on their team that’s helping kind of explain the history. And our CTO always goes through history and architectural deep dive with every new engineer. So, you know, we try to account for things that come up like that as best we can.

Jovian: Yeah. Yeah, that’s amazing. I guess also like having a people ops can also kind of help because there’s this one person that kind of owns like, if there’s a problem, even though it’s within the engineering team and then this person, and then this can take notes and probably give some advice for improvement.

Megan: Yep.

And I would say one of the best things that Help Scout did as we grew, actually before we even really grew, was to over-optimize for people ops.

So we had three people on the people ops team when the company was still less than 40 people, which I think a lot of startups do differently, right? They usually like HR people ops is kind of like, “Oh, we’re at 50 people now,” or “Oh, you know, we have enough people that we need to hire this person.” We did that from the get go and it was an invaluable decision because it did give support to new people and it allowed us to, you know, really embed the culture across the team as we grew.

Jovian: Right. Yeah. And also, this is the thing about remote companies, like it’s about the people, this sounds super cliché, but the other company that I found out also put a lot of emphasis on people ops or explain employee experience is TaxJar. So I chat on the very first episode of “Outside the Valley.” It was Mark Faggiano, CEO of TaxJar. TaxJar is a similar size with Help Scout or at a hundred plus people. And what I found really fascinating is that Mark as the CEO, he personally onboarded every new hire until it hits like 20 something people. Like it super intrigued because usually at this early kind of stage, like founders will either focus on product or focus on sales.

But Mark personally onboarded like 20 new hires for training and then he realizes, “Oh, I cannot do this like anymore because, you know, capacity and whatnot.” And then he hired up some people ops, one or two, in which around like 30 or 40 something. So I just found it fascinating and I felt like it only happened at remote teams. I’m probably wrong. I’m probably wrong actually. But yeah. Cool.

And next thing. Okay. We’ll talk about the hiring process and the onboarding. So let’s talk about the internal, like whole team specifically engineering and product team. So Megan, as a VP of engineer, let’s get back to the basics, how would you describe your responsibilities and does being remote somehow makes it more challenging to finish just responsible, not necessarily like super challenging, but it’s like the difficulty is slightly higher.

Megan: Sure.

I would say the bottom line, I am responsible for enabling people to do their best work. That means I am facilitating a team that is empowered and focused, making the right decisions. I feel successful if everyone understands what their priorities are, has the right access to information and people to make decisions and to get their job done.

And lastly, probably most importantly, I want the team to feel like they can do their best work at Help Scout. I want them to feel satisfied with the work they’re doing. I want them to feel like they’re growing their career and they enjoy working on our team. There’s obviously hundreds of details that go into making that a reality, but at the end of the day, that’s my responsibility is, you know, empowering the team to do their job.

I think in a remote environment, in terms of challenge, I think it takes a lot of empathy and good listening and good communication. And there’s nothing specifically unique about remote. I think just, that is what allows leaders to work with their teams and empower them to do their best work.

I can say that, you know, in remote, the challenge is you must be intentional with all those things. Because anytime you make a mistake, it’s a little bit harder to recover because you have to, you know, set up a video call. You can’t just like grab someone and, you know, go for a walk and chat about it.

But yeah, so there’s some intentional work that needs to be done there. But otherwise, I would say being able to build that trust between, you know, me and my team and between each of the team members really goes a long way to overcoming those challenges.

Jovian: Right. What are some workflow or processes that you think is either quite unique to you or Help Scout as a company that you think makes you take for the engineering team or the product team? It can be anything.

Megan: Well, you know, I can always go back to our values, right? Helpfulness, ownership, excellence. It is really infused in everything we do. And this is very clear with how we get work done on the engineering team. You know, from test cases to documentation and code reviews, working with customers. We put a lot of care into everything we do and we really honor the craft of software development. Again, I don’t wanna come off as pretentious, but you know, we consider it very important, what we do, and that practice of excellence really, it’s an organic fallout of our passion to take care with everything that we create.

Jovian: Well, you mentioned about code review. So, when I was doing my research, this article written by one of your team members. Okay. Let me just out read out the title. I, Me, We, Us: Creating Team Ownership with Better Language. Can you share a bit more about, especially code reviews, right, if you’re literally in a way “criticizing” other people’s work? How did this come about? Like when did you decide or your team decide, “Hey, we need to write an article about this?”

Megan: The engineer who wrote the article, Craig, has been with us for many years. He was one of the original engineers on the team and he wanted to write a blog post and this was near and dear to his heart and most of the engineers on the team. And so it seemed like a good topic for blog posts, this practice of using, you know, inclusive language in removing the first person when we talk and when we leave comments on code reviews has been a practice of ours since the beginning. So he felt it was important to share and I’m glad that he did.

I think if we all could move through the digital life with a bit more empathy and inclusiveness, that would be a better place.

Well, I did forget one piece of our onboarding that has been really helpful in helping us work better as a remote team. When everybody is hired, they go through this process of generating an Arc profile? A-R-C, this is a company that does sort of behavioral pattern analysis. They ask us a bunch of questions that seem relatively like innocuous and then they come up with this gigantic description of our personality that is scarily accurate. And then we share those with each other.

And one of the things that comes out of it is we learn who on our team is a contextual communicator, who just wants the information and then wants to move on. And that definitely helps us be more thoughtful and mindful when we communicate.

Jovian: So Megan, so you are the first VP of engineering in this “Outside the Valley” podcast. So any piece of advice that you will give to engineering managers or everybody around the world when it comes to helping your team to do their best work?

Megan: I think if I had to boil it down to one thing, it would be, I guess this is kind of two things, be vulnerable and trust. I think the more trust you have between yourself and your team members, the easier it is for anything to get done. And that trust comes from being vulnerable and, you know, bringing your full self to work and seeing everyone that you work with as full humans with lives outside of, you know, the Slack room. And yeah, I think that’s kind of at the heart of it.

Jovian: Yes. Awesome. So yeah, I think that’s a good end to this episode. Megan, thank you so much for the time today. I really learned a lot and I really hope the audience can learn a thing or two from this conversation.

Megan: Thank you, Jovian, this was great.

Jovian: Right. And how can anyone find you online or where can anyone read more about Help Scout.

Megan: Definitely on our blog. There is a ton of wonderful content there that’s not just about Help Scout. So I would highly recommend digging through that. In terms of finding me, probably the easiest is LinkedIn. I’m horrible at Twitter and yeah, I think that’s about it.

Jovian: Okay, awesome. Again, Megan, thanks so much for your time.

Megan: You’re welcome.

Jovian: And that’s it for another episode of “Outside the Valley,” brought to you by Arc. We created this podcast with the hope that in each episode, you can learn something new from other remote startup people. So if you have any feedback or suggestions, please don’t hesitate to reach out to me at jovian@arc.dev. It’s jovian@arc.dev. Or you can find us on twitter at @arcdotdev. See you next week with another episode of “Outside the Valley” and ciao.

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