The importance of fostering a dynamic remote company culture with Darcy Boles of TaxJar

Maren Kate
Today my guest is Darcy Boles. She is a thought leader around remote work and company culture and previously worked at Airbnb in business and brand development. We met at the conference a few months back in San Diego and had some amazing conversations around remote work, remote company culture, candidate experience so I'm super, super excited to have you on the show today, Darcy.

Darcy Boles
Thanks Maren. I'm super happy to be here. It was so fun to meet you where I live in San Diego.

Maren Kate
Yeah, yeah, absolutely. So first question, I always love asking people this, what was your first job?

Darcy Boles
My first job was at doing dishes at a college dorm room cafeteria where I had to wear a hairnet.

Maren Kate
Oh, my goodness. Awesome. And then what? So going from there to what you're passionate about today, how did you fall into the remote work world and also just on the people side of business?

Darcy Boles
Yeah. So for me, I guess you could say my first job was technically in hospitality, right? Like I was working in a kitchen. And I've always had a deep love for people. I'm an only child and my parents are much older than me and so, as a kid, I kind of had to be really curious about the world and discover a lot of things on my own because I didn't really have a brother, or sister, a lot of people my age around to understand how the world works. And so I was a really curious kid and it allowed me to just meet everyone. I just learned as a kid to be able to talk to anybody, like, I could talk to a wood door. And so after working in a cafeteria for a summer I kind of fell into summer jobs in really high-end hospitality, working for wineries and restaurants, and started to learn how to create a welcoming and positive experience for guests and people. And I was fascinated by that concept. And I also learned that if I could be a really good server, or bartender, or create that experience, I can actually do that anywhere in the world. And so it kind of really bit me in the travel bug and I just started traveling everywhere. I traveled to 40 countries in a year and just works in different experiential restaurants and hotels and hostels and just learned where different cultures had similarities. And I always found that was between food, values, experience, and just connection. And after working at Airbnb, I started to really realize this can actually be translated into the workplace. And that's where this light bulb went off in the last, I'd say, four to six years of my career where I was like, maybe I could take this lens of high-end hospitality and create a working experience that, frankly, doesn't suck. And where people feel comfortable in and they feel aligned to and they feel like they have everything they need to be successful. And they know where the best restaurant down the street is. And they don't have to ask a lot of questions because their basic needs are taken care of.

Maren Kate
I like that. And so in terms of when you think of that, it's like you're taking the kind of hospitality, that experience thing, and you're porting it over to the workplace. And I guess when you think of an employee, we think of their lifecycle with the company, it starts when they're being recruited and then it goes through onboarding and then it goes through the entire time they're with the company and then also even into the alumni. They've worked with a company for years and then they go off and do something else. How do you think companies, especially remote ones, how can they create that experience? How should they be thinking about it?

Darcy Boles
I think number one, consistency is key, right? And that's number one. I call the lifecycle really from hire to retire and that's everything you just talked about. And what I've really seen work well in remote companies and see it's being fairly scalable is, the companies who want to create this long term connection, longevity, loyalty to the company, especially remote is codifying the company values and making sure that those values are the north star and are a map for mapping that hire to retire lifecycle. So the way I really look at this, you know, customer service teams have a customer journey map, right? Many do. The moment of truth for the customer where X team needs to deliver. And this is the moment of truth where X team needs to deliver. Well, the employee lifecycle is very, very, very similar and, in remote, those values and the words and language that is used to shape that experience is incredibly, incredibly important. And I think even more importantly, we hear a lot about people joining companies say, ‘Oh, the office looked beautiful and I heard all of these great reviews’ and they get in and it's nothing like they actually read about. It's kind of, in some ways, a bait and switch. Unfortunately, that happens all too often. And with remote, I think there's such a beauty in being extra transparent about things and making sure that the sentiments that are put on the recruiting pages and in the employer brand match the sentiments of the remote employees. And that all comes down to a translation of feeling and consistent DNA. What is that red thread? What isn’t good, what is good, and being really, really, really clear about the things that might not be great but people are working on and matching the skill sets and the people who want to be there. Instead of just saying “comfortable with ambiguity”, cool, we all need to be comfortable with ambiguity, but being really specific about what's needed and really transparent about the actual sentiments of the culture.

Maren Kate
So it's almost like, as we're talking I'm thinking of a matrix of like, there's the values a company espouses, there's like, the anti-values, because if we really believe in transparency what's the opposite of that, right? And then it almost seems like pros and cons kind of, right? Because that's always going to be a thing. There's always going to be a, just in every relationship whether it's a personal one or a professional one, in all parts of life, there's that meeting in there that yang. There's some good parts, there's some bad parts. So are you saying that companies should actually, especially remote, remote-first, and remote-friendly companies, should kind of lead with that? Or how do you imagine that being translated to somebody, especially from the point where they're looking at would I even be interested in working here?

Darcy Boles
I mean, I think that all comes through in employer branding and the design of the employee experience, right? And I think there's a lot of things that we can do to “try before you buy”. And that is, I don't know if it's necessarily a newer concept, but it's one I've seen work really well, a contract to hire. Remote is still really, really new for a lot of employees. Especially in the U.S., we're socialized to think that we need to be at our computer nine to five. We're seeing massive burnout in remote work. But I think that allowing people to kind of explore the environment and make sure that it's the right match both for the employer and the employee, paid, of course, is a really important way, and a really good way, to be able to find the right alignment for a future together. And that comes through flexibility. And again, employee experience design, right. And with remote, it's even more important because think about it, we're hiring people from all different, whether it be in part of the U.S., all different states, all different parts of the world, are coming from all different types of cultures, they have different daily experiences every day, you're not just walking into an office and you see the same coffee shop and you see the same friendly mailman every day. There's very little shared experience that happens on a daily basis for a remote employee. And so creating and being very clear of what this shared experience is going to be and what is expected and behavioral codification of how to thrive in it is essential in remote work.

Maren Kate
What would be examples that you've seen either of companies that have done this really well and/or of specific actionables? Someone who's listening to this, who's in the people function, who's building a business, who's creating the recruiting function within their company, what are things people can do or examples they can look to help guide that? As it is, kind of, so new.

Darcy Boles
Yeah. I think the number one thing I would say is creating an employee experience that is one of over-permission. I think that we assume, I know that we assume a lot of the time, especially if you've worked in the tech world and have worked in an office, maybe in San Francisco or Austin or wherever it might be, there is a certain type of behavior expectations that we just adopt, right? But let's say we're hiring somebody from the middle of Iowa who's never left their state before; taking the lens of that employee and then designing the experience to be much more inclusive. So when I say over-permission, I mean, getting nitty-gritty even to things like ‘we don't expect you to be online all day, I don't need you to tell me if you are going up to pick up your kids’. Like very, very small things that we think should be assumed that everybody should be comfortable doing that. We don't know people's past working experiences. We don't know their past working trauma and in a virtual environment, my mentor says this all the time, “words make worlds”. And so be very, very intentional about the worded design and the behaviors these people want their employees to exhibit. Because, in remote, there's no or very little mutual or shared understanding of what the environment should look like. So back again, I think I'm just repeating myself is just ‘words make worlds’ and being incredibly consistent and intentional, and saying, describing things that you wouldn't think you need to describe.

Maren Kate
Yeah, I mean, it goes back to kind of almost over-communication, but also documentation. That's one thing we noticed at Avra. We've always been very big on over-communicating. And I would say in the last year, we've actually started to add documentation on to that where it's like, we can communicate this but if it's going to be communicated more than once it should also be documented. And there should be a point of truth to point to and we use notion a lot with that. And so what we're able to do is we're able to say, you know, someone asked the same question, we can say, ‘hey, I can answer it here on Slack, and then I can also point you to where the most updated version of this lives’. And in that updated version, we're saying like this was created by Maren or this was updated by Erin and on this day. So we're able to, ideally, the goal is everybody can kind of have a point of truth. And as things evolve, and things grow, or maybe something's questioned, or there's pushback, we can say, ‘Oh, alright, actually, we're going to edit this. And this is the person that edited it. And this is what was added’. What are some of the tools, like the online tools, the collaboration tools, that you are excited about, that you've used in your career to make this happen?

Darcy Boles
Yes, so one tool, that tool is only as good as us, right? One tool that I've used consistently over the last four years that I've really found to be a great space for collaborating async communication but also synchronous communication is Basecamp. I've really, really enjoyed the way that it is set up to also include imagery. I think that's something that's really important that we lose a lot of the time maybe in Slack or other tools is, you know, we're talking about values, about behaviors, again, in remote, people could hear that and read that 100 times but unless they see it, whether it's somebody posts a photo of their baby on their lap during a meeting, or whatever, that might be within a thread that is consistent. I think that the thing that I loved about Basecamp and tools that are similar to it is it almost can create this visualization or feeling of different rooms or departments that have their own architecture. And it's not replicating an office, but again, you can kind of create those feelings instead of perhaps in Slack, where you just kind of have, you know, I saw a meme the other day and it was like ‘Slack’s just an all-day meeting with no agenda’. But it creates a little bit more of an architecture and an environment for people to feel like they can poke around in instead of having to follow a consistent thread if that makes sense.

Maren Kate
Yeah, It's almost the idea of, I mean, it's a little bit nerdy, but you think of like the metaverse or something, it's like even people need to more or less, humans need to have an understanding of their place in space-time and that manifests itself in a lot of different ways. But when you're in a room, you can say ‘I am here, I am in San Antonio in this room looking at blank’. And when you're working online, everything's remote and you're hearing either a disembodied voice, or you're doing Zoom, or you're typing. It is nice to have some, it's almost like creating rooms and spaces, but fully online.

Darcy Boles
Yes, so I'll use the ‘words make worlds’ example again and we're gonna give you two examples here. One was we had a channel or basically a basement project where I've worked before and it originally was called Demos & Releases and we were seeing all of the engineers just post their demos and releases there. Great, that's awesome. But one of the goals was not to silo our teams. We wanted to have more visibility into what's marketing doing, what's customer success doing, what is that? And so we changed the title of the project to, You Oughta Know, like the Alanis Morissette song. So we took something that was kind of a socially known, for some people, construct and it immediately opened up that channel for other people other than engineers to post in. And so it kind of, again, created that comfort blanket of ‘oh, I'm allowed to be in here’, and that was really interesting. And another, the analogy that I use a lot for remote company culture is, you're hiring somebody; you need to tell them what to pack. You need to tell them what the environment is like.

Maren Kate
Where their desk is in a real-life situation.

Darcy Boles
Where their desk is. Is it in Antarctica? Do I need to bring a puffy jacket? Am I going to Hawaii? Do I need to bring a bikini? And so letting people know, again, even with those titles, and getting creative with that. What is accepted and allowed and what you can bring into those spaces is like I found to be a really helpful way for employee experience professionals and recruiters and people who work on people design to get their head into that headspace.

Maren Kate
Yeah, and it seems also like the way, the best way, to do this is to start with the candidate experience before someone is an employee to start with. We're noticing this; we've seen a lot. We interviewed someone from Notion a few weeks ago and Notion has a phenomenal, the way, they have candidate guides and outline exactly what their process is so it seems like that immediately starts to orient a person and get an understanding of ‘Ah, like this is how things are, this is how information is going to flow, this is what I need to know, this is what I'll need to know if I get this job, is this a fit for me or not’, and it feels like the companies that are going to succeed in fully or partially remote environments are going to need this. And probably, in reality, even as this happens more across companies, even companies that are mostly co-located will need to start building out these spaces online as people work from home more.

Darcy Boles
Absolutely. And I think also the beauty in that and that this is on the rise is that it also holds people teams accountable to reacting to the information that they have put out there. So if you've got this hiring guide out that you're talking about, here's step one, here's step two, here are the tools we use, then it also is, kind of, an if this, then that for the recruiting team and the people experience team of saying, are we in alignment? We're always checking back on the information that we have put out to the public on our employer brand and it's just this back and forth, which I think is an incredible way to hold accountability.

Maren Kate
Yeah, absolutely. Yeah. And that is a great way and we need to be held accountable because I think often and it usually, rarely people mean this maliciously, but things just get dropped and the experience suffers. So if you can point back to that and say, ‘hey, this was the expectations, that's how it wasn't met’, that's gonna create a really good feedback cycle.

Darcy Boles
Exactly, exactly. And it also helps with Glassdoor reviews and reviews that may come in and out and saying, ‘Okay, where did we drop the ball here if we did, or where didn't we, and where can we cover ourselves here in response’. And I think that as long as, and it comes down to the authenticity, and again, matching the inside to what's put on the outside.

Maren Kate
So, switching the gears and thinking in the terms of a job seeker, I mean, we just hit another record months of people quitting jobs because I think a lot of times people are like, ‘I want to find something that is more aligned with what I want, meets my needs in better ways’. And so it's like, I know, from what we've talked is values, alignment, and matching is something that you think about a lot. I'd love to hear how you would coach an individual job seeker when they're looking for a new role. How can they be approaching the job search from a, like, how can they start understanding this stuff about companies? Especially because most companies, very few companies have this done perfectly.

Darcy Boles
Yeah. And I think we're gonna see more and more companies start to write down their cultures and their values, especially with the rise of remote. But for job seekers, I think one of the most beautiful parts of the world being much more accepting of remote, you know since 2020, is the ability to find much more direct alignment between employee mission, I’m sorry, employer mission and employee intrinsic motivation. And so I think that for a job seeker, I would highly recommend doing a couple things. One, start to discover what your core values are. I think a lot of people know what makes them happy but they actually haven't done a deep dive into, do I really value accountability over something else, or being a part of a team. You know, there's some people who just like to be individual contributors. So starting to really, really understand what lights you up and paying attention to how those words feel in your body when you say them. And also, I would go back. This is something, I was working with a woman recently, or just chatting with her, she had previously been a domestic violence counselor but she really wanted to get into the tech world and she felt like she didn't know where to go, right? She had been working in a shelter for years and we kind of went through and broke down, what were the things that she absolutely loved working in that shelter and really learned it was community. It was helping. It was these core values that were actually her DNA that are actually transferable skills into the tech world. And so looking back at your past roles, things that you have deeply found that you, there were moments you felt like you had a massive impact in your role, and then seeing what that is, writing it down, and then now you actually have your own personalized guide to then look for companies and jobs that offer these things.

Maren Kate
I love that. I think that is so valuable. And it's interesting, it's not something we are taught to think about, like, when we're in school when we're in university. We're not taught to think of like, what are your values, and how would those potentially align with these careers you're looking at, and where will you thrive, and where won't you? And it's so important because, you know, there's a company and there's a role that one person will love and thrive in and feel fulfilled and another person will feel suffocated. And I think it comes down to not only the company's culture but the company's working style and then specifically how the role ties in with what you want, what you need, your values, and your working style.

Darcy Boles
Totally. Another benefit, I mean, there's so many benefits to values matching but one of them I see all the time as well is, it's actually less expensive for a company to hire somebody whose values align with theirs as long as their operating system is in the truth of those values and how they work is consistent because when you're intrinsically motivated there's so much less need for extrinsic motivation. Like throwing money at people, sure it works for a couple months, but that's not going to keep you a long-standing longevity employee. As everybody who's probably listening I'm sure knows or is learning, it costs three times the salary to fire somebody or let them go and hire somebody new. So it's really important to find that right match.

Maren Kate
Wow. Absolutely, absolutely. And it's like you think about it, well we call them recruiting funnels, and as you're building out a recruiting funnel for a role you need to be not only vetting for skill, experience, working style, but you need to be vetting for that values match and communication style.

Darcy Boles
Exactly, exactly. And in going back to does the way the individual works, especially in remote. So again, it comes down to how you work, and is that going to be in alignment with how the company works because not all remote companies are created equal. I’ve seen a lot of remote companies who are just basically working from home and they're on Zoom all day. It is not an asynchronous-first operating rhythm. And that might not work for somebody who is seeking a true remote asynchronous-first job because they like to design their life around their work. But some people want to be in a completely synchronous work environment. So again, getting really clear on how you want to work and finding companies that operate in that similar cadence.

Maren Kate
Yeah, and I like that you mentioned, I was recently reading an article that you had interviewed on, you mentioned designing our lives around work versus the other way around. And how do you personally approach that?

Darcy Boles
It honestly, has been one of the bigger struggles that I have faced and I have talked to a lot of people that they have faced as well. I think the assimilation process into a fully remote environment comes with a massive amount of freedom that you have to give yourself. So it took me almost six months to be comfortable going on a bike ride in the middle of the day and nobody was telling me that I couldn't do that, nobody. And so that was really eye-opening for me. So I started actually, when I first started working remotely, I would test myself. I would try to challenge myself to do something scary in the middle of the day. Like maybe cook a really long lunch or maybe like go surfing for two hours in the morning. And I started to find my rhythm. I started to say, ‘Okay, I actually work really well when I check my emails in the morning then I take a two-hour break or Mondays are not great for me to have meetings, if possible, with my team because I feel like I need to get really grounded for the week’. And so I started to learn and just pay really close attention to when my consistent meetings were and what type of headspace I needed to be in to show up at my best. And so then they would start to test and design what are the things that gave me energy and kind of active recovery outside of work and put those on my calendar as kind of ‘do not schedule over’ as long as there wasn't a big deadline or whatever it may be. And that was something that was really helpful. I just treated myself like a giant remote work experiment.

Maren Kate
I love that. I think that's awesome. And when you find that it is just a game-changer. I mean, it really changes not only your work but it changes your life. I think for years I struggled even though I've been working remote since I was more or less like 20 and I've started a few remote-first companies. But for years when I was in the Bay Area it very much, especially the time I was in the Bay Area, which was 2010 to 2016, it seemed like there was very much a culture of go, go, go, you're constantly on calls. I remember sometimes there would be another CEO that would show me their calendar and they had 10 or 20 calls, I kid you not, in one day just back to back to back. And I remember thinking ‘oh man, I'm clearly dropping the ball here, I need to be doing more work like they do’ and it just absolutely destroyed my productivity. It destroyed my creativity. And I realized, similar to you, is like my mornings need to be clear. I try to not have anything scheduled before noon because those first few hours are where I get the most creative, I get my best work done. And then the rest of the day, I can do meetings, I can give feedback. But if I don't have that morning time, it really throws off the rest of my day, week, etc. Granted, like as the boss so to speak, I have the ability to do that. But it is important for everyone, regardless in what area they are in the company, to be able to have that ability. Because when you get in sync with the way you do your best work everyone wins. The company will win, you'll win, your co-workers will win and it really does but it takes a very trusting workplace.

Darcy Boles
It takes a very trusting workplace. It needs to be modeled by the leaders. You know, I was reading an article, I can't remember where it was, the other day and it was all about managing your energy, not your time. And I think that's really the crux of it is, how do we start to create culture and model as leaders that it is more important to manage your energy than your time. Because if I'm going to start a company and hire people, I want people to be at their best. If that’s at midnight, then that's at midnight. Who am I to say, where you work when you work best?

Maren Kate
Yeah. So my final question, first of all, who or what, it could be a person, it could be books, it could be, whatever, what has impacted your thinking about this employee and candidate experience the most?

Darcy Boles
That’s a good question. I would say one of the books I read when I first started in the remote world was Patti McCord’s Powerful. She was the VP of Culture at Netflix for 14 years and she really influenced me in understanding the setting of expectations and values alignment and creating that experience of freedom and flexibility. And the way that I call it now is freedom in the framework. Create the framework and then people can have freedom in it. And that's really, really impacted me, that phrase in and of itself. It is my job or the people experience team or the recruiting team’s job to codify and design the framework so people are able to be free within the bounds of what the company has decided they want that to look like. But without that framework, the culture will grow 10 heads. People won't know how to behave. And that's been so so so essential to designing a virtual environment that thrives.

Maren Kate
Yeah, I mean, it would be like saying, ‘hey, you need to win at this game but there's no rules but we will tell you when things aren't working’. I love that. I've actually not read that book so I just added that to my Goodreads list. What product or tool do you rely on the most to do your best work?

Darcy Boles
I mean, honestly, I would say. This is a hard one for me because I use a lot of tools. I will say Google Docs and the Notes app. And that might seem really, really, really simple but I’m somebody who has a lot of thoughts and I have a hard time putting them down into one place. So I will use my Notes app, even if I'm at home and I don't have my work computer but I will have my Notes app saved, where I will just throw in ideas, I will throw in words, I will just kind of barf my thoughts or my dreams or whatever that might be. And then I'm able, when I'm in the right headspace and ready to kind of do some deep work, I will take everything I've written and then organize it in whatever format I need to organize it in. And so it might sound like throwing paint on a wall and I would probably liken it to, it's probably very Jackson Pollock-y, but I definitely thrive in organized chaos. I like to build. I like to pull words and themes out of things. So I will just barf everything out onto a Notes app or Google Doc, and then I'm able to then extract the threads that I really feel like are the ones that I'm going to design around or I'm going to implement or whatever that might be.

Maren Kate
And it seems like the vital thing with that is being sure to be disciplined about processing that mind sweep, that kind of brain dump. Like there has to be some sort of cadence around processing, right? Yeah. And I would say that

Darcy Boles
Yeah. And I would say that happens when let's say I'm designing a remote company on site, which is one of my favorite things to do, and that's a whole nother conversation we can have, but it's one of my biggest joys. But what I'll do is I will just throw everything onto a document, then I know that the due date for the on-site is, you know, four months out, so then I've got a project tracking system within Basecamp that I know I have certain milestones I need to get done and so I'll just use my barf doc and check in every week. Sorry, I keep calling it a barf doc. I'll keep checking every week, and then I'll be able to pull things out. And it's just this master document that I'm able to just always come back to and it's cool to see and pull from because I will probably have 10 pages at the end of it where I've rewritten everything. And I've seen where it started and where it got to and that's something that's really fun for me in my process. And I think the other thing to note is that I've been very clear with my team who I'm collaborating with that this is the way that I work best. And so I have a girl on my team in the past who is very, very detail-oriented and needs a spreadsheet for everything. But she and I have learned to work together where she'll take the points from my barf doc and then put them into her spreadsheet because that's what works for her. So I think, again, it comes down to communication and making sure that your methods of working are going to work with the people who are supporting you.

Maren Kate
That's awesome. I love that you call it a barf doc. I call mine a brain dump or a mind sweep so there's definitely a theme. Darcy, this has been so awesome. How can people find more about you online? Where can they find you?

Darcy Boles
Yeah, so I'm most active I would say on LinkedIn and you can just search Darcy Boles. It's Darcy Boles and feel free to connect and shoot me a message. I love growing my community. I love talking to people about remote culture, the future of work. I'm so thrilled to just see so many more people be able to do and create their lives around what matters most to them, but also have thriving careers and make a really big difference in business.

Maren Kate
I love it. That's awesome. And we'll be sure to put a link to your profile in the podcast notes and also in the blog post. Darcy, thank you so much.

Darcy Boles
Thanks, Maren. Really appreciate it. This was fun.