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Remote Work

The Magic of Remote Work at Digits

Back in early March, before the full extent of this pandemic set in, I kicked off our introduction to remote work at Digits as follows:

To be sure, working remotely is not for every business, and not for every individual.

Little did I know how soon so many businesses and individuals would be forced to make do, and how quickly fully-remote work would become mainstream.

It’s been an abrupt transition… and for many, it hasn’t been easy.

Over the course of the year, I’ve heard from countless startup founders, small business owners, and team leads looking for more advice on how to build effective, collaborative, productive, and happy fully-distributed teams. The last, of course, being the most challenging.

For those of you that have held-off implementing major process and collaboration changes to optimize for remote work, the time to reconsider is now.

While there may soon be light at the end of this tunnel — thanks to the incredible vaccine development efforts by scientists and researchers worldwide — I foresee no quick reversion to “normal”. Remote work is here to stay, and every industry that can do so will embrace it.

Success in 2021 and beyond will be defined by those who adapt to remote work most effectively.

Here’s what we’ve learned at Digits.

If you’d rather listen than read, Stanford University has published a full interview covering our approach to remote work, as well as a short 7-minute summary as part of their free Entrepreneurial Thought Leaders podcast.

What We’ve Learned, Remotely

Digits went fully-remote the day we started the company in 2018, with my co-founder Wayne in Los Angeles and I in San Francisco. We knew it would be a fools-errand to try to build the company we envisioned in just one city (there’s simply too much great talent everywhere) and we both shared distinct, negative prior experiences managing multiple remote offices: the “second-class citizen” effect felt by those not frequently present at HQ is hard to overcome.

So (and despite distinct skepticism from a few of our investors — don’t worry, we appreciated the push-back!), Wayne and I made the decision to embrace remote work wholesale: Digits would never own a physical, shared office, and we would design our approaches and processes from the ground-up to champion distributed work.

After seeing so many different attempts at remote work by so many companies over the course of this year, and after reflecting on the most effective aspects of our own culture at Digits, it’s become more clear to us than ever what’s really important.

There are now thousands of online articles pitching countless techniques for improving the remote work lifestyle — it’s overwhelming.

As founders, here are the practices we believe have had the most positive impact at Digits, and the ones that we would recommend you try out with your teams today, even if you’ve previously preferred an in-person work experience.

Embrace Synchronicity

For many, remote work is black and white: you’re either in the office together, or you aren’t. But degrees matter. Time zones matter.

In our experience, productivity and happiness go hand-in-hand with collaborating live, so we’ve made a conscious decision at Digits to agree to all work roughly the same hours: in our case, US Central Time. Folks out West tend to fire up their computers a bit earlier than they otherwise would, and those back East tend to stay on a bit later, or check back in after dinner, or once their kids are asleep. There is still a bit of skew on each side, but to have our entire team online together, every day, simultaneously, for the core hours of US Central Time is magical.

Sure, there are downsides. There are incredible folks (and former colleagues from prior companies!) in EMEA and APAC that we would adore the opportunity to work with, but we have assembled an incredible team that can collaborate live across North, Central, and South America synchronously. The pros outweigh the cons dramatically, and we communicate this upfront in our recruiting materials: when you join Digits, you’re free to move wherever you want within continental American timezones.

For those of you who already have colleagues spread around the globe, our advice would be to strive for team synchronicity. Here’s how.

The Buddy System: Scaling Synchronicity by Shrinking Teams

The traditional “two-pizza” team of 8–10 folks gathered around a conference table may work well in person, but we’ve come to realize it’s unwieldy on Zoom.

Even on fast Internet connections, latency often makes it awkward to get a word in edgewise in group settings, and inevitable background noise from pets, children, construction, or everyday city life motivates a default-to-mute culture, which adds another layer of friction to highly-participatory group dialogue.

That’s ok — we’ve never found large group meetings to be productive to begin with 😉

At Digits, we consciously break teams down into their smallest possible units: every project is tackled by tiny teams of 2–4 people, and in practice we found that 4-person teams often self-divide pairwise to get work done more effectively. We call this the Buddy System.

Working on something by yourself is lonely.

Working on it by yourself, in your home, with nobody else around, is just sad.

Working on it with a buddy is awesome.

In practice, substantially everything we do at Digits is tackled collaboratively by 2–3 people. They work together, synchronously, throughout the day, and decide when they want to pair on Zoom, Tuple, or Slack Audio, and when they want to go heads-down and sync back up in an hour or two. But they always know who they can count on to brainstorm with, or get feedback from, or have review their work, and they know they won’t have to wait around for it because that person isn’t elsewhere working on something else.

Yes, this means we take on fewer projects simultaneously than we otherwise might, but in exchange, each work-stream gets completed far faster, at a far higher quality level, and the work day is far more enjoyable.

We default to coordinating work between teams asynchronously: via shared Google Docs and Trello, in order to minimize meetings and maximize flow. Input is welcomed, and actively sought from broad groups across the company, but that doesn’t take a meeting to accomplish. Let people chime in on a doc when they have time, and then grab time with them and their buddy directly if it deserves a live conversation. After all, they’re unlikely to be in another meeting…

The Maker Schedule, Writ Large

One of the most challenging aspects of almost any large organization is the meetings. An endless parade of prescheduled time-blocks, which require abrupt context switching and leave little time for thought, creativity, or even a snack. How easy it is to end the day exhausted, yet with the gnawing feeling that you didn’t actually accomplish anything of note?

For those with the maker mindset — with roles that require creativity and execution — this sparks terror. There is no better way to ruin the productivity of your design and engineering teams than a few poorly placed meetings. Losing half a day or more due to a couple preset commitments is not an exaggeration. At large companies, it’s a way of life.

At Digits, we discovered something we hadn’t realized: scarce resources are largely to blame.

Conference rooms are evil.

At a traditional company (all of Silicon Valley included), I need a place to hold a meeting. It would be rude to stand around and make noise somewhere public, where others are trying to work, so I book a conference room. Genius.

Except, conference rooms are in high demand, so I must reserve one in advance, and my meeting must conform to the room’s list of available slots. Without thinking about it, my meeting must now be 30 minutes or an hour long, and the time it will happen is now fixed on the calendar and broadcast in advance.

This is a nightmare.

It turns out that the maker schedule is not all that disrupted by the meeting itself… but rather by the presage of said meeting.

There is nothing more distracting than seeing a hard-stop on your calendar in 90 minutes. Do I have enough time to build out this feature before then? Can I really sink my teeth into this design problem in less than two hours? Should I just spend this time replying to email, or triaging bug reports, or grabbing coffee?

Don’t worry, I’ll dive into my real work after that meeting. (I tell myself)

Oh no. I also have a 2pm!?

At Digits, we have full-company, all-hands meetings 3 times a week, spaced every 48 hours:

  • Monday morning Kick-off (30 mins)
  • Wednesday morning Check-ins (30 minutes)
  • Friday afternoon Show & Tell (75 minutes)

They are scheduled to fall at the beginning or end of the day, to minimize disruption.

More importantly, we aim to schedule no other internal meetings.

Sure, interviews need to be booked, and customer and partnership calls need to happen, but it’s easy to distribute interviews across the team (and monitor how frequently any given engineer is pulled into an interview) and external-facing roles tend to be less maker-schedule driven.

This does not mean people don’t talk! Instead, we highly prioritize an ad hoc, interrupt-driven culture. Remember, the meeting itself is far less painful than the upcoming hard-stop on the calendar. And with no conference rooms to book, there’s no need to schedule anything in advance, so we don’t bother.

Much to our initial surprise, this has lead to a bit of a utopia: our typical “meeting” is 5–7 minutes long, includes less than 6 people, and happens with just a couple minutes of notice. Everyone is typically available because they’re all working US Central Time, and they aren’t tied up with any other pre-scheduled commitments, so why not join? And in just 7 minutes, they’re right back to being productive, because the meeting wasn’t long enough to “page out” or forget what they were doing and shift them out of flow.

This sounds too good to be true. It isn’t. It’s reality.

Remote Work At Digits

Taken together, our days and weeks at Digits look like the following:

  1. High-bandwidth all-hands, every other day, so we all know what everyone else is working on and how it’s all progressing. The complete, cross-functional visibility these provide builds confidence that the whole company is rowing in the same direction, and immediately surfaces any duplicate or conflicting efforts.
  2. Empty calendars, devoid of pre-scheduled internal meetings, so everyone can stay in flow and focus on getting work done.
  3. Tight-knit, synchronous collaboration with a buddy, day-in and day-out, so you’re never alone during the day, and you always have someone you count on to brainstorm with and get feedback from.
  4. Asynchronous, cross-team collaboration via shared Google Docs and Trello cards. Input and feedback is actively sought, but never blocked on, and each team is empowered to deliver their work end-to-end.
  5. Ad hoc check-ins throughout the day, as needed. With no notice or preparation that takes you out of flow, it’s trivial to pause for 5 minutes and share an update, or get input from another team and then go right back to being productive with your buddy.

Spreading the Word

A few months ago, it was an honor to be invited by Stanford to share Digits’ approach to remote work as part of the university’s Entrepreneurial Thought Leaders lecture series, and they have published the full talk here.

With 2020 coming to a close, Stanford eCorner just recently published a recap of their key entrepreneurial takeaways from this year, and I was floored to be featured again. Thank you Tina 🙂

Join us at Digits

We’ve been heads-down for the past two years, building out our full vision for Digits, and we can’t wait to share it with the world in 2021.

If you’re excited to join a passionate, fun-loving, fully-remote team that’s obsessed with building delightful business finance software, we’d love to get to know you! See our open positions here.

A New Definition for Remote Work

To be sure, working remotely is not for every business, and not for every individual.

If your team needs to huddle together to prototype a physical product, that will be tricky. Or if you work for a biotech startup with special lab equipment, it’s likely infeasible to provision it for every home-office. Or if you’re a big-time extrovert who lives for lunchroom gossip and 5pm team socials, this work-style may not be your cup of tea.

But remarkably, we’re now at the point where most software/digital/service-based businesses, and most knowledge-based employees, are well-suited to going fully-remote, and many will be better off if they do! In fact, remote work has already jumped 159% in the past 12 years, but that’s just the tip of the iceberg.

Wayne and I founded Digits 2 years ago to create the next generation of delightful, powerful business finance software, and we had a choice: how should we structure the business? When we landed on building a fully-remote startup, even some of our closest supporters were skeptical.

Can a fully-distributed team be productive?

Won’t everyone just slack off all day?

How do you brainstorm and make product decisions?

But, but… whiteboarding??

We immediately faced these and countless other questions, but we were convinced that we could not build the scale of business we envisioned in San Francisco, and we had a strong distaste for the known challenges of distributed offices.

With the full benefit of hindsight, we could not be happier with our decision. Working as a fully-remote team has been a joy, and we have relentlessly iterated on the tools and techniques we’ve used to make it so.

Here’s just a few of the lessons we’ve learned over the past 2 years building a fully-remote company:

The Key Difference: No HQ

“Remote” isn’t new, and isn’t great. “Fully-remote” is a totally different concept.

Most peoples’ understanding of remote work has been a scattering of remote employees and a big HQ somewhere. As a result, the remote teams miss out on a lot of the ad hoc conversation/culture that develops in the colocated offices, are frequently left out of some meetings (sorry, who forgot to dial-in?), and inevitably begin to feel like 2nd-class citizens.

Trust me, I’ve been there.

A fully-remote team, by contrast, means no conversations are happening in an office somewhere to miss out on. At Digits, the pulse and culture of the company is pushed online for everyone to partake in: what would normally be hallway conversations now happen in some digital form. Chats are quickly upgraded to voice/video calls when written communication is not enough—and there is no stigma towards, or friction preventing, those who were passively following along in the chat room now asking to join live. Everyone is on the same level playing field.

This makes our fully-remote team feel like we aren’t remote at all. We’re all working right next to each other, at adjacent desks, despite being thousands of miles apart. Our remote interactions are a real and meaningful replacement for stopping by a coworker’s desk to chat something out or chasing them down in the hallway.

The moment any part of your team is physically together in an office, all of these critical distinctions begin to break down.

The Buddy System

We aim to run all projects at Digits in micro-teams of 2-3 people. Sometimes 4, but in practice we’ve found they tend to immediately split themselves into pairwise sub-teams.

The major benefit is you always have a buddy. From the moment we kick off the week, you know what your goals are and who you’ll be working with to achieve them, so you can dive right in together.

On the engineering side, this means you always have a designated code-review partner to keep things moving. It varies, but over the last 2 years many of our teams organically started to pair-program (yes, fully remotely) to further align and accelerate their work.

On the business and product sides, it’s the same story. We pair on strategy docs, product wireframes, marketing copy, blog post drafts—you get the idea. And pairing makes the work way more fun! You’re not sitting in your house toiling alone; you’re talking with at least one other colleague constantly, and you’re both working together to achieve a common goal.

It’s easy to think we’re wasting time having at least 2 people tackle every task, but the opposite is true: quality is much higher, each project moves at a faster pace, and in a distributed world, redundancy is critical to increasing the odds that someone knowledgeable about a thing is online and available.

The benefits have been dramatic: nobody is lost in their own world either slacking off or making unilateral (mediocre) decisions. Ideas are iterated and improved rapidly as they are discussed in small groups and then raised for broader awareness. And there is no unwanted overhead or design-by-committee: each micro-team is empowered with their own goals for the week, so they know the direction to head in and are trusted to seek input when and where they need it. If they haven’t, it will become very obvious at our next group check-in 🙂

The Death of 30-Minute Time Slots

To stay in sync and highly aligned as a remote team, we do (short) all-hands meetings every 48 hours. Apart from that, we aim to have no other scheduled meetings.

Of course, interviews do need to be booked, and external customer/partner meetings get scheduled, but the principle holds: work within one’s micro-team is fluid and synchronous—you’re constantly on and off ad hoc video calls or pairing sessions with your buddy, but work between teams is async: via Google docs to review, large PRs that need broader buy-in, blog drafts that need editing, etc.

It becomes the ultimate Maker’s Schedule, for a single reason:

Digits is fully remote, has no office, and owns no conference rooms. This fact is critical.

Without conference rooms, there are no scarce resources to book, which means meetings don’t need to be planned in advance, which means they don’t need to be 30 minutes or an hour long. Chats can happen when the necessary people are available (which in practice is typically within minutes, because teams are small and independent, and no one else is over-scheduled either). You can add people to meetings when they are needed, and they drop off if the topic moves on. There is none of the awkwardness, friction, or wasted time of traveling between, waiting outside of, entering, or leaving, physical conference rooms. It’s truly remarkable.

This has made our typical internal “meeting” last on the order of 5-7 minutes: you hop on, get your questions answered or share your perspective, and return to execution. With the elimination of Parkinson’s Law, the Maker’s Schedule is complete: meetings usually aren’t long enough to knock you out of flow.

This flips the typical work day on its head: rather than running between recurring meetings and trying to “get stuff done” in between, we’re all free to focus on executing until pinged by someone who needs input. And since those interrupts are typically quite short, they aren’t disruptive—you’re right back at it without forgetting where you left off.

All of this creates an interesting reality: we’ve felt that we’ve reliably had more face-to-face interactions with colleagues than we ever did in physical settings. Everyone is more available. There is less friction to chatting—you don’t need to walk across the building to catch someone at their desk. And because the interactions are shorter, they tend to be much more frequent: I’d much rather chat with my teammates for a few minutes every day than a half hour once a week in a standing meeting!

The Remote Work Toolkit

Productivity tools often border on religious choices for many people and organizations, so I hesitate to make specific recommendations.

Instead, it’s more important to focus on the “jobs to be done”—what use case is each tool meant to solve—and then standardize on an answer for each, so everyone on the team knows where to go.

Over the past 2 years, we’ve converged on the following core roles for our tools:

  1. Asynchronous & semi-synchronous lightweight chat (no important decisions, no expectation of reading scrollback)
  2. Decision recording & lightweight knowledge sharing
  3. Long-form strategy and documentation
  4. Synchronous all-hands video meetings
  5. Synchronous 1-1 (or small group) video/audio chats
  6. Pair programming
  7. Whiteboarding
  8. Work-tracking/project management

We have preferred to find specific tools that really excel at each of these distinct use-cases (even if we only use a tiny fraction of the tool’s functionality), rather than consolidating on fewer tools that might be less ideal. In practice, we’ve not had much issue forgetting where something is because the use cases are sufficiently distinct and obvious.

We also constantly evaluate and explore new tools, as the pace of innovation in remote collaboration is currently exploding.

For those who insist on asking, our current toolchain at Digits is:

Digits uses: Slack, Basecamp, Google Docs, Zoom, Tuple, Pixelboard, Trello

…but it can and will change as new options come on the scene 🙂

We do not use email for anything other than customer support, and I can hand-count the total number of internal emails we’ve sent since starting the company.

A New Set of Employee Benefits

As founders, Wayne and I care deeply about showing company personality through employee benefits. Above and beyond health insurance and 401ks, we try to embrace the remote-work lifestyle to ensure every team member’s day-to-day is as delightful as possible.

Wherever You Work Best

Not everyone “works remotely” the same way. Some people have a home office they have used for years, but that’s really not typical. Usually it’s a difficult choice—do I take over a spare bedroom or underutilized corner of my house or apartment, or do I find a co-working space nearby? Countless factors go into this decision and it would be unfair for us to motivate one over the other.

So we happily support both!

Every new Digits employee gets the choice: if you’d rather work from home, we give you a $2,000 budget to outfit your home office. A great chair. A new desk. Houseplants! A side-table with a coffee bar. Really anything you feel would make your day-to-day more enjoyable. Conversely, if you’d rather go the co-working route, awesome. Pick your favorite spot and we’ll cover your monthly membership fee for a desk.

The Need for Speed

Regardless of which direction you go, we have another perk up our sleeves. We’ve found that everyone works from home sometimes, for many reasons, even if they prefer a coworking environment. And ISP quality varies widely across the country.

Starting last year, we rolled out a new benefit: Digits pays for every employee’s home Internet service, and we immediately upgrade it to Gigabit (or the equivalent fastest available plan)!

Never have you seen a more butter-smooth video-chat experience from so many different homes across the country…

The New Power of Team Travel

Gone are the days of traveling between distributed offices for alignment sessions or making the monthly trek to HQ.

There’s no office at all, so there is nowhere you have to go just to make an appearance or get face-time! Instead, all internal business travel can be deeply intentional, and optimized for creating amazing shared experiences.

At our current stage, we’ve found the ideal cadence is quarterly. 3 times per year, we host our Digits Onsites: we rent a series of AirBnbs (or hotels, as we’ve scaled) and we bring the entire team together somewhere in the country for a jam-packed week of strategic planning, knowledge sharing, in-person work and collaboration, and fun team-building activities and celebratory dinners. During the 4th quarter, we throw our annual holiday party.

And what we’ve learned is that working remotely makes these in-person moments together even more memorable. Time is punctuated by Onsites. Product milestones are marked by the strategy we discussed at each one. Team members’ start dates are recalled by which Onsite they first joined.

There’s always the next one on the calendar to look forward to, and we go to great lengths to make each one special, in some way or another. With no corporate budget dedicated to facilities or inter-office travel (indeed, one month last year our cash burn was 91% payroll-related!), we instead shift those resources to Onsite logistics, with great effect.

The resulting work-life balance has been magical: we are home with our families, with no commute to speak of, day-in and day-out, with flexible schedules and an unlimited vacation policy, and then we’re all together each quarter, exploring someplace new and aligning on our next chapter.

The Future of Work

Without question, we will be forever adapting and refining our approaches to remote work with each new level of scale and degree of business complexity, but we foresee no structural reasons that would cause us to change this basic approach. Indeed, great companies such as GitLab, Invision, Buffer, and many others have pioneered this path with well-recognized success.

At Digits, we’re extremely energized by the growing interest in remote work and the explosion of new tools that are being built to facilitate it, and we’re excited to join the community in sharing and iterating best practices.

These past 2 years have honestly surpassed our wildest expectations: one of our teammates recently expressed that they don’t see themselves returning to an office environment for the rest of their career.

Everyone else nodded in agreement.

If you’re excited to join a passionate, fun-loving, fully-remote team that’s obsessed with building delightful business finance software, we’d love to meet you! See our open positions here.