We'd like to think we've worked remotely pretty successfully: we raised a seed round, we've come in first place on the Pioneer leaderboard for a record-breaking 25-weeks in a row, we publish at least five pieces of content each week (check out our blog and YouTube channel!), and we’ve grown our team to 7 full-time hires. (We’re currently seeking to hire a few more full-time hires!)

We've learned a lot! As companies and employees grapple with the choice of how (and even whether!) to return to the physical office, we wanted to share some of the tools and structure we’ve used to work remotely successfully.

Quick background: Our team currently has seven full-time employees with a number of people doing additional contract work. We’re distributed across five states and two time zones. We use a combination of technology, “fun” team activities, and “business” team activities to ensure we’re a happy team that gets a lot done. We hope this will be helpful to your team and your whole organization!

Technology: Sidekick, Slack, Zoom

  • Sidekick: Our video devices that enable us to cowork side-by-side – remotely. Imagine an iPad with a steel arm that supports it sitting on the side of your desk, on which you’re able to see your colleagues. That’s basically what Sidekick is! The goal: replicate an office setting while allowing your team to work remotely. It's kind of like a FaceTime or Zoom meeting that you're all in at the same time. However, it's in the background with no volume, so it's not like you're overhearing everyone on their calls while you're trying to work. If you want to talk to one of them (kind of like tapping someone on the shoulder in the office), tap the screen to jump into a DM with them. If you want to go into “focus” mode so someone can’t do the electronic equivalent of “tapping you on the shoulder,” you press a button. Your team can set expectations around core hours – for example, “everyone should be on Sidekick from noon to 3 p.m. on Monday, Wednesday, and Friday.” For our team’s size, we haven’t yet set those core hours (people come and go throughout the work day), but imagine we may set expectations as we grow.
A few members of our team, including one of our team's dogs.
  • Zoom: One of the go-to video conferencing platforms. While Sidekick is great for coworking and feeling like we’re connected from different time zones, we’ve found it isn’t a substitute for Zoom calls for meetings. When we do team meetings like our daily stand-up or calls with customers, we choose Zoom as our video platform. We’ve found the ability to share screens and reacting with emoji to be really helpful as we get things done.
  • Slack: An instant messaging service with direct message and group chat capabilities, among others. Not all communication can (or should!) be on video, and the written record of Slack is preferred for most communication. We err on the side of putting notes or comments in channels as opposed to direct messages, with the goal of increased transparency. Many of the channels we’ve created are specific to work functions like #hiring and #bugs; we also have more “fun” channels like #memes, #music, #out-of-context (for quotes taken -- you guessed it -- entirely out of context), and #stonks for stock tips. We also use Slack-integrated apps to improve the work experience, including Donut. (More on that below.)
#out-of-context message from June 2020: "I love that we were on a Zoom with the founders of [redacted], and the highlight of my day is that I met an Iowan."

Fun Team Activities: Weekly Lunch, Donut, Raccoon Awards, Book Club

  • Weekly Lunch: Every week, we schedule a half hour during which we all join a Zoom call and have lunch together. We’ve instituted a “no checking in on work stuff” rule so that people aren’t asking about how far someone is on a task. Often we talk about things going on in our lives; other times we’ll play games. (One of our current favorites: an online version of the game Wavelength.)
  • Donut: Connecting you with one coworker each week. Each week, we set aside a half hour for connecting with one coworker. We use the Donut Slack integration to randomly group each employee into pairs and “introduce” them. During this set time, we talk about… literally whatever! It immediately precedes our weekly sprint planning, so we often spend the first few minutes of spring planning talking about what we discussed. My first Donut chat, we dove into really deep topics like philosophy and outer space; in the second Donut chat we took a “Which Sex and the City Character Are You?” quiz. Most weeks, we all take a quiz (recently: “Which Hogwarts House Are You In?”) then discuss results. One nice functionality with Donut: you can (secretly) specify if you don’t want to be paired with a certain person.
  • Raccoon Awards: Celebrating wins for the week. Our mascot is a raccoon, which spurred the name "Raccoon Awards." Each Friday, we vote (anonymously via Google Form) to decide who did something excellent this week. The last thing we do each Friday is that our CEO tallies up the votes, reads all of the submissions, and then awards "the raccoon" to the person with the most votes. Since we're remote, we add a raccoon emoji next to the person who earned it. Ties are broken with a randomly selected trivia questions. It's surprising how positively motivating this process is!
  • Book Club: We just started a Roboflow Book Club, in which we all read a book and then discuss it together. Given the size of our team, we each propose a book, briefly describe what the book is about, then vote (again, anonymously via Google Form) to select which book we’ll read. For our first book club, we each had about a month to read Inclusify, by Dr. Stefanie Johnson. We set aside 90 minutes to discuss our thoughts and takeaways. Turns out, 90 minutes wasn’t enough and we keep discussing the book in later meetings!

"Business" Team Activities: Weekly Lunch, Donut, Raccoon Awards, Book Club

Despite categorizing these team activities as either “business” or “fun,” we think our “business” activities incorporate a great deal of fun as well!
  • Stand-Up (w/Weekly Warm-Up). Every morning, we have a daily stand-up where we describe what we did yesterday, what we're doing today, and what blockers we have. It works pretty quickly; every Monday we have a longer stand-up to provide macro-level team updates. For example, we describe what the sales team goals were last week, how the sales team did, and what their goals are for the coming week. We repeat this for all teams.
  • One-on-one meetings. One-on-ones are crucially important to every team. We currently have teammates conduct a one-on-one (abbreviated 1:1) every week, alternating between the CEO one week and the CTO the next week. As we scale, we've discussed having meetings "cascade" so that information flows upward throughout the week. For example, perhaps directors have 1:1s with their reports on Tuesdays, VPs have 1:1s with their reports (often directors!) on Wednesdays, and our C-suite conducts 1:1s with their direct reports (e.g. VPs) on Thursdays. In this case, things flagged to directors on Tuesday should get flagged to the C-suite by Thursday.
  • Sprint Planning. Following the Scrum methodology, we have one hour-long meeting each week where we describe what we'll do for our next sprint. Sprint planning is fairly well-known, so we leave describing sprint planning to the experts.
  • Pioneer: the network for ambitious outsiders. Each week, our team sets explicit goals as part of Pioneer. It's similar enough to sprint planning, but we think of Pioneer goals as "those which must be completed." See some of our goals from a recent week:
A recent weekly set of goals to accomplish, shared on pioneer.app.

Our goal is to do at least those 13 bullet points in the "Planned" section. Each week, we share and update regarding if we met our goals, missed them, or exceeded them. (Spoiler alert: we never miss our goals.) After submitting our update, other Pioneer teams will vote on which updates are more impressive/have more done, which turns into points that each team accrues. Did we mention that we've come in first place in the Pioneer leaderboard for a record-breaking 25-weeks in a row? It's also a great way to source feedback on your team's work and goals to help you keep pushing forward.

These are some of the things we use as a remote team to keep executing against our goals and stay on track! Obviously not everything can be distilled down to one blog post, but we'll continue to share what we've learned moving forward. We'd also love to hear from you what your team does to accomplish your goals!