How To Build a Remote Startup

What it’s like to work at Osano.

Osano is a fully distributed (remote) company. Although we have an office address, it is primarily the place we pick up packages and occasionally rent a conference room.

In the past, I’ve written about how using the phrase “remote” does a disservice to describe the modern distributed company. Work is remote if you have a central office, work is distributed if the entire company operates this way.

When I built my first real company in 1997, we started out with offices, but due to some lean months early on, and some key hires who were in other parts of the country, office space was seen as something of a luxury. At that time, there was no co-working, and getting a lease was not easy for a broke 20 something. In the mid-2000s, when our business was doing 50M in ARR with a full-time staff of fewer than 20 people, I was often asked how we operated. Sadly at that time, the best we had for remote communication was phone calls and ICQ (a precursor to Skype/Slack/WhatsApp)…. and boy oh boy did we use ICQ but we didn’t have many processes.

Fast forward to 2020, and it is now possible to fully replicate the in-office experience. Even with great tools, building a distributed team requires a great deal more discipline and process early on in the company than if it’s 5 people sitting in a WeWork together. Osano, as of this writing, is a team of just under 30 people. We get to hire for skills not location and we get to hire from the massive ocean of North American talent rather than the pond of Austin.

Our view of team building is that we are building an army of high performers. The keyword there is “team,” not family. We are working together for a purpose, not goofing around to pass the time until happy hour. We operate in a highly structured, disciplined way. This is how we do it at Austin, Texas-based Osano:

1. Do not hire more than two time zones away. Crossing substantial time-zone differences to support a customer with an occasional request is hard enough. Working with team members who are just 2 hours ahead or behind creates challenges for coordinating meetings. So suffice it to say that crossing substantial time-zones differences for full-time employees is a show stopper. I tried, and it doesn’t work. Save yourself the trouble.
2. The Standup is Gospel — Every single morning at 8:30 AM in the time zone you live, StatusHero will ask you a couple of quick questions. At 10:30 Central time, everybody’s answers are posted in a shared standup channel. Everybody, including the founders. These standups create transparency into what everybody is working on so that nobody needs to be micromanaged. Miss a standup and we notice, miss two and we’ll have a conversation, miss three, and you’ll be looking for work elsewhere. Aside from transparency, this also ensures that everybody is butts in seats working at the beginning of the day.
3. Mark time — We mark time in weeks, and we do it with bookended all-hands on Mondays and Fridays. Monday morning at 9:15 AM sharp, every single team member is on a Zoom sharing our prior week’s accomplishments, mistakes, and what we hope to achieve this week. I also use this as an opportunity to give a repetitive 5-minute speech about what we do, who we do it for, and why we are doing it. Fridays at 2:30 PM are product-focused, one-hour Show & Tell Zoom meetings. This meeting serves as a platform for anybody who needs to share all-company information. However, practically it’s mostly engineering & product sharing what features & fixes from the current week. Engineers love showing off their work, and doing this helps keep support, sales, and marketing up to date on product changes.
4. Video not Audio — Every single Zoom meeting is a video meeting, with no exceptions. We’re replacing the office, not hiding that we’re human. Is it weird getting used to lots of video meetings? Yes, but no stranger than getting used to a new office and meeting new people. Some peer CEOs at distributed companies prefer Google Meet, but we had too much trouble with prospects being able to get Meet to work, whereas Zoom has become ubiquitous. Zoom is more expensive, but it is much better, in my humble opinion.
5. Channel, not DM — Unlike some companies, we are not militant about how Slack is used, but we do ask that the team use channels rather than DM for any non-private conversations. We do that because having a searchable record of what people talked about is a big part of Slack’s value prop, and it comes in handy to avoid people asking duplicate questions. Threads are how the channels stay manageable. As well, we have a handful of team-specific channels, a bunch of logging channels (e.g., social media alerts for brand mentions), and two special channels. The special channels are #announcements and #tech-work. Announcements are read-only except for admins. Tech work is a public channel, but the only people who can talk in that channel are the @engineers — we have a separate #tech-talk channel where the team can communicate with engineers. This gives the engineers autonomy and the ability to put on their virtual headphones while remaining part of the team.
6. Structured Onboarding — We used Asana for some time but found that from a price and purpose-built perspective, Donut was a much better solution for onboarding. Role dependent, we have additional mandatory training (e.g., HubSpot certification), but for HR training, we use JustWorks and its built-in bias, diversity, and harassment training. For security training, we use Ninjio — we don’t love Ninjio, but it works.
7. System of Record — Most roles have a system of record in which we can track progress and projects. At Osano, our engineers use Club House and GitHub, marketing and sales live in HubSpot, support lives in HelpScout, product lives in Asana.
8. Get FaceTime — The goal of distributed work isn’t to avoid seeing eachother. Not all of the team are all introverts. With all of the money we save on offices we can afford to take the team on some awesome getaways that would otherwise be out of our budget. Twice a year we meet up for a few days in one location. The team votes on locations, cuisines for restaurants, and books their flights on LOLA — then our shared assistant from Zirtual takes care of putting together an amazing itinerary. These events are not hokey ropes courses and trust exercises, but rather they are quality time hanging out at the beach, enjoying great meals, and participating in some (actually) fun group activities like bowling & going to baseball games.

These are just a few of our approaches to managing a distributed team. Our team is happy and productive. Nobody sits in rush-hour polluting the planet while their bloodpressure rises, and rarely does anybody prefer to leave for lunch. We get to work beside our pets, walk the kids to the bus, and make their snacks after school. We are there to help with homework. Nobody’s packages get porch pirated because we are there to answer the door. Our coffee is made precisely the way we like it. The temperature in the office is exactly what we each prefer it to be. The chair at our desks are the ones that fit us. Our comfy shoes is our work atire. We make that mid-morning yoga class. The music is whatever pleases us and it’s as loud as we want it to be.

Our approach like all things in a startup is constantly evolving, but at the end of the day, our process works for our team; perhaps it will work for you too. Oh, and we’re hiring.