Remote Work @ SidelineSwap

Like most companies, SidelineSwap went fully remote when COVID-19 disrupted life as we know it back in March. The transition for us has been relatively easy. We’re a small team and we’ve always been very flexible when it comes to our work-from-home policies (prior to COVID 20% of the team already worked remotely). That meant we already had most of the tools and processes in place to enable a smooth transition, but we’ve significantly improved those processes over the past few months.

We’re finding that our team is more productive than it’s ever been, and with hours back in our days, many of us have found better work-life balance. The lease on our office in Boston was set to end this summer, so we quickly decided that we would work from home for the foreseeable future.

When things do eventually return to normal, we’ll be a remote-first company. We may open a small “hub” in Boston (and eventually elsewhere) for team members who want to work from an office, but that will be optional. If team members currently in Boston want to move, we have no problem with that. And going forward all hires will be remote. The only caveat is that we’d prefer people continue to work on east coast hours.

Remote works well for us because we have a strong culture built on trust, but also because we’re constantly fine tuning our processes and tools to enable efficiency and transparency. Here’s what I mean by that…

Trust is deeply rooted in our culture

Remote works best when you have a high degree of trust built into your culture. We hire great people who work hard and are passionate about their crafts. By having the right people on the bus, we don’t need to spend time thinking about individual productivity.

We set goals, and revisit them often

We’re are very data-driven and very goal-driven. We use quarterly OKRs to set clear objects at the company and departmental level, and establish key results that are measurable and transparent. By frequently aligning on the long term vision and medium term objectives, team members can prioritize their work effectively.

Communication tools and best practices are clearly established

Slack is our primary form of communication internally. Slack is well organized to enable transparency without creating too much noise. Team members can snooze slack alerts outside of core work hours so that it’s easy to escape when needed.

We use Google Hangouts for scheduled meetings and ad-hoc chats. We’re quick to jump Hangouts as needed, especially when a Slack topic is getting too noisy or context is getting lost. Every team member should be able to identify this as it happens.

For communication within product and engineering, we use Jira and Confluence. Larger specs typically start in Confluence before they’re broken out into Jira tickets, while small features and bug fixes start in Jira.

Our UI / UX team shares wireframes and designs in Figma, and we use comments within those tools to discuss feedback. We use Figjam for whiteboarding and collaboration.

(We almost never use email internally.)

You own your schedule (and disruptions are ok)

We’ve always been pretty flexible when it comes to accommodating people’s personal lives — whether it’s a doctors appointment, a work-from-anywhere week, or leaving early to coach your kids games — as long your work gets done. It’s easy for us to do this, because our team works really hard and enjoys what they do (back to our strong foundation of trust).

Family always comes first, but especially in times like these. When your nanny cancels or schools close, we get it. We’re cool with kids (and dogs) popping in for a call. And if you want to wear your pajamas until 3pm, no one is going to think twice.

A commitment to just the right amount of meetings

Huddles: Each team starts their day with a 20 minute huddle where we sync up on priorities, and clear blockers. We try to make these light / fun, but efficient. Longer conversations that don’t involve the broader group should be “parking lotted” until the tail end of the meeting.

Highlights: Every Wednesday afternoon, we host a company all-hands meeting. Anyone can use this time to demo a project they’re working on. We use it as an opportunity to share progress, solicit feedback, and brainstorm where a project could go next. We also use this time for updates on KPIs so everyone knows how the business is performing and how we’re tracking towards OKRs.

1-on-1s: Team members do weekly or bi-weekly 1-on-1s with their manager. These are a combination of status updates, personal check-ins, and career development.

Donuts: Each week, team members are randomly matched for a 30 minute virtual coffee. There’s only one rule in donuts… no work talk.

Product weekly: On Thursdays engineering leads meet with business stakeholders in a highly collaborative, broad ranging discussion of all the projects we have in flight. This meeting typically has a strict agenda for status updates shared by each project lead, and a set of deep dive topics at the end.

Sprint Planning: Our engineering team works in weekly sprints. Every Friday morning the team spends 30 minutes to an hour quickly recapping last week’s sprint, and reviewing work planned for the coming week.

Team leads blog weekly updates

When possible, blog it instead of scheduling a meeting to share a status update. Each week, department leads share a detailed status update. All team members have access to these. Conversations often take place within the comments of a document.

Meetups are encouraged, and quarterly retreats are a lot of fun.

Being remote doesn’t mean we don’t want to see each other. In fact, one of the toughest parts of going remote was not getting to see the team.

With some inspiration from the teams at RemoteYear and Basecamp, we committed to quarterly retreats. So far, these have been 3 day outings in a social distance friendly setting (like a large tent outdoors) and have been within an hour drive of Boston. Team members from out of town stay overnight. These serve as an opportunity to step back from the day-to-day and think about the longer term vision, as well as have some fun. (Matt & Alex are the reigning lawn olympics champions.)

For the team in Boston, it’s easy to meet up in person for an afternoon brainstorm, lunch, or coffee.

We’ll continue to refine this over time, and eventually some team members may end up back in an office if enough of us want to do so. We imagine this will be a smaller “hub” in Boston, or other locations where we have a cluster of employees. But the future of work at SidelineSwap is remote by default, and we’re excited about all the opportunities that will bring.