Annie Tsai

Our company has been fully remote since early 2019 (a few months before I joined) to reduce lease expense liability on the balance sheet. We used to have an office downtown Oakland. It was as stereotypical of a bootstrapped startup office you could imagine – small, needed a paint job, kind of smelly, cheap. 

I love seeing the photos from before that time. The team at lunch, collaborating on a whiteboard, at happy hour, laughing together or huddled around a screen very seriously. 

Initially, everyone was grateful for the change. People had been commuting in from Dublin, Pleasanton, and San Francisco. Getting over an hour back every day was a dream. But for our early career employees, the shift eventually proved to be hard. 

We had ambitious and extroverted team members who were energized by being around each other and fed off the energy in the room. When they were the only energy being emitted in the room (besides the computer monitor), the days got longer and lonelier. The work became less interesting and our customers felt further away. We started talking about ways we could support connection and trust, and implemented more casual 1:1’s, all hands meetings, and quarterly offsites so we could get together. 

Our first offsite was in Santa Cruz December 2019. It was a much needed break from staring at the screen all day every day. We got to take those photos of sharing a meal together, collaborating over a whiteboard, and laughed together. It was the first time I had met most everyone in person. We called it a success and started planning quarterly offsites.

Then the pandemic hit. We felt surprisingly prepared with a year of having lived the remote work culture life (although I was definitely not prepared to be going through a complicated pregnancy with my second while teaching my school-aged child while I was helping run a software company). But it was the lack of any physical interaction that eventually took its toll on all of us. 

Managing the team and all of our initiatives with zero opportunity to work in person meant an overinvestment in administrative coordination. Trust was the most important thing – as leaders, we had to trust that the team was working towards the outcomes that they were charged with delivering against. 

We invested in more tools that helped us stay organized and became even more transparent with business planning and metrics. Engineers and go-to-market talked more and releases involved a cross-functional team to test and provide feedback representing customer personas. Our team became more cross-functionally collaborative, not less. It paid off – our company has grown 3x since 2019 while extending our runway by 4x.  Today, we have team members across six states.

So what have we learned about navigating a successful remote work culture? Here are my 5 lessons: 

1. Leadership must believe that remote work can work

This may be the single most important thing. The truth is, if you don’t believe something will work, it probably won’t. Across the board, executives need to believe that a remote workforce can and will deliver or exceed targets, and will do the work to regularly assess what’s working and not and evolve practices and policies to further engrain this belief into the culture. 

2. Systems are in place to establish and reinforce trust

In support of evolving old practices to new, it takes systems, tools, and mutually agreed upon definitions of success to reinforce the above belief. These systems enable the ease of access to information, support accountability, trust and business velocity, and accelerate decision making.

3. Employees know which communication method is best for the topic or problem

Some conversations are better had in person. Others email. Or chat. Or a virtual meeting. Or asynchronously through documentation. Applying the best channel for the topic gets the most productive outcome.

4. Your company culture focuses on and rewards outcomes

A remote workforce that spends too much time focusing on aligning on every single tactic, all the bits and bobs and the tiny details of project execution will simply never successfully embrace remote-first. The culture needs to be able to let go of some of those details and empower your team to run.

5. More people “doing” than “talking”

Let’s be honest – when the workforce has been designed to be top heavy on “driving alignment” as opposed to executing strategy, remote is going to be less effective.

My hope is that more companies choose some blend of remote-friendly schedules. It’s better for working families and better for mental health. But, leadership needs to believe it’s possible – and it definitely is.