Our New SF Office and In-person vs Remote

Over the past two years, we have struggled with our identity of being a remote company or an in-person company. I’m writing this to share our journey of starting remote to now having a 5,500 sq ft SF office with 15 people in-person.

2023

Tennison and I started Truewind in January 2023. After YC and raising our seed round, we wanted to build an in-person company. What followed was months of struggles and disappointment hiring in San Francisco. We needed the engineering resources to keep up with growth, so we tapped out and started hiring outside of SF. Our first engineers were in NY, Denver, Seattle, and Brazil. Despite failing to build our team in SF, we had a tight-knit community of early stage YC founders.

2024

I hadn’t given up. We got a 1,600 sq ft office and kept trying to find the best people to join Truewind in San Francisco. It was pretty awkward for half a year with just me and Tennison in a 1,600 sq ft space. Then, things started to turn. 

Richard joined us in June. Renato visited SF for a month. Jina joined us in July. Anthony and Greg joined in August. Plus a few other valued team members who’ve come and gone, we were 8 people in San Francisco. It was starting to feel like an in-person team.

2025

In January, we had three team members visit and suddenly it felt *very* crammed. It was time for a new office. And that brings us to where we are today:

Welcome to our new office at 577 2nd St, across the street from the South Park Blue Bottle. 2nd Street is hustling and bustling, every seat in Blue Bottle is filled. And in the past month, we welcomed 5 new team members, all in San Francisco. Truewind is now 15 people in SF with offers out to 4 more, all in SF. All are either already in SF or relocating to be with us in-person. We’ve turned the corner. 

My Reflection

Just to be clear, we’re not 100% in-person. We have people across Canada, LatAm, SE Asia, and Europe—all important team members. When the remote team members are working with each other, it works well: Everyone meets on Zoom. When the in-person team members are working together, it’s even better: Go to a whiteboard. 

It gets tricky when the majority of a team is in San Francisco but key contributing members are remote. In fact, it’s harder to have six people in a conference room with two joining individually on Zoom than it is to have everyone on Zoom. People in the room end up speaking to their laptops, and you can’t use the whiteboard because the Zoom participants can’t see it.

You might as well have everyone on Zoom so it is a level playing field and everybody can interact in the same format.

How do I reconcile this? Truewind is a place for the best people to do their best work. This means surrounding them with the best teammates and the best environment. 

For the early employees who joined remotely, relocating to SF remains an ongoing discussion. While I believe it’s simply better to have every employee in SF, I respect the challenge of relocating their family and support system, particularly because they didn’t expect to relocate when they joined. 

With that said, my commitment to building an in-person company has not wavered since the beginning. I’ve seen the transition from remote to in-person and how powerful it is to have critical mass within the same four walls. This means, we prioritize hiring in San Francisco and building together in-person. And our remote team members remain essential to our business. 

San Francisco

San Francisco is a great place to be and it is significantly cleaner than 3 years ago. All trends point to San Francisco attracting talent back into the city. 

• At a macro level, the Bay Area accounted for 11 of the largest U.S. office leases in 2024, making it the third leading market after Manhattan and D.C.

• On a regional level, the industry titans are leading the way. Salesforce and JPM Chase are requiring employees to return to the office. YC is 100% in-person again with in-person retreats, office hours, and more. This means 500+ new startups start in SF every year. 

• On a micro level, Truewind tripled its real estate footprint and all of our new hires are relocating to SF. A small contribution I am very proud of. 

Keep an eye out for an invite to our office warming party. As a way to give back to the community that has given us so much, we’d love to host events. If you regularly host meetups or gatherings, we’d love to volunteer our office space. 

In Closing

Thank you to Samantha Low and Peter St Geme Jr. at Cushman & Wakefield for finding us this location and closing in 3 weeks—incredible! Fun story: We met on X when Samantha posted this cool phone booth gondola. Sam and Pete were a pleasure to work with; let me know if you’re looking for an office space and want an intro to them. 

Interested in learning more about Truewind and our AI-powered solutions? Chat with our team to get started.