I’m starting a new job as a CTO of a Series A tech startup in LA and one of the many challenges I’ll face is how to shift the product and engineering team into being remote-first.
The company has been around for about a year and the current ProdEng team is 12 people. They are all currently co-located and I have very limited data on how they work and what challenges moving to remote-first will bring. Needless to say, I’m feeling pretty anxious to jump in and start figuring this out.
Why go remote-first?
There is an immediate personal need that I need to solve for. My commute to the new office is an hour and fifteen minutes. Spending two and half hours a day in LA traffic is just not an option. I have a one year old at home, so time is a precious commodity.
Critically, I made this a key point during my job negotiations, so I have the support from the company leadership. This, in my mind, is one sine qua non for going through this transformation.
I have a phrase that I dish out way too often, and regularly get the ‘seriously, dude’ look from others, so I’m going to have to self-administer it and show that I do eat my own dog food.
Every crisis is an opportunity
I want to use this challenge as an opportunity to not only fix my personal situation but help the whole team. I can’t do this alone, so we’re all going for a ride together. I hope that the pitch of better quality of life, increased productivity, freedom to live in more places, and no commuting will convert most of the team. We will also be growing the team quite rapidly over the next few years, so access to more diverse and high quality talent will be a key part of the sell.
What will be my approach
I’m going to be spending the first month at the office. This will give me a chance to meet the team, build relationships, understand challenges and network with the rest of the company.
During this initial period, beside the normal on-boarding as a CTO of a tech startup, I’ll be focusing on the remote-first topics quite heavily. Figuring out how we work, what our processes look like, how we need to modify them to accommodate the remote-first mentality, etc. is going to mean more work up front, but that’s what I signed up for, so no complaints here.
I’m a huge fan of iterating on pretty much everything, so as the team comes on-board with the idea, we’ll start slow, one day a week, see how it goes and then ramp it up from there. There’s one absolutely key point here, working remotely is an option for everyone, not a requirement. Since we do have a physical office, people are free to use it as much or as little as they want. Having a physical space will also allow us to bring people together regularly for important innovation and planning meetings, as well as social gatherings.
As I don’t have enough room at home for a dedicated work area, I’ve started looking at co-working spaces in my area. Having a good workspace is critical, so that’s one thing I have to figure out sooner rather than later. I’ll probably start with some sort of a flex plan where I can come into a co-working space ten days a month and use the common area. As I ramp up my time working remotely, I’ll most likely get a dedicated desk and potentially a small private office.
I’ve also been doing a lot of prep work. Mostly reading and talking with people who work remotely. Here are some of the highlights that I would recommend:
- Oldie but goodie: https://www.amazon.com/Remote-Office-Required-Jason-Fried/dp/0804137501
- A must read: https://klinger.io/post/180989912140/managing-remote-teams-a-crash-course
- Good tactical advice: https://www.bearer.sh/blog/how-to-make-remote-a-success
- If you have TC Extra Crunch: https://techcrunch.com/2019/12/09/effective-ways-to-ensure-your-remote-team-feels-like-part-of-hq/
- Great practical advice from a remote company: https://open.buffer.com/category/inside-buffer/
- Another great guide from a remote company: https://about.gitlab.com/company/culture/all-remote/
- Pros and cons: https://toggl.com/out-of-office-why-go-remote/
I’m starting the job next week, so stay tuned for a lot more details from the remote-first trenches.