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What Goes Wrong With a 100% Remote CTO

Remote first means, "now we have a remote employee we will pretend that every team member is remote and work accordingly".

What Goes Wrong With a 100% Remote CTO

I joined Searchspring in 2019 when the CEO, Peter Messana, asked me to help him join two ecommerce companies together (read more about these struggles in a future blog post). The company’s headquarters are in San Antonio and at the time, the main engineering departments were in Denver and Toronto. I’m located just off the coast of Canada on Vancouver Island.

I started at Searchspring five months before the pandemic forced everyone in the world to suddenly be remote. Fortuitously, I was immediately invested in the problems that the pandemic would subsequently throw at us. This blog post will talk about the problems with me being 100% remote.  

Remote First 

A good adage to live by when you have a single remote worker is that a department or individual will not succeed if you are remote-friendly. Your department and/or company has to be remote-first. The distinction is important.

Remote-friendly means, we have a remote employee and we tolerate it. Remote first means, now we have a remote employee we will pretend that every team member is remote and work accordingly. Fortunately for me, everyone in engineering reports to me so I could make sweeping changes to allow for this style of work. Fortunately for our company, these changes gave us significant resilience during the pandemic. 

Problem 1 – The Whiteboard

Comic - Man: Don't clean the whiteboard in the conference room. It has my project timeline. Janitor: I can't promise that. I slip into a sort of zombie reflex mode when I do this job. Man: I envy you. Janitor: Would you like a few minutes to say goodbye to your timeline? 

An unfortunate, and difficult thing to put on the chopping block, is the whiteboard. A whiteboard is a great tool for collaborative brainstorming and problem fixing and is hard to give up. The problem with a whiteboard and remote work is that no matter how HD a webcam is, pointing a laptop at a whiteboard does not allow the remote employee to interact with the discussion that’s happening at the board. People stand in front of the whiteboard and it’s impossible to move it to get a better angle. As people move around to go up to the whiteboard, the distance from the microphone changes and loses important snippets of conversation and we can’t point to something specific on the whiteboard. When the meeting is over, best case, you can get a picture of the whiteboard post into slack before eventually becoming lost forever.  

Our team decided on Realtime Board (now called Miro), as a really great whiteboard simulation. In Miro, users have shared cursors so everyone can see what is currently being looked at and so much more. As our team became familiar with the tool, it greatly helped our communications density and velocity and we now use it as a standard part of any project. 

Problem 2 – Timezones

Comic - Boss on the phone: I'll call you back in one hour, Irene. You're in a different time zone so you'll get the call in...umm...three hours. Really? You're three hours ahead? Then that means...whoa! You're freaking me out here.

Searchspring has development in Krakow, Toronto, Calgary, Denver, San Antonio, Colorado Springs, British Columbia, California, and Portland. Our teams are split across these cities and this can pose a couple of problems. 

  1. At all times, engineering wide meetings are outside of office hours for someone.
  2. Some teams are split across time zones making their working-hours overlap smaller than normal. 

To combat the first issue we changed meeting times around on a regular cadence to make sure the pain either getting up early or working late is split. For example, if there is a monthly repeating meeting, one month it will be at 7am Pacific and the next it will be at 7pm Central Europe. The lucky people in the middle don’t have to change their working hours.

Specifically for me, I use the Google Calendar feature to set my work hours differently per day. On Monday and Tuesday, I work 6am – 2pm Pacific and on Thursday and Friday I work 9am – 5pm Pacific. Wednesday’s I leave open and decide what I’ll do with my time at the beginning of the week and weigh factors of where I want to spend my time that day. Starting work at 6am is a bit of a grind, but it is lessened by getting some really good lamps that brighten my work room.

Problem 3 – Disconnection

Comic - Man: I significantly increased my visibility at work today, Dogbert. Yesterday I was invisible to my management. But today I'm known by all. Dogbert: You screwed up, huh? Man: Oh yeah. Big time.

A large part of the role of Chief Technology Officer is to ensure effective communication and identify and solve issues. Having an engineering team split over multiple time zones makes it easy to get disconnected from the daily struggles of team members. Combatting this lack of visibility requires a multi-pronged approach.

  • Read Everything

A large portion of Searchspring communication is in Slack and we push to have messages in public channels. I join nearly every channel and read most of the messages. This gives a scattergun approach to what is happening in the engineering department and our organization as a whole. This habit also allows me to cross-connect departments where things are getting stuck.

  • Hierarchy

 Making sure we have good team leads, directors, and a solid Vice President of Engineering provides insight into what is happening and if any troubles may be on the horizon.

  • Skip Level 1:1’s

The Searchspring engineering department has quarterly 1:1’s with employees who report more than one level below the next person. This is a good temperature check to gauge general troubles, where managers are struggling, and offers help in career development.

  • Town Halls

Engineering and product get together once a month for a presentation of what we’re doing and a space to have an Ask Me Anything where anyone can answer burning questions anonymously.

  • Manager Review Surveys

A quick ten question survey of 1-5 scales about an employees manager that gives a manager and me insight into where we can do better.

  • Travel

This didn’t work out because there was a pandemic but we hope to get back out there in 2022!

  • Coffee Dates 

Searchspring has a system where we are randomly connected with an employee outside of our department for a 30 minute coffee date each month. During these “coffee dates” we learn about that person’s roles, struggles, life ambitions, and much more.


There are many ways the Searchspring engineering department increases connectivity, but those will have to wait for another blog post.