How I found an awesome remote only job

Posted on Tue 28 November 2017 in Jobs


It's been over three months since I left my position at Caterpillar, but leaving that job wasn't as simple as finding a position and changing jobs. Since my initial post that I was changing positions, I've gotten questions from several professional contacts that were also looking to move, but weren't entirely sure of the process I used to find my new job. I hope to answer some of those questions with this post.

New Job Criteria

One of the advantages I had during this search was that I had a job already. This allowed me to hunt for a job at my own pace. I didn't need a new position immediately. The slower pace also let me set my own criteria for what I wanted in a new job.

Full time work from home

At Caterpillar, I worked from home one to two days a week. I did this for several years and enjoyed it. I found that I was much more productive. I was able to focus on the work that needed to be done that day because the distractions of working in a cube farm weren't present. I didn't hear the side conversations that I wasn't involved in. I didn't get the "hey can you help me" questions that could be solved with a few seconds of trying some new code. I was able to concentrate on the task and not context switch frequently.

Additionally, the drive to and from the office was consuming almost two hours a day. In the winter, this was brutal. I was leaving as the sun rose and getting home well after it had set. I wasn't seeing the family.

My most important criteria was born from these two. I wanted to be able to work from home, full time. I was not opposed to the occasional yearly get together, but I didn't want to go into an office on a regular basis.

Pay and benefits must improve

Caterpillar had great benefits. I don't remember ever worrying about health coverage, or prescription drug coverage. Pay was "industry average", which always seemed a bit lower than what sites like said I should make. Part of this was due to the yearly bonus I was eligible for. This was dependent on the business performance and not guaranteed. It also fluctuated a lot. The fact that Caterpillar went through nearly five years of poor market performance didn't help with those bonuses either.

A new position would need to meet or exceed the health benefits I had. The pay would need to improve too. Working from home would have the advantage of not paying for gas for the car as frequently. It'd also reduce the maintenance costs of putting so many miles on the car.

Something challenging

A new position is going to bring new challenges. It's new. You don't know the job. But, I wanted it to be challenging after I made it over that initial period of adjustment. I started looking for a job that would utilize my programming skills, leadership skills from the projects I've led, and maybe some of the community management skills I had from Team Vipers and various StackExchange communities I participate in.

I had my initial, if broad, criteria defined. The next step was to start the hunt. I utilized several sites to help with the initial search and to help narrow down the list of companies I'd really like to talk with.

  • remote|ok - A job board that updates throughout the day, yet doesn't have thousands of postings. It is specific to the "IT-ish" world. This was helpful in finding companies that are open to remote jobs, because I'd see those companies listings repeatedly over the course of my hunt.
  • We Work Remotely - Another "IT-ish" job board that updates one or two times a day. It has multiple categories of jobs and usually is pulling in positions from other job boards. I preferred using this over the source sites because this had a much smaller set of jobs and was restricted to my area of interest.
  • Stack Overflow Jobs - I have a love/hate relationship with Stack Overflow Jobs. On the one hand, it had so many UI/UX issues. On the other hand, it makes it really easy to find remote jobs and narrow it down to only jobs I'm interested in. This is where I eventually found the posting for the job I took.

UPDATE: Stack Overflow Jobs shut down in March 2021.

If I'm being honest, my search for a job took over eighteen months. I found several jobs that were interesting and that I applied for, but the process was slow. There were several false starts, several job applications were ignored, and several interviews that didn't move forward at either my choice or the company's choice.

Keeping it all straight

I put out a lot of job applications. This meant that I needed to adjust my resume and cover letter to each company. I needed to keep track of when I applied, who I interacted with, when interviews were scheduled, and when to give up on a job.

Enter: Trello

Trello Job Search Board

  • Prep: This is a reminder to update resume and cover letter for each position, and a list of the labels I utilize. The colored labels made it easy to identify the current status, and whether this was a local or remote position. After searching for about nine months, I started to consider office positions in a few specific cities.
  • Interesting Positions: All new jobs I was considering would go here. It'd consist of a link to the job posting. This was made really easy by utilizing a bookmarklet provided by Trello that would send any link to this list on this board.
  • Companies to watch: As my hunt continued, I found several companies that seemed interesting or that had expressed interest in my skill set. I set up links to the job pages for each of these companies so that I could see if anything new and interesting was posted.
  • Submitted applications: After updating my resume and cover letter, filling out the application forms, and pressing submit, a job posting would be moved from "Interesting Positions" to "Submitted Applications".
  • Interviews: When a company liked an application and scheduled an interview, I'd move the card to this step. Additionally, I'd add a comment with the name of the people I'd be talking with - Human Resources representative, technical leads, managers - so that I knew who I'd be talking with.
  • Recheck opening availability: If a card sat in "Interesting Positions" for a period of time, I needed to check if the position was still available before finally submitting an application. There were many times that I'd mark a job as interesting and then never apply. This list helped keep the viable list of positions down to what was still available.
  • Cold Opportunities / Rejections: Just as I ignored positions, my applications were ignored many times. Other times, an interview process would just fizzle out. These seemed like the company didn't want to send a rejection notice and hoped that ignoring me would provide a hint. It was unprofessional, and I wouldn't look at those companies again. Other times, official rejection responses would be sent back. I appreciated these, even though they were rejections.

Butler for Trello

The last list on the board was Butler for Trello. This is the system that automated a lot of the moving of jobs through the process and applying proper labels. When a new job was added to the "Interesting Positions" list, a due date was added for one month from now. Triggering off this due date, the butler would move cards to "Recheck" if the due date was exceeded.

When a card was moved to "Submitted Applications" the due date was changed to be three weeks from now. The thought here was that if I haded heard from the company in three weeks, I was probably being ignored and thus rejected.

This automation helped keep the board clean and usable. I was always presented with a list of openings I was interested in that were current. Moving through the interview process, the cards would be moved if a period of time was exceeded. I didn't need to remember to move stuff based on when I submitted an application, or when the last interview was. It just happened.

It was amazing.

Getting the job

As I said above, this was a long process. That list of cold opportunities and rejections is pretty long. I talked to a lot of different companies and went through a lot of different interviews. Eventually, though, I found a job advertising a Senior Integration Tester at a new start up.

The interview process consisted of 4 interviews - one with the Senior Vice President of Development, and three individual interviews with team leads (my peers). I also needed to submit a project demonstrating how I'd test the API.

The interviews felt like conversations. We discussed my project. I had to defend a few decisions, but there were no wrong answers. Everyone was professional, yet personable.

After all of this, an offer was presented and after some last minute "do I really want to make a big change in my life" doubts were squashed, I accepted. I love the job.

- is a father, an engineer and a computer scientist. He is interested in online community building, tinkering with new code and building new applications. He writes about his experiences with each of these.