Relentless Review + Learnings from an older tech jobseeker
Last year I found myself on the job search in my middle 50’s. It was the first time I had ever had trouble finding my next gig. Technically, I was very proficient, but I also was looking for a higher level management position and that, due to my family needs, relocation wasn’t an option. That left me with the option of local companies or fully remote work. When I was younger, if I got an interview, I got the job. Now I found myself stuck. I reached out to have my resume rewritten and it got marginally better responses, but I still was getting ghosted a lot. I realized that recruiters were not helping me - they worked for the hiring company and I needed to find a team to be in my corner.
I reached out to a company named “Relentless” - they charged a high initiation fee and had expensive pricing but ultimately helped me get a job. In the process of getting this job, I learned why what worked for me in the past didn’t work anymore.
- The goal of your resume is to get you in the door - treat it like marketing material not a biography.
This was one of the most important thing I learned. My resume read like every tech resume I had ever seen. It was full of technical details about projects, languages I knew, Operating Systems, etc. but it didn’t say the right things. Earlier in my career, this was important, but now it wasn’t so much. What I needed was a resume that caught recruiter’s eye so that they would want to jump on the phone immediately. That meant that my summary needed much more than a bland description of a “manager” position. I had worked at NASA, Capital One, Corning, Anthem, and more but none of that leapt off the page. Additionally, I needed to show the business value I brought out from my projects.
With a resume that is built for marketing, things began happening
- Once you get to the screening call, the goal is to get to the next interview
The screening call is just a filter. Your job is to progress the sales process. This means you need to ask questions as much as you talk about your history. Find out what they are looking for in the person filling the role and then you will know how to sell yourself. To sell yourself, you need to pull stories out of your history that show your ability to meet their needs.
- Stories are super important
Dry facts won’t progress you as well as detailed stories. Stories are memorable. I learned to pick out various examples from my history and have a good story to tell. For example, in my job at Anthem I had to design a new architecture for a team and I needed the team to accept the design. I had two people on the team with seemingly opposite goals. John was a former Navy guy and really liked rules. He did not want to make design decisions, he wanted rules to follow and he would happily follow them. Jie felt that to be successful for our customers meant to be super fast. A bunch of rules would slow him down. There was a third person in the group who was very well respected and wanted to be seen as the smartest person on the team. These observations made me design a system with just enough rules but not to the point of overkill. I took that design and had the 3rd person try it out. When he approved and promoted it, John and Jie were 100% on board. In fact, John came up just a few weeks later and told me how much he enjoyed coding the new design because it let him make his code better.
A good, detailed story helps people remember you and shows you really did the work.
- Job titles can be handcuffs
Your job title doesn’t have to be the one that the company assigned you. If you were doing the job of a manager, but your company job title was individual contributor, don’t feel that you have to use the company title. It will hold you back. Likewise sometimes companies will create job titles that are “unique”. These titles will not pass through the automatic resume screeners. Use industry standard titles to get around the filters.
- Be honest, but remember job hunting is a sales activity
Don’t lie on your resume. Absolutely. However, you must put yourself in the best light possible. In tech, for example, our work isn’t always about making something that is sold - many times it’s about saving money. Tech people often do not recognize how to accurately quantify their contribution to the company bottom line. This is certainly something I learned during this process. My projects had large impact on the company bottom line over the projected life of the project. I needed to understand how to estimate those numbers and they really helped sell me to recruiters.
Think about it this way, which is more captivating:
My team developed a logging system in NodeJS that had a 700ms response time
Or
My team developed a logging system that is projected to save 10MM.
The second sentence will grab the eyes of reviewers because it puts the work into how it relates to business value. How would I come up with that amount? I estimated the cost savings over the course of 7 years - not just hardware, but time savings. In a sales position, you will see them talk about 50MM contracts, even though that contract spans multiple years - tech people need to learn from this.
So, as you get older in the tech business, you must learn to adapt. What used to work for you as a younger engineer, may not continue to be successful. There are fewer positions in the job pool at the higher levels, and so by changing your approach, you can have a more successful job hunt.
Posted Aug 13, 2026, 4:36 PM UTC