Getting a Job in 2026

The job market is tough right now in tech. You hear about it everywhere. Whether it's due to AI, over-hiring due to ZIRP, or *waves hands broadly* the economy, getting a job is a journey these days. This is how it went for me.

I recently wrote about automating my actual search process, but for catharsis I wanted to go into a little more detail. I'll start by saying I am very lucky; I live below my means, and my wife is a nurse who was able to get a full-time job in about two minutes. I'm extremely thankful that this gave me room to breathe.

Challenges

It took me about four months from the time I was laid off to accepting a new job offer. In that time, I never really rested and enjoyed the time off. Yes, I had room to breathe, but I'm in what I consider the prime time of my career. I didn't enjoy spending that effort looking for work because I wanted to work on real problems, especially since I'm so passionate about applying AI these days.

I purchased LinkedIn Premium and it showed me how many people were applying to the same jobs I was applying to. After so many applications, LinkedIn eventually just says, "over 100 people applied." Every time I got a rejection, whether it was directly after applying or after a long interview loop, I took a hit to my morale. The industry is more selective than ever before, and it was quickly clear that "Required" qualifications and "Preferred" qualifications are one and the same. 

These rounds of interviews are very long. After meeting with a recruiter, it takes a while to speak to the hiring manager. Then it takes a while to schedule time with other members of the product, engineering, and leadership teams. Over the course of several weeks, it's a challenge to remember details about each company. Taking copious notes helped. The larger the company, the longer and more formal the interview loop. I learned to love smaller companies even more.

Even with the mindset "my job is finding a job," it was hard to find time to actually search for a job. Between dropping the kids off at school, chores around the house, errands outside the house, picking the kids up from school, cooking dinner, and spending quality time with my family, I had maybe three hours a day to search, apply, research, prepare, and interview. Automating that process helped a lot.

What helped

The best thing I did was also one of the first things I did shortly after getting laid off: I hired a career coach. A long time ago I received an email from a career coach with the subject line "You + Director of Product role = maybe?"

I generally dislike this kind of cold outreach. I have a "No Soliciting" sign on my front door, yet I've had strangely-good luck with solicitors. Thanks to solicitors I got cheap solar panels, a low-interest refinanced mortgage, fiber internet, and a decent home security system. Maybe I should take that sign down?

The reason I pulled the trigger and laid down the money is because I know I'm good at being a product manager, but communicating that in an effective way for an interview is a distinct skill. Career coaches know what lands and what doesn't. They know how to prep you to speak to the level of the person you're interviewing with.

I learned to break out of my humble shell and clearly articulate the value I can bring to a company based on what I've done before. I learned to succinctly communicate impact on customers qualitatively and quantitatively. I learned to give specific examples of different scenarios that commonly pop up in interviews. I learned to address follow-up questions before they're even asked. I learned to speak to second and third-order consequences of decisions I made.

As a bonus, all of these skills will help me in my career going forward. I didn't change fundamentally as a person or a product manager from the beginning to the end of my job search, but my communication skills improved overall.

I spent a lot of time on cold outreach. It appears other dislike it as much as I do. As I detailed in my other post, standing out is a real challenge. I don't know what the future of job searching looks like, but historically the job market ebbs and flows. Hopefully this was the most difficult search for me.

Highs and lows

Early in my search process, I was flown out for an on-site interview. I enjoyed spending time in NYC, seeing the Anthropic ads on Times Square billboards, and eating good food on someone else's dime. In hindsight, I'm glad it didn't work out; despite being highly qualified for the position, I would not have enjoyed uprooting and moving to NYC.

After one interview loop, I was told they were excited to move me forward with an offer. After a couple days, that offer was rescinded. That one hurt. 

Near the end of my journey, at the end of an interview with an engineering manager, he said, "Have you had media training? You're very polished." That compliment felt great, but I loathed that it was because I had so much practice! 

One interview loop was directly started because I wrote something that reached the front page of Hacker News. That was a great unexpected benefit of just writing for myself! 

A happy ending to my story

At the end of my search, I received two offers for a Director of Product role. Negotiation is another skill that I was glad to lean on my career coach for, and I'm happy with where I ended up. For both companies, I was introduced to the position via networking. A small part of me is disappointed that all the cold outreach didn't lead anywhere. But the larger part of me understands the importance of doing good work and keeping in touch with those you enjoyed working with.

To celebrate, once I accepted a new role I decided to finally build my Christmas gift.