Deciding to leave

It look be a long time to mentally get to a place where I wanted to leave my former employer. It could be summarized as a bunch of smaller pain points that slowly accumulate into something severe. A few things that really cemented the decision was the departure of some of my closest friends and respected colleagues, feeling undervalued in my role, and an inability to change teams internally to continue growing.

Preparing for interviews

Advent of Code, which I have been doing for the past few Decembers, was the soft start to interview prep. As I got into the meat of it, I religiously used Leetcode and a physical copy of Cracking the Coding Interview. Interview Cake also provided a light introduction to topics and some new questions. The best preparation was actually doing interviews. I tried to schedule my interviews so that the ones with companies I was most interested in were later to so I could be as prepared as possible.

Timeline

Between Thanksgiving (traveling to Morocco and Spain) and Christmas (biking from San Francisco to Los Angeles), the holidays were not the best time to mentally prepare for interviews. Therefore, most of December was setting up technical screens for January and ramping up the studying.

In January, there were several major circumstances that fought for my time. First, I had signed up for an online programming course that started that month and lasted 24 weeks, in part to help prepare and more generally to learn, but the lectures and assignments ended up taking up a good amount of time without contributing much additional knowledge for my interviews (~8 hours/week). Second, I had to move at the end of January, which was not great timing. Instead of being able to focus on the weekends on studying, I was making trips to check out new apartments, finding roommates, and shuttling stuff between places. Third, I was in the middle of a big project at work which was needed to be code complete at the end of January. The stress of having to do all of these simultaneously meant that I could not procrastinate and I was as quite effective with my time that month.

It also meant that my on-sites happened primarily in February. Although I had tried to group my interviews together, it was difficult to foresee how long certain companies would take to get back to me. I concluded the search on 2/25, weeks after I had originally anticipated.

Reflecting on my calendar, I spent nearly every day in January and early February talking to some company. In total, I spent 18 hours talking to recruiters or potential managers as part of the interview process, 17 hours in technical screens (primarily over phone or video), 43 hours in 8 on-site interviews, and 12 hours team matching post-offer.

Making the decision

The most important, non-negotiable criteria for my next role were:

People and culture
Learning opportunities
Product team (after being on a Growth team for the past 2 years)

These ended up being rather broad criteria and subjective to evaluate against.

I was deciding between 6 companies. In no particular order:

Company A: I originally put this company on my “safety” list, but they came in higher than I expected with compensation. However, nothing stood out to be as particularly interesting about working here during the interview process.
Company B: I was referred by a friend who vouched for the great work culture - and I definitely noticed it in my interactions. I was blown away by the technical caliber of my potential future coworkers, but the compensation was too low and risky as an early startup.
Company C: Similarly, I was referred by friends. It was clear that leadership was thoughtful and I liked the direction they were heading as a mid-stage startup.
Company D: A large company that I have long admired, and I got matched with a team where a friend could provide insight into. It fulfilled my core search criteria, but meant giving up some “nice-to-haves” such as unlimited PTO and being in the city.
Company E: I had seen this company grow tremendously from the last time I was doing interviews and had faith that they would continue in that direction. However, I wasn’t particularly interested in the team and upcoming projects.
Company F: Another company that I am a regular user of the product and will have a bright future innovating. However, the team matching process took so long that I never got to the end of it.

I ended up choosing Company D. I had to ask countless friends for their input and even still vacillated between options. In the end, any decision could be a right decision; it was a mostly gut feel as to where I saw myself, so I’ll avoid overanalyzing. I can’t wait to see how I grow in my new role :)

Insights

Be willing to say no

I should have turned down interview requests earlier. For smaller startups, there simply is not much information available about them on the internet. Even after talking to CEOs and whatnot, it could still be difficult to understand what I would be getting into. If I were to do this again, I would have focused more on companies where I had insight through my personal network. For others, I went midway through the interview process and had to withdraw simply because I had too many to juggle. After having industry experience, I can afford to have strict search criteria and be extremely selective about opportunities to pursue.

Timing is key

As mentioned above, one company made an offer, but never followed through with team matching. Another responded to my application 2 months too late, as I wrapped up my job search. Yet another was looking for a team lead and did not have a need for an engineer at the moment. As with any other criteria in the job search, I won’t take it personally if it doesn’t work out this time, but I’ll keep tabs on companies I’m still interested in for next time.

Take meticulous notes

Some days, I talked to 3+ companies back to back. It’s a lot to juggle all of the information thrown at you and continue to sound (and be) interested by re-sharing information you know about their company. It is also helpful to keep track of questions (I asked and was asked) and trends to find areas to improve on, topics to study for the next one, etc.

Strategically negotiate

I ended up applying to a wide range of companies because my search criteria was broad. A comment that I heard from recruiters/hiring managers was that they were willing to match offers of similar-size and similar-stage competitors. My list meant that it was difficult to compare apples to apples in the most effective way. I was still able to negotiate to a compensation that I am more than happy with, but next time, I will be more strategic about how I choose companies to apply to.

Thanks

Shout out to all my wonderful friends for sharing their interview experiences, introducing me to their companies, and moral support throughout the decision-making process.