“Target the right team, not just the right company”: Lessons from a successful COVID-19 era job search

Michael Senkow
6 min readMar 4, 2021

Over my career, I’ve had a few dumpster fire interviews, but I’ve only had one interview during an actual dumpster fire.

As the photo below can confirm, this isn’t a joke. This actually happened.

View from my old apartment during one of protest nights on Capitol Hill.

This was the scene outside my window in Seattle on September 23rd. Inside, I’m trying to relax after a day of work and prepping my portfolio for upcoming job interviews. Outside, I’m experiencing my second dumpster fire in one summer.

These things happen, I guess, but it’s not the sort of event you want to deal with when you’re also trying to convince a hiring manager you’re the best fit for a role the next day. Despite all this, only 5 weeks later I’d be starting at Facebook.

Honestly, nothing that big. But when you’re also in the middle of 5 companies job interviews it can be good to layout ways to cope with the world’s added stress.

The experience marked an auspicious end to a fraught, six-month job search that taught a lot about both what I wanted from my career and how to obtain it. Here are a few things I’ve learned, and how you can apply them to your own search.

Target the right team, not just the right company

I have a general approach to long-term career goals. Instead of one goal, you should always have multiple mini-career goals rolling at the same time. Hunt for that job to pay the bills. Got it? Okay, now hunt for your dreams….while also hunting for the job that will help you build your dreams. My first internship in undergrad at Kimberly-Clarke had nothing to do with software design, but I realized the report creation, data visualization decisions, were the things I really lived. I didn’t even fully know what my dream was at the time, but I knew it would involve design and technology.

One of the hardest parts about searching for a new job is constantly having to juggle the romantic with the realistic.

This is especially true in the current job market. With so many people out of work because of the economic contraction caused by COVID-19, job opportunities feel like they are few and far between. As a result, it’s hard to blame anyone for taking the first offer that comes their way. Doing otherwise would be crazy.

Or would it? Having landed my dream role after navigating a lengthy job search process, I’ve come to realize that, while the job market is in a rough place right now, that shouldn’t mean pressing pause on your ambitions to land the “right” gig.

This was a lesson that learned the hard way. As someone with roles at both Microsoft and Apple on my resume, I can say with confidence that working at a great company means nothing if you’re not happy with your projects and your day-to-day. At Apple, for example, I worked on the company’s Information Systems & Technology team, which created internal technical tools. And while I loved working for Apple, I didn’t love the work I was doing AT Apple.

Everything was fine.

I experienced a similar dynamic working Microsoft, where I worked on the MyAnalytics/Workplace Analytics sub-team in the Office group. It was a good experience, but there was a general dynamic to the company that didn’t work for me. My manager would ask how I was doing, and I’d answer honestly. It wasn’t great. It wasn’t good. It was okay. I felt constantly as if something was wrong, but not what or why.

I wasn’t alone in this feeling. Many of my friends had shared similar stories about their experiences at large orgs. Many of us had discounted that working at a prestigious brand can’t make up for being unengaged with your output.

If you love math and numbers, and ended up in software design, look into analytics and financial software. If you love helping people, look into HR and healthcare. Think about what you love about other aspects of your life and make sure that your career connects with it. If it doesn’t, start looking for your exit strategy.

For me, I didn’t specifically know I wanted to be a software designer when I was in school. I just knew I loved design and technology. In many ways, I’m designing analytics software now because my favorite part of my Kimberly Clarke internship was making the final data reports.

My experiences were invaluable because they taught me to be more honest with what I wanted from my work, and less willing to compromise on it. I don’t regret this one bit.

Portfolios are the key to interviewing at scale

I’m the kind of person that only updates his resume when it’s time to search for a new job. When I graduated from my undergrad and started my job search, my biggest issue was not having a central repository of my work. It cost me multiple opportunities. Chances are you’ve fallen into the same trap.

First portfolio: Just a PDF a bunch of random work.

One thing my recent job search confirmed time and time again is the importance of having a central repository of my work. While portfolios are a useful — and often essential — way for companies to see the full breadth of your capabilities, they’re also important for another reason: they allow you to effectively take on more interviews.

Evolution over time, into a hand-built website (worth doing at least once but…if you’re not a Front-end Dev it starts to get less useful).

As my interview pipeline filled up, having a single repository of my work allowed me to take more interviews simultaneously. With examples readily available in Figma, I was able to pull together customized subsets of my output that best reflected what each company I spoke to was looking for. In the age of COVID-19, this meant that I could juggle not just 3–4 but 5–6 job interviews at the same time.

The most recent site, easier to update…

Another note: Always have both a cloud backup and a downloaded copy of your work. Whether it’s a corrupted file, a Verizon outage, or a vodka and coconut cocktail spilled on your laptop, accidents come in many forms. Having multiple backups ensures they don’t derail your interviews.

And the actual Portfolio for interviews…Figma is your friend and I’ll have a future article detailing exactly why.

You’ll probably burn out — but that’s okay

The importance of both of my above points is heightened further during COVID. Not knowing what I wanted from my career and not having my portfolio ready-made job searching during this stressful time even more harrowing early on.

But eventually, I realized that the job search, like life, is all about finding those small optimizations that can eliminate stress and move you closer to what you really want. When you narrow your search, you expand your focus.

Remove those roadblocks, one by one, and be true to what drives you.

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