Sisyphus goes job hunting
I’ve felt like Sisyphus lately. In the myth, Sisyphus is punished for his hubris by pushing a boulder up a mountain that would inevitably roll back down whenever he neared the top, condemning him to an eternity of fruitless repetition.
13 months ago, I parted ways with the company I helped build from a pre-product-market fit startup to a Series B company selling to some of the largest companies in North America. When I left, I was feeling pretty good about my resume and my track record and figured I’d find my next role right away. Queue the boulder.
I had a verbal offer aggressively rescinded when I asked for an official offer letter before accepting. I went all the way through a virtual onsite before learning the head of product had never cleared a new hire with the founders and my role didn’t exist. I received advice like aiming for hundreds of applications a week or doing preemptive, unsolicited work for companies — 12 hours per day per company, 5 days a week, with a wife and toddler — and sending them that work to separate myself from the pack. I got dozens of messages from the LinkedIn vultures selling “professional services”, asking for thousands of dollars up front from the unemployed to help them become employed. My pet peeve was the boilerplate rejection emails after I’d sunk dozens of hours into a place, and all of my requests for feedback were met with silence. The lack of empathy was exhausting and the lack of progress was maddening.
So what is there to do? My dad, a pediatric surgeon who sometimes operates on 400 gram babies, has a rule: If you ain’t got a lot to work on, work a lot on what you’ve got.
What I’ve got
There’s a simple temptation in blaming the terrible job market or the poor judges of character and talent who get to make hiring decisions, but the more I dwelled on any of that, the worse I felt. Strangely, it felt better to operate under the assumption that it was 100% my fault that I wasn’t getting any offers, because it meant that I controlled my destiny, and all I had to do was put in the work to earn my next shot.
I began asking advisors and friends what I could do better. The answers covered just about everything, including my LinkedIn profile and resume or how I was decorating my office for video calls, but I noticed a few major categories:
My interview answers weren’t focused or brief.
My critical eye came out in unintended places and made me sound negative.
I wasn’t talking enough about fundamentals.
To be honest, this wounded my pride at first. It hurt to hear my shortcomings from people whose opinions I respected, not because I was unhappy with them, but because I wasn’t as good as I wanted to be. It also gave me clear goals, and simply the act of trying to hit them did more to erase my feelings of futility than everything else I did combined.
Focused roles, focused efforts
I have long thought of myself as a devoted generalist, but pitching myself as someone who could do anything was ineffective. My first real act of focus was highlighting my specific experience in user onboarding, feedback funnels, system design, and product strategy. I found that people responded better when I told them exactly what I was great at and how I could fix their problems, which concentrated my prospects. Instead of having 10 roles where I would fit okay, I had a couple where I'd fit extremely well, and suddenly I was getting past the recruiter screening calls and into the interviews.
It's also worth noting that nearly all of those wins came from a focused effort. When I started my job hunt, my Monday morning routine was scouring LinkedIn, www.workatastartup.com, Otta, and Built In for open roles. I applied to over 100 of these roles, got a recruiter screen or intro call for four, and into the actual pipeline for just one.
Meanwhile, I had referrals or warm leads to around 30 companies. Almost every single one led to at least an email thread with a recruiter or an intro call. About 75% made it to the interview pipeline, and I made it to the final round at a dozen of them. It took me six months before I abandoned cold outreach and blind applications so I could focus on warm leads, and I wish I had done it sooner.
Document everything
I naturally struggle with certain types of interview questions, usually the general ones like “What are you looking for next?” After airballing that exact question on a couple calls, I made a list of what I was going to talk about the next time it came up:
A mission or product that aligns with what I care about.
An opportunity to grow as a manager and mentor while still building products.
A culture of driven, talented people who are hungry to win.
The flexibility to keep my family schedule.
It grew from there. I started a Google doc and wrote bullets like these for every question that tripped me up, and soon I had outlines for:
What’s your favorite product?
Tell me about yourself.
How do you work with sales/design/engineering/any other org?
How do you think about the product life cycle?
This document became the central source of truth for all my interviews, and my goal became to prepare for any question I might be asked. I saved every question that came up, with notes on how I answered it and anything else I'd change if I got it again. If I ran into a question that I didn't have a framework ready for I'd find one afterwards.
That document stands at 34 pages and has a list of every product I have strong opinions about, positive or negative. Populations of continents and countries, market shares, and revenues for Fermi estimates. Notable metrics for strategy or analysis. Categories for user segmentation. Market analysis frameworks.
The more ambiguous and high level the question was, the more I benefited from having a plan on how to answer it. It kept me focused and brief, and let me build on top of the fundamentals. It might be worth a write-up all on its own, but these are some of the most valuable frameworks that I used:
SPSIL (Situation, Problem, Solution, Impact, Learnings) for situational questions. STAR is perhaps the better known strategy, but I like SPSIL a lot better. It was more flexible, let me focus on the parts that my interviewer cared more about, and most importantly, made sure I always included what I personally learned from the situation.
Five Cs for market analysis — customer, company, collaborators, competitors, and climate. SWOT is a bit superficial and inflexible (since I found each C can contain all the elements of SWOT), and Porter’s Five Forces struck me as a bit outdated, or at least more focused on industry than tech.
Diego Granados’ Product Design/Product Sense framework for any question about analyzing, improving, inventing, or designing products. Like all my other preferred frameworks, it’s flexible, simple, but comprehensive.
It’s a popularity contest
I am a problem-solver at heart, and strongly value honesty in the workplace. That means that when I get asked interview questions, I tend to pick it apart and get to the creamy center of the problem, and when talking about past events, I'll try to paint as truthful a picture of the world as I can - good, bad, or ugly. I had an advisor point out to me that answering like this is optimizing for showing off my PM toolkit, which is enough to get to final rounds, but reminded me that an interview is inherently emotional. Someone gets 30 or 60 minutes with you to decide if they want to work with you for years on end. That cannot possibly be a rational decision, and if I wanted to get that offer, I needed to instead optimize for being liked, while still letting my PM skills shine through. For me that meant a few things:
Brevity. Nobody wants to work with the version of me that won’t stop talking.
Using positive, inclusive language and only talking about how I worked with the right people on the bus instead of the wrong people who weren’t on the bus.
Focusing more on relationships, learnings, and self-improvement instead of being black and white and declaring things right or wrong.
On top of the mountain
The uphill battle was worth it — I ended up with three offers and reached the team match stage with Google. I start my new job as a head of product later this month. I have my prep doc I made that I’d love to share. I learned to love the fight. I made it through a hard time.
I could never have reached this point without the help of so many, but a few deserve special recognition. Clif Claycomb has been a stalwart friend and fierce advocate who I am tremendously excited to get to work alongside again. Glen Lipka has been a generous mentor whose only request was that I pay it forward. Kirsten Bunch, my coach and counselor, helped me find my way and reminded me to always be curious. Most importantly, my wife Jill never wavered in her belief in me, and never let me push the boulder alone.
Crushing truths perish from being acknowledged. The struggle itself toward the heights is enough to fill a man’s heart. One must imagine Sisyphus happy.
