Job Search Diaries No.5―Director of Product
The long-tail impact of Green Card timelines, how gym swole-ness begets interview clarity, formal post-interview self-debriefs, and the importance of a light lunch before a big interview.
Welcome back to JOB SEARCH DIARIES, where we shadow someone’s tech job search for an entire week. Ride the highs and lows with these job seekers and get the scoop on fresh tools and tactics for job searching in tech.
👋 Hey, it’s 📣 Coach Erika! Here with a quick, important update. This post is a 🔒 subscriber-only edition🔒 of The Career Whispers. You’re going to see a lot more of these in the future.
Moving forward, free subscribers will get ONE free post per month, and the rest of TCW will be reserved for paid subscribers. Free subscribers still get previews for most posts, but they’ll encounter the paywall earlier in each post and more frequently (in all but one post per month).
A great deal of research, energy, and expertise goes into every post on The Career Whispers, and I hope you’ll spend the two-latte equivalent to feed your brain and upgrade your subscription.
If you do, you’ll get access to all 3-7 monthly posts, across these thoughtfully crafted career experimentation series:
JOB SEARCH DIARIES
THE WEEKLY WHISPER
DEBUGGING YOUR JOB SEARCH
MVIP (MINIMUM VIABLE INTERVIEW PREP)
CLEVER GUERRILLA
BONUS EDITIONS and more (see all the paid subscriber benefits here)
Now, onto the diary!
Today, we have a Bay Area PM Director who went from Big Tech to startups later in his career because of the Green Card wait game. Now, he’s looking to explore the middle ground in late-stage startups (pre-IPO and early Public).
About me: I am passionate about building products that make a difference in users’ lives. I spent the last 13+ years crafting successful products in the payments, e-commerce, marketplace, and monetization domains.
My location: Bay Area, California
Role I'm seeking: Director of Product or Senior Manager of Product (depending on the company size and role scope)
Target company stage: Public / Late-Stage / Pre-IPO
Target industry(ies): E-Commerce, Payments, FinTech
Passive or active search? Active
When I started my job search: February 2024
Number of applications so far: 20+
Number of HR or recruiter screens: 8
Number of first-round interviews: 6
Number of final-round interviews: 3
Average time spent weekly on job searching: 20-30 hours
What drove my job search: After working at a big company for 10+ years (while earning my green card), I wanted to join a product-led (PLG) pre-IPO company, and I did. In January, the company pivoted to a sales-led growth model, which didn’t align with my interests. I decided to leave and take a short break after 13+ years of continuous work.
A note: I wanted to move to a smaller company earlier in my career, but I chose to wait an insanely long time to get a green card. If I had moved companies before I got a green card, I would have had to restart the process, opening myself to unnecessary risks like the new company going out of business, laying off (which impacts filing green cards), facing unnecessary audit risks, and visa stamping uncertainty because of smaller companies.
Day 1
7:00 am
Woke up at 7 am (it’s usually the same time every weekday). Started the uphill task of getting my kids ready for school. Coffee. Breakfast. Pack Lunch. School Drop.
9:00 am
Last week, I provided my availability for a second round interview with a large e-commerce company for Sr. Manager, PM role. Today, the recruiter sent the calendar invites (Wed, Thurs, and Fri this week). Spent some time to confirm interviews, move around meetings on my calendar, and get organized for the week.
10:30 am
Some reading on Medium (for fun), The Career Whispers (for interview prep), and Lenny's post on representing business as an equation (for PM skill sharpening).
11:30 am
I've always wanted to try my hand at entrepreneurship, so decided to explore an idea that I had nursed for some time: building an iOS app for home gardeners. Decided to use OpenAI, so I got started.
12:00 pm
Lunch
12:30 pm
An expertise network reached out and wanted to invite me to share some expertise in a paid interview. Worked on scheduling that. I learned that once accepted, my profile would be available to all of their client companies to book interviews to glean from my knowledge.
1:30 pm
LinkedIn job search. My strategy: reach out to network for the roles where I have a connection; blind apply when I don’t know anyone in a target firm.
4:00 pm
Gym group workout - functional strength and isometric strength movements combined with high-energy circuit training
5:00 pm
Kids pick up, dinner, and wind down. My partner and I want to ensure we eat home-cooked meals with the kids. So a decent amount of time every evening is spent making fresh food (Italian today). We hope this will help our children make healthy choices.
9:00 pm
Handle some complaints about how the younger or older one is not sharing. Wind down with some silent me time. I reflect on the day, taking care of payments/renewals/etc, and plan for the day ahead. I note down learnings from my networking and recruiter interactions. I refer to these before key interviews.
Total time job searching today: 3.5 hrs
Day 2
7:00 am