Job Search Diaries No.4―VP of Product
Job searching with a full-time exec role, reporting to a founder at an early-stage startup, burnout shame (and growth), and building job search systems.
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.
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Now, onto the diary!
Today, we have a VP of Product at a Series B real estate tech startup.
About me: I’ve spent 9+ years building digital products as a PM, but I stumbled into product management after my first career in architecture.
My location: Atlanta, Georgia
Role I'm seeking: Because I’m currently at a Series B startup, I know that if I go up or down in company size, my title will adjust to reflect the relative scope. Thus, I’m looking at a range of titles: PM/Senior/Staff/Lead/Group/Principal Product Manager.
Target company stage: Late-stage (pre-IPO) start-ups or public companies with a strong tech team
Target industry(ies): Consumer tech. Mission is important to me.
Passive or active search? Active
When I started my job search: 2/1/2024 (actively); since 2022 (passively)—rage applying on bad days.
Number of applications so far: 3
Number of HR or recruiter screens: 0
Number of first-round interviews: 0
Number of final-round interviews: 0
Average time spent weekly on job searching: 4, after my work day.
What drove my job search: I've been at the same company from seed through Series B. My growth and motivation have stagnated, and I'm also increasingly frustrated with leadership. I stuck around due to my team (whom I love) and the general inertia of comfort. My dissatisfaction at work is seeping into my personal life, and I’m hyper-aware that I'm no longer bringing my best to my role. My attitude in this role makes me feel ashamed. I want to spend the best hours of my day motivated rather than grunting with frustration at Slack messages. I’m not just job searching, I’m searching for a new sense of purpose. It’s time for a change.
A note on crippling imposter syndrome: Without an engineering background, I struggle daily with imposter syndrome. I've grown to be confident in my ability through experience and driving actual results, but job searching still intimidates the heck out of me. I'm a first-generation immigrant and come from a family of academics and doctors. I live in a second-tier city (not a tech hub), so I’m acutely aware that my network isn’t as deep and that I’m competing with other high-caliber remote talent. In short, many fears that I’ve pushed away for a long time are now bubbling to the surface, and I hope this diary helps others who face similar fears.
Day 1
6:45 am
Rolled out of bed. Switched on coffee and washed my face. Sat down with coffee and my journal to do my morning pages (3 pages of stream-of-consciousness writing the moment I wake up). I started reading "The Artists' Way" a few weeks ago, and so far have made it to…just the introduction 😬, but the morning pages are helping me already.
9:00 am
Sat down to work at my full-time job. Started by checking my schedule and answering email.
9:30 am
Gym. I started weight training a few months ago, and I love it. Sharper mind, sharper body, stress burning. The hardest part is to fit it into my schedule. I note that my bench press weight has been the same for over a month. Chronic left shoulder issues, plus the fact that I cheated for the first few weeks is probably why I’m stuck. I will add weight slowly and not worry about it too much. Focus on form and pulling the barbell down all the way to my chest. Elsewhere, I've been adding weight quickly and making strong progress.
11:00 am
Logged on to Slack and email. Getting pinged. Most of them I can ignore until later.
I start each week by writing out my work goals. I use a format called MVW (minimum viable work), which distills the minimum work to achieve the most critical goals. I always do more than what’s on the list, but identifying the highest-leverage work upfront in my week keeps me focused on what matters most.
MVW
(annotated)
* Reviewing all product design candidate portfolios & ping the recruiter
* Property Score meeting with data team
* New format for release notes
* Public newsletter article & send to marketing
* Kick-off sponsored listings research/follow-up
I layer in 1 hr of email + Slack and 1hr of small/busywork tasks each day.
OK. Goals set for this week. The rest of my time, I can focus on my job search.
Job search goals
* Organize Notion
* Apply to a role at a construction tech startup automating the permitting process (first: check to see if the job is still open, reach out to CTO, create role/company research plan)
* Start networking for another role at WikiMedia. Review application requirements and do LinkedIn research to see if I have any second-degree connections.
2:30 pm
Just jumped off my last call and on to the final task of the day! Will review designer candidates until 3:45 pm and jump over to job search work from 4:00-5:30 pm. Turning off Slack now. Haven't gotten around to the emails, but a quick glance says nothing is urgent and can wait.
3:00 pm
Reviewed product design candidates for 1 hr (allocated time). It’s odd to be on the other side of the hiring process, and it’s nerve-racking to understand just how many candidates are out there. Also, I momentarily consider that it’s probably bad karma that I'm rejecting so many people. But we can only hire one person, and hiring the best talent is part of my job.
Got caught up figuring out the details of a bug last minute but was able to wrap things up before 4pm.
4:00 pm
Read the construction tech startup job description for the nth time. Copied and pasted the application questions into a Google doc to draft answers. My process:
Write → Manual edit → Feed through Claude AI to check grammar → Manual edit again
These questions are much easier than the application I filled out last week which took 16+ hours. Is it a trick? Should I be spending more time on it? I don't know.
Worked on a connection request blurb for the Hiring Manager (the CTO) on LinkedIn. It turns out I do have a secondary connection, but I don't trust them to be discreet about setting up an intro. Sent connection requests to both the CTO and recruiter (with the blurb).
5:50 pm
A role at a cool green/climate tech caught my eye. I did a deep dive into their website, read the job description, and I am definitely excited/interested in the role. Scrolled through the employee list and found three with mutual connections. Reached out to the mutual connections via LinkedIn to ask for intros. Fingers crossed!
I also contacted another connection to see if they know the CTO at the construction tech startup. They're not connected, but they seem to have been in the same accelerator program around the same time.
These warm intro requests are quite painful. I do them because I know I need to, but they make me squirm internally. The discomfort is what it is. I want to improve at networking (both giving and receiving).
~6:05 pm
Aiyeee!! The CTO at the construction tech startup just accepted my request on LinkedIn. He asked if I applied via Ashby. I quickly followed up with an answer and told him I'd love to connect and talk more and offered up some times.
I hope I don't come off as too pushy, but I knew I'd regret it if I didn't ask....major squirm.
~6:15 pm
Turning off the computer now. I know that this job search will be a marathon and not a sprint. I'm trying to schedule blocks and avoid obsessing, burning out, or getting discouraged. I did a lot today:
1) Wrote out an application for a job and applied
2) Researched another position I'm interested in
3) Reached out to mutual connections regarding the job I just applied to and the job I want to apply to.
Time to change into my non-work clothes and start dinner.
Total time job searching today: 2 hours
Day 2
6:45 am