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
Coffee. Morning pages…got cut off in the middle due to the electrician coming at 8:00 am, so I had to hustle and clean out the bathroom and leave home to go to a co-working space.
8:45 am
Answered email and Slack. Jumped on stand-up. Have three follow-up items to do (write/send story to engineer, send bug update, set up 1:1 with teammate, check “done” column and tag to appropriate release)
9:30 am
MVW for work today:
(annotated)
* Follow up on stand-up items
* Set up quick property score v.3 data review
* Update one-pager/content for property score v.3
* Check on release and draft release notes, set team up for demos
* Review PD candidates. Send over shortlist to recruiter.
9:45 am
Job search status update:
* Saw that the CTO of the construction tech startup replied to my follow up for his connection request. He gave a generic “my team will review and contact…” I did see that he checked out my LinkedIn profile, so I assume he wasn’t impressed enough to take me up on my offer to have a call?
* Mutual connection says he does know the CTO of the construction tech startup and will set up an intro. I thanked him and asked him what he thought about the team.
* Mutual connection for the climate tech startup says he doesn't know the connection personally and feels awkward setting up an intro with him but if it's anyone in his network that he personally knows, he is more than happy to make an intro. I wrote back thanking him for his offer.
* Stil waiting on another connection for the climate tech startup. I'll wait until tomorrow and send a follow-up. I might get impatient in the meantime and just reach out directly on LinkedIn....never sure what the best strategy is.
Job search goals for the day:
* Update LinkedIn profile
* Look up climate tech startup application requirements
* Read up more on climate tech startup
* Refine blurb for climate tech startup
* Create cool down routine
* Create “leading indicator” tracker
Had a good talk with Andrew (partner) last night regarding my job search. It's hard not to be obsessed, check my email all the time, scroll through job openings, and regurgitate areas I could have done better. The goal is to get a new job, but I need some leading indicators I can control, to encourage myself and have peace of mind on the journey. Part of today's goal is to reflect and create just that.
11:00 am
work, work, work
12:30 pm
Checked personal email during lunch and saw that another mutual connection for the climate tech startup got back to me and agreed to set up an intro. Sent a quick thank you note and my blurb to forward easily.
1:00 pm
work, work, work
3:00 pm
Work done! Moving on to my job search tasks now.
4:00 pm
Deep dive into sustainable agriculture and MRV (measurement, reporting, validation). Edited blurb for the climate tech startup. Updated Linkedin. Double checked to see if connection replied back. No response. What do I do? Should I go ahead and apply? I don't see a referral field in the application so maybe? Should I reach out to the Hiring Manager directly on LinkedIn? I decide to do that.
4:15 pm
Rewrote/ massaged blurb and sent a connection to the VP of Product and Head of Product at the climate tech startup.
I think that's all I'm going to do regarding active job search today. I’ll spend the next hour creating leading indicators to measure success for the Process and not just the Outcome.
5:00 pm
Packed up from Co-working space. Some colleagues are in town for the new sales training so there's a happy hour. Headed to the happy hour.
Total time job searching today: 2 hours
Day 3
7:10 am
Slept in a little bit. Coffee. Washed face. Morning pages. Made breakfast (yogurt bowl), and organized the kitchen (put away dishes). Then put on workout clothes so that I can go to the gym right after working. I try to get 30 min of full focus time before workouts on the days I have them scheduled. The deadline really pushes my focus.
9:00 am
Contact I reached out about getting an intro to the climate tech startup texted me and asked if I would be interested in the head of product role at a fintech start-up his friend is investing in.
Thought it couldn't hurt to talk, so I said yes.
9:30 am
Worked out 💪
11:00 am
Jumped straight into meetings after the gym.
12:00 pm
Just set a meeting with the investor. Scrolled through the website, a tad disappointed that the company is not US-based. But it's an opportunity to make connections and practice interviewing. Plus, I'm trying to keep an open mind and see where this journey takes me.
1:30 pm
Final meeting of the day! Now, I can get some work done...
A connection got back to me and looped me into a LinkedIn thread with a PM from a product design platform. I wrote back asking if we could connect and talk about the company and what they look for in product people.
I want to focus on work, but I get distracted by these messages and often feel the pressure to make a timely reply.
1:35 pm
Finally getting around to MVW. It’s going to be a busy work day, it seems.
* Write a story for a new fee penalty reduction feature
* Check up on backend bug
* Set up product feature release notes with Appcues
* Review feature recording and set up the next steps
* Schedule a standing meeting with CX
* Ping teammate about operator's call
* Clean out inbox
* Look into a recruiter request
Goal: finish by 4pm today.
Job search status update:
* Fintech startup: meeting set for Thursday
* Climate tech startup: Waiting on a friend to loop me in with his contact. None of the three people to whom I requested connections accepted 😕
* Product design platform: Wrote a reply to the thread. No other updates.
Job search goals:
* Respond to any inbound messages or connection acceptances.
* Look for one more target job. Load to Notion tracker and find contacts.
* Set up a clean Calendly link for intro meetings
2:00 pm
work work work
4:00 pm
Noticed that the VP of Product at the climate tech startup to whom I sent a LinkedIn connection request and an intro blurb has accepted my request (!)
Set up a personal Calendly link and messaged him, thanking him for accepting the connection request, expressing my interest in the role, and asking if we could connect via video chat (along with the Calendly link). I also attached my resume. Hope it's not too much. But then again, it’s rare to get a response to these messages, so I might as well give everything.
4:45 pm
Gotta finish some tasks that came onto my plate while I was clearing out my plate. Standard PM life.
5:30 pm
Scheduled some time tomorrow to get to a big task that I couldn't figure out today. Closing the computer and packing up now.
Total time job searching today: 1 hour
Day 4
6:20 am
Wake up. Coffee. Wash face. Morning pages. Had a brief but intense discussion with Andrew (partner) about a real estate investment opportunity that came up. We haven't waded into anything beyond 401K, IRA and index funds, so this is an interesting learning opportunity. Not sure if we have the risk appetite for it.
7:45 am
Pilates. Been taking weekly pilates lessons for ~5 years. The pilates has really helped stabilize (dare I say, improve?) my back muscles.
9:00 am
Thursdays are for meetings. 50% of my meetings for the week are scheduled on Thursday. It’s exhausting, but I prefer this over constantly being interrupted during the week and not getting anything done. To ensure I have the stamina to pay attention in all the meetings, I walk around between meetings. Knowing that I won't get meaty work done during the day takes the pressure off, but I still face Thursdays with a bit of dread.
First meeting: Stand up.
9:20 am
Got upset during standup. Code freeze is tomorrow, and we have 31 items still in QA. I snapped and said we need to get at least all the bugs in the QA column out. The rush of emotion and the shame of snapping completely exhausted me. I have a bit of a temper which, to be honest, has helped me stand my ground as a female PM who mostly works with male engineers. Being an asshole is not a role I enjoy. This is the wrong tone for the day.
~9:50 am
Completely forgot I had a 10am call with the investor from the fintech startup that my friend put me in contact with. Andrew (my partner) took a look at me in my foul mood and told me to go outside and walk around for 5 min, which I did. It helped.
~10:40 am
Had a pretty good call with the fintech investor. We have some mutual friends, so the icebreaker was easy. Talked about my background and experience and asked him about the company, why he invested...etc. He said he'd put me in touch with the CEO/founder. We'll see where things go.
~11:10 am
Got off a call with my boss, the CEO of the company. It was a blazing reminder of why I started looking for a job. I love my team, and I'm hugely invested in this company that I helped build. Sadly, I find that my role has become 80% CEO wrangler. Everyone on my level is basically a human shield for the rest of the company, and I am utterly exhausted. Days like today make me want to quit on the spot. The only thing that stops me is the irrational fear that I will never find another opportunity. The call ran over, and both of us were late for the next meeting, which we're both part of...
12:30 pm
Meetings, meetings, meetings (10 min lunch break)
2:30 pm
Cancelled one of my 1:1s because I really needed a break to walk around and cool down the emotions that have been bottled up since this morning. The walk helped, but only slightly. My frustration is deep-rooted and hard to slough. I really need to leave this job.
4:00 pm
Short break until the last meeting of the day. Took the opportunity to take a quick peek at LinkedIn. I noticed that the Hiring Manager at the climate tech startup took a look at my Linkedin profile but never replied to the message I sent him. Is that a good thing? I don't know. No word from my connection yet. I think I might just apply.
5:00 pm
Last meeting got canceled. Extra time, hooray! It's a beautiful day. I think I'll go and get my nails removed. I got them done three weeks ago for a wedding, and they've grown quite long and are impeding my typing. I’m not really in the right headspace to be doing anything substantiative. Hopefully, I feel better after that. Planning on updating my Notion Job Tracker with the job search success criteria I wrote out the other day in the evening.
Tomorrow is Friday, yay!
5:10 pm
I reflect that for every job I've held, the work itself has always been the easy part. It's the human component that's difficult and stresses me out. Having a good team and a good manager really impacts the quality of one's life, and I realized that being a good manager and teammate is one of the most positive impacts I can have in the industrialized world. I try to be that, and perhaps everyone is trying, but oh man, why is it so hard to be one and to meet one?
Total time job searching today: 1 hour
Day 5
6:30 am
Wake up. Coffee. Morning pages. The first page is always easy. The second page is a struggle; I have nothing to say. It's the third page that's always magic. Somewhere in the dredges of my unconscious are these beautiful thoughts that are waiting to come out. I was feeling really down about my career and job search, but wrote about how I want to gain confidence and perspective during this process and work through it with no regrets as a growth opportunity. I didn't know I was such an optimist. 😏
9:00 am
Made a personal job search success criteria tracker in Notion. Found a position I was interested in at a food tech company. Reached out to two people for networking opportunities (I have only one connection: an investor in our current company, sigh). Rewrote blurb to make it relevant to their industry. Sent an email to the fintech investor yesterday thanking him for the talk.
9:30 am
Personal training
11:00 am
Meetings for my full-time job
12:00 am
Interview with a PD candidate. It's odd to be sitting on the other end of the hiring process. He’s a perfectly nice candidate with a great portfolio. He said all the right things, and although I'm going to send him to the next round, I'm not that excited about him. The thing is, I can't really say why I'm not excited. The vibe just isn't right. It makes me uncomfortable to think that, on the other side of all of my rejections, there is someone like me who cannot articulate why they are rejecting me. I’m reminded that hiring is a subjective process and I shouldn't take things personally. It’s not entirely comforting. So much depends on luck, your network, and intangible “vibes.”
12:30 pm
Meetings for my full-time job
2:30 pm
Another interview with a PD candidate.
4:00 pm
I didn't create an MVW list this morning, so naturally, the day devolved into a day filled with busy work: cleaning out my inbox, follow-up items, answering Slack and comments in JIRA, etc. I want to spend the remaining 1 hour of work reviewing some job search-related articles from “The Career Whispers” so that I can craft my strategy for next week.
Last week, I spent an enormous amount of energy and time writing a single application (it had 10+ essay questions). I was pretty exhausted afterward, and I won’t survive this search with that level of exhaustion. I set a goal this week to apply Cal Newport’s Deep Work principles (great book!) to enable me to search during work hours. For the most part, I think it worked! I was focused and productive at work, and I had time and energy to job search as well.
I haven't heard back from any job this week which is pretty discouraging. In my experience, when a company wants you, they rarely take more than a week to get back to you. I tell myself it’s ok. It won't happen until it happens, and all I can do is my best (which I am doing).
5:30 pm
Just refreshed on some articles regarding networking that I read a few months ago. Good reminder. I was motivated to send a second follow-up message to a hiring manager who accepted my connection request a few days ago. I'm hoping to nail sounding confident yet persistent and not thirsty and desperate―fingers crossed.
Ended up scrolling through a product community channel and reaching out to someone whose startup resonated with me. I'm not looking for opportunities per se but I’m trying to build a broader network and sharpen my outreach skills.
Total time job searching today: 2 hours
What I learned this week
#1 Job search during work hours is possible without your current work suffering. Write out goals for the week/each day and schedule your job search tasks.
#2 Get over the awkwardness of putting yourself out there. It gets easier, and people are generally supportive/positive in their responses.
#3 Focus on what you can control and give yourself points for taking measured steps in your job search.
#4 Continue putting yourself out there so that unexpected opportunities/experiences can find you (ie, the head of product position at an early-stage fintech startup). Even if it leads nowhere, it's pretty cool to feel like the energy you’re putting into the universe is returning.
What I’ll adjust for next week
Iterate on my intro blurbs
Be more active in reaching out to people. Develop a better system so I don’t forget to follow up.
Keep warm intros warm. Make them your friends (maybe that's pushing it too far?)
I'll experiment with finding an online community
Tell us more
How would you describe your job search strategy? What's working? What needs adjustment? For two years (2022 til now) I was rage-applying to any opening I saw whenever I got frustrated at work. It hasn't worked. And worse, I developed a defeatist attitude about myself and my search, ie: "Any job I want, they won't hire me because of X reason, and even if they do, it will probably suck." This mindset is hurting me, and it’s rubbed off onto every aspect of my job search.
This month, I'm trying to get back into the mindset of being positive, optimistic, and strategic:
I look forward to doing more research into companies and roles and allowing myself to get excited about them as I learn more.
Networking has always been a weak point, and I want to strengthen this.
There are unseen “systems” for every aspect of life, and I'm interested in learning how to crack the job market instead of relying on luck 🍀
How many hours a week do you spend on your job search? Can you break this into rough buckets? Rage applying was cheap and quick (~4 hours a week) but yielded no results. I’m pivoting my job search strategy, but I do still have a full-time job. I plan to dedicate 7-11.5 hours per week to the job search:
1-1.5 hrs each weekday
2 hrs each day on the weekend
Here’s how it breaks down:
Interview prep (highly recommend the First Round Ready course)
Deep research into 1-2 companies and roles per week (giving up my spray-n-pray approach!)
Networking
Honing my job search strategy (it’s a skill, so I plan to make adjustments as I go)
How much of your time do you spend sharpening your skills? How do you do this? In the past, I did mock interviews with other people online 2-3 hrs/week because I was so nervous about interviews. I also spent 1.5 hrs/daily working on case studies and talking through them with peers and my partner.
This time, I'm starting with my “Why” to establish what I want from a job and career. I need fuel for what may be a months-long search for the ideal role. I'm also doing a lot of writing these days, thanks to morning pages.
What is the best part about job searching? The forced self-reflection is painful but good. Having the opportunity to assess myself against concrete goals (why, what skills, how to structure time) is always an incredible growth opportunity.
What’s the worst part? Facing my internal ghosts...and always feeling like I'm falling short somehow. This comes in many forms: scrolling the LinkedIn profiles of people who hold positions I want at companies that I'm interested in, reading the requirements on job posts, working on my own resume and blurb, reaching out to/meeting up with people and trying to “market” myself, etc. I feel as raw and vulnerable as when I was an awkward, chubby teenager in high school.
What are your current favorite job search tools, and how are you using them? Finding jobs: LinkedIn. I haven't turned on alerts because LinkedIn does an incredible job surfacing job postings similar to the ones that have caught my eye.
I've also quietly told a couple of people that I'm on the hunt, and they've given me resources from alumni channels that I find fascinating. It's eye-opening to discover the alternative channels that companies use to find talent.
What's one tool or service you couldn't imagine living without in this job search?LinkedIn (of course), and 1:1 coaching with Coach Erika. She offers tactical guidance, pushes me, holds me accountable, and points out where I can do better.
What's one thing you regret spending time on while job searching? Self-loathing. Regrets about past choices. I have to remind myself: “Be confident! You can't change your experience or the past! Own your current self and focus on what you can improve!”
Advice for other job seekers in tech? Have a schedule. If you're not feeling confident or are lost, spend resources hiring someone who can help you. Navigating a soft job market is a skill worth learning, and it will give you confidence.
Anything else you’d like to add? Searching for a job is another learning and growth opportunity. I've been extremely lucky that blind navigation has offered great career opportunities so far, but it's worth building the skills to search with more self-determination and agency. After all, work is what we spend the majority of our waking hours doing.
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I loveeeee these. Keep them coming 🙏🙏🙏