Job Search Diaries No.1―Staff Product Manager

Welcome to our new series JOB SEARCH DIARIES, where we peek into someone else's job search. This week: pickleball, Claude.ai, and cozying up to recruiters.

Welcome to our new series JOB SEARCH DIARIES, where we shadow someone’s tech job search for a full week. Ride the highs and lows and get the scoop on fresh tools and tactics for job searching in tech.

👋 Hey, it’s 📣 Coach Erika! Welcome to the once-a-month ✨ free subscriber edition✨ of The Career Whispers. Each week, I tackle reader questions about tech careers: how to get one, how to navigate them, and how to grow and thrive in your role.

If you’ve found your way over by some miracle but are not yet subscribed, here, let me help you with that:

Now, onto the diary!

---

To kick off our series, we have a Staff Product Manager with a stellar career history at Yelp, Okta, and Twilio.

Staff PM Job Seeker Diary.

About me: I'm a seasoned technical product manager with 15+ years of experience in enterprise, consumer, and platform products.

My location: San Francisco Bay Area, California

Roles I'm seeking: Staff/Lead/Principal Product Manager

Target company stage: Late-stage, pre-IPO, or public companies

Target industry(ies): I’m fairly industry agnostic, but my skillset is best used on large enterprise or consumer platforms

Passive or active search? Active

When I started my job search: October 2023 (passive), January 2024 (active)

Number of applications so far: ~150

Number of HR or recruiter screens: 50

Number of first-round interviews: 12

Number of final-round interviews: 8 (6 completed as of the week documented, 2 future scheduled)

Average weekly job search commitment: 20-30 hours

Day 1

8:30 am

It's Saturday morning. I just drove home late last night from South Lake Tahoe to avoid the upcoming storm. Looking to relax and rest before preparing for the upcoming week of active job searching.

4:00 pm

Review my calendar to check for interviews I need to prep for.

• Monday & Wednesday: initial recruiter calls with Series C companies (Company A: digital healthcare & Company B: website design software).

• Tuesday: final-round interviews with two public companies (Company C: social networking & Company D: financial services).

I hope to land an offer with one of these public companies but still need to work my job pipeline in case both fall through. I'm also scheduling a 2nd round interview with another public company (Company E) later in the week (Thursday or Friday).

I realize that I'm currently interviewing with nine companies(!). It's been a struggle to balance all the interviews and prep work. To stay sane, I've stopped applying to any more PM jobs as I feel nine is a sufficient pipeline to land at least one offer.

I finished final-round interviews with another public company (Company F: B2B SaaS) last week, but the Hiring Manager has not decided (it’s been 6 days). The recruiter told me I'm in the top two and that the HM will decide tomorrow morning (Monday). I wonder if I should send a last-ditch email to the HM to express my enthusiasm for the role (which I already did last week). I plan to ask some colleagues for advice and ask Claude.AI (which has been a much better interview prep tool than ChatGPT).

5:00 pm

I called my best friend for advice about whether or not I should email the HM at Company F a second time to express my enthusiasm for the role. My friend has founded multiple companies, including a job listing site. He has a lot of experience in recruiting and being a people manager, and I trust his perspective.

6:00 pm

I've decided not to take action on Company F. I don't want to sound over-eager, and I think letting things play out is the best strategy in this situation. After all, I have other final-round interviews lined up this week. There isn’t a guarantee I'll get a decision tomorrow, so the timing may work out to my advantage if I don't push things too hard.

Total time job searching today: 2 hours

Day 2

9:30 am

I was scheduled for an initial screen with the Hiring Manager of an e-commerce company (Company G) tomorrow, but it's being rescheduled. This works well because I can now focus my energy on the two final-round interviews tomorrow.

10:00 am

Met a friend at an indoor Pickleball Club to relieve some stress and play pick-up games.

2:00 pm

Took a video call in my car with another company I am interviewing with. They just had layoffs. The HM contacted me directly and assured me that the role is still a key hire and that the team is working on some of the top corporate priorities. The layoff news initially spooked me, but this new information helps allay my concerns.

3:00 pm

Got an email from the recruiter of the B2B SaaS platform company (Company F). The HM still has not made a decision yet. The recruiter says he will keep me posted if he hears anything. I'm now less optimistic about landing this role.

11:30 pm

Finally looking at my Inbox to review all the emails I've gotten. I have another HM interview with a delivery platform (Company H) on Wednesday, and a recruiter contacted me with another opportunity for an online ticketing company (Company I). I feel like the market is improving because recruiters are starting to proactively reach out to me, rather than me having to submit applications.

Still no word from the recruiter from Company F. I plan to spend my entire morning tomorrow preparing for my two final round interviews in the afternoon.

Total time job searching today: 2 hours

Day 3

8:00 am

Just heard from the recruiter this morning from Company F. They aren't moving forward with me and will instead re-open the position. Ouch. This is the third company where I didn't get an offer after finishing the final round. It's a bit dispiriting, but I'll use it as fuel to make me stronger and improve.

I have two final rounds later today. I hope to close at least one of them.

Also, I heard that I made it to a final round for the digital healthcare company (Company A). Things are moving fast.

One of my former PM co-workers is now a HM at a different company (Company J). I just saw a post that he is hiring. I'm tempted to reach out. I remember that I have eight job opportunities in the air, so I decide not to reach out yet. Let’s see how I perform today in the final rounds at Company C and Company D.

3:00 pm

Just finished the final interview with the financial services company (Company D). The final round was a presentation with Q&A. I think it went well. I had a follow-up call with the recruiter. I should have the results by the end of the week (Friday).

I have my 30-minute final round with Company C (the social networking company) in one hour. I realize that I need to decompress and mentally prepare.

5:30 pm

Final interview with Company C is done! I think I did OK. I messed up one question, but I’ll try to salvage the situation by sending a thank you note to the recruiter with a detailed, corrected response in case my one error becomes the deciding question. Better late than never.

6:00 pm

Reflecting on the day, I realize I made a mistake by scheduling back-to-back final-round interviews within an hour of each other. I'm exhausted.

Next time, I should give myself a longer gap between interviews in a single day or schedule final rounds on different days.

7:00 pm

I sit down to review new interview questions. I just got an interview request for a digital mortgage platform company (Company K). I will probably start the process as a backup if the other eight in-flight processes don’t yield an offer.

As an aside: I never know when to stop filling my interview pipeline. Nothing is guaranteed in the talent market. In the past, I haven't gotten offers from interviews where I thought I performed outstandingly, and then I got offers from companies where I felt I underperformed.

Interviewing can be hit-or-miss depending on the mood of the interviewer and your own mental clarity and mood. It’s not ideal, but I have to get comfortable with this. The way I manage the uncertainty is by having multiple interview processes running.

7:30 pm

As a backup for the two final rounds that I completed today, I schedule a final interview with the digital healthcare company (Company A).

Last week, I proactively reached out to a PM at Company A to say hi and inquire about the company/product culture. She just responded! I plan to have an informational chat with her later this week (which I will treat as an informal interview), before my final-round interview next week.

8:00 pm

Went to play pickleball tonight to relieve some stress. It really helped.

Total time job searching today: 6 hours

Day 4

7:30 am

Last week, I asked to reschedule an interview I had with a marketplace platform company (Company L) because (1) the company wasn’t my top choice based on what I know of their work culture from negative reviews on Glassdoor and Blind and (2) the interview was a presentation for a take-home assignment that I hadn’t done yet.

The recruiter just reached out to ask if I could present on Friday (in two days). I’m unsure if it's worth my time/energy to squeeze this in and disrupt my week or if it’s better to hold a firm stance and tell them next week so I have enough focused time to prepare.

Also, I should get an outcome by Friday regarding my final interviews at Company C and Company D. If I land either of them, I will most likely withdraw my application from Company L. I need to think about this.

8:30 am

I've decided to push back on the marketplace platform company (Company L) and tell them I'm unavailable until next week.

Trying to cram a take-home assignment and an interview this week is not great for my mental health. I need some time & space & energy to breathe a bit after yesterday, especially given that Company L isn’t a top choice for me.

Instead, I’ll wait for feedback from my final interviews yesterday.

9:00 am

I’m taking time in my unemployment to improve as a PM. I am attending a webinar from Roman Pichler: "Product Strategy — Common Missteps and How to Avoid Them," which I find interesting. I’m also in my 3rd week of a Product Strategy & Leadership course at Gigantic. Honing my product strategy skills should help me with interviewing since the Staff/Lead/Principal PM role criteria tend to weigh more toward strategy/vision than execution.

10:30 am

Had an initial recruiter interview with a website design software company (Company B). I thought it went well, but it's a Series C company, so the equity isn't liquid. I would prefer public companies if possible. I should hear back in a few days

11:00 am

Had an OK interview with a public marketplace platform company (Company M). The HM was a bit under the weather, but it’s a key hire so the HM did the interview anyway. I got the standard questions:

• Project I'm most proud of

• Resolving conflict with a stakeholder

• My PM super power

I also got a tricky question: “In which PM skill am I the strongest: strategy, execution or team collaboration?” The HM said there was no "wrong" answer, which threw me off. I should've said strategy or team collaboration, but I said execution which is probably not the "right" answer for my level (staff PM). I suspect that strategy probably was a better answer, but oh well....let's see what happens.

12:30 pm

Met a friend to play some Pickleball. I’m relieved to have no more interviews for the rest of the day.

And I only have two calls tomorrow (a relief!):

1. the informational interview with a fellow PM at the healthcare company where I’ve got a final round next week (Company A)

2. a recruiter call for the digital mortgage company (Company K)

Right now, my Friday is completely open except for my weekly live mentor session for my Product Strategy course. This is partially a relief and partially a stressor because I always wonder if I should have more opportunities in the pipeline.

3:00 pm

Got back from Pickleball. I normally check LinkedIn daily because my feed always seems to have PM job openings in my network. Interestingly, I see a PM lead role for an e-commerce platform company that I've talked to before. I quickly submit an application and email the recruiter directly, since I already had her info.

Noteworthy: this job description wasn’t even posted yet on the company’s public website. I’ve learned that I need to FOLLOW product leaders on LinkedIn for the companies I’m interested in. They often post/comment/repost job openings that may not be live on the public site yet. By getting there first, you can get a head-start in the process. This is important because every new PM job posting on LinkedIn seems to get "Over 100 applicants" in a few hours—crazy times.

Total time job searching today: 3 hours

Day 5

8:30 am

I am nervously awaiting the final decisions from the social networking (Company C) and financial services platform (Company D) from Tuesday's interviews. I plan to send a nice note to both HMs to share why I’m excited about their role. I already asked the recruiters for these companies to forward my thanks, but it doesn't hurt to send a direct note to these HMs to show my excitement (and why I'm a good fit for this job). It might push me over the line if I'm on the border.

9:00 am

Info call with a PM on the healthcare company I'm interviewing for next week (Company A). It went well.

9:20 am

Sent a note asking the recruiter for the healthcare company (Company A) to share guidance on what topics will be covered for my final round next week. I already passed the product sense and product execution rounds, so I’m unsure what's left.

9:30 am

Recruiter call with the digital mortgage company (Company K) goes well.

1:30 pm

A sourcer at a large software development company (Company N) just contacted me about a Principal PM role. I was a bit surprised by the proactive outreach because the market is so soft that I’m surprised to see big companies sourcing—they probably have a ton of inbound applicants for the role. I’ve looked at some jobs at this company before and wouldn't mind working for them. I asked to set up a call later today.

She agreed, and our phone chat is set for 2:30 pm.

2:30 pm

Just got a text message from HM of the financial services company (Company D). I sent a big THANK YOU text to him this morning. He thanked me for the message and wanted to talk, but I told him I was busy until 3:30pm due to the sourcer call that I’m hopping on now for Company N.

3:00 pm

Just got off the phone with the Company N sourcer. It looks like a potential fit, but the interview process may take two full weeks. I told her I’m late stage with other opportunities, so she agreed to schedule the first round hiring manager screen early next week.

I’m about to text the HM of the financial services company (Company D) that I'm ready to talk. Crossing fingers for an offer...

3:05 pm

HM from Company D says he needs 10 minutes. I have two different browser windows open now, depending on what happens:

1. Message box to HM of Company N to offer my availability for a call next week (if I don’t get an offer from Company D)

2. Email to all open final round opportunities to share that I have a verbal offer and ask for their responses soon.

3:30 pm

Just finished the HM call for Company D. Good news and bad news.

Bad: The HM really liked my presentation, but the rest of the panel didn't think I had enough deep storytelling around product strategy. He shared that the company has a hiring committee approach and that he wouldn’t be able to successfully pitch my candidacy given the current interview feedback.

Good(ish): He offers to allow me to present one more time, but the catch is that I have to present a different project. I tell him honestly that I'm unsure if I want to do that and I need to think about it. It’s more work for me, so it depends if I really want this job or not. He asked me to get back him soon “but dont take too long…”

If I get the offer from the social networking company (Company C), I would likely accept it. I'm not optimistic about landing that one, though.

Kind of a rough day so far...

Total time job searching today: 5 hours

Day 6

9:00 am

Attending a live mentoring session for the product strategy course.

9:30 am

Just got an email from the social networking company (Company C). They aren’t extending the offer to me. I’m disappointed. Recruiter offers to share feedback, so I will schedule a call next week to understand how I can improve.

This was a rough way to end the week, but I still have a lot of interviews in process, and job searches take time in this market. The right opportunity will come along at the right time. I remain optimistic, but I’ll admit that I did not expect this week to end with no offers in hand.

Reflection

What I learned this week

1. I need to space out my interviews to give sufficient time to prep before and time to decompress after each interview. I was trying to do multiple interviews at a time in an attempt to land multiple offers. I’m learning that this is just not a reality in this market.

2. In general, the job market is much tougher now than in my last job search ~2 years ago. There is more competition due to tech layoffs, which forces companies to ask tougher questions, introduce homework assignments, and take extra time to try to optimize their decision. You can't expect to get feedback from final interviews within 1-2 days like in the good old days. In this market, it can take up to a week.

What I’ll adjust for next week

1. I’ll block out entire days where I do no job hunting whatsoever. On those days, I will play pickleball and decompress/relax. 

2. I need to take time to reflect on why things didn't go well in my final interviews and write down how I can address those shortcomings based on the feedback I've received so far. Reflection is important.

Tell us more

How long have you been job searching?

I have been looking passively for four months, but I started actively applying for jobs in January 2024. Recruiters/HM were in and out late last year for the holidays, and there weren't as many JDs open until this new year. I was told by a lot of my colleagues that new headcount opens up in early 2024 after budgets get approved from annual planning in Q4 2023.

What drove this job search?

I decided to leave my last job to take a mental break. I had been heads down for many years and needed a breather. But my work is important to me, so now that I’m refreshed, I want to get back into it.

Do you recommend this path (leaving a job without another one lined up)?

I only recommend this if you have the financial means to live without a paycheck and benefits for at least 6-9 months. The job market is a lot tougher, so candidates need to expect a longer job search than in the past.

How would you describe your general job search strategy?

I only search for jobs that align with my:

• level of experience (Staff/Lead/Principal roles)

• company requirements (Series C or public since I want stability)

• compensation goals ($200K+ base salary)

• job goals (targeting Technical PM roles like API or Platform roles where I have deep domain expertise)

How many hours a week do you spend on job searching? Can you break this into some rough buckets of how you spend this time?

Since I am unemployed, I spend at least 20-30 hours a week on job searching. It roughly breaks down into 60% on sourcing opportunities and preparing for interviews and 40% on job interviews and take-home assignments. I probably do too much prep, but I tell myself that being overprepared never hurts.

How much of your time do you spend sharpening your skills? How do you do this?

I spend a few hours each week watching selected YouTube videos, and I also sharpen my skills by taking interviews with lesser-priority companies to gain confidence and practice. I don't do mock interviews, which is probably a bad practice.

In your opinion, what is the best part about job searching?

Learning more about companies that you have never heard of or getting deeper into the companies that you know of. It's interesting to see all the innovation that is taking place in the world across all industries. I do so much product strategy research on the public companies I interview with, I could probably make some money by investing selectively using my research.

In your opinion, what's the worst part about job searching?

REJECTION, hands down. Interviewing is like dating. You are introduced to a company, then you learn more about them, then you start to get seduced by what they do and you start to see yourself contributing to their vision. Sometimes, you fall in love, hard. And sometimes you get rejected. It hurts, but you have to move on.

What are your current favorite job search tools, and how are you using each of them?

Finding jobs: LinkedIn. I turn on app and email alerts for new jobs that get posted matching my job title.

Interview prep: Claude.AI. I do this by pasting the job description and asking Claude: “What are the top interview questions I could get based on this job description?”

I also develop my own questions based on the JD and ask Claude to adopt the persona of a top 2% staff PM qualified for the role, then answer my questions. I really like Claude.AI vs ChatGPT. I use the free version.

I also use:

• Google Sheets to track my job search progress

• Google Calendar to block times for me to prep

• Google Docs for more detailed interview prep notes

What's one tool or service you couldn't imagine living without in this job search?

Probably Claude.AI. It has helped me tremendously with interview prep: giving me sample questions and answers I can use as a starting point. I also ask it to give me summaries about a given industry. These are decent and save me a ton of time. Like any LLM in 2024, it is not (yet) something you can use verbatim. You have to use it as a guide, give good prompts, and filter based on your own experience. I also use Claude.AI to help draft follow-up emails to recruiters to help make my copy more precise and succinct.

What's one thing you regret spending time on while job searching?

I often regret over-preparing for job interviews. I’ve learned to ask the interviewer about the interview type (behavioral, product design, product sense, data analysis, or a case study) so I can focus on the given interview style.

Advice for other job seekers in tech?

Consider load balancing the cognitive and emotional load of your job search, whether you are employed or fully available for job searching. Here’s what I’ve found to be my max daily loads in this search:

• 3-4 informational chats or recruiter screens

• Two hiring manager interviews

• One final round interview

Is there anything else you would like to add?

Some tips for others who are actively searching:

Tip #1: Reach out to your PM colleagues. Get referred.

Referrals are the best way to get your application noticed by recruiters. Before applying for a job, double-check if you have a connection there. Ask if they can send you a referral link.

Tip #2: Don't go through this journey alone.

I've grouped up with three colleagues who are also actively looking for a job. It’s helpful to have a support system to share war stories, vent, and seek outsider feedback on your draft take-home assignments. 

Tip #3: Do research on the company.

Look at company blog posts, videos of their most recent annual conference, and podcast interviews of their leaders to get more information about the company.

Tip #4: Be nice to recruiters. Build relationships with them.

They will want you to succeed. At each stage, ask them about common pitfalls where candidates fail for your next round of interviews. You'll be surprised how much information they share if you ask!

UPDATES from author, 3/28/2024

Tip #5: Waterfall your interview questions

Use the questions at the end of each interview to prepare for the next one. For example, if I am talking to engineering and I have product interviews next, I ask engineers questions like: “Where do feature ideas come from,” or “How do you collaborate with PMs,” and other leading questions. These questions give me valuable insider context I can use to shape my responses in later interviews, ie: if I can get a better sense of how a company operates, then I can map my responses to match the company lingo, culture, and product development process and make it clear that I will fit in.

Tip #6: Do 80% of take-homes before submitting

I recently asked a recruiter about the common pitfalls for a given take-home assignment with a panel-style presentation. He gave me great advice: keep it high(ish) level.

He shared that if the idea is too high-level (pie-in-the-sky), then candidates will get grilled on execution questions by the panel (which are easy to plan for and have backup slides/FAQs prepared). But when candidates present a very detailed idea, they always get asked about alternate solutions and get stuck because they spent all their time planning this one idea end to end and didn’t consider alternatives. Thus, it's best to make it detailed enough but with enough ambiguity for you to back it up in the actual presentation.

Submit at 80% complete and spend the remaining 20% of your time preparing for questions and building some backup content after submission (as slides or FAQs).

Tip #7: Post your take-home assignment to a website

I did this once, and it really impressed the interviewers and showed I was invested. When someone showed up to the panel and hadn’t done the pre-read, I shared the URL right then and there, rather than having them dig through their emails for a PDF.

Here’s how:

1. Create a simple site (sites.google.com). Use a standard theme that is reasonably well-designed.

2. Embed slides or text (or copy text from docs and paste it into a text box on your new site).

3. Publish the page.

4. (if you want to get fancy) Buy a domain (product.XYZ) and redirect your sites.google.com URL to the new domain.

Tip #9: You’re not crazy. Take-home assignments do take longer than advertised.

Homework assignments will take you an entire day even if the guidance is only 2-3 hours. I find it takes 1-2 hours alone to research the company/industry, and then you need to design and craft your response to the prompt, which can take 2-3 hours. It always takes me two days because I can't work at my best for 5 hours straight, and I also take time to get feedback from friends in my field so I can iterate.

It sucks, but that's the reality. I think it’s better that we talk about this, because I would hate for other job seekers to feel stupid or slow or incompetent when it inevitably takes you longer than you are told it “should” take.

---

I invite you to use the comments to share your thoughts or to ask a clarifying question.

---

Want to nominate a noteworthy job seeker (including yourself)? (It’s anonymous!)
Fill out our JOB SEARCH DIARIES form.

---

Check out coacherika.co for free resources, resume help, and coaching options, including my very popular TUYJS Workshop. Follow me on Substack, YouTube, and LinkedIn to stay in touch. Subscribe to this newsletter to receive a steady stream of tech career advice and experimentation ideas 💛