Job Search Diaries No.3―Jill of All Trades (Program/Product/BizOps) Manager

Returning to a job search after hiking 2,653 miles on the Pacific Crest Trail. Pivoting into a new industry, becoming a first-time landlord, and the jitters of moving away from a tech hub.

Mar 31, 2024

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 Swiss Army Knife tech worker with a diverse background in product management, program management, and operations management at Uber and Airbnb.

About me: I’ve worked in tech for eight years, at Airbnb and Uber. I was in consulting before tech. I’ve held several different roles in tech: operations, insights, program management, and, most recently—product management.

My location: Oakland, California (currently); relocating to Portland, Oregon (soon)

Role I'm seeking: Product manager, program manager, business ops roles. Remote!

Target company stage: <500 people

Target industry(ies):

Climate Tech - home electrification, measurement
Government - DOE, state-level clean energy programs

Passive or active search? Active

When I started my job search: February 2024

Number of applications so far: 6. I do a lot of research and networking before applying, so this number might seem low to people who do a lot of cold applications.

Number of HR or recruiter screens: 1

Number of first-round interviews: 0

Number of final-round interviews: 0

Average time spent weekly on job searching: 10 hours. I’m concurrently packing all my belongings, renting out my house in Oakland, and finding a new place in Portland.

What drove my job search: I left my job at Airbnb last spring to hike the Pacific Crest Trail, one of my lifelong goals. I am grateful I could step away from "real life" for six months. I was ready to move into Climate Tech before the hike, and now that I’m back in civilization, I’ve geared up my search.

Day 1

8:00 am

Woke up and tidied up the house while my partner made delicious eggs and potatoes—great way to start a Monday!

9:00 am

I met with a city inspector to check my new heat pump installation—the climate-friendly alternative to a gas furnace + air conditioning. While unemployed, I've been doing home projects because I have more free time to research incentives and meet with installers.

10:30 am

Applied to a job: Strategy & Operations Manager at Reunion. The job description stresses the "ability to get a high volume of work done quickly."

...I like moving fast, but pushing speed and volume so openly in their job description raises a flag.

11:30 am

Tool Lending Library + Home Depot to buy caulk to repair the trim around my garage door. Helped someone jump their car in the parking lot 🧰💪

12:30 pm

Lunch - just a Cliff bar while catching up on emails and browsing.

1:00 pm

Read a whitepaper on the solar development industry from two former colleagues. I saw they referenced the company I just applied to this AM. Great timing!

1:30 pm

Found five more jobs to apply to using Climate Tech network; saved them to Teal (later, I’ll share links to all the tools I use in my job search).

3:00 pm

Brief catch-up with a former colleague from Airbnb. I noticed her new job announcement on LinkedIn and left a comment saying congrats. She immediately reached out to see what I was up to post-Airbnb and recommended joining her new company noting the strong, steady leadership. I shared what I was looking for (climate), and she offered her network. It’s a good reminder of the value of staying in touch with former colleagues.

3:30 pm

I got rejected from a state Department of Energy role I had been excited about.

Rejection for a job I was really excited about. Oof.

I wonder what part of my application made them decide to pass. Was their decision personal or impersonal? Did they already have 5 good candidates so they auto-rejected everyone else? Or is there something I should change, i.e., was my cover letter too passionate or too personal for a government job?

It stings not to get feedback when you get passed up, especially since I always put a lot into my job applications.

4:00 pm

Did PT / strength workout.

5:00 pm

Early dinner before dropping my partner off at the airport.

8:00 pm

Looked at more jobs from 8-10 pm. Cut myself off and forced a wind-down by putting on a podcast while falling asleep

Total time job searching today: 6 hours (strange—it felt like much less!)

Day 2

8:00 am

Get a text from a friend reminding me of how stressful work can be! As stressful as looking for a job is, I remember how it's not actually a cakewalk on the other side either…

This conversation was a health reminder that, while job searching is stressful, so is having a tech job.

9:00 am

Grocery store run.

10:00 am

Weekly call with other job seekers as part of the Never Search Alone method. I formed a job search council with a high school friend who works as a PM in the Bay and two of her friends. It’s helpful to share where we are all at and get advice + connections for jobs we are interested in.

11:00 am

I research who to vote for in the lower offices of the California elections (due today!). Read through several voting guides online.

12:00 pm

Drop off my ballot and the tools I borrowed over the weekend

12:30 pm

Lunch: grab tacos at this new place near my house.

1:30 pm

Get paint match for the garage trim.

2:00 pm

Start customizing my resume for the jobs I found yesterday.

2:30 pm

Search LinkedIn for connections to my new target companies: Powin Energy, ChargePoint, Building Decarbonization Coalition. I don't see anything promising in terms of 1st or 2nd connections, which disappoints me. I’ve heard (and feel!) that sending applications without a referral results in nothing happening, (maybe your resume isn't even reviewed?).

3:30 pm

Call dermatologist offices to schedule an appt for a melanoma removal 🤕

4:00 pm

I was supposed to hear back today about an interview I did last Friday. The recruiter mentioned the note would come from their recruiting system (Lever) and warned me to check spam. I checked multiple times throughout the day but didn't see anything. It’s a nagging thought in the back of my head all day, and both my partner and my mom ask me about it. The wait is hard.

5:00 pm

Send friends a few jobs that I came across that are a good match for them.

5:30 pm

Pull all my tax docs together to send to my accountant.

8:00 pm

Look at jobs for myself. I keep tweaking my resume and looking for connections on LinkedIn. I start to get in my head. I worry that all the best jobs are hybrid in the Bay Area and that I won't find a good remote job that allows me to move to Portland to be with my partner.

8:30 pm

I’m planning to rent my house in Oakland when I move to Portland. I follow up on an ask from a potential property manager for references. I notice that similar properties in my neighborhood are still on the market two weeks later, and one dropped their rental price. I tweak my expected P&L spreadsheet to model a lower price, just in case. I check PG&E to estimate the utility bill before I bought solar. I paid a lot for solar upfront ($20k), and I want to charge tenants the previous price of utilities rather than passing on the discounted bills so I can recoup some of the investment over time.

10:00 pm

Wind down by listening to a podcast, cleaning the kitchen, and having a late snack/dinner (girl dinner?) of cottage cheese + pesto + tomatoes on toast.

Total time job searching today: 4.5 hours. Today felt less productive because I didn’t apply for any new roles, and I didn't hear back about the interview. Also, I regret not doing my PT / workout. I'm not working, you'd think I'd be able to make time for this!

Day 3

7:30 am

Wake up, do Wordle, look at new houses in Portland that went on the market overnight.

8:30 am

Get up, have a cliffbar, make my to-do list. Three main categories:

Rent Oakland house (decide if/which property manager, decide on rent price and what's included—utilities, pets, etc)
Apply to jobs
Organize the move (sell furniture, schedule moving pod)

I hope to get another interview, but adding more interview prep feels overwhelming given what’s already on my plate.

9:00 am

Taxes last night made me feel nervous about my finances. All my accounts are still open in different tabs on my computer, which brings back the worry. I send a note to a CFP friend to double-check that I'm doing my IRA rollover right. Check Wealthfront to see the financial impact if I don’t land a job until September 2024.

10:30 am

Decide to get a job app out of the way. I don’t want to go another day without filling my pipeline! Select one of my favorites from my list compiled on Monday. I'll reach out to one of my connections who knows the CEO. Two options for connections:

ex-boyfriend who's in the industry 😬
former colleague, but I can't tell how well he knows the CEO

I decide to go with the ex-boyfriend, and then I notice that the job is already gone! Taken down in 2 days. I guess I was too slow?

10:50 am

My regret is interrupted by a call from a potential property manager. We discuss the agreement, ask for references, go over my question re: utility costs. I schedule more time for Friday to discuss this in depth.

11:15 am

Inspector + electrician are back. He signs off on the heat pump installation immediately ✅

11:30 am

Start a doc that looks curiously like a PRD to help organize my research and decide how exactly to rent my house. Maybe this is good practice to brush off any PM skill rust from my 6 months in the wilderness?

12:00 pm

Lunch - reheat leftovers of turmeric chicken + rice, bake a sweet potato.

12:30 pm

Got up the nerve to reach out to an old colleague to see if she'd be up for an intro to her 1st-degree connection at Building Decarbonization Coalition (they are the ones who make The Switch Is On).

12:45 pm

Very quickly get a "we haven't talked since college" response from my former colleague, so that was a dead end. I try to figure out how to word a cold outreach message...

1:00 pm

Work on my “renting a house” PRD.

3:00 pm

Take pics of my house.

4:30 pm

Walk with a friend around Temescal Lake. Catch up on all things moving + job related. She offers to intro me to a few people she knows, and we talk about outreach strategies + the job market overall. She's passively looking too.

7:00 pm

Grab dinner after the walk.

10:00 pm

Back to my house. I’m behind on my list but feeling happy + rejuvenated after spending time with a close friend.

Total time job searching today: 1 hour

Day 4

7:00 am

Wake up to my cat purring in my face. Eat some toast with basil from my garden + cottage cheese + tomatoes + sea salt flakes.

7:30 am

List my space on Zillow! Add pictures, draft a listing description, decide rent price.

9:30 am

Double-check new laws about security deposits + tenant screening.

10:30 am

11:30 am

Start answering lots of questions and setting up showings! Tomorrow is going to be busy!

12:00 pm

Talk to my friend in NYC about his experience renting out his place in SF. Hear about people fishing for lawsuits to get newbie landlords in trouble. This makes me uneasy.

12:30 pm

Lunch

1:00 pm

Get landlord insurance quotes. I learn quickly that California is not the place to be if you want new insurance. Call four places, keep getting routed to talk to an agent because insuring in California triggers extra friction. They literally laugh at me.

2:30 pm

Open a new bank account for my rental income and expenses.

3:00 pm

3:30 pm

Set up six more showings and answer questions from potential tenants.

It’s nice to have so much interest in my house. I’m happy that I don’t have to settle for lower rent despite renting in the low season.

4:00 pm

Talk with friend who referred me to the climate company he just joined. I realize I’m getting mixed messages of working remote vs working in person. Seems like the CEO is pretty hardcore about requiring people in the office, despite managers and recruiting pushing a very relaxed message: "Come in occasionally if you want. Some people are full-time remote.”

4:30 pm

Paint the side of my staircase + chat with my neighbor about her new foster pup.

6:30 pm

Get a rental request from someone who works in Climate! And knows Coach Erika! What a small world.

7:00 pm

PT + strength workout while watching Summer House.

9:00 pm

Talk to my partner about our days and discuss logistics for the move.

11:00 pm

Make a to-do list for all the viewings tomorrow.

Total time job searching today: 0—I realize this is turning into a moving diary rather than a job-seeking one! Moving took center stage this week, I realize.

Day 5

6:30 am

Wake up to kitty purrs and remember that today is the big showing day!

7:00 am

Get up and prep for the tours. Vacuum the house again, wipe all counters, and stack the boxes I'm gifting to my Buy Nothing group. Keep trying to look at the house from a tenant's perspective. Does anything seem weird? Too personal? I turn a few self-help books around so you can't see the title on the spine 😬

10:30 am

Get a rejection email from the climate tech company my friend referred me to 💔 I cancel my scheduled follow-up email asking for an update. I try to remember all the excellent candidates I referred to Airbnb who got rejected too. Instead, I try to find the nuggets of constructive feedback. Even though I spent a few hours prepping, I think I may need more practice. I wonder what else they would say. I decide to ask for feedback from the recruiter.

I also reach out to the friend who referred me to let him know the outcome and to thank him for the support. He's disappointed, noting it's their loss. I realize that it wasn't meant to be! I'm moving, and asking for a hybrid role to be fully remote seems like an uphill battle.

11:00 am

Met with the first potential tenant! I try to take note of the types of questions she asks, what areas she's most interested in so I can point them out in future viewings. I realize I forgot to move some tools from the half-bath downstairs.

11:30 am

Bring tools down to the basement. Leave the lights on and the side door open for smoother entry. I see that the tenant from the first showing already sent a quick email saying thanks and asking for an application asap!

12:00 pm

Meet with a second potential tenant. It’s a couple who work in tech. They have a healthy income and no pets. They have many questions and push back on some policies in my listing description. I sense that we have differing expectations and think this may be a relationship with more conflict than I want.

12:30 pm

Respond to the influx of requests and questions I received from more people wanting to set up viewings over the weekend. I realize the built-in tools in the Zillow Rental Manager app don't let me see the schedule in order. I have to click on each message to see when the tour starts. I start a doc to keep track of times and notes from each set of tenants.

1:00 pm

Keep adding to my rental options document. It's looking increasingly like a PRD from work (some habits die hard).

I dove deep into becoming a landlord. It’s a minefield!

I realize I need to understand the timing requirements for the Rent Adjustment Program, which is the rent control program that affects practically all buildings in Oakland. I notice that they take 5 business days to review applications. I email them to confirm that I must register before signing the lease. I'm unsure what last-minute negotiations may affect the terms of the lease or the timing of it.

2:00 pm

Meet with a third potential tenant. It’s two friends, and they are super nice. I feel like we would be friends in real life. Their living needs probably aren't the best fit for my house, though. They would need to use both bedrooms full-time, but one of the bedrooms has a built-in Murphy bed and is intended to be used mainly as an office/guest room.

2:30 pm

Take notes on all the tenant meetings before I forget key details: who has a dog, who mentioned something relevant about what they're looking for, who balked when I shared I'm planning to sell when the market rebounds (🤞) in 1-2 years.

3:00 pm

Meet the fourth potential tenant: a quirky, hyper-cool couple. We work in adjacent industries, and they offer to connect me with people who work in climate tech. It’s the small world of tech in the Bay. Career connections can come from anywhere!

3:30 pm

While waiting for the last potential tenant to come (who ultimately ends up postponing until tomorrow), I can’t help but consider the similarities between job interviewing and house interviewing (both from the tenant and landlord standpoint).

It's all about fit and researching the market (pricing my place, understanding what a good deal looks like in my Portland search)
It’s also about putting my best foot forward (as both a landlord and a tenant, it’s definitely not one-sided!)

Job searching and tenant searching aren’t so dissimilar. Sometimes it doesn’t work out for reasons outside of your control.

4:00 pm

It's such a nice sunny afternoon. Friends who live a few blocks away ask if I want to do an early dinner outside. I offer to have them over for homemade pizza in my backyard. They happily agree and note it might be one of the last times we can do this! I head out to pick up some dough and toppings.

5:00 pm

We have a lovely impromptu dinner party in my backyard! It’s great to see friends and their 2.5-year-old. I appreciate having friends of 10 years around the corner to take advantage of sunny afternoons like this 🧺

Total time job searching today: 0.5 hr. Really, it was just reading the email.

What I learned this week

How similar job searching and renting a house are:

the preparations before a house viewing (interview prep)
the expectation-setting in a listing (job descriptions, resumes)
assessing a fit on both sides (and how sometimes it's personal and sometimes it's circumstantial)
process steps and navigating advancement to the next step (interviews)
navigating new tools (screeners vs scheduling tools)
the legal angle (what am I allowed to ask?)
the financial angle (what can I afford? how much can I go outside my budget if it's a perfect fit otherwise?)
the reference checks, credit checks, background checks

I also reflected on the benefits of writing things out to help process big decisions. I had been spinning over the risks and the 50+ decisions needed to set up a house rental. Writing a good old-fashioned PRD-like document helped me track my research and process the pros and cons of each decision. It also helped me get feedback to uncover any factors or options I missed (sharing the doc was easier than explaining it all to each friend I asked for advice).

What I’ll adjust for next week

Next week I will likely still be in house mode as I’ll be in Portland looking for a house to rent. But when I pick up the job search in the coming weeks, I'll try to:

be clear on my expectations, I will consider writing them down in a private doc to process my goals as clearly as I did with this rental PRD.
remind myself that the first interviews aren’t always going to work out, and it’s good to learn what needs to be smoothed out
not take rejections personally. Sometimes it's really just not the right fit. One door closes, another opens.

I'll also strive to be more proactive and go outside my comfort zone when reaching out to prospective companies. They are hiring and want excited, qualified people to apply!

Tell us more

How would you describe your job search strategy? What's working? What needs adjustment? My search is hyper-targeted. I only apply to jobs that are a perfect match, and I customize my resumes, write a bespoke cover letter for each role, and always take the time to get a referral (when I can find a connection!).

How many hours a week do you spend on your job search? Can you break this into rough buckets? 4-5 hours a day, but I don’t search every single day.

2-3 hours sourcing opportunities and researching the company
30 minutes reaching out to connections to ask for intros/referrals
1 hour customizing my resume & cover letter for the most exciting prospects

How much of your time do you spend sharpening your skills? How do you do this? To prepare for my interviews, I write out all the answers to questions that I expect to receive, record my responses, and then practice aloud with a family member.

What is the best part about job searching? It’s fun to see new roles, learn about different companies, reconnect with old colleagues, have flexible time to travel (hello, ski season!), and do other life projects.

What’s the worst part? Rejection 🤕, fear for the future, self-doubt.

What are your current favorite job search tools, and how are you using them? Here are 5 of my top tools:

Teal: to track jobs I want to apply to and track where I'm at in the process
Claude: to respond to emails + draft cover letters
LinkedIn: to see who I know at a target company and reach out for intros
Climatebase & ClimateTechList: to find jobs in climate. Climate spans many industries and roles, which makes it hard to look for on LinkedIn. These niche lists are more searchable when you have specific areas of interest within a larger industry.

What's one tool or service you couldn't imagine living without in this job search?LinkedIn. It’s hard to imagine how I'd figure out who to contact for intros and referrals without it. Pros: core functions are solid: finding out who works where (1st, 2nd, 3rd-degree connections!) and being able to message them. I also find great inspiration from other people’s profiles, ie, how to describe myself and my accomplishments. Cons: Job filtering doesn't work great for my search because it’s quite niche, and the endless newsfeed scrolling can be addicting and wasteful.

What's one thing you regret spending time on while job searching? Any cold applications. They don’t seem to work for me.

Advice for other job seekers in tech? Enjoy the time off while you have it. You can apply for jobs and get outside for a bit each day. Try to stay refreshed and enjoy the moment.

That’s a wrap! I invite you to use the comments to share your thoughts or to ask a clarifying question. If you know someone who would love to read this, share it with them.

Job Search Diaries No.3―Jill of All Trades (Program/Product/BizOps) Manager

Returning to a job search after hiking 2,653 miles on the Pacific Crest Trail. Pivoting into a new industry, becoming a first-time landlord, and the jitters of moving away from a tech hub.

Day 1

Day 2

Day 3

Day 4

Day 5

Tell us more

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