Field notes from the job hunt

My time at Ness ended on July 17th. After roughly four months, I’m excited to share I start my new full-time role on Nov 27th with Paytient. I honestly couldn’t have found a better fit; more on that in a future blog post.

Today, I wanted to share some ideas and references that I found helpful while navigating the emotional rollercoaster that is job hunting.

On one hand, the break was…nice. I was able to be there for my family. Our oldest started Kindergarten, and I had the flexibility in my schedule to do drop-off and pick-up every day. When our youngest picked up hand-foot-and-mouth, I was there for that, too. I also had my fair share of relaxing days spent hiking, meeting friends, and reading.

On the other hand, it was incredibly tough. For better or worse, my professional life is a big piece of my personal identity. I enjoy working! I missed the daily cadence of building something amazing with a great team. At the same time, I experienced the highs and lows that come with finding a new role—mountains of applications, interviewing, checking email dozens of times per day.

With that context in mind, here are some ideas. Two quick notes. First, your mileage may vary. This is just what worked for me! Second, I was very fortunate that I could take my time finding the right role. Your situation might be different. Context is everything.

Don’t start applying immediately.

I did what I assume many other people do when they’re laid off. I applied for ~30 jobs in the first week. I received 0 interviews, which left me feeling quite frustrated. If I’m being honest, I didn’t even want 50% of the jobs I applied to; I just wanted any job. I would recommend against this approach. It was wasted effort that felt productive at the time.

Develop your support system.

It helps to have friends supporting you throughout this journey. My support groups fell into three buckets:

  • I joined a free Job Search Council (more on this in a moment)
  • My friends and family were always there to listen and build me up
  • Professional relationships that helped with support, advice, and introductions. Keep a list of these people (I use folk). You’ll want to keep them updated as you progress through your search (more on this below).

Spend time figuring out what you want.

Broadly, I see two ends of the spectrum for finding a new role.

On one side, you have the volume approach—applying to 10+ places a day, tailoring your resume for ATS systems, and hoping to land an interview. On the other side, you have the tailored approach—sending 5-10 applications per week that you’re uniquely suited for. I tried the volume approach for ~3 weeks and had very little success. I wish I would’ve shifted to the tailored approach sooner.

I targeted my approach through two different processes:

  • The Mnookin two-pager and Candidate/Market Fit exercise through the Job Search Council mentioned above.
  • I took Erika Klics’ Focused job search course

There’s a lot of overlap between the two resources. In general, you’re combing over your past experience, identifying the overlap between what you enjoy and what you do best, and aligning that with the job market through research and specific conversations (recruiters, past colleagues, etc.). This alignment includes role-specific responsibilities and also company-level or industry-level details.

Now, instead of a scattershot approach selecting jobs based on title alone, you’re really clear on your fit. Honestly, this took me about six weeks to dial in. I spent a lot of time walking my neighborhood just thinking.

Figure out your tooling.

It’s a good time to be in the job search tooling market. There are an endless amount of resources available. I used the following tools and ignored everything else:

  • Teal – Creating resumes and cover letters
  • Google Sheets – Tracking applications
  • Dropbox – Dedicated folders for each application to hold my cover letter, job description, and resume
  • Obsidian – This was already part of my core toolkit, but I set up a separate folder for collecting interview notes
  • ChatGPT – Mainly for preparing for interviews
  • LinkedIn – Connecting with hiring managers and recruiters
  • Otta – The primary way I found new opportunities
  • Since I was focused on the fitness/wellness and healthcare worlds, I also used niche job boards like Fitt Jobs

Outside of paying for LinkedIn, I used the free version of everything. Unless you have a great reason to switch, don’t hop tooling. It feels productive in the moment, but I found it was ultimately a waste of time.

Define your schedule.

When you’re in a full-time role, you naturally have a rhythm and structure built into your day. When you’re unemployed, you have to define this for yourself. Otherwise, it’s easy to lose a full week aimlessly doing stuff.

I’m a big fan of Cal Newport’s weekly/daily planning cadence. Each week, I sat down and laid out some goals. Generally, that consisted of eight to ten applications and five coffee chats. Then, each morning, I laid out a daily schedule in service of my weekly targets. I boxed my job search to four hours per day, roughly broken out like:

  • 9:00-9:30: Admin and email
  • 9:30-11:00: Find and apply for opportunities
  • 11:00-11:30: Break (walk/eat)
  • 11:30-1:00: Either coffee chat, prepare for interviews, or identify more opportunities
  • 1:00-1:15: Admin and shutdown

This schedule varied depending on what I had going on. For example, if I had several simultaneous interviews, I spent less time applying for new opportunities and more time preparing (and vice versa).

Find opportunities and apply.

Once I had my “fit” (described above), I was able to quickly find new opportunities and submit an application. There’s a lot of pre-work before getting to this step. I skipped this pre-work initially and had a 0-10% interview rate, never really making it beyond the recruiter screen. After doing the pre-work mentioned above, I was getting a 50-60% interview rate. Slowing down really did help me speed up.

With my Mnookin and Candidate/Market Fit statement plus Erika’s course, I could quickly triage possible opportunities. As Erika describes in her course, I only considered an application if I met 70% of the requirements and had at least one key area of overlap. To find areas of overlap, I’d dig through my past experience and find commonalities. For example, I worked at on CMS systems for 7 years. I’ve also worked on Developer Platforms at Zapier. If you’re a SaaS CMS tool building a Developer Platform, I’m a unique fit (real example).

It took me ~30 minutes to comb through job boards each day and triage opportunities. I’d find 2-3 good fits and apply to those. Each application took 20-30 minutes. Again, I used Teal for managing my resume and wrote the cover letters myself (using these templates).

I know many people that agonize over each line of their resume and use ChatGPT to whip up cover letters. I kept my edits lightweight; I was playing the targeted game, not the volume/ATS game. I lightly edited my resume each time, tailoring it to the role, and highlighted my unique overlap in the cover letter. Once I applied, I took a screenshot of the job description and dropped my resume, cover letter, and the screenshot in a dedicated Dropbox folder.

After applying, I found the hiring manager on LinkedIn and send a brief message outlining my background and my unique overlap. If I couldn’t find the hiring manager, I found someone adjacent to the role. I received responses about ~30% of the time.

Track your applications.

When I first started, I tracked all of my applications in a massive spreadsheet with a single “status” column. This was a big mistake. I had no easy way of recognizing patterns or learning from my approach.

Following Erika’s guidance, I started breaking out applications by week and getting granular about my funnel performance. Each week had a separate tab. The tabs tracked each application (linking to the Dropbox folder) and the progress across four stages:

  • Recruiter Screen
  • Hiring Manager
  • Late Stage
  • Offer

Now, I could roll up each week into a summary tab and see my overall performance (factoring in a ~two week lag). What percentage of applications where landing recruiter screens? Of those recruiting screens, how many were progressing to the hiring manager stage? (Erika provides good targets for each of these stages, by the way.)

This was incredibly helpful. I could now investigate “problem” areas. Was I having trouble landing recruiter screens or getting beyond the hiring manager interview? Those are two separate issues with different tactics.

Meet people.

Seeking out and applying for roles was half of my approach. The other half was building connections with people. I have a whole separate post to write about what I’m calling “small n networking,” but this podcast is a good starting point.

As a brief overview, I tried to meet four to five people per week for coffee, blending old friends and new. I didn’t focus the conversation on my job search. Instead, I asked about their lives and professional ambitions. Then, I tried to help wherever possible. In some cases, I made introductions. In other cases, I sent along articles or references I thought they would enjoy. Inevitably, my job search would come up though, and I would ask three specific questions:

  1. Clarify my interest and ideal role. I viewed every person I met as an advocate. I wanted to give them the information necessary to source roles on my behalf. “I’m looking for a PM role” is not very helpful. “I’m looking for a PM role on a Series A/B startup in healthcare” might bring some connections to mind. I’d frame my ideal role and then make a broad ask like, “If you learn of any available roles, I’d love if you could keep me in mind.”
  2. Ask specific questions. Generally, I was speaking to other product managers or product leaders. These connections either had gone through product hiring loops or run hiring loops themselves. I’d ask for specific feedback on aspects of the hiring loop. Often, I focused on the case study portion of product interviews.
  3. Ask for my next connection. I’d phrase this like, “I’m interested in meeting new connections within the product space, specifically within healthcare. Who should I talk to next?” I usually heard 2-3 names and an offer to make an intro, which kickstarted my next chats.


I spent a lot of time preparing for interviews. For early rounds (recruiter and hiring manager), I’d prep for 45 minutes per round. For later rounds, I’d spend 60-90 minutes or more depending on if the round had a project component.

During this prep, I focused my energy on:

  • Understanding the company, the product, and the surrounding market
  • Combing through the job description and my past experience to identify stories that align well with the responsibilities
  • Doing “mock” interviews with ChatGPT combining these two ^

Over time, I grew a database of experiences following the STAR++ format described in this Lenny post. Then, I could pick and choose which stories were most appropriate ahead of an interview. I found interviewing with ChatGPT to be very helpful, particularly if I was new to an industry and needed context.

Send bi-weekly updates.

This is my single biggest tip and the best “hack” I found along the way (from Never Search Alone, the book behind the Job Search Council process).

As you progress through your job search, you’ll build a growing cheering section. I visualized this as an army of supporters willing to make connections, provide referrals, and generally be helpful in any way possible. I can’t tell you how many conversations would end with, “Well, let me know if I can ever help.” Two things are true. These individuals mean well, and they are busy.

With this in mind, I had two goals 1) grow the army of supporters and 2) tell them how they can help.

I did this through bi-weekly updates sent individually through email. The title was “Job Search Update,” and the content took ~45 seconds to read. I included emojis and stripped out any unnecessary text to keep it brief. Generally, I had three bullet points:

  • 🤞 I’m currently interviewing at these companies: ABC and XYZ. The next big milestone is…
  • 🔍 This week, I applied for roles at COMPANY and COMPANY. I’d love an introduction…
  • ❤️ One way you can help is…

Most of the time, the person would either not respond (remember, they’re busy!) or send back positive words of encouragement. That’s okay! I’m staying top of mind.

More times than you might imagine though, I’d get a hit. Someone could put in a word or new someone that had a connection. Often times, these connections were invisible to me (not on LinkedIn). I really can’t underscore how powerful this was as a tool.

Again, this is what worked for me. It all sounds very linear and organized, but I promise there were dozens of false starts. Finding a job is an inherently messy and emotional process. This eventually gave me some structure that produced a very positive outcome.

If you’re searching for a new role, I hope these tips help. If you need a sounding board or just someone to listen, I’m here for you! Email me at jeremeylduvall-at-gmail. You got this!

Photo by Matt Ragland on Unsplash

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