How I Found a Job in This Brutal Market (and What You Can Steal From My Strategy)

No gatekeeping. Here’s exactly what worked—resume tactics, LinkedIn hacks, and tools that got me interviews.

When I first launched this newsletter, my opening post mentioned the last job I left and the new season I was stepping into.

What I didn’t share was how I actually landed that job.

The last five years has been a rollercoaster in the job market. We went from a candidate’s market in early 2020, with remote work becoming the norm, quiet quitting trending, and people juggling multiple jobs, to a market where folks are applying to hundreds of roles and getting zero callbacks. And those still employed? Often asked to “do more with less.”

I remember “doing more with less” well. I recall being in a work ‘Town Hall’ where our CTO literally said we had to do so, verbatim.

At the height of my last role, I was operating as a Product Lead within a 100k+ person org, meeting daily with 30+ engineers, pushing strategy, driving deadlines, and delivering high-stakes projects. It was also the year I earned more gray hairs than I care to admit (no, seriously). Eventually, I realized it was time for my next chapter. But how do you make a move in 2025?

The rules have changed. Gatekeepers are shifting. And competition is steep.

In my case, I was fortunate to get several interviews, largely thanks to a great resume rewrite and some very intentional bullet points. But even landing interviews with hiring managers wasn’t always enough. I made it to multiple final rounds and still didn’t walk away with an offer.

That’s [one] part most people don’t tell you.

Eventually, I found myself with options—and accepted a role I’ve been genuinely excited about. One where I feel seen, heard, and like I’m leaving a real impact. I can’t say what the future holds, but today? Today feels good.

So how do you navigate this job market chaos?

I won’t pretend to have all the answers. But I will share exactly what worked for me, as a job seeker in the U.S.—no gatekeeping. Here is Part I of this II Part Series.

Let’s get into it.

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What Worked for Me

Quick point of clarification: This mainly references my experience as someone working in the tech & software development portion of several industries, which is no way represents all industries ( I can think of a few where this would mean little). Roles like Program Manager, Project Manager, Product Manager, Sales Rep, Cybersecurity Analyst, Marketing Manager / Analyst, etc. are all in scope here. I acknowledge certain industries such as education, media, the medical field, federal government, typically have their own unique systems and intranets that job seekers must frequent. I don’t know much about those, but the things I do know, I will share:

Here’s the honest breakdown of what I did to get traction—today we’ll focus on LinkedIn, and then later, we’ll go beyond it. No fluff, and no pretending any one thing was a magic bullet. It was a system, not a shortcut, that worked. It also did not happen overnight, it took several months of getting in front of the right teams, then getting a comfortable interview posture, and then getting to offer stage. The in-between was beyond frustrating. So remember: This is a marathon friends.

I also practiced what I call the ‘100 no rule’. Until I heard ‘no’ from final interviews 100 times, I believed the role just wasn’t mine, and the right one was on the way. If you are reading this because you need it, I’m asking you to first, believe. Within the 100 no rule, I also had to adapt. If you’ve made it to ‘no’ 27, it may be time to review and understand what parts of your workflow, resume, interview, or overall presentation isn’t working and kept adjusting. Easier said than done, I know. But don’t give up.

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I Paid for a Resume Template, & Used AI to Update It Over Time

I know people say design doesn’t matter unless you’re going for a Marketing role. But presentation does—especially when recruiters are scanning 300+ resumes in an hour.

I hired a resume writer, who provided a modern template and it immediately leveled up the clarity of my resume. Worth every dollar (I initially did this in 2021, but the template still did it’s job, even 4 years later). The other real value came from doing the heavy lifting on the content: quantifiable wins, strong verbs, no filler - less fluff.

No funds for an expensive rewrite? You have a few options (1) There are tons of free tools that will help with templates such as Cultivated Culture Templates or Canva (yes, Canva has resume templates). AND/OR (2) Insert AI tools such at Claude, or ChatGPT to begin leveling the playing field. As of today, Chat can be used for free, with $20 for the premium membership for 1 month. For my latest resume rewrite, I took the template I had from 2021 and used Chat to update and optimize each bullet point. Why else should you consider this? Because your competition (everyone else applying to jobs) is doing this right now. By not considering methods involving where the overall market is headed, we risk being buried under a pile of other ‘qualified leads’.

Need some prompts within Claude or ChatGPT to get started? Here are two prompts that I used more than once.

Rate My Current Resume, & Help Me Update it to an A+

Prompt: You're a seasoned tech recruiter and hiring manager with 15+ years of experience at top companies like Google, Meta, and Amazon [OR INSERT YOUR INDUSTRY/COMPANY HERE]. Act as a brutally honest expert. Evaluate this resume and assign it a letter grade (A–F) based on:

1. Clarity & Structure – Is it easy to skim in 6 seconds? Is the layout clean and modern?

2. Relevance – Does it match current job market demands for [insert role]?

3. Impact – Do the bullet points show measurable achievements or just responsibilities?

4. Language & Tone – Is the language concise, powerful, and aligned with seniority level?

5. ATS Optimization – Will it pass applicant tracking systems?

Then answer:

• What’s the letter grade and why?

• What are the top 3 issues holding this resume back?

• What are 3 specific changes that would raise the grade?

Here’s the resume:
[Insert or attach resume content]

Then, based on the feedback, ask for update recommendations and execute as necessary.

Cross Reference My Resume With The Job I Want & Help Me Optimize

Note: Prior to starting this prompt, take the text for the job description you want and have it at the ready, as well as your resume.

Prompt: You're a senior recruiter and resume optimization expert with 15+ years of experience placing top talent at companies like [INSERT YOUR INDUSTRY COMPANIES HERE].

Step 1: Review the uploaded resume and job description.
Step 2: Cross-reference them and assess how well the resume aligns with the job description, focusing on:

• Keywords and technical skills

• Role-specific responsibilities

• Industry terminology

• Level of seniority

• Quantified results vs generic duties

Step 3:

• Give a match score out of 100 and explain the score

• Identify the top 5 gaps or mismatches

• Rewrite 3–5 key resume bullet points or sections to better align with the role (using strong action verbs, quantifiable impact, and relevant language)

Input:

• Resume: [Paste or attach resume]

• Job Description: [Paste or attach JD]

Be precise, strategic, and bold — the goal is to maximize alignment and get interviews.

Based on the output, then ask for assistance aligning your resume with the job description to make you a 100% fit for the role.

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I Set Job Alerts on LinkedIn (and I Applied FAST)

Every time a new job in “Privacy” or “Product Management” dropped, I was one of the first applicants. LinkedIn job postings move quickly, especially the good ones—so I made it a rule to apply within 24 hours of a listing going live. The truth here is that execution is necessary. With many roles (especially in Tech), once you have _x_ number of viable applicants, it is virtually impossible to get in front of the hiring manager. In this environment, we want to apply before the job has been active for 1 full day if able, and no later than a week since it’s been opened.

How did I keep track of all of this with different jobs and different resume versions? I had a resume folder, and within that, subfolders for each company I applied to and a version of my resume that was updated for that role. So when I got a callback, I could reference the resume that was submitted.

Pro tip: set notifications for specific job titles, not just broad categories. You’ll get a notification once per day from the LinkedIn app this way, and you can review daily instead of hour by hour.

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I Turned on “Open to Work”—Privately

LinkedIn lets you quietly signal to recruiters that you're open to opportunities. I turned that on (but did not turn on the green ‘Open to Work’ banner — I did not want to signal to my current employer that I was looking) and updated it every single week to keep my profile circulating (turned it off and back on). This helps you come up as a fresh new ‘Open to Work’ to recruiters. I also refreshed my Skills section with keywords aligned to the jobs I was applying for. Small moves, big visibility boost. You want to be seen? Update the part that people using LinkedIn for recruiting care about. This helped some, though I admit mainly for contract roles in 2025 (not Full Time roles with benefits). Still, if you are actively searching, this is still good. In the past (think 2017), this alone was enough to be found for a Full Time role (which was a huge promotion at the time). Don’t sleep on this.

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I Used Boolean Search on LinkedIn

Here is where I started doing things that I did not see my counterparts doing also in the job search. Want to skip the fluff and find people actually hiring?

Try this:
Go to the LinkedIn search bar and type:

‘hiring’ AND ‘INSERT JOB TITLE HERE’

For example, I would insert, “Hiring” and “Product Manager”

or

“Hiring” and “Privacy”

Look specifically at “posts”.

These search results will show you real humans who’ve posted about open roles that have those keywords in the roles/post—often right after those jobs hit any board. You can then filter by those who have posted in the last 24 hours. Using this process, I learned that all companies don’t have a huge budget to pay for LinkedIn job postings when each role opens. We can use this to our benefit to find jobs that may be fitting to you before anyone else sees it, or even jobs that never actually made it to the ‘jobs’ portion of LinkedIn, only existing on company websites.

Note: Results here can potentially be broad. E.g. When searching for Product roles, I typically found roles globally, vs just the U.S. (where I’m based). So it’s not fool proof, and it still requires review.

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I Reached Out Directly

When I found someone hiring for my kind of role (using the above boolean), I messaged them. Not a generic pitch. I referenced the role they shared, connected the dots between their needs and my skills, and kindly asked for 30 minutes of their time to learn more. I was specific and granular in less than a paragraph. I also messaged them on a Saturday (in my defense, the role was posted on a Friday — but I had no shame in reaching out if it meant a great opportunity).

Pro Tip: Shoot Your Shot. The worst that can happen is you don’t get the job and you never see this person again in your life.

In this case, I was afforded 15 minutes with the Hiring Manager. This is vital if those are 15 minutes no other applicant received. Don’t sleep on advocating for yourself if you meet a need an org has and you are confident about it.

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I Used My Network

Let people help you. I know it can feel awkward to say “I’m looking,” but when I let my trusted network know I was exploring new roles, the support was real. The hidden job market is real—and more generous than we give it credit for.

In a situation separate of this one, I have been fortunate to see this at play. An opportunity that literally never made it to a job board. If you are in a role that you like currently, network! Meaning, build strong relationships with each and every person you come across, and if possible, you can help each other in scenarios such as this one, should the opportunity arise.

If you are reading this with a substack account and your own newsletter, I’m looking at you. Network.

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Final Word — For Now

If you’re in the thick of a job search right now: I see you. This market is no joke. But you are not helpless, and you’re not without power.

Be strategic. Be visible. Be early. Be real. And be relentless, but also rest when you need it.

You deserve to land somewhere where you’re seen, valued, and paid.

And if you’ve read this far, please remember, I'm rooting for you.

Come back for my next installment of this 2 part series, where I’ll show you how to get to the bottom of finding your next job, outside of LinkedIn. Looking forward to seeing you friend, and I hope you found something here, Just For You.

Justin

Was this helpful? Not helpful at all? What tips would you add? Which ones did you have a different experience with? If you don’t live in the U.S., how is the process for finding quality work different or the same? Let me know — I’d love your thoughts.

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