Reading · Black Tech Pipeline

The job search is not easy, and there are plenty of approaches that claim to make it easier, especially with AI. My honest take: the traditional way will always win, but building ease into that process makes it a lot less stressful.

I’ve been experimenting with different strategies, and none of them let you remove yourself from the process. No tool or service that claims to handle it for you actually works well. What does work is having a smarter system. Here’s one that at least helps:

I run around 10-15 LinkedIn job alerts using Boolean strings that Claude and ChatGPT helped me build. My phone goes off all day, and while that gets annoying, it surfaces opportunities quickly. Here’s how to set it up:

Using ChatGPT, Claude, or both, upload or paste an anonymous version of your resume and submit this prompt:

Here is my resume: [paste or upload resume]

Roles I’m targeting: [titles, seniority level]

Industries I want: [list]

Industries I want to avoid: [list]

Role types from my past I do NOT want: [list]

Main Task — Targeted Roles

Generate 5 to 10 LinkedIn job alert search strings I can paste directly into LinkedIn’s job search bar.

Rules:

Only use AND, OR, and quoted phrases
Only use job titles that appear in my resume or in “Roles I’m targeting”
Minor title variations are allowed (e.g., “Program Manager”, “Program Lead”, “Director of Programs”, “Programs Director”)
Do not assume or infer anything beyond what is provided
Reflect industries I want using relevant keywords
Avoid unwanted roles by not including related titles or keywords

Additional Task — Role Discovery

Identify 3–5 additional roles I may be a strong fit for based on my resume.

Rules for this section:

You MAY introduce new role titles, but they must be directly supported by my experience
Do not suggest roles that require skills I have not clearly shown
Stay within my preferred industries
You may include adjacent industries only if the role function is identical and clearly transferable
Do not introduce entirely new industry categories
Avoid roles I explicitly said I do not want
Prioritize roles adjacent to my experience (not drastic pivots)

Then for each suggested role:

Provide the role title
One-line justification tied to specific experience
1 Boolean search string using that role
Include 2–4 relevant industry keywords in the Boolean string

Output Format

Section 1: Targeted Roles

Boolean string
One-line note on what it surfaces

Section 2: Suggested Roles

Role title
One-line justification
Boolean string

Paste the generated boolean strings into LinkedIn’s job search bar, click on the ‘jobs’ only page, then apply your filters before saving it as an alert. Set it for roles posted within the past 24 hours, your preferred locations, and anything else relevant. Keep in mind: the more specific your filters, the fewer alerts you’ll get.

Once you find a role worth pursuing, go directly to the company’s site to apply. Don’t apply through LinkedIn.

Once you’ve found roles worth pursuing, the next step is tailoring your resume, and no, there’s no tool that does this for you in a way that actually works. What I built gets you closer though.

Resume Tailor is a free GPT built into ChatGPT (no downloads or sign-up required) that takes your resume and a job description and gives you:

Newly developed bullet suggestions to make you more appealing for the role
An honest read on how well you actually fit, strengths and gaps included
Ways to elevate your transferable skills
Guidance on how to position your skills and experience
Examples on how to strengthen specific bullets for that specific role
A way to turn your resume from a list of tasks into a cohesive story of your history

Tailoring is exhausting and time consuming. This won’t do it for you, but it’ll cut down the time it takes to figure out where to start.

Check out Resume Tailor🔗

A referral is still the most effective way to land a job. Before you apply anywhere, check whether anyone in your network is connected to that company.

Here’s how to find out directly on LinkedIn:

Go to your personal LinkedIn profile
Click on your ‘connections’ in your LinkedIn header
Click ‘search with filters’
Click the ‘Current companies’ filter
Type the company you’re interested in and click ‘Show results’

This filters your connections by company affiliation. Even if you don’t know them well, reach out. A referral from an acquaintance still carries more weight than a cold application.

Here’s a message you can send even if you rarely interact:

“Hi [Name], I saw the [role title] opening at [Company] and I’m applying.

Quick context: I have experience in [1–2 core relevant things], and this role lines up well.

If you’re open to referring me, I’d really appreciate it. If not, no worries at all.

Happy to send my resume to make it easy.”

None of this totally removes the work of the job hunt, but incorporating these steps makes the process less chaotic.

1. Go-To-Market Recruiter | Remote in U.S. | $108,000– $130,000

2. Principal Product Marketing Manager | Remote in U.S. | $157,000 - $210,000

3. Sr Product Marketing Manager | Remote in U.S. | $145,000 - $190,000

4. Product Manager, Synthetics | Remote in U.S. | $160,000 - $180,000

5. Prototype Design Engineer | Remote in U.S. | $170,000 – $210,000

6. Sr Product Manager, Kentik NMS | Remote in U.S. | $190,000– $230,000