My Job-Hunt Stack: LinkedIn, AI, Airtable, and Coffe

I wanted to spend a little bit of time talking about the job hunt since I’ve been back in the States. It's been about a month since leaving Emirates after heading up their digital product design organization and getting back into the flow of things. What I’m seeing is that the market is rough. The combination of layoffs across digital and AI isn’t making it easy for anyone on either side.

The Current State of the Market

Organizations are using AI to prescreen CVs before they hit a human, and candidates are using AI to generate CVs to interface with the Applicant Tracking System (ATS) being deployed by organizations. Getting in front of a human is the first hurdle in an already challenging market.

My Job-Hunt Stack

Your network will be your biggest asset. Since being open to work, my job-hunt stack has included LinkedIn, Airtable, Claude, Gemini, Slack, and Twin Cities metro-area coffee shops. So, how does it all come together?

The Step-by-Step Process

Step 1: Sourcing & Organization

• I’ve been using LinkedIn for a horizontal view of what openings are open.
• I’ve set up a variety of job alerts with different keywords and different locations.
• This fills my inbox with a daily digest of open roles in the design leadership space.
• If I come across something that feels like a good fit, I’ll set up a folder structure in Google Drive to help organize the documents.
• Inside each folder is a notes document and a CV document.
• The notes document contains a tab with my vanilla CV, a tab with the role job description, and an empty tab to be filled in later.
• I’ve then been using the role's job description and pasting it into the job description tab.

Step 2: The AI-Assisted Resume Tailoring

With those two tabs in place, I’ll head over to Gemini or Claude and have it help create a tailored CV for the role based on my actual CV and the job description.

The "Tailor-Fit" AI Prompt. Copy and paste the text below into Gemini or Claude, filling in the bracketed information with your own details.

Prompt: Act as an expert executive recruiter and ATS (Applicant Tracking System) optimization specialist. I am applying for the [Insert Job Title] position at [Insert Company Name].

I will provide the job description and my current "vanilla" resume below. Your goal is to help me tailor my resume to this specific role. Please do the following:

Keyword Extraction: Identify the top 6-8 critical skills and keywords from the job description.

Resume Tailoring: Rewrite the bullet points under my work experience to naturally incorporate these keywords and emphasize the experience most relevant to this role.

Action-Oriented Impact: Ensure the new bullet points use strong action verbs and highlight quantifiable achievements (e.g., increased X by Y%).

Strict Boundaries: Do NOT invent, fabricate, or exaggerate any experience. Only use the facts and history provided in my current resume.

Output: Provide the updated resume in a clean, simple, ATS-friendly text format.

Here is the Job Description: Tab #2 in the Doc

Here is my Current Resume: Tab #1 in the Doc

The output from that exercise then goes into that empty Google Doc tab in the notes document. This gives me a very raw but tailored CV for the role I’m getting ready to apply for.

Step 3: The Human Touch

The next bit of the process is critical. Now that I’ve got a raw CV, I need to make sure it’s accurate and that it fits my voice and tone for how I’d like to position myself. Running the raw CV through a human-in-the-loop quality assurance flow helps keep me in the driver's seat. After I’ve got the CV in a good spot, I’ll bring it into that second Google Doc titled CV document.

Step 4: Application & ATS Alignment

• Now that I’ve got a CV tailored to the specific role, it’s time to log in to the HR software and apply.
• What’s nice about coworking with Gemini or Claude is that the CV output tends to be ATS-ready, which means the autofill feature in HR software (Workday, Ashby, SAP, etc.) tends to work pretty well.
• Fields are accurately populated 90ish percent of the time.
• After the software autopopulates the fields, I go back through and do another round of QA on the inputs.
• If everything checks out, I hit the submit button and move on to the application tracking part of the journey.

Tracking the Journey

For application tracking, I’ve been using Airtable. I came across a great base template from Jeff Maddux called “The Ultimate Job Application Tracking Tool” (opens in new tab). It’s well structured and simple to use. It's been good to have a bird's-eye view of the application journey. There are fields for materials submitted, salary range, role title, company, and a lot more. It’s quite robust. As I hear back from companies, whether with a rejection or an interview opportunity, I update the tracker to keep things current and organized.

Closing Thoughts

The current market is busy and loud. There is a lot in motion across the entire digital space. Keep things positive and don’t take it personally. Hiring managers are just one piece of the puzzle and they are swimming upstream in a sea of red tape.