Meet My Job Search Aide "Claude": Using AI Assistants to Organize and Assist In Your Job Search

Well... at least it's honest

If you are currently on the job hunt right now you know one thing for certain - the amount of information you are trying to keep track of at once is overwhelming. In today's market of constant applications and rejections I have found it hard at times to even remember when I have applied for a job already and been rejected (I guess that at least means I wasn't losing sleep over the rejection, right?)

When I was two months into my last job search I ran into a good problem to have: I had so many interview requests to schedule and prepare for. And I didn't want to lose track of new positions that were becoming available in case none of these worked out how I wanted, so I needed to still be applying to great opportunities as they came up. Overall, I was finding that my job search was becoming an all-consuming project that I needed to schedule out time for while still maintaining the work of my current 8-5 job and did not know where to start.

This was where Anthropic's Claude came in.

I know what you are thinking. If you work in basically any sector of corporate America right now, "AI" is being shoved down your throat at every opportunity and you are probably sick of even hearing the word anymore. I am right there with you. Let me assuage your fears from the onset that this is not me convincing you that AI can do everything for you and serve as a replacement for all current corporate workers (sorry executive overlords).

What AI can do (and especially LLMs) is be a fantastic thought parter, skilled writer, and organizer of project work. And those capabilities are what you need the most when tackling a job search. Whether it be helping to write a cover letter, reviewing a job posting to see your interview selection likelihood, or prep you for an upcoming interview, tools such as Anthropic's Claude, Open AI's ChatGPT, or Google's Gemini are fantastic LLMs to get you organized and on the right track with how you are applying.

Below are just some of the ways that you can use these tools in your job search (with some of my own personal anecdotes of what works well and what not so much) to get you off to races when looking for a new job.

Resume & Application Materials

• Write, rewrite, or tailor a resume for specific roles or industries

• Optimize resume language with relevant keywords for ATS (Applicant Tracking Systems)

• Suggest better action verbs and quantifiable achievements

  • Resumes need measurable words to prove that you succeeded in your role and weren't just there for the paycheck. Let the AI assistant suggest places where specific numbers can help clarify the role that you had and what it helped your company achieve

• Format and structure resumes for clarity and impact

• Write targeted cover letters from scratch or customize templates

  • WARNING - this is where I found the most "hallucinations" during my process. Both Claude and ChatGPT were prone to adding in experience I did not have based on the job posting that I was applying for. Review every section very carefully so that you are being honest with your experience for a recruiter.

• Draft LinkedIn summaries, headlines, and "About" sections

• Write reference request emails

• Create a portfolio bio or personal brand statement

Job Research & Strategy

• Explain what a specific role, title, or industry actually involves

  • This is fantastic if you are thinking of making a career pivot and not sure what is out there and what roles you would be looking for.

• Compare career paths (e.g., "What's the difference between a data analyst and a data scientist?")

• Identify transferable skills from one field to another

• Suggest job titles you may not have considered based on your background

• Explain company culture, business models, or recent news about a target employer

• Help prioritize which roles or companies to pursue

  • This ended up being very helpful for me. Some positions would list a job with the same title as I currently had but when Claude cross-referenced the job posting to my resume there was actually little in common with the posting and my current role. Other job titles were sometimes the opposite and matched my experience perfectly with a different title. Allow the LLM to assess how good a match your resume is to the posting to assess how well you actually fit the position with your experience.

• Outline realistic salary ranges and compensation expectations for a role/region

Out of 100's of applications, Claude assessed the positions that most matched my resume. Notice how none of these job titles are remotely close to each other!

Interview Preparation

• Generate likely interview questions for a specific role or company

  • Additional tip - in addition to having the LLM generate a set of interview questions based on the job posting, I would sometimes review the GlassDoor interview section for the company to see commonly asked questions as well and have Claude generate some possible ideas for answers.

• Help craft and rehearse answers using the STAR method

• Conduct mock interviews (ask questions and give feedback on answers)

• Help prepare for behavioral, technical, case, and situational interviews

• Suggest smart questions to ask interviewers

• Help you talk about gaps in employment, career changes, or weaknesses

• Debrief after interviews to identify what went well and what to improve

Be sure to practice these answers so that they feel more natural!

Networking & Outreach

• Draft cold outreach messages to recruiters or professionals on LinkedIn

  • If you use Easy Apply on LinkedIn and notice a recruiter is attached to the job posting, send them a message to let them know how interested you are in the position.

• Write follow-up messages after networking calls or coffee chats

• Help craft a concise "elevator pitch" about yourself

  • I have never done an interview where I have not been asked "So tell me a little about yourself". Having this nailed down and flow naturally is a great way to come off personable and put together from the outset.

• Suggest how to reconnect with old colleagues or contacts

• Draft thank-you notes after interviews

• Help prepare for informational interviews

Skills & Career Development

• Identify skill gaps for a target role and suggest how to fill them

• Recommend courses, certifications, or projects to strengthen your candidacy

• Help you learn or brush up on technical skills relevant to your field

• Explain industry jargon, tools, or concepts you're unfamiliar with

  • I applied for a role that would be reviewing data on customer service agents and Claude added information about possible industry standard KPIs that are used that could come up in the interview and many of them did! Way to go Claude!

• Help you build a portfolio project or case study to showcase your work

Negotiation

• Explain how to evaluate a job offer holistically (salary, equity, benefits, PTO, etc.)

• Draft a salary negotiation email or talking points

  • Salary negotiations are hard because you want to come off the right amount of forceful but friendly. Let the LLM assess your response to see if it sets the right tone for what request you are making.

• Help you think through counteroffers and walk-away thresholds

• Role-play a negotiation conversation so you're prepared to respond in real time

  • I won't lie, when I didn't hear back after a day with my request to negotiate for a job I started to have a doom spiral that they were going to rescind the offer. Claude actually wrote down a timeline of what could be happening in the background that would take time to resolve and that this was normal. It certainly helped with my anxiety over the situation!

Attempts to talk me off the proverbial ledge were appreciated (if not a little overdone).

Organization & Planning

• Help build a job search tracker or suggest how to structure one

• Create a weekly job search schedule or action plan

• Set milestones and accountability checkpoints

• Prioritize tasks when you're feeling overwhelmed

Mindset & Emotional Support

• Help reframe rejection in a constructive way

• Offer perspective when motivation is low

• Help you articulate your own value when imposter syndrome sets in

• Think through difficult decisions (accepting an offer, leaving a job, etc.)

  • This was the one I found the most helpful, as the other three are more geared to the type of people who do not find the fawning that the LLM speech does over a person nauseating. This one allowed me to create pros and cons of different options and let me visualize what I really wanted out of my job search.

AI: A Useful Tool But NOT A Substitute For You

After reading through all the above, you probably are of the mind that you can just let that AI assistants take over the job search fully. Let it completely write every cover letter, assess whether you should apply or not, and send every email.

But there is something to be said in this new day and age about coming off as a unique individual. Recruiters are being inundated with resumes, cover letters, and emails that are indistinguishable from each other. Some are saying that professional summaries and cover letters are actually becoming useless because they are just "AI slop" of word salad that no longer has any meaning.

While these are great tools to help you think through your responses and documentation, let them assist in the process but not takeover. One of the best ways I found to do this was in the instance of cover letters. While I would let Claude write out a bullet summary of my experience for the middle, the first paragraph and last paragraph were uniquely written by me. This allows for my personality and thoughts to shine through while allowing AI to write the more fact-based portion of the cover letter.

Should I pay for a subscription?

When I started my job search I was using the free version of Claude. I started running into the limits of requests fairly quickly when I was deep into the job hunt at night and trying to process as many applications as possible. I switched to ChatGPT to help take on additional questions and then started to hit the limits there as well. This became frustrating as I only had certain hours of the day to dedicate to my search and this was causing a significant slowdown of what I could accomplish.

In my case, I did end up paying for the Claude Pro Plan at $20 a month to make it easier to get the work I needed to get done in one sitting. But depending on the veracity of your search, this may not be necessary for you. It may be worth it to temporarily budget this expense while looking for work and then cancel once you have the new employment offer in hand.

Ready to Employ Your New Assistant?

If you came to this article overwhelmed or not even knowing where to start, I encourage you to test out different prompts and see what of the above tasks could start being an asset to you in your job search. Remember that now more than ever that job searches can be long and arduous processes, let your new AI helper get you on the right track to success!