Dougherty said job seekers have to stay proactive; applying and hoping to get picked won't work.

This as-told-to essay is based on a conversation with Dan Dougherty, a 46-year-old sales director from New York City. It's been edited for length and clarity.

I jumped into the job hunt immediately after losing my sales job at a startup and set a goal to land a new job in 60 days.

I applied to some jobs on LinkedIn to test the waters and received rejection after rejection, even on jobs I was fully qualified for. I realized I'd need to be more strategic and intentional if I wanted to stand out, so I decided to treat the job hunt like a sales cycle.

I treated it like a sequence of steps to follow to close a deal with a customer. Only this time, I was the product. I realized that being intentional and strategic is crucial to landing a job in this market.

Per a friend's suggestion, I signed up for a Crunchbase subscription and spent about a week prospecting 200 to 250 companies in the startup or scale-up phases. I figured they were most in need of salespeople.

Then I narrowed my list to 70 companies that had a high run rate, a solid leadership team, and were in an industry I was excited about. I logged each company's information into an Excel spreadsheet.

I checked their website for any specific job openings, but I planned to reach out to all companies regardless. I gathered recruiter emails and used Hunter.io to find emails of CEOs and VP-level people to reach out to.

I'm not much of a grammar person, so I bought a $19 monthly subscription to use Kickresume's AI function to optimize my résumé's grammar and formatting and to store multiple résumés. I also hired a few people on Fiverr at $50 to $100 each to make me a résumé.

I compared the Fiverr résumés to Kickresume's suggestions and kept the commonalities. I found Kickresume to be more useful because I needed to customize each résumé.

Finally, I used ATS scanner sites to scan my résumés and flag any errors that would prevent it from passing through the first round.

If I were applying to an enterprise sales representative role, I'd edit my previous job descriptions to highlight my work as an enterprise rep and use the keywords and phrases that were listed in the job posting.

Even though my job experience isn't explicitly a ton of enterprise, I think it's important to tell a consistent story in my résumé to grab the recruiter's attention.

I typically emailed the recruiter and CEO of each company I was interested in. I knew my emails could get passed around their organization, so I made sure to customize every message.

In an email to a CEO, I might personalize the message by saying that I noticed their company was raising money and working with XYZ VC groups, meaning they were likely in need of salespeople. Then I'd describe how I could specifically help.

I used ChatGPT to draft example emails. I asked AI what its response would be if it were a CEO receiving my email, and it typically gave me formatting suggestions or ways to reduce word count.

I typically sent my emails late at night because I figured the CEOs would either see them at night when their inbox wasn't being flooded or it would be at the top of their inbox in the morning. I'd also follow up each email with a LinkedIn message stating I shot them an email and was looking forward to catching up.

I was meticulous about following up. On weekends, I'd send emails with catchy subjects like "I know it's a Sunday morning..."

I used email trackers that notified me every time someone opened my email or forwarded it to someone else. I also knew recruiters would go to my LinkedIn after looking at my resumé, so when I'd get a notification that my profile was viewed, I'd reach out to them and say something like, "I noticed you checked out my LinkedIn profile. I'd love to connect more."

My targeted approach helped me get interviews with recruiters and C-suite level people, and I interviewed with various companies before getting officially hired on day 57 as a head of sales.

The biggest takeaway from my job hunt is that applying and hoping to get picked won't work. You have to be proactive whether you want to or not. I sold myself using my sales skills, but I encourage people to leverage whatever skills they have to stand out.