Small startup founder has ChatGPT pick the top applicants from 150 and draft first messages to them

What they did

He posted a role on LinkedIn and on Upwork and got 150 applicants. Instead of reading every one, he gave his ChatGPT agent, which already knew a lot about the role and his business, careful access to his Upwork account and his Tally application forms. He asked it to evaluate the applicants, rank the top three from Upwork and the top three from LinkedIn and Tally, and prepare a first message to each. The same session also planned his week, drafted a re-engagement email to a contact he'd let slip, made first-draft one-page sheets for the new part-time sales rep and updated his Attio CRM.

How it went

He calls it "awesome"; the shortlist and outreach drafts came out of one rainy-day session instead of hours of reading applications.

Worth knowing

• He worked out that even two minutes per application would take 5 hours, but he doesn't report how long the agent took. Read the shortlisted applications yourself before reaching out, and watch for good candidates the agent ranks low. Only give an agent the account access the task needs.
• Price check: ChatGPT: free plan; Go: US$8/month (checked Nov 1, 2026); Tally: free plan; Pro: US$29/month, or US$24/month on a yearly plan (US$288/year) (checked Oct 26, 2026); Attio: free plan; Plus: US$44/month, or US$35/month on a yearly plan (US$420/year) (checked Oct 26, 2026).

Paying for ChatGPT? See cheaper ChatGPT alternatives.

Try it yourself

Paste this into a chatbot, then add your own details underneath.

Here is the job description and the applications I received. Score each applicant from 1 to 5 against the must-have skills, with one line explaining the score. Give me the top 3 with their strongest evidence and any red flags, then draft a short, friendly first message to each inviting them to a 20-minute call. Don't send anything.

Original post

See Jon Cowley (@whatifi_io)'s original post on X → (Oct 24, 2026)