Prompt to Offer: A Practical AI Workshop for the Job Hunt

The job search is a numbers game, and AI is supposed to make it easier, yet most of the time, it makes everything sound generic and predictable.

Leighton Anderson, a Senior Product Manager in health-tech, ran into that problem firsthand when he was trying to reenter the job market in the first half of 2025. He wanted to use AI to get more applications out and prep for interviews, but everything it produced sounded generic. It didn't know his career. It didn't sound like him. He didn't want his resume to read like AI slop, so he figured out how to give the tools real context. The interviews followed.

On Wednesday, May 20, he's bringing those workflows to SOST for a hands-on workshop with our community. No conference vibes. No TED talk energy. Just practical tools you can use the next day.

What you'll leave with:

• A workflow for tailoring your resume to any job in seconds
• A workflow for cover letters and application essay questions
• An outreach approach that doesn't sound like everyone else's
• An AI interview coach you can practice with out loud
• Personalized prep guides for any interview, any role
• Email support for 3 days after the workshop

What to bring: If you want to participate live and try the workflows in real time, bring your laptop and a copy of your resume. If you'd rather just listen and ask questions, come as you are.

Details:

Wednesday, May 20

5:00pm - 8:00pm

Resto Lounge, 2nd Floor

1901 9th St NW, Washington, DC 20001

SOST | @sost.dc

Free to attend. RSVP to reserve your seat.

Follow @l8onanderson. Sounds by @konshince

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Host or Publisher Leighton Anderson