Automating the Art of Career Transformation with AI

Navigating a career change can be overwhelming. From crafting a standout résumé to positioning yourself on LinkedIn, the process often feels uncertain, repetitive, and time-consuming.

Sam Waterfall, a career coach with 22 years of experience and founder of Obvious Candidate, used the AI Upgrade for Creative Professionals course to turn that pain into possibility. His capstone project? A custom AI-powered system that transforms raw client input into a suite of polished, job-ready materials—in just six seconds.

The Problem: A Manual Process That Didn’t Scale

Before AI, Sam’s coaching was deeply personal but highly manual. Writing each client’s résumé could take 6–8 hours. Multiply that by hundreds of clients, and you’re looking at thousands of hours lost to formatting, phrasing, and rewriting.

“It was excruciating,” Sam said during his final presentation. “So many mental decisions—do I write this word or that word? The machine could take some of that pain away.”​

His capstone goal?
To make his method scalable—without losing the personal touch that made it so effective.

The Innovation: The AI-Powered Career Engine

With help from Kris and Peter during live coaching sessions, Sam used prompt engineering and iterative design to build what he now calls “The Waterfall Guide to Greatness.”

Here’s how it works:

• Step 1: Clients upload transcripts of coaching calls, existing résumés, and LinkedIn links.

• Step 2: The AI system parses the content using Sam’s methodology.

• Step 3: In six seconds, it generates:

  • A custom résumé

  • LinkedIn “About” section

  • Cover letter

  • Personal brand elevator pitch

  • Social media content strategy

  • Speaker bio

“I just plop it in,” Sam said. “And seriously, six seconds later—it gives me a résumé, a LinkedIn section, and a ton of value-added material. It even swapped out engineering terms for teaching language in one client’s alternate version.”​

The Breakthrough: AI That Feels Human

Sam’s system doesn’t just copy-paste credentials. It preserves voice, values, and nuance—customizing for different tones, industries, and goals.

The impact has been transformative:

• ⚡ Clients save 6–10 hours per application

• 🧠 AI captures more consistent messaging across all materials

• 💼 One senior client at AmEx landed an interview within days

“I tested it on real client sessions,” he explained. “And they couldn’t tell which résumé I wrote manually and which was AI-generated.”​

Scaling Value, Not Effort

Sam’s project isn’t just a résumé writer. It’s a scalable personal branding platform—designed to empower clients with a full suite of communication tools, including:

• 10 thought leadership LinkedIn posts

• A one-page speaker bio

• A 30-second elevator pitch generator

And that’s just the start. He’s already working on new features:

• Industry-specific customization for résumés and cover letters

• Real-time job market integration

• A SaaS product for instant, AI-powered career coaching

“It’s not perfect yet,” Sam admitted. “But I’ve built something that used to take hours—and now takes seconds. And the quality? Still mine.”​

AI That Empowers, Not Replaces

At The Upgrade Academy, we believe AI should amplify human expertise, not replace it. Sam’s project is proof: he didn’t outsource his coaching practice—he upgraded it.

“When I arrived, I was full of concerns and fears about AI,” he reflected. “But now I’m much more positive and optimistic about the potential. I just needed a system that let me scale my magic.”​

Want to Build Your Own Career-Supporting AI Tool?

Join the next AI Upgrade for Creative Professionals cohort.
Learn to automate what slows you down—so you can focus on the work that moves you forward.

AI isn’t here to take your job. It’s here to help you land the next one.