The 21 Hats Morning Report

The 21 Hats Morning Report

Deciding to Go AI-First

With AI already reshaping his industry, Rob Levin has concluded its time to transform WorkBetterNow: “Any workflow that can be done by AI will be done by AI.”

Loren Feldman's avatar
Loren Feldman
Mar 19, 2026
∙ Paid

Good morning!

Here are today’s highlights:

  • There’s a huge gap between how much employers and employees trust AI.

  • Looking for a loan? Ami Kassar encourages you to view your business through a lender’s eyes.

  • Even the oil industry is worried about the spiraling increase in oil prices.

  • Portland, Oregon, it may surprise you, has come up with a way to help home-builders make money.

ARTIFICIAL INTELLIGENCE

Rob Levin explains why WorkBetterNow has begun its AI transformation: “​​WBN is a talent company. What we do, finding, vetting, and placing great people, is exactly the kind of work AI is beginning to reshape. ... A growing part of our value is placing ‘AI-enabled’ certified professionals who are equipped to support our clients’ own AI efforts. We can’t do that credibly without going AI-first ourselves, and that single reality, more than anything else, is what drove the decision.”

  • “I’d been thinking about a problem we see constantly: small and midsize businesses generally aren’t great at writing job descriptions. They’re often not compelling enough to attract the right candidates, or not accurate enough to help us make the right match. A weak job description makes finding the right fit harder for everyone. So I built a custom AI tool designed specifically to improve job descriptions. Clients appreciated the clarity and accuracy of what it produced, and our recruiting team found it led to better matches.”

  • “AI-first, as we define it, means that any workflow that can be done by AI will be done by AI. The key distinction is that we’re not taking existing workflows and tweaking them. We’re rebuilding them from the ground up, with AI doing the work and humans designing, overseeing, and continuously improving those processes, with AI’s help in doing that too. And it’s not just about efficiency, though that matters. It’s equally about effectiveness, getting better outcomes, not just faster ones.”

  • “Our finance team has deployed several AI-first workflows and is saving approximately 140 work hours per month. As a result, a department we had planned to staff with two additional people to accommodate our growth now needs one.”

  • “Our IT department is worth highlighting for a specific reason: unlike most companies our size, we handle our own IT support internally. The team rolled out an AI chatbot to handle routine first-level support tickets that previously required a person, freeing them to focus on helping other departments build their own automations and AI workflows.” READ MORE

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