Last Friday (October 2nd) we joined Jason Averbook and Jess Von Bank for the Now of Work Digital Meetup — live every Friday at 1pm ET with operators, CHROs, and builders talking AI, HR, and the future of work.

It was fun, a little nerdy, and we got into the real questions: headless software, whether to rip-and-replace, AI pricing, and universal basic income.

Watch the replay here:

E326 Replay: Now of Work Digital Meetup with Meg Bear & Amy Wilson

If you want to join live on Fridays, register here:

Now of Work Friday registration

1. Are we finally at headless software? Jason shared how he's now doing almost everything through a personal agent — decks, email, expenses — instead of opening apps. Amy talked about what's still missing: a dashboard for agents running across processes & workflows and shared UIs for teams working together with agents, not just solo in ChatGPT or Claude.

2. Rip and replace vs. rip and repair? Meg's take: companies that invested in data, integrations, and tech discipline over the last 20 years are in a better spot to get value now. It's not a durable lead — you can't coast — but you're starting from the right foundation. Companies that just kept the lights on will have a harder time moving.

Amy added a preview from Stacey Harris (episode 58): HR teams that did the work on efficiency and plumbing are seeing better business outcomes with AI. Teams that skipped that and went straight to bespoke, custom apps are now struggling to get outcomes.

3. Can UKG, ADP, SAP, Oracle, Workday evolve and stay relevant in 2027 and beyond? Amy’s quick answer: unlikely without starting over.

Meg noted that Workday, Oracle, and SAP took more than a decade to make the on-prem to SaaS shift. That kind of rebuild takes years of investment and focus. Tinkering with what exists won't be enough — it will take a separate bet, new architecture, and tight customer partnerships with folks willing to be early.

4. Jason posed the the AI pricing question every leader is asking: what the heck are tech vendors doing?

Our take: vendors do have real costs to cover for models, agents, and API scale, so it's not fair to say it should all be free. But they have to be transparent about what it costs and how it's priced. And buyers: start with strategy and the lever for growth — don't start with "what cool widget should we buy?"

Jess nailed it: companies moving the P&L with AI aren't chasing marginal efficiency. They're pursuing growth and innovation.

5. Universal high income? Jason asked about Elon's line that advanced automation requires not just to universal basic income, but universal high income.

Amy shared why she's working on this via the Income to Support All Foundation — it's not left vs. right, it's how capitalism keeps working if paid labor shifts. Everyone needs economic dignity and purchasing power to participate.

Meg zoomed out to an economists' view: capital markets risk, chips that depreciate in 5 years vs. railroads/fiber that lasted decades, smaller future workforce, and why it's time to invent what's next from every seat.

Where to jump in — timestamps

All times from the replay:

Thanks to this community

Thank you to Jason, Jess, and everyone who joined live and dropped green/yellow/reds and One Big Things in chat. Congrats to you on 326 Fridays in a row of showing up as humans.

If you listened, tell us: what was your One Big Thing this week?

— Meg & Amy

P.S. New to our show? We're Meg Bear and Amy Wilson, former tech execs (PeopleSoft, SAP). We host The Meg and Amy Show with bold takes and operator expertise on AI, leadership, and modern work.

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** Typos and poor grammar either because I'm too lazy to edit properly, or to make you feel confident this was written by a flawed human and not AI generated.