OP #303: Dual-Track Persuasion and Smart Measurement: This Week’s OP

A summer check-in on what it means to persuade both humans and AI — plus why the smartest marketers I know obsess over outcomes, not activities.

Author

Darren Herman
July 22, 2025

Vibe Song: Hot Damn (Paul Cauthen)

If you’ve been around The Operating Partner for a bit, you know I usually take a Summer Siesta — a little time off from writing and sending the OP. This summer’s been a bit different. I did step away last week, but only because I was moving my son into a summer college program where he’s getting a taste of college life before his senior year of high school.

I can’t remember the last time I set foot in a dorm room — maybe when visiting my younger brother after I’d graduated — but it’s been a while. I’m fired up for him and the experiences ahead. Even better? Some of his classes hit pretty close to home: social media marketing and AI in the classroom. I’m hoping he comes back ready to teach me a thing or two.

Speaking of learning, my friend Tyler at Shopify passed along a sharp read: “Persuasion Isn’t Dead” by Susannah Shipton. If you’re in B2B or B2C marketing, it’s worth your time. The core idea? In today’s world, you’re not just persuading people — you’re also persuading AI agents. Both matter.

“Persuasion hasn’t vanished, it’s just doubled its audience. Brands that master both languages — the logic of machines and the longing of humans — will own the next era of commerce.”

Susannah Shipton

I wrote a long piece about the New York Knicks in OP #299 but wanted to highlight the latest episode of The Roommates Show (podcast) that just dropped last week. Jalen, Josh, and Matt talk about the new coach, new teammates, and a bunch of other rambling. I’m excited for the 2025-2026 season and believe we made some good upgrades so far this offseason.

Speaking about excitement, anyone in the OP community going to any Oasis concerts? I promised myself that if the Gallagher brothers ever reunited, I would absolutely go see them. I am planning to go solo to the Chicago show as it’s the only show that works for me… anyone else going?

Here’s a few articles to get us started this week…

And for those watch enthusiasts amongst us, here are three links to check out:

I hope you enjoy this week’s OP. For those subscribers who are Silicon Alley Sports participants and are playing in the Silicon Alley Tennis Invitational, I’ll see you tomorrow - Wednesday!

Darren

A longtime friend asked me to write a piece for his upcoming book on marketing and advertising. I met him when we were both working for MDC Partners agencies (now Stagwell Group) and we became fast friends… nearly two decades ago!

Here is the piece I wrote while on a recent flight…  curious to get your take.  I will share it here in the hopes of making it better with your feedback.

Smart Measurement

I’ve sat on every side of the marketing table—marketer, agency, investor. The one constant? I’ve always been close to the CMO seat. And if there’s one thing I’ve noticed over the years, it’s this:

The CMO has finally become a measurement executive.

Not just a storyteller. Not just a brand steward. A growth driver, with numbers to prove it.

But here’s the catch: marketing is absolutely measurable—just not the way most companies do it.

Too many teams still obsess over activities: clicks, likes, impressions, bounce rates. All the things that feel busy but don’t always move the needle. I call these activity traps.

You think you’re making progress, but you're just walking in circles.

The smartest marketers I know—across our portfolio and beyond—start from a different place. They ask:

What are the outcomes that actually matter to the business?

Then they pick 2–4 KPIs max. That’s it. Not 17 dashboards. Not a BI tool with every toggle flipped on. Just a tight set of outcomes that map directly to business goals.

Everything else? Should ladder up to those few KPIs. If it doesn’t, it’s noise.

This isn't just a reporting issue. It’s a leadership issue. Because when you measure the right things, your team focuses on the right things. You get clarity. You get accountability. And you get momentum.

The marketers who get this—they’re usually the ones winning. The ones buried in vanity metrics? They’re often the ones wondering why growth feels stuck.

If you’re leading marketing right now, here’s what I’d do this week:

  • Sit down with your CEO or CFO.

  • Ask: What does success look like for the business this quarter?

Then translate that into 2–4 marketing KPIs you can own.

Everything else is execution.

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Two AI players are releasing web browsers:

Thank you for being part of The Operating Partner. I’m grateful you make the time for it — I hope it’s delivered a useful insight or two along the way.
If you want to catch up on past editions or search through topics, you’ll find everything since January 2024 right here.

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