Tom Wentworth has been an advisor to RevSure since the Recorded Future days. Over the years, we’ve had dozens of conversations about marketing measurement, attribution challenges, and what it actually takes to run a revenue-focused marketing organization.
Last month, when we sat down for the first episode of Moneyball CMO, I wanted to understand how Tom thinks about the CMO role in the age of AI - now that every marketing team has access to the same tools and automation.
What came out of that conversation surprised me.
The more interesting part is how he’s doing it and what he thinks separates the next generation of CMOs from the ones running the same playbook job after job.
Tom’s background is unusual for a CMO. He majored in computer science and began his career as a sales engineer. He later moved into product marketing and demand generation at Adobe, HP, Optimizely, and Acquia before becoming CMO at Recorded Future, which was eventually acquired by Mastercard. Now, he’s at incident.io, building the marketing function from scratch once again.
The New Math for Measuring Marketing Success
He gave me a formula that I haven’t stopped thinking about:
Marketing Success = AI Adoption × Taste²
His point: everyone is going to adopt the same AI tools. That advantage scales linearly. But taste - the ability to build memorable brand experiences, tell compelling stories, and create moments that stick - scales exponentially.
In this conversation, Tom breaks down his measurement framework, how he aligns with his CRO and CFO without attribution battles, why he believes B2B is three to five years behind B2C on tactics that actually work, and what he learned at Recorded Future that led to a 40× ROI on pipeline ahead of the Mastercard exit.
Here’s what stood out:
The Metrics That Actually Matter
He does not believe in vanity metrics. Tom’s measurement framework is brutally simple:
CMOs lose the trust of their CFO and CRO because most of the time they’re measuring the wrong things, or they can’t get alignment on what the right things are.
When I asked him, how does he work? His reply was pretty simple - Tom and his CRO aligned on different marketing metrics before they started measuring anything.
“In my first week, my CRO and I made a pact,” Tom explained. “We’d never point fingers at each other over attribution. If the business is hitting numbers, we both win. If it’s not, we fix it together.”
This is the lesson most CMOs miss: Attribution only becomes a political weapon when you don’t define the framework upfront. When marketing, sales, and finance agree on what metrics matter and why, before you start reporting, attribution becomes a planning tool instead of a blame game.
The companies that figure this out early are the ones where CMOs actually have a seat at the revenue table.
How to Actually Align Marketing with Revenue
Most CMOs talk about “alignment” with their CRO. Few actually achieve it.
Here’s what Tom did differently:
1. He started at the point of most friction.
Not at the top of the funnel. At the handoff between marketing and sales.
“Did the demo request go to the right person? Did they have the right context? Did they follow up fast enough?”
Tom obsesses over the mechanics of the engine. If your reps aren’t getting qualified leads with proper context, nothing else matters.
2. He defined his own measurement framework - before finance did.
Tom explained his metrics proactively. He showed the CFO how inputs (spend, campaigns) drive outputs (pipeline, revenue) with a lag model.
“The CFO should look at CAC,” Tom said. “But they shouldn’t be looking at cost per MQL or legacy vanity metrics. Those don’t tell the real story.”
CMOs who own their measurement framework own their narrative.
3. He treats budgets like a zero-based model.
Tom doesn’t pretend to know where every dollar will go in 2026. He has directional targets, but his actual spend is based on what’s working.
“If things are working, I’ll spend more. If they’re not, I’ll spend less. It’s what’s working that we double down on.”
Why B2B Marketing Is Becoming B2C (And Why That’s Good)
I asked Tom about the shift we’re seeing: B2B marketing tactics looking more and more like B2C.
His answer was blunt:
“B2B marketers have always thought our job was somehow different. That was the mistake.”
The brands Tom admires - Apple, Patagonia, even challenger DTC brands, figured out years ago that you win by standing for something, by being consistent and authentic.
Then I asked him what channel he’s most excited about.
His answer was Influencer marketing.
“Look at what B2C companies have been doing for years,” Tom said. “Influencer marketing at scale. Guess how many B2B companies are doing it? Almost none.”
He pointed to Cluely, the Andreessen Horowitz-backed AI startup that built its entire growth engine on creator partnerships.
“They hired hundreds of creators to flood TikTok and Instagram with content. It’s sketchy in their case - they were literally helping people cheat on interviews, but the underlying tactic works.”
Tom’s version for B2B won’t involve stunts or staged demos. It’ll be authentic partnerships with people who actually influence his target audience: developers.
“If I can activate creators in a real, authentic way, that’s a massively underutilized channel in B2B.”
He’s putting the real budget behind it in 2026. We’ll see how it works.
The pattern is clear: B2B marketing is 3-5 years behind B2C in adopting tactics that actually work. He sees B2B marketers embracing, influencer marketing, brand storytelling and the overall consumerization of the buying experience. The CMOs who figure this out first will dominate the next decade.
The Future CMO: Engineers or Brand Builders
I asked Tom who he’d hire as a CMO today.
His answer surprised me:
“I wouldn’t try to hire another me. I’d hire someone who’s built a big brand at a B2C company.”
Tom thinks the next generation of CMOs comes from two paths:
Brand Builders: CMOs who’ve built memorable brands at B2C companies. People who understand storytelling, taste, and creating cultural moments. Give them the right AI tooling and budget, and they’ll do for B2B what they did for consumer brands.
Engineers: Technical CMOs who can build AI agents, automate workflows, and think in systems.Tom showed me a Claude code prompt that he had built right before our call, it automatically scans Linear tickets, finds website instances of a phrase he doesn’t like, and fixes them in the CMS on the fly.
“I just removed 52 instances of ‘seamless integration’ from our website in seven minutes,” he said, laughing.
Clearly, the pattern matching CMO era is over.
What Recorded Future Taught Him About Financial Discipline
Tom spent years at Recorded Future before it was acquired by Mastercard.
This is the one lesson which stuck with him:
“Every company builds a model that says, ‘To hit our number, we need N sellers ramped by Q3,” Tom explained. “But that model is fiction. Hire sellers when you have enough pipeline to keep them busy. Don’t hire them because a spreadsheet says so.”
That financial discipline led to something rare: A profitable, sustainable SaaS business in an era of “growth at all costs.”
The result? A successful exit to Mastercard and a 40x ROI on pipeline generation.
Tom’s bringing that same discipline to incident.io with lean marketing teams, every dollar scrutinized and not hiring until the pipeline justifies it.
The Takeaway
Tom’s been at this for 20+ years. He’s seen the playbook change multiple times.
Here’s what hasn’t changed:
What is changing- the tactics, the tooling, and the type of person who becomes CMO.
The future CMO is either a brand builder from B2C or an engineer who can automate everything. The operator running the same playbook job after job - is disappearing.
In an AI-democratized world, taste and systems thinking are the only sustainable moats.
The best CMOs aren’t the ones with the prettiest dashboards. They’re the ones willing to kill their existing playbook and build something new.
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