ASKJAMES.
★ 3X CMO2 EXITSAI-NATIVE GTM

Ask James
about his campaigns|

Two decades building B2B go-to-market — with strong opinions on GTM, AI, and what actually compounds. Plus a few stories involving a knife thrower, a Bachelorette parody, and a coffee-truck hijack of Qualtrics.

— Or start with one of these

6 starters

— Why James

AI innovator, human believer. The tools change monthly — the edge doesn't. The single greatest differentiator is taste: judgment, creativity, and knowing what's actually worth building.

A rare whole-brain GTM leader — fluent in both halves of the job.

The art

Brand · Messaging · Positioning

Product marketing, competitive intel, positioning, and ICP/persona work — the creative demand creation that makes a market feel something and gives capture its moat.

The science

Demand · Growth · AI

A real ICP, demand capture, compounding growth, AI-native systems, plus the data analysis, reporting, and revenue & pipeline forecasting that make growth predictable.

See both sides in the frameworks →
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Humanity in business, always — I've worked through two exits and up to eight acquisitions, and what I'm proudest of isn't the metrics. It's the teams we built, the user manuals we wrote to understand each other better, and the customers who became friends. Every win on this page belongs to the people I had the privilege of working alongside.

Explore
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Real Campaigns

The creative work — on video, with receipts.

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Written Articles

Published thinking on brand, accessibility & GTM.

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Frameworks

How compounding growth & AI-first GTM actually work.

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References & Testimonials

What leaders, peers, and teams say about the work.

Go Deeper

The last two chapters, in depth.

Want the full story on Flip and Bloomerang? Open either one for the challenge, what I did, and the results.

How I Lead

Every teammate writes their own User Manual.

On the teams I served, every person writes a personal User Manual — how they work, what they value, how they want feedback. Then we share them with each other.

It's how I make sure we lead with humanity, not just headcount. Real example from a teammate (anonymized) →

— Anonymized Example

The User Manual

How I work

  • It's a journey: My brain doesn't work linearly — that's the beauty. Don't put me in a box.
  • Collaboration: I feed off the creative energy of others.
  • Warn me: Ask before calling. Unexpected calls put me in stress mode.
  • Time blocks: My best work happens with uninterrupted blocks.

What I value

  • Responsibility: I thrive with autonomy and impact.
  • Transparency: I struggle when I don't trust the team.
  • Respect: Everyone gets a chance to speak — regardless of title.
  • Experimentation: Same way as always = no innovation.

Feedback

  • Constructive & private, please. And warn me before tough conversations so I can prepare.
Voice
Forbes Contributor

Published thinking on AI, CX & modern GTM

Member of the Forbes Communications Council. Multiple articles on customer experience, voice AI, and the future of go-to-market.

Read on Forbes
Podcast · Still Running

Banking on Experience

Founded at CRMNEXT. Drove the show to 100+ episodes and built it into a category-leading podcast for credit unions and community banks. Still running today.

Listen
YouTube · Lightning Strike Recap

The Big Flippin' Reveal challenges

Yes, that's actually James in the robot costume in an ice bath. Yes, those are real knives. The full recap of the reveal challenges — proof that sometimes the absurd builds the most anticipation.

Watch
Archive · No Longer Producing

Spamming Zero · Sweets of CX

Two more industry podcasts I founded and hosted — Spamming Zero at Flip CX (Voice AI, available on YouTube) and Sweets of CX at CloudCherry. Combined with Banking on Experience, the three drove $55M+ in attributable pipeline.