3X CMO, two exits, 20+ years of B2B SaaS go-to-market. James owns the whole-brain GTM system: AI, demand, pipeline math, data, and RevOps. He scaled Flip CX from $500K to $8.5M ARR and helped create the Voice AI category, and led a GEO/AIO motion that ranked a B2B SaaS brand #1–2 across ChatGPT, Claude, Gemini, and Perplexity.
We treat AI as an operating model, not a tool. Small autonomic teams, each augmented by dedicated AI agents, so a 12-person team produces the output of 30. We put AI to work where it moves the numbers: qualification, routing, content, and the agents that capture and serve customers.
Revenue compounds across the full lifecycle, not just the top of the funnel. The bow tie re-widens after the close through onboarding, retention, expansion, and advocacy. Net-new and expansion don’t add, they multiply. We’ve owned both: 68% expansion revenue contribution and expansion velocity from 52 to 22 days.
Find the one place AI moves the numbers most and build it. Tighten the demand engine and the pipeline math. Sharpen positioning so you’re the obvious choice. Not an open-ended science project: a focused build with outcomes you can measure - revenue captured or hours saved.
“James is one of those rare marketing leaders who actually delivers transformation.”
“He has command of the funnel and the numbers behind it unlike any demand gen leader I've worked with, and he uses that fluency to drive real outcomes.”
“He was early on GEO long before most of our peers were paying attention, and defined our strategy with enough conviction that we now have a real competitive advantage in AI visibility.”
“The combination is rare. I'd partner with him on anything.”
“I knew his work before he joined, and I put my own name behind him to get him in the door at Bloomerang. I would do it again.”
“The growth engine needed real work. He led demand generation and turned it around - he rebuilt how we generated and tracked pipeline and made the numbers something the leadership team could actually plan against. The motion went from unpredictable to something you could count on.”
“He never treated brand as an afterthought to demand. For a demand leader, that's rarer than it should be.”
“He gets things done, he grows the people around him, and he's honest about what's working and what isn't. I'd refer him again tomorrow.”
“I am pleased to recommend James Gilbert without reservation.”
“He never approached sales and marketing as two separate functions operating in parallel - he approached it as a shared mission with shared accountability. That kind of partnership is rare.”
“James has one of the more comprehensive understandings of AI's role in a modern GTM motion that I've encountered - he can cut through the noise and help leadership make confident, specific decisions rather than chasing the next shiny thing.”
“He is exactly the kind of marketing leader that a sales organization wants as a partner.”
“James and I partnered closely, building real alignment between demand gen, BDR, and sales that drove the overall GTM engine and growth.”
“What stood out most was his creativity with AI - he built a real strategy around it, grounded in results rather than buzz.”
“He thinks big about what demand gen can do for a business and brings serious cross-functional energy to the work.”
“James is a strong leader, a true collaborator, and one of the more creative thinkers I've worked with.”
“James delivered a full year of consistent overperformance - finishing 2025 at 121% of the bookings plan with ~30% year-over-year unit growth, including a company-record close.”
“He led early adoption of AI across our go-to-market motion - getting the AI vision on paper and bringing cross-functional teams and the executive leadership team around it.”
“When an experiment wasn't delivering, he recognized it, shut it down, and recovered the budget. That decisiveness is exactly what scaling organizations need.”
“It is not an overstatement to say James and his team put Flip on the map.”
“There was never any ego, just pure desire to do whatever he could to help the business achieve its goals.”
“He has one of the most beautiful biases for action I have ever seen in a leader.”
“James would be an awesome fit as your CMO… he is the real deal.”
“He just gets it - and even more importantly, he understands how important the relationship between marketing and sales is.”
“He's a born leader. Not only can James light a fire under the team, but he's a fantastic mentor too - with the vision and guts to make unconventional decisions.”
“In a nutshell, I'm totally sold on James as your CMO.”
“I worked closely with James on a daily basis during his time at Flip, where he poured his heart, soul, and mind into the work.”
“James is a CMO and highly creative brand builder with a legendary bias for action - he gets stuff done.”
“He was instrumental in rebranding RedRoute to Flip, kickstarting our Spamming Zero podcast, and standing up a demand gen effort - Email, Partners, and Outbound - that repeatedly builds quality pipeline.”
“It's been my absolute privilege. I wholeheartedly recommend him for any company looking for a talented and extremely well-connected marketing exec and leader.”
“I recommend James without hesitation - across multiple organizations, one of the most innovative, hard-working, and genuinely gifted professionals I've worked alongside.”
“His approach to marketing and demand gen is cutting edge - he doesn't just keep pace with industry trends, he anticipates them.”
“His ability to own a room, command the data, and drive teams to action is something I rarely see at any level.”
“He operates with integrity and honesty that's refreshing and rare, and brings a rising-tide mentality that makes entire organizations better. Any org that brings him on gains someone who elevates everyone around him.”
“James is simultaneously one of the most forward-thinking minds in go-to-market strategy and one of the most grounded, human-centered leaders I've encountered.”
“He was developing and executing AI-driven GTM strategies months before I saw other practitioners begin experimenting with them - not as a talking point, but as a real, integrated approach to driving business outcomes.”
“In a world full of CMOs who speak in sweeping narratives about what they can accomplish, James brings specific, substantiated proof points. He has done the work, measured the results, and can articulate the impact with precision.”
“He is that exceptional and increasingly rare individual who brings both the technological sophistication to lead at the frontier and the humanity to make the people around him better for having worked with him.”
“He has been for me a trusted mentor, a steadfast leader, and a friend - always going to bat for me and our team. Above all, he leads with compassion first, creating an environment that's supportive, trusting, and fun.”
“James has always been one of the best leaders I've ever worked with. He invests in his people and helps them grow. There's a reason I keep following him.”
“James was always a fantastic leader. He leads with empathy and pushes you to grow in the areas you want to grow.”
“James took a chance on me and helped me develop into a career I never imagined. He's fantastic to work with and always has his team's back.”
“James has a fantastic understanding and passion for all things marketing, and his enthusiasm inspires and energizes everyone who works with him. He's a tremendous leader - fostering innovation and bolstering his people to shine. I highly recommend him; he'll be an irreplaceable asset to any team.”
A free 30-minute consultation: we map your highest-impact use case, pressure-test your positioning and demand, and leave you with the plan - work with us or not.