James Gilbert 🙏🏻

I am the current VP of Demand Generation at Bloomerang with a background as a 3X CMO. I have with a proven track record of helping companies scale from early stage through late growth, building marketing functions that drive sustainable scale. I thrive at the intersection of brand, demand generation, and AI-driven go-to-market strategy, translating innovation into market momentum.

Start-up stages: Seed to Series D & $1M - $150M
Enterprise experience at Cisco, Verizon, and AGCO

Core expertise includes:
- Building and scaling global marketing and growth organizations
- Harnessing AI as a growth engine, with hands-on experience in agentic AI models, Voice AI, and leading platforms such as Claude, ChatGPT, Gemini, Perplexity, and more to transform marketing, customer experience, and operational efficiency
- Partnering with CEOs, boards, and investors to guide companies through critical growth inflection points
- Positioning organizations for long-term success through strategic storytelling, brand building, and market leadership

In addition to my executive roles, I serve as an advisor to founders and leadership teams, an investor, and an author on the future marketing, AI and modern go-to-market strategy. These roles keep me deeply connected to emerging technologies and the evolving growth landscape, enriching the perspective I bring to every company I help scale.

I bring a balance of strategic vision and operational rigor, ensuring marketing not only shapes the narrative but also drives measurable business impact in revenue not just pipeline. Today, I am focused on helping organizations harness AI and modern growth strategies to reach their next stage of expansion with clarity, momentum, and scale.

Vice President Demand Generation

Empowering fundraisers and nonprofits to do what they love and build a world inspired by giving

No Decks. No Fluff. We Rebuild Revenue Engines for B2B Teams Stuck Under $20M!  Building systems that convert and close. We use GTBM, Go To Bigger Market strategies and implement them.

Most revenue problems don’t show up in the numbers first.

They show up earlier.

In decisions that feel reasonable at the time.
In momentum that looks healthy on the surface.
In activity that stays high while progress quietly slows.

By the time the numbers confirm it, the real mistake is already baked in.

That’s the moment I work in.

I get brought in when growth feels possible but unstable.
When pipelines look busy but don’t feel real.
When teams are working hard, yet leadership keeps circling the same decisions.

Not because people aren’t smart.
And not because effort is missing.

But because the system underneath the business can’t support the decisions being made on top of it.

That’s the work I do.

I help leadership teams see what’s actually happening before momentum locks in and options narrow.

Most teams start with the Next Move Diagnostic.

It’s a focused working session that pressure-tests one core KPI to show whether decisions are actually executing, or just sounding right in meetings.

Not with decks.
Not with theory.
And not by “optimizing” surface-level activity.

The work lives in:
- pressure-testing real decisions
- clarifying who the business is actually built for
- separating movement from noise
- setting rules that force reality into the room
- creating an operating rhythm that holds under pressure

Most teams reach out when something feels off, but they can’t quite name it.

Pipeline meetings get heavier.
Forecasts swing without explanation.
Execution slows even though effort increases.
Decisions keep getting revisited instead of resolved.

At that point, more activity doesn’t help.

Clarity does.

I started working at 14, running a barber shop on my front porch.
Since then, I’ve built and scaled businesses and worked alongside elite performers where pressure exposes what’s real fast.

That perspective still shapes how I work.

I don’t sell growth.
I don’t promise scale.

I help teams see what’s real, decide cleanly, and stop paying for hidden mistakes later.

If you’re leading a company where growth feels close but not clean,
and decisions feel heavier than they should,

we’ll probably have a useful conversation.

No pitch.
No performance.

Just a clear look at what’s actually happening before the numbers make the decision for you.

taplio

The Battle

James Gilbert 🙏🏻

Judd Borakove

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