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 start in the numbers.

They start in decisions that felt reasonable at the time.

Pipeline looks active.
Activity stays high.
Meetings multiply.

But momentum quietly slows.

By the time the forecast reflects it, the real mistake is already baked in.

That’s where I work.

I get pulled into revenue teams when growth feels possible but unstable.
When pipeline looks busy but doesn’t feel real.
When leadership keeps debating whether the issue is strategy, execution, or something deeper.

In complex organizations, those look identical.

But they require completely different decisions.

Most teams respond with more effort.
More oversight.
More process.

That only makes things worse if the diagnosis is wrong.

Revenue doesn’t stall by accident. It stalls by design.

My work isolates where the breakdown actually lives:

• Strategy
• Execution
• Structural constraint

Once that’s clear, decisions get simpler.
Forecasts stabilize.
Meetings shorten.
Momentum becomes predictable.

If revenue feels unstable and the diagnosis keeps shifting, we should talk.

Judd Borakove

Your competitor doesn't have a better product.

They just made theirs feel inevitable.

You're explaining features. Building case studies. Sharpening your differentiation.

They're shaping belief.

Peloton didn't build a better bike. They made home fitness aspirational.

Warby Parker didn't make better glasses. They made optometrist shops feel obsolete.

Goop didn't create better wellness products. They created a movement where not buying felt like self-neglect.

They made choosing anyone else feel like a mistake.

In the video, someone asks what to do when life gives you lemons.

Make lemonade?

No.

Stockpile lemons. Create scarcity. Launch campaigns making lemons culturally necessary. Build the empire. Then sell it.

Most GTM strategies are about how to compete.

The best ones are about how to stop competing.

Competition is what happens when nobody owns the narrative.


🎥VC: humanifys

#sales #Marketing #GTM

Revenue doesn’t stall by accident. It stalls by design.

Most bad decisions don't come from bad thinking.

They come from rushed thinking.

There are always two sides to a choice.

The thoughtful one.

And the rushed one.

Pressure doesn't usually push people toward the wrong answer.

It pushes them to answer too quickly.

The installation in this video shows it perfectly.

A giant rock labeled anxiety sitting next to a small one labeled reality.

Two versions of the same moment.

The one we end up standing next to is almost always determined by how much time we gave ourselves to choose.

When pressure gets loud, the natural instinct is to move.

Do something.

Give the room an answer.

But the leaders who build things that last learn a different discipline.

They slow down.

They don't let the noise decide.

They don't let the deadline think for them.

They create just enough space to see clearly.

Because the decision you make under pressure is usually the one you live with the longest.

Pressure doesn't always change the situation.

But it can change which side of it you see.
🎥VC: andreaolivari

The lumberjack story is wrong.

Not the lesson. The assumption underneath it.

Everyone remembers the moral: stop and sharpen your axe.

But that's not what kills teams.

What kills them is this: The person who stops swinging gets questioned.

When someone says, "This isn't scaling." "The math doesn't support it." "We need to fix the foundation."

They're told: We don't have time. We just need more.

More leads. More activity. More output.

So they keep swinging. Or they leave. Or they get replaced by someone who will.

Nothing improves. It just gets louder.

Here's the part nobody says out loud:

The leader at the top won before.

So when it stops working, they don't question the playbook. They question the effort.

Same axe. Different forest. Swing harder.

You don't have a productivity problem.

You have a leader who mistook a winning season for a permanent formula.

And until someone is allowed to say that out loud, no hire, no campaign, no playbook fixes what's broken.

The axe isn't dull because nobody knows how to sharpen it.

It's dull because you punish the person who stops to try.

🎥VC: figuringout.co

#sales #Marketing #GTM

Three weeks of following up got nothing.

One reminder closed it immediately.

You see it in every stalled negotiation.

Features presented. Value explained. ROI mapped out.

Still nothing moves.

Because asking puts you in a position of need.

And need weakens every negotiation.

In the video, three dogs pitch for treats. Features. Value. Tricks they know.

Nothing.

Then one shifts: We also know where you sleep.

Dog with bat. Standing over him in bed.

Next scene: they have treats.

The deal didn't close when they added value.

It closed when they stopped asking and started reminding.

Asking is what happens when you forget you have leverage.


🎥VC: aguyandagoldenn

#sales #Marketing #GTM

Helping leadership teams isolate revenue breakdown | Strategy vs execution vs system failure

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The Battle

James Gilbert 🙏🏻

Judd Borakove

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The Battle

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Judd Borakove

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Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Judd Borakove's LinkedIn Performance

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