An enterprise sales point of view

I've spent 20+ years betting on disruption.

From cloud to cybersecurity, I've consistently chosen technology companies that challenge the status quo and change markets.

AI in the enterprise is the next bet.

Caroline Gregory
Cloudflare
Okta
VCE
Workday
Sungard Availability Services
01 — The Shift

The best enterprise sellers don't just solve today's problems. They forecast what a company's ambition requires.

Information is abundant. Clarity isn't.

Customers can research products and competitors themselves. AI can explain technology before a salesperson enters the room.

The bar has been raised, and the value of the seller has changed.

Now simply getting in the room requires connecting ideas and patterns others don't see and bringing a point of view that changes how people think.

02 — What's Next

My next career bet is an enterprise AI company with the potential to define the next era of technology.

The right company will combine technical credibility with commercial discipline. It will have a clear position about where the market is going and the ability to back it up.

The people matter just as much. I want to work with business-first technologists who are naturally curious about how companies operate — where they're headed, how decisions are made, and where conventional thinking needs to be challenged.

Selling disruptive technology requires creating opportunities, not simply qualifying them.

The best leadership teams give experienced sellers genuine ownership. They have personal conviction about where the market is going, and they're able to meaningfully contribute to both business and technology discussions with customers.

They design territories thoughtfully and enable great salespeople to consistently win.

03 — My Approach

Every account starts with the same question: What's the strategic big bet?

  • What's been promised to investors?
  • Why now? Why hasn't this happened before?
  • Where is the greatest tension between ambition and execution?
  • How does this impact the operating model?
  • Who has the most at stake?
  • What has to change inside the business for the strategy to work?

Those questions tell me what's true about the business. The next ones tell me whether I can change the outcome.

  • Where can we create disproportionate value?
  • Who cares enough to make something happen?
  • Is there a real reason to act now?

I'm purposeful with resources. Every meeting, technical evaluation, and commercial decision should earn its place by moving the customer and the business forward.

I also believe the way we share content is just as important. Our champions and executives want more than static PDF attachments and generic PowerPoint decks. Creating mobile-friendly, interactive microsites to share ideas and build business cases has become an important lever for getting results.

Technology ultimately becomes part of the story, not the story itself.

04 — The Results

I've spent my career turning disruption into enterprise adoption: building new markets and successful customers.

The bets paid off.

82%
GREENFIELD TERRITORY
40%
NAMED ACCOUNTS CONVERTED TO CUSTOMERS
TOP 10%
CLOUDFLARE SALES TALENT
$74M
CUMULATIVE SALES REVENUE
Resume

Listen to the microsite