How I Think About Enterprise Sales

I've spent 20+ years helping disruptive technology become enterprise standard.

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
Cloudflare
Okta
VCE
Workday
Sungard Availability Services
01 — The Shift

Enterprise selling has changed. The seller's value is increasingly in forecasting what a company's ambition will require.

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 a credible chance to define how enterprises actually use AI.

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