How Oracle rewired $455B into its future

Hi Transformers,

Welcome to the debut edition of Revenue Rewired, the newsletter for ambitious Startup CEOs, CROs, and sales leaders who refuse to settle for incremental growth.

My mission is simple: to arm you with insights that help you scale faster, win enterprise deals, and create enduring impact for your clients.

By joining Revenue Rewired, you’ve signaled something bigger. You’re here to lead transformation. To rewire growth. To take on the goals others call impossible… and make them inevitable.

As I was shaping ideas for this newsletter, Oracle stunned the market. Shares surged 40% in a single day, adding more than $250B in market cap, the largest one-day leap in its history.

For years, Oracle wasn’t even in the conversation when people talked about the top cloud players. Most had written them off. But while the market dismissed them, Oracle kept building and never gave up on its ambition.

To put it in perspective, here are three catalyst milestones that reshaped their journey.

During their earnings call, Oracle revealed $455 billion in Remaining Performance Obligations (RPO) — contracted future cloud revenue that customers already owe them.

That’s bigger than Microsoft. Bigger than Amazon. It was a jolt to Wall Street and Silicon Valley alike: the “old guard” had not only survived but outmaneuvered the supposed front-runners of the cloud era.

But let’s face it: As you may have noticed from the timeline above, this “overnight success” was 10 years in the making. And it’s a masterclass in enterprise sales strategy that every founder and sales leader should study.

Go back a decade, and Oracle looked like a dinosaur. AWS and Azure were sprinting ahead in cloud. Google was pouring billions into infrastructure. Startups were ridiculing Oracle as bloated, slow, and trapped in the past.

Larry Ellison himself once mocked the term “cloud” as meaningless. But when Oracle pivoted, it pivoted hard. It built Oracle Cloud Infrastructure (OCI) from the ground up, with a second-generation architecture optimized for performance. It invested billions into capacity. And crucially, it didn’t try to copy AWS or Azure. It played a different game.

Oracle positioned itself as the specialist for what’s coming down the pike… the biggest jobs: databases at global scale, mission-critical enterprise apps, and — as it turns out — the AI workloads that suddenly exploded in demand.

But technology wasn’t enough. The real unlock was a transformation in how Oracle sold.

1. Giant Whale Hunting
In Q1 FY2026 alone, Oracle signed four multi-billion-dollar AI contracts — with OpenAI, xAI, Meta, and others. These weren’t $5M SaaS deals. These were commitments worth hundreds of billions spread over multiple years.

Instead of chasing thousands of smaller logos, Oracle went after the whales that could rewrite its trajectory. And it landed them.

We often chase volume. But sometimes one transformational client can do more for our business than 1,000 small ones.

2. Partnerships Over Pride
Rather than fighting AWS, Azure, and Google head-on, Oracle built multi-cloud partnerships. They colocated Oracle services inside their competitors’ data centers, offering customers the ability to run Oracle alongside their existing cloud.

Result? Multi-cloud database revenue grew 15× in one year.

The initial instinct is always to compete. But if partnering can accelerate growth, could it be the smarter play? As Oracle proved, the answer is a resounding yes.

3. CEO-to-CEO Selling
Larry Ellison himself picked up the phone. At 81, he personally helped close these mega-deals. Because when you’re asking for a $300B contract, the client expects to hear from the top.

Executives buy vision and commitment as much as they buy technology. And when it came from Ellison — with decades of credibility and bravado — it landed.

As a founder or CEO, there are deals only you can close. Step into the arena.

Oracle’s breakout wasn’t about a cloud product. It was about thinking bigger in sales.

They proved that “legacy” doesn’t matter if you have the right strategy. That one whale can transform your entire company. That partnerships can be more powerful than rivals. And that sometimes the CEO’s voice is the most valuable sales tool.

If Oracle can reinvent itself after 40+ years, what’s stopping you from aiming higher today?

Think about your pipeline. Ask yourself:

👉 What one customer, if we won them, could transform our business and 10x our growth?

Small wins matter. They build momentum and keep the lights on. But don’t stop there. Start mapping the path to your big whales. Oracle just showed us all how transformational that path can be.

I hope you found this edition valuable. Hit reply and tell me what you’d like to see next.

—Ram Himmatraopet

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Coming Soon
📖 My new book Lead With Transformation launches October 2025.