Caitlin
Epstein

A Burrito. Three Billion Dollars. One Forbes Story.

When Twilio announced its acquisition of SendGrid in 2018, the deal was worth roughly $3 billion. In transaction terms, it was a straightforward cash-and-stock merger. In PR terms, it was an empty room waiting for a story.

The Twilio CEO had brought the SendGrid CEO a breakfast burrito. A small gesture - the kind of thing that happens between two people who genuinely like each other. Epstein saw it differently. She saw a $3 billion breakfast burrito.

She pitched that angle to Forbes. It ran. The story gave a heartbeat to a corporate announcement that would otherwise have been processed and forgotten. That is what Caitlin Epstein does: she finds the moment inside the milestone.

This philosophy - stories need faces, deals need hearts - has guided nine years of work at one of Silicon Valley's most developer-beloved companies. When Twilio went public in 2016, Epstein was inside the communications operation. When acquisitions landed, when crises needed navigating, when Twilio needed a voice that didn't sound like a press release - Epstein was the one writing it.

Building a Career on Human Narrative

Caitlin Epstein studied Communications, French, and International Studies at Santa Clara University. The combination is telling. French implies patience with complexity. International Studies signals an awareness that context changes everything. Communications was the obvious choice - but the others explain why she approaches it differently than most.

She came up through Eastwick, a technology-focused PR agency in the Bay Area. Four years of agency life - associate to senior account manager - is a particular kind of education. You learn how clients think about PR from the outside. You learn the distance between what a company says it wants and what it actually needs. You learn how to work fast. And you learn, if you're honest with yourself, when a pitch is wrong.

A brief stint as Director of Communications at InVisionApp in early 2015 gave her in-house experience before Twilio came calling that August. She joined as Public Relations Manager. The job she holds today - VP, Corporate Communications, earned in March 2024 - is nine years and several titles later.

Six Principles That Shaped Twilio's PR Machine

Over years of interviews and talks, Epstein has articulated a clear communications philosophy. It isn't about volume. It isn't about press releases. It's about what actually works - and what looks like PR but isn't.

1. The Human Story Always Wins

"Humans want to hear about other humans." This sounds obvious until you see how B2B companies communicate: feature lists, customer logos, performance benchmarks. Epstein's constant push at Twilio was to move the human to the front - not the platform, not the API, the people using them and the people building them.

2. Patience Is a Media Strategy

She once spent nearly a year cultivating a relationship with a Financial Times journalist before a story ran. No pitch, no pressure - just consistent, genuine relationship-building. In an era when PR is measured in quarterly coverage volume, this is almost a provocation.

3. Surgical Over Scatter

Mass pitching is noise. Epstein's approach is targeted: the right reporter, the right story, the right time. She describes this as "surgical storytelling" - a phrase that captures both the precision required and the discipline of resisting the urge to spray.

4. Internal Press Releases as Culture

Twilio used internal press releases celebrating wins as a way to encourage executives to participate in PR activities. It turns the comms function into a culture function. When leaders see their stories celebrated internally, they become more willing to share them externally.

5. Measure Effort and Outcomes Separately

Track how many outlets you're building relationships with. Track the quality and sentiment of coverage you're landing. Volume metrics and impact metrics are different numbers measuring different things - treating them as the same is how comms functions drift toward busywork.

6. Know When to Kill It

The discipline to abandon a pitch is as important as the skill to write one. Four rejections is the signal. Hanging on past that is ego, not strategy.

The Arc

What She Actually Says

Caitlin Epstein on Camera

Why B2B PR Is Harder - And How She Does It Anyway

Enterprise technology communications is a genre that rewards clarity over charm. The readers are buyers and analysts, not general public. The stories are about integration specs and pricing tiers, not human drama. And yet Epstein has spent a decade arguing - and proving - that this is exactly where human stories matter most.

Twilio sells APIs. Its customers are developers. Its value proposition is technical, its differentiators are architectural, and its competitive moat is developer trust built over years. This is not the stuff of viral campaigns. And yet Epstein found ways to make Twilio human: through founder storytelling, through the faces of engineers who built the platform, through customers whose businesses ran on Twilio infrastructure.

The breakfast burrito story is the most famous example, but it's not an anomaly. It's the output of a consistent philosophy applied at scale: find the human moment, build the relationship that earns the platform to share it, and trust that readers will respond to people over products.

That philosophy earned her a VP title. It also earned Twilio nine years of coverage that reads less like press releases and more like a company that actually has something to say.

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