Oct. 28, 2025

She Rebuilt Zocdoc Overnight - Now She’s Running Cascade

What do you do when your company goes dark - literally?

For Anna Elwood, now COO of Cascade, it meant turning a Sheraton ballroom into a temporary headquarters overnight.

Back in 2012, when Superstorm Sandy flooded lower Manhattan and took Zocdoc’s office offline, Anna was in Scottsdale, running point. Within 24 hours she found a hotel ballroom north of the blackout zone, hauled in Wi-Fi boosters, and recreated a 300-person HQ from scratch.

That story captures who Anna Elwood is: an operator who runs toward the mess, finds calm inside chaos, and builds the systems that keep everyone moving.

From Broadway to Boardrooms

Anna didn’t plan to end up in operations. She started as an actor in New York, pounding the pavement with an Equity card and a dream.

But theater taught her something critical: how to read a room, build trust fast, and deliver under pressure - skills that map perfectly to leading teams.

Her jump to tech began at Zocdoc, when the company still had “beta” in the corner of its site. She joined as an operations associate and spent nearly a decade helping it scale into a unicorn. From there came Knotel, Teachable, and now Cascade - each stage a new lesson in how to design rhythm into growth.

The Rhythm of Execution

At Cascade, Anna’s first move as COO wasn’t some flashy new initiative - it was rebuilding the company’s operating rhythm.

She noticed the basics were missing: no weekly leadership meeting, no shared cadence for decisions, no visibility across teams scattered between New York and Sydney.

So she did what great operators do - she created structure:

Weekly leadership reviews anchored in data
Clear accountability loops for initiatives
A hybrid model that brought teams together in-person when it mattered

Her goal? Make decision-making predictable so people can focus on customers, not coordination.

Governance Without Red Tape

Every scaling company wrestles with the same tension: governance versus speed.

Add too much process and you choke creativity. Add too little and you drown in chaos.

Anna’s answer is balance. She uses Cascade’s own framework - the five pillars of strategic maturity - as a mirror for both customers and her own team:

Visibility, Alignment, Focus, Accountability, and Speed.

If one pillar weakens, the whole company wobbles.

AI as an Operational Multiplier

AI isn’t a buzzword inside Cascade - it’s built into how the team operates.

With just sixty people, they function like a company twice that size.

“AI is the teammate that jumps with you,” Anna told me. “It helps us analyze data faster, summarize discussions, and free up humans for judgment and creativity.”

It’s a glimpse of what every modern COO is facing - how to pair human intuition with machine leverage.

Strategy Is Everyone’s Business

Ask Anna who owns strategy, and she doesn’t hesitate:

“It’s everyone’s business - but the CEO and C-suite have to model it first.”

In Cascade’s world, strategy isn’t a PowerPoint deck that lives on a shelf; it’s a living operating system. One that connects long-term goals to daily execution and keeps everyone rowing in the same direction.

The Takeaway

Anna Elwood’s story is a masterclass in operational resilience.

From rebuilding a company overnight to designing rhythms that keep teams aligned, she embodies what modern operations looks like: grounded, adaptive, and quietly relentless.

She doesn’t chase calm - she builds it.