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How Zendesk Rebuilt Communications During PE Transformation: The 9-Month Playbook

Four days after Zendesk‘s private equity acquisition closed in November 2022, ChatGPT launched. For Sarah Gavin, who would join as Chief Communications Officer two years later, this timing created an unexpected advantage: the company had already accepted radical change as the new normal.

In a recent episode of The Narrative, Sarah shared how she rebuilt Zendesk’s communications and marketing functions during the post-acquisition period. Her approach—doubling the team to 40 people while eliminating all agency spend in nine months—reveals a counterintuitive principle about organizational change: maximum chaos enables faster transformation than incremental adjustment.

Why Consolidated Change Beats Incremental Transformation

When Sarah joined Zendesk in 2024, the company was still processing its acquisition by Hellman & Friedman and Permira. Leadership had changed. The business model had shifted from public to private. And ChatGPT had upended assumptions about the customer service software category.

Most operators would introduce changes gradually to avoid overwhelming the organization. Sarah made the opposite bet: execute all major changes simultaneously.

Within nine months, she doubled her communications team to 40 people, eliminated all agency relationships, and pulled everything in-house. The consolidation wasn’t about cost—it was about decision velocity during a transformation window when rapid iteration matters most.

“If you’re going to change things radically, just go do it all at the same time,” Sarah explains. “You can undo things much easier than you can add one thing after the other.”

This approach came from her decade at Expedia, where she managed communications through a 15-month period when the company acquired Hotels.com, HomeAway/VRBO, Orbitz, Travelocity, and multiple global brands. Each acquisition brought its own PR infrastructure, creating an opportunity to rebuild the entire function rather than integrate piecemeal.

The insight: teams process wholesale change more effectively than they handle slow-rolling disruption. A single major reorganization sets new expectations. Incremental changes create perpetual uncertainty about when the next shoe will drop.

But there’s a deeper pattern here about how crisis creates permission structures. When ChatGPT launched days after Zendesk’s PE deal closed, the timing actually helped the organization. “We were already in this position where we were already saying, oh, shit, right?” Sarah notes. “And in some ways there’s a gift of saying, hey, you’re on this holy shit moment. Here is a North Star that’s also mildly terrifying if you don’t go figure it out.”

The compound crisis—PE transition plus existential AI threat—made it easier to justify radical moves. The organization didn’t have to debate whether change was necessary. Everyone already knew the old playbook wouldn’t work.

Psychological Safety as the Constraint During Transformation

The structural changes were straightforward. The harder challenge was rebuilding capacity for risk-taking after organizational trauma.

Instead of focusing on pipeline, conversion rates, or brand metrics, Sarah made psychological safety her primary KPI. Over several quarters, the marketing team’s psychological safety scores increased 8 points.

“The number one thing they needed from me was not to tell them where to spend this dollar,” Sarah explains. “They needed some psychological safety. They needed to feel like they could go take risks.”

This reframes what limits performance during transformation. It’s not execution capability or resource availability—it’s willingness to experiment when the consequences of failure feel uncertain.

Sarah’s experience building Expedia’s communications program from scratch prepared her for this. When she started, the function literally didn’t exist beyond an expense line item. One senior lawyer refused to let her sit down during their first meeting, telling her: “I’ve never met a PR person I liked and you should just be prepared that I’m going to say no to anything that you want, because all you’re going to want is making trouble.”

Building credibility required demonstrating value repeatedly while teaching the organization how to engage with communications. During Expedia’s acquisitive period, Sarah created a training on “bridging and deflection.” She made everyone stand up and practice “can’t hands”—physically putting their hands out while saying “I can’t answer this question,” followed by their natural redirect phrase.

Years later, former Expedia colleagues still reference “can’t hands” when they see Sarah. The physical gesture created muscle memory that survived beyond the training itself.

The broader lesson: during transformation, leaders need to actively rebuild the team’s permission to fail. Execution frameworks matter less than creating conditions where people will actually use those frameworks.

Hiring for Business Intuition Over Communications Craft

Sarah’s hiring approach challenges conventional thinking about communications roles. She actively recruits people with sales backgrounds—including retail jobs from high school—rather than prioritizing traditional PR credentials.

“There’s a difference between being a comms person who serves the business and being a business person whose craft happens to be comms,” Sarah explains. “And that is a just radical different mindset shift.”

The distinction matters because sales experience teaches several things simultaneously: understanding influence mechanics, managing customer dynamics, handling rejection, and developing business curiosity. Someone who sold in a mall at 16 learned to connect their daily actions to revenue outcomes in ways that traditional PR training doesn’t emphasize.

“I don’t really care if they can read a P&L,” Sarah says. “I look for people who have the curiosity to learn about the business more than do you already know about the business.”

This screening criterion produces communicators who optimize for business outcomes rather than media placements. They make better executive advisors because they frame recommendations in terms of commercial impact. They tell stronger stories because they understand customer economics, not just messaging frameworks.

The inverse matters too: communications people who think like service providers will always struggle to influence at the executive level because they’re optimizing for the wrong outcome. A cool story placement doesn’t matter if it doesn’t connect to pipeline, brand perception among target accounts, or competitive positioning.

Using Customer Research to Navigate Political Decisions

Before the 2024 election, Zendesk faced the question every B2B company confronts: should we take a public stance on political issues?

Sarah’s framework bypasses the usual debate about corporate values and authenticity. Instead, she commissioned Morning Consult to research what Zendesk’s customers actually wanted.

The data showed a 50/50 split—customers were evenly divided on whether they wanted the company to be politically vocal. This informed Zendesk’s decision to stay relatively quiet during the election cycle.

But the research served a second purpose: it gave leadership concrete evidence to share with employees about the decision. Rather than making a values-based argument that some employees might disagree with, they could point to customer data.

“What do your customers want? What do your customers want? What do your customers want?” Sarah emphasizes as her three-question framework.

This differs from the common approach of aligning political stances with company values. At Expedia, Sarah did take strong public positions—but only when issues directly affected the company’s core business. When 2016 immigration restrictions threatened to prevent people from traveling to the United States, Expedia opposed the policy because it contradicted their fundamental operating principle: “free movement of people all around the world.”

The decision tree is simpler than most companies make it: Does this issue directly impact your business model? If yes, consider taking a stance. If no, research what customers want before deciding.

Crisis Response Requires Capability-Based Deployment

During COVID’s early weeks at Expedia, Sarah managed more than a communications crisis—she managed a humanitarian crisis. Thousands of travelers were stranded worldwide with no way home. Some needed to book hotels for six weeks because flights weren’t available.

Sarah’s response reveals a principle about crisis management that extends beyond communications: deploy people based on capability for the specific crisis, not job title or steady-state expertise.

“Those crisis moments are when you sort of learn that no one is too good for anything and everyone is good enough to help,” Sarah reflects. Her PR team wrote customer communications while she personally negotiated messaging with airlines.

This works because crisis response requires different skills than business-as-usual operations. A PR person might excel at customer empathy under pressure while a lawyer struggles with it. A finance person might be excellent at rapid scenario planning while a product manager freezes.

The key is recognizing that crisis capabilities don’t map to organizational hierarchies. Your most senior people might not be your most effective crisis responders for a given situation.

The Case for Agency Experience Before Going In-House

Despite building 40-person in-house teams at both Expedia and Zendesk, Sarah strongly recommends agency experience for people starting communications careers.

“When you go to an agency, you learn everything from at 1pm you’re prepping the CEO and at 1am you’re down at the FedEx making copies,” Sarah explains. “That boot camp of agency life even for just a couple of years is so good.”

The value isn’t just the range of experiences—it’s learning what you don’t want. “There is so much freedom that comes from knowing what you want to say no to,” Sarah notes.

Agency work exposes you to multiple industries, client types, and problem sets in compressed timeframes. This creates pattern recognition that’s hard to develop by spending five years at a single company.

But the transition from agency to in-house requires learning something agencies don’t teach: how to be the decision maker rather than the advisor. In-house, you don’t have to say yes to every internal stakeholder request. That shift can be difficult for people trained to serve client demands.

What Communications Leadership Actually Means

Sarah’s dual role as Chief Communications Officer and Acting CMO reveals what communications leadership looks like at scale. It’s not about message development or media strategy—it’s about understanding how communications functions as a business lever.

The Zendesk transformation demonstrates this in practice. When Sarah prioritized psychological safety over marketing KPIs, she wasn’t ignoring business outcomes. She was identifying the actual constraint to performance: the team’s willingness to take risks after major organizational trauma.

When she consolidated all changes into a nine-month window rather than spreading them over years, she wasn’t being reckless. She was recognizing that teams process wholesale change more effectively than incremental disruption.

When she hired communicators with sales backgrounds instead of traditional PR credentials, she wasn’t lowering standards. She was selecting for business thinking over communications craft.

These decisions only make sense when you view communications as a business function whose craft happens to involve words, stories, and relationships. The moment you position it as a service function that supports the business, you’ve already lost the ability to influence at the level Sarah operates.

For founders building communications functions, the playbook is clear: hire people who think like business partners, consolidate major changes instead of implementing incrementally, measure the constraints that actually limit performance, and remember that crisis response requires capability-based deployment, not title-based assignments.

The through-line in Sarah’s experience—from building Expedia’s program from nothing, through managing COVID’s travel crisis, to rebuilding Zendesk during PE transformation—is that communications leadership means understanding which organizational constraints matter most at any given moment, then systematically removing them.