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Zendesk CLO Shana Simmons: Empathy is the new superpower for AI leaders

Zendesk

Zendesk's Chief Legal Officer Shana Simmons has reframed governance as a cultural imperative rather than a legal compliance checkbox, signalling a fundamental shift in how enterprise organisations should approach AI adoption. Speaking at Zendesk Relate 2026, Simmons positioned governance as an umbrella spanning privacy, security, AI guardrails, accountability and data quality—but crucially, she embedded it within organisational culture rather than treating it as a legal department problem. This represents a departure from the industry's historical obsession with data infrastructure; governance has quietly become the primary blocker to enterprise AI adoption. For CX teams already managing autonomous agents or considering deployment, this means the conversation with your legal and product teams should centre on shared accountability and cultural integration rather than post-implementation compliance audits. The question becomes whether your organisation has genuinely embedded governance into product development workflows, or whether you're still operating with siloed legal reviews that slow deployment cycles.

Simmons' approach to workforce transformation offers a counterpoint to automation anxiety that pervades CX discussions. Rather than viewing AI as a displacement mechanism, she advocates identifying repetitive work and upskilling teams to focus on high-value interactions—a philosophy she applied when visiting her Manila legal team. Her hiring criteria now prioritise AI literacy and agency (the willingness to learn and solve problems) over pure productivity metrics, reflecting a recognition that the future of work is fundamentally about human-AI collaboration rather than replacement. For support team leads and CX consultants, this reframes how you should evaluate automation opportunities: the goal isn't to eliminate roles but to identify which tasks drain your team's capacity and prevent them from delivering the empathetic, nuanced customer interactions that differentiate your service.

The broader implication centres on authenticity and character as competitive advantages in an AI-saturated market. Simmons explicitly rejected the notion that empathy is a weakness to suppress in corporate leadership, instead positioning it as a superpower for understanding customers and building effective teams. She evaluates candidates not on credentials alone but on how they treat people they perceive as less important—a metric her executive assistant often informed. For CX professionals, this suggests that as vendors commoditise AI capabilities and proof-of-concepts become ubiquitous, your organisation's ability to embed genuine respect and engagement into customer interactions—and to hire and retain people who embody those values—becomes the actual differentiator. The technology evolves rapidly, but the fundamentals of trust-building and human connection remain constant.