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Erin Casali

Senior Director of Product & Design at Xero (formerly Head of Design, Jetpack at Automattic)

ExecutiveLeads from the backOld schoolOrgProductAI
She pairs a people-protective leadership identity with an active, grounded AI practice — writing the frameworks for 'designing with AI' and steering Xero's AI tooling so it lifts craft and teams rather than replacing them.

Signature win. Helped scale Automattic's design organization from 200 to ~1,500 people by building leadership through trust and agency, while shipping products that reach 40%+ of the web.

The case

editorial · CCBEI · with sources
Craft17+ yrs designing for millions (WordPress reaches 40%+ of web, WooCommerce mobile app 4.7/5); contributed to Calypso/Gutenberg foundations; built a 'critique-as-craft' framework that defines quality as goals-aligned, research-informed, constraints-aware — judgment over pixels.8
CommunicationProlific writer/speaker (Intense Minimalism, A List Apart, Leading Design); distills org complexity into shared frameworks (trust equation, presence framework, design critique vocabulary) — directly the clarity/legibility thesis.9
BusinessSr Director shaping Xero's global Tax portfolio strategy (LUCA Awards 2022/2025); NED at Audience Agency Tech Ventures; ties design to outcomes and durable orgs; patent holder cited 200+ times.8
EducationHelped grow Automattic design org from 200 to ~1500 by 'trusting people and giving them agency'; writing centers on growing managers, team health, and reskilling — the people-protection axis is her core identity.9
InnovationAuthors 'designing with AI' primer and 'five levels of AI engagement' org framework; advocated Xero's Anthropic/JAX partnership; frames AI as material that must lift rigor and people, not replace craft — elevate, not hollow.8

Endorsed by peers

illustrative · opens with verified accounts
OverallI'd work for them102
CraftRaised my craft bar98
CommunicationMade the case for design110
BusinessMade design matter to the business98
EducationTaught me something I still use110
InnovationShowed me a new way to work98

Verified peers only — one tap with LinkedIn. Names stay private; we show role and industry. Bars are illustrative until the participation backend is live.

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