Summary
Today’s design organizations continuously face increased scope, complex deliverables, challenging people dynamics, and pressure to hit business goals. For this reason, it’s important to reevaluate how DesignOps leadership is supported so that they can be as efficient and effective as possible. An emerging solution to this challenge is the Chief of Staff role — DesignOps practitioners skilled in values-driven leadership at scale, ruthless prioritization, and building trusted partnerships, who can serve as an advisor, proxy, and operational leader to the heads of large design teams. Here’s what Isaac has learned while defining this new leadership path in DesignOps at Salesforce. Takeaways: How to lead your team as the scope of your responsibility widens How to build trusted operational partnerships How to navigate complex situations on your team as you scale up
Key Insights
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The Chief of Staff role was formalized to help executive leaders manage rapid UX team growth and operational complexity.
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Isaac Hayvin and Jason Day have collaborated since 2010, highlighting the importance of a trusted partnership in this role.
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Salesforce’s UX team doubled overnight from 80 to 170 members, driving the need for expanded design operations leadership.
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Chief of Staff personas include goalkeeper, operator, implementer, integrator, proxy, and advisor, enabling versatile support for executives.
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The Chief of Staff bridges executives, design program managers, and executive assistants to maintain organizational cohesion.
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This role focuses on strategic prioritization, organizational planning, program operationalization, and communication across teams.
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Emotional intelligence, data competency, and communication skills are critical for a successful Chief of Staff.
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Chief of Staff and Design Program Managers share many skills, but the former supports executives at an organizational level, not just project teams.
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Once UX teams exceed around 100 practitioners, a Chief of Staff becomes valuable to help scale leadership operations effectively.
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Spreadsheets remain a core tool for resource allocation and planning due to their flexibility despite the role’s strategic complexity.
Notable Quotes
"The trusted partnership between the Chief of Staff and the executive is critically important."
"These changes were effective immediately — going from 80 to 170 people overnight was a shock but also an opportunity."
"The Chief of Staff serves as a bridge between design program managers, executive assistants, and UX and product COOs."
"The Chief of Staff acts as a goalkeeper helping to triage and prioritize strategy and work for the executive."
"Emotional intelligence is key to navigating situations with senior leaders multiple levels above you."
"I love being heads-down deep in a spreadsheet — data is my happy place."
"The Chief of Staff creates consistency and confidence in key programs like talent review and budget planning."
"When your UX team surpasses about 100 people, that's a good threshold to start looking for a Chief of Staff."
"Slack helps consolidate communication but still requires careful curation to keep leadership aligned."
"The Chief of Staff role is a natural expansion of design ops leadership with a shift in mindset from project to executive support."
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