Expand DesignOps Leadership as a Chief of Staff
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
-
•
The Chief of Staff role in design ops focuses on enabling the executive and leadership team to scale operations and strategy, not just managing individual projects.
-
•
Isaac Hayvin partnered for over a decade with EVP Jason Day, exemplifying the trusted partnership critical to the CoS role’s success.
-
•
Salesforce’s Customer 360 UX team grew from 30 to 170 practitioners almost overnight, prompting the formal creation of the Chief of Staff role.
-
•
The CoS serves multiple personas: goalkeeper, operator, implementer, integrator, proxy, and advisor, tailoring support to executive needs.
-
•
Chiefs of Staff operate closely with executive assistants and design program managers, forming a triad essential to operating a large design org.
-
•
Operational tasks for a design CoS include talent reviews, budget planning, quarterly business reviews, and global team investment strategies.
-
•
Spreadsheets remain the primary flexible tool used for resource allocation and strategic planning despite their low-tech nature.
-
•
Emotional intelligence and strong communication skills are vital for a CoS, who works across multiple leadership levels and teams.
-
•
The Chief of Staff role can be a natural next career step for Design Program Managers, expanding from team-level to organizational leadership support.
-
•
Adding a Chief of Staff is advisable once a design leadership team surpasses about 100 practitioners or undergoes rapid growth requiring dedicated executive support.
Notable Quotes
"The trusted partnership between the chief of staff and the executive is critically important."
"We went from a team of 80 to 170 overnight, and that was a wide open cheeks flushed moment for me."
"The chief of staff serves as a bridge between the design program managers, executive assistants, and other ux and product chiefs of staff."
"The persona of a goalkeeper is helping to triage and prioritize strategy and work for the executive."
"Emotional intelligence is key to navigating situations with senior leaders multiple grades above you."
"A lot of our work still happens in spreadsheets, because they’re flexible and dynamic."
"The chief of staff is the bridge between our executive leadership team and the design ops practitioners."
"If you’re managing over 100 design practitioners, it makes sense to start looking at a chief of staff role."
"The chief of staff can be a natural next step from a design program manager or design ops leader of one."
"Communication is an integral part of the chief of staff role, whether with leadership, the org, or partners."
Or choose a question:
More Videos
"Guardrail metrics help catch unintended consequences like increased customer service calls despite higher conversions."
Erin WeigelUX Lessons from running more than 1,200 A/B Tests
July 10, 2024
"Safe money has solid returns, so fiscally responsible companies demand higher returns from new investments especially with inflation."
Mike OrenWhy Pharmaceutical's Research Model Should Replace Design Thinking
March 28, 2023
"Future UX includes designing for user discovery in conversational and augmented interfaces, not just clicks."
Lija Hogan Milan Mijatovic Sam Proulx Louis RosenfeldThree Years Out: Perspectives on the Near-Term Future of User Research
March 15, 2024
"Alice often perceives Charlie as just another barrage of alerts filled with jargon she doesn't understand."
Heidi TrostWhen AI Becomes the User’s Point Person—and Point of Failure
August 7, 2025
"The studio is designed for whole teams to work together, not just the design team alone."
Adam CutlerPeople + Places + Practices = Outcomes
June 8, 2016
"Anyone can become a person with accessibility needs at any time, so inclusivity should be a default."
Rittika BasuAge and Interfaces: Equipping Older Adults with Technological Tools
February 23, 2023
"By designing products through the lens of edge cases like disabilities first, they often become better products for everyone."
Saara Kamppari-MillerDesignOps for Inclusive Design and Accessibility
May 26, 2022
"We want you to leave feeling like all those missed Slack messages and emails are worth it."
Bria AlexanderTheme Two Intro
October 3, 2023
"Junior roles represent only one percent of design ops roles, raising the question if we are missing opportunities to cultivate new talent."
Laine Riley Prokay Lisa GordonCarving a Path for Early Career DesignOps Practitioners
September 9, 2022
