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
"This tool radically automates user research steps so that no facilitation is needed, it’s actually automatic."
Joerg Beringer Thomas GeisScaling User Research with AI: Continuous Discovery of User Needs in Minutes
June 10, 2025
"I sometimes avoid the word participatory because it can sound scary; I just call it research and let it be participatory by default."
Nidhi Singh Rathore Amber DavisEmbracing participation to unlock deeper truths in commercial research
March 12, 2025
"Heat maps showed users clicking on areas they thought were clickable but weren’t, resulting in click rage."
Mackenzie Cockram Sara Branco Cunha Ian FranklinIntegrating Qualitative and Quantitative Research from Discovery to Live
December 16, 2022
"We are talking about climate solutions to displace things that are incompatible with thriving life, not just add more options."
Jamie Beck Alexander Nina Gregg Shawn Petersen Bill DeRoucheyHow can you find your role in climate?
January 17, 2024
"Getting executive buy-in is so critical to the success of research, yet it remains a challenge for many."
Caroline VizeThe State of UX: Five Lessons from 2021 to Accelerate Digital Experience in 2022
March 9, 2022
"Design ops has the opportunity to set a new default future, not follow the path set by the past."
Dr. Karl JeffriesThe Science of Creativity for DesignOps
January 8, 2024
"Including human stories alongside numbers helps business leaders grasp the complexity behind the metrics."
Alberto FerreiraMaking it Count: Developing a custom digital metric framework that works
October 15, 2021
"AI is not just speeding up what I used to do, it's changing what I used to do."
Shipra Kayan Robert Kortenoeven Eileen TangEmerging principles for using AI in Design: What the product design team at Miro has learned from deeply integrating AI in their workflow
June 11, 2025
"Identifying the right success metrics is the number one challenge teams are facing today."
Dana Bishop2022: The Year UX Demonstrates its Business Impact
March 11, 2022
