Rosenverse
Expand DesignOps Leadership as a Chief of Staff

This video is only accessible to Gold members. Log in or register for a free Gold Trial Account to watch.

Log in Register

Most conference talks are accessible to Gold members, while community videos are generally available to all logged-in members.

Expand DesignOps Leadership as a Chief of Staff

Gold
Thursday, September 8, 2022 • DesignOps Summit 2022
Share the love for this talk
Expand DesignOps Leadership as a Chief of Staff
Speakers: Isaac Heyveld
Link:

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."

Ask the Rosenbot
Paul Pangaro, PhD
Systems Disciplines: Table Stakes for 21st Century Organizations
2023 • Enterprise UX 2023
Gold
Peter Van Dijck
Hands-on AI #1: Let’s write your first AI eval
2025 • Rosenfeld Community
Sam Proulx
SUS: A System Unusable for Twenty Percent of the Population
2021 • Civic Design 2021
Gold
Mujtaba Hameed
Frameworks for Excellence: Using Visual Thinking and Communication to Elevate Your Research
2024 • Advancing Research 2024
Gold
Rebecca Gimenez
Work in Progress: Service Design at Airbnb
2024 • Advancing Service Design 2024
Gold
Dantley Davis
Leadership & Diversity—A Fireside Chat with Dantley Davis
2020 • Enterprise Community
Jemma Ahmed
Theme Three Intro
2023 • Advancing Research 2023
Gold
Saara Kamppari-Miller
Inclusive Design is DesignOps
2021 • DesignOps Summit 2021
Gold
Lija Hogan
Practical Principles of Inclusive Research
2023 • Advancing Research 2023
Gold
Gabriela Barneva
Operationalizing Inclusive Design in Service Design
2025 • Advancing Service Design 2025
Gold
Maria Rosala
Research Repositories
2026 • Advancing Research 2026
Gold
Amy Jiménez Márquez
The Atypical UX Manager Path
2020 • Enterprise Community
Jason Mesut
Shaping design, designers and teams
2018 • DesignOps Summit 2018
Gold
Sheryl Cababa
Expanding Your Design Lens with Systems Thinking
2023 • Enterprise Community
John Maeda
About Design Organizations
2019 • DesignOps Community
Jilanna Wilson
Distributed Design Operations Management
2019 • DesignOps Summit 2019
Gold

More Videos

Shipra Kayan

"We had to push through analysis paralysis and trust our guts as customer-facing teams that knew the business."

Shipra Kayan

How we Built a VoC (Voice of the Customer) Practice at Upwork from the Ground Up

September 30, 2021

Peter Morville

"Categories are dangerous but not bad."

Peter Morville

The Architecture of Understanding

May 13, 2015

Renee Reid

"Only one internal hire on the UX team was a huge misopportunity for us."

Renee Reid

Becoming a ResearchH.E.R (Highly Enterprise Ready)

June 3, 2019

Dane DeSutter

"The environment can disrupt critical interactions, like when Stacey gets caught up in cords and takes her eyes off the patient."

Dane DeSutter

Keeping the Body in Mind: What Gestures and Embodied Actions Tell You That Users May Not

March 26, 2024

Sam Proulx

"The four Cs—consistency, convenience, confidence, and customizability—are not just good for accessibility, they make a great experience for everyone."

Sam Proulx

Online Shopping: Designing an Accessible Experience

October 3, 2023

Andrew Custage

"It costs less to keep the customers you have than to acquire new ones."

Andrew Custage Michael Mallett

The Digital Journey: Research on Consumer Frustration and Loyalty

March 29, 2023

Shelby Switzer

"Be present, put devices down, turn off Slack notifications, and really engage."

Shelby Switzer

Making Space for Community Knowledge-sharing in a Distributed World

December 10, 2021

Llewyn Paine

"Right now, there’s a fear of being replaced by AI, and while a lot of that’s overblown, researchers have a legitimate reason to feel uncomfortable."

Llewyn Paine

Coexisting with AI: A practical guide for researchers to navigate tools, ethics, and integration

March 11, 2025

Robin Beers

"Researchers make customers visible inside the organization, but also help the organization learn about itself."

Robin Beers

Navigating organizational systems: Rethinking researcher’s role in driving change

March 13, 2025