From Designer to Executive

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Today, in 5 Minutes or Less ⏰

You’ll learn the mindset shift that turns creative focus into leadership success, how to overcome impostor syndrome by focusing on judgment rather than expertise, and the strategy for creating an experience-delivery system (EDS) that guarantees executive buy-in.

Executive Insight with Phil Clevenger 🔍

At the time of our interview, Phil Clevenger was the Vice President of Product Experience at DocuSign, leading a team of over 150 professionals. His deep experience includes 17 years at Adobe, where he designed the first versions of Adobe Lightroom, and a pivotal early career mentored by the renowned designer Kai Krause, who taught him the enduring lessons he uses to shape digital experiences today. The full interview with Phil is included in my book, Leading by Design, in the chapter "How to Get the Top Job."

The Individual Contributor (IC)-to-Leader Shift

“As you transition from Individual Contributor (IC) to a managerial role, you face a profound challenge: shifting from a "24-hour cycle of worry and stress" focused on your own deliverables to a leader responsible for political standing as well as securing and directing resources. One salient mindset shift is to be consistently cultivating your "oxygen supply" -  the executive sponsorship that validates design as a business asset, rather than a cost center.

Phil’s Executive's Thesis

Phil's thesis is that leadership is a tremendous liberation from being a "prisoner of me" (the self-oriented designer) to being focused on service and scale. The reward of an executive role is having "far more impact on a broader scale than I ever did as an individual contributor" by elevating others and using design judgment and resources to solve large-scale business problems.

1. The Strategic Translation: Linking Design to Revenue

Phil Clevenger's strategy starts with a clear mandate: understand the business's financial goals, then build a design strategy to meet them.

Example Problem: Adobe's SaaS products were largely vertical and often not well integrated for a variety of reasons. The business needed to break them into flexible, composable UX microservices to increase revenue and gain a competitive advantage—allowing for custom sales bundles and bespoke customer environments.

The Design Solution: Phil and his team created what they called an "Experience Delivery System." This system, a large step beyond a conventional design system, was a set of standards and infrastructure meta-components necessary to deliver a unified, frictionless experience across all existing services and to embrace new or incoming services. Design built the foundation that enabled the new financial strategy.

2. Translating the Business Goal into a Design Imperative

Phil recognized that simply breaking apart the back-end code would create a Frankenstein's monster on the front end if design didn't intervene. His design objective was twofold:

• Improve CX (Customer Experience): Ensure the experience matches the specific needs of each customer (addressing the "bespoke environment" goal).

• Reduce Friction: Drastically reduce the learning curve for users by creating a frictionless, consistently understandable user experience, regardless of which services they are utilizing.

3. The Solution: The Experience Delivery System (EDS)

The EDS was the strategic design initiative Phil championed to solve the technical and customer-facing problems simultaneously. It went beyond the scope of a typical Design System:

4. Gaining Buy-in: Prioritizing the Invisible Work

Phil's insight lay in how he advocated for this major undertaking. Instead of simply asking for budget to "build a design system" (which sounds like an internal expense to finance), he framed the EDS as the critical enabler for the C-suite's explicit revenue goal:

• The Argument: "We cannot achieve the goal of flexible, integrated services and increased competitive advantage unless the customer experience is equally seamless. The Experience Delivery System (EDS)  is not a design tool; it is the necessary foundation for delivering the bespoke, frictionless experience that will drive user adoption and retention across our new product architecture."

• The Priority: He ensured the EDS was a top-tier priority on the design strategy sheet, directly linking its objectives and milestones to the overarching Adobe business objective. Phil ensured the design team "knew and needed to do" this work to accomplish the stated business goals, securing the mandate without waiting for the business to explicitly request the infrastructure.

By connecting the EDS to the quantifiable goals of increasing revenue and strengthening competitive advantage (via better CX and faster development), Phil transformed a foundational design project into an indispensable business strategy project.

Use Phil's Tips Yourself: 4 Tactical Steps for Design Leaders 🪜

1. Focus on Service to Find Success

When worried about losing your creative spark, shift your focus from self-orientation to kindness and empathy for your team's growth, which Phil found to be a massive source of personal energy and inspiration. 

2. Lead with Judgment over Expertise

When leading non-design teams (e.g., Research, Content Strategy), overcome impostor syndrome by remembering that successful leaders, like politicians, rely on informed judgment and the specialized knowledge of their staff, not personal expertise.

3. Cultivate Your "Oxygen Supply”

Recognize that executive sponsorship is crucial. If key leaders retire or move on, the environment can shift, forcing you to "spend time educating them, proving yourself all over again”. Always be building and maintaining connections across your organization.

4. Determine Resourcing Scientifically

“Avoid the "Wicked Witch's throne room" trap of fixed ratios. Instead, focus on the ratio of designers to feature-level Product Managers, starting with a 1:1 assumption and adjusting based on transparent project scope and needs.

5. Apply the Right Metrics & Measurement

How the leader connects design work to business KPIs; Phil assesses the design team not on constant shipping speed, or whether designs get shipped at all, but on two equally important factors: 

1) The quality of their work and 

2) Their ability to build positive relationships. 

“The ultimate measurement of a kick-ass team is the positive impact seen in the business, which is evident when engineering or product management partners voluntarily reach out with gratitude and appreciation for the design contribution and collaboration."

Phil’s Leadership Lesson ✍🏽

The essential mindset shift for an executive leader is to "free yourself of some of the fears" you had earlier in your career. Stop worrying about being right or being the best. Instead, "lean back a little bit, take it all in, listen hard, use your best judgment, delegate well, empower others, and move to the next thing." This non-personal approach allows you to focus on the work as a role, not a personal drama, and enables greater impact while reducing stress.

Phil Clevenger’s experience teaches us that the highest form of design is leading people and strategy. His insights are a roadmap for turning your fear into freedom and your function into a true business driver. 

Dive deeper into Phil Clevenger's full interview in my book, "Leading by Design: The Insiders Playbook for Tech Leadership.”  Order your copy today! 

That's it for this week!

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