Webinar Recap: Driving Enterprise Outcomes as a Design Executive in the AI Era

Design Executive Council | Webinar Recording

Webinar Recap: Driving Enterprise Outcomes as a Design Executive in the AI Era

Webinar Recap: Driving Enterprise Outcomes as a Design Executive in the AI Era

Design Executive Council | Webinar Recording

October 23, 2026
Webinar Recap: Driving Enterprise Outcomes as a Design Executive in the AI Era
Summary

As AI takes on more of the hands-on production work, who decides what's worth building, and what is design's role in it?

Listen to leaders working through these challenges at the enterprise level

For DXC's first open webinar, Gordon Ching, the Founder of the Design Executive Council (DXC), brought together four design executives to unpack how the role of the design executive is evolving, what businesses are now asking of design leaders, and what driving enterprise outcomes looks like in practice in the AI era.

DXC's mission is to advance the strategic role of design leadership in global business. Much of the conversation in design has centered on functional leadership: how to make great experiences and great products. As leaders ascend in their careers, the conversation moves into business leadership and board directorship, and roles shift from influence to accountability and to governance. This session looked at that shift through the lens of what businesses are asking of design executives as the AI era changes expectations and the work.

The conversation featured the panelists: Andy Vitale (Taxwell), Heather Winkle (Delta Air Lines), Catherine Winfield (Autodesk), and Matthew Menz (Fmr. Amazon Web Services).

  • Andy Vitale is the VP, Head of Product Design & AI Center of Excellence at Taxwell, where he leads design across TaxAct and Drake Software and drives AI enablement across 18 business areas. The platforms support tens of millions of tax returns each year for more than 90,000 tax professionals and 3 million DIY filers. His work covers new product development and core platform modernization across professional and consumer tax, including the TaxAct Claude Connector and an agentic product-development pipeline.

  • Heather Winkle is the Vice President of Digital Experience at Delta Air Lines. Heather leads a multi-skilled organization of Product Managers, Designers, Analysts, and Developers in the strategy, design, and delivery of Delta's digital products. In partnership with commercial and operational teams across the Delta ecosystem, they create human-centered tools that empower confident and elevated travel.

  • Catherine Winfield leads Experience Design and Product for Autodesk's digital direct business, a $1B+ global engine spanning e-commerce, AI monetization, and a third-party marketplace. She owns the experience end to end, from strategy through execution, aligning engineering and go-to-market leaders across the company. A builder at heart, Catherine treats design as a formative function, one that shapes how people behave and drives impact the discipline is too rarely trusted to deliver.

  • Matthew Menz is the Fmr. VP of Customer Experience at Amazon Web Services (AWS). Matthew leads a multidisciplinary UX team at AWS that guides the product experience across all channels. His content, design, research and engineering teams partner with nearly 300 services including AI, robotics, storage, and data analytics. Matt believes in the transformative impact of design at scale.

What we covered in the webinar

  1. What businesses are now asking of design executives: What the new business context asks of design leaders, and what is different between the prior era and this one.
  2. Leading through AI-driven change: What it means to take accountability for enterprise outcomes rather than influence them, and how the AI era has shifted that as more leaders take on greater responsibility.
  3. The investment case for design: How to understand design and its value heading into 2027, as design executives stretch beyond design into analytics, product management, growth and revenue, and customer experience.
  4. The big questions that remain: What the panelists are still wrestling with about the shape of the work, and how it gets done, in 2027.

What businesses are now asking of design executives

The leaders agreed the business is asking for more, and faster, and that what hasn't changed is the need to understand people and solve meaningful problems.

  • More and faster, without lowering the bar. AI has reset expectations of what a team can produce, and leadership wants to see it show up in faster builds, more deliverables, and shorter cycles. In a seasonal business like Taxwell's, when you deliver is part of the value you deliver, so teams have to ask where customers are getting stuck and which problems deserve the limited time available. Prototyping in code has cut the time to get an idea in front of customers from two to three weeks to under three days.

  • Experimentation in place of the three-to-five-year vision. Long-range visions now seem almost laughable, and with designers in Claude Code, paper prototypes are hard to imagine. Rapid iteration takes their place. Design and product still need to imagine the future and hold an ambitious vision, one that may be more real now that complex experiences can be built faster. AI is a tool, and it can make long-imagined experiences like personalization and dynamically rendered experiences real.

  • Out from behind the tool. Tools at our fingertips risk putting designers back at a desk, when they can enable a different kind of conversation. Design can show up at new points in the product development lifecycle, such as working through a call scenario on paper, side by side with a customer care agent. As more people use these tools, design's job is to bring years of practice and judgment into how tools are teed up, how models learn, and how others make choices, letting that almost invisible work take the stage.

  • Platforms, not services. At the enterprise level, where experiences span tens or hundreds of companies, design can no longer run as a service. Instead of reviews, redlines, and adoption campaigns across 300 teams, leaders build mechanisms that make the right, vetted, proven way the easiest way to build, unlocking tens to hundreds of teams with far fewer hands on keyboards.
"People hand us financial details. So the thing that still matters most is trust."  Andy Vitale, Taxwell

Leading through AI-driven change

With code shipping faster than ever, the leaders described accountability as owning outcomes across functions, and proving them, rather than only influencing the work.

  • Taste, judgment, and humanity as seams collapse. Design's value is taste, judgment, humanity, and systems thinking. As seams collapse, some design moves into engineering and some into product, while other functions tip into design too. Leaders who can see across them are needed. Two practices help: hypothesis reviews in place of activity-based design or product reviews, asking whether this solution will solve this problem for customers, and moving design systems teams toward design engineering.

  • Adoption is not the finish line. Taxwell's AI Center of Excellence enabled 18 teams through a four-level fluency rubric (curious, assisted, enabled, native), an AI ambassador in every function, and a weekly, bottom-up AI spotlight that costs nothing. Beyond adoption, efficiency is table stakes. Leaders should name what the saved time made possible: a customer problem resolved, a product in customers' hands earlier, an assumption tested before more resources were committed.

  • Knowing which experience actually works. When interfaces are cheap to generate, the scarcity is knowing which one works. Connecting the design system (the vocabulary), instrumented analytics (the proof), content systems, and a context engine creates a feedback loop from creation to actual customer behavior. Design shifts from anticipating behavior to curating the response, moving past vanity metrics like active users and bounce rates. Leaders can also take intentional slices through journeys and ecosystems, experiment quickly, and keep the work traceable and observable, so the lineage of value can be traced.

  • The owner's mindset and shared outcomes. What got you here won't get you there. At the next level, your function is one piece of the puzzle, which can mean redirecting design resources to engineering so things actually get built. Heather Winkle described a shift to shared KPIs for the customer, the employee, and the operation, rather than divisional ones. For many, the hardest move is from functional to cross-functional leadership: pushing past imposter syndrome to ask deep technical questions, and treating your function as one lens on the organization's problems.

  • Holistic ownership and tight loops. Owning a design system from customer ideation to vended code, rather than across 12 partners and three roadmaps, makes holistic ownership powerful. Governed, automated feedback loops from SDK to design systems to analytics let teams learn and iterate continuously. Every company is at a different point, and leaders earn their way into closer continuity and governance.

  • Raising the next generation. It is easy to over-rotate on tooling and undervalue how the next generations of designers, researchers, and content writers are nurtured and mentored, when their first engagement with the craft may be a text prompt.
"It's not about your team, it's about company or organizational division resources, how they get allocated." Catherine Winfield, Autodesk
"Shared metrics gives you an eventual answer, shared ownership gives you a boardroom to sit in, and accountability changes it by 3 PM." Matthew Menz, formerly Amazon Web Services

The investment case for design

As design executives stretch into analytics, product management, growth and revenue, and customer experience, the leaders saw design's value heading into 2027 moving toward context, systems, and judgment, with investment following capability.

  • Owning context. Who owns the knowledge graph of customer outcomes and the experience? Today that context lives in data, analytics, business, and product teams. A meaningful experience model, grounded in context that the engine uses to build experiences, is where design could be, offered as a strong opinion, loosely held. The goal is not an ETL data connection but a mental model of journeys and continuity across sales, support, professional services, and product or go-to-market, because how you change a business is how the business thinks.

  • Formalizing how designers have always worked. Designers have always worked through the possibilities: how someone enters a workflow, the contextual clues they use, their likely next move, and whether it succeeded. That work can now be formalized, moving design from a suggestion you hope gets built to a layer that informs the building.

  • Systems thinking as the number one skill. Journey management, service design, and systems thinking form a connective tissue layer designers can now step fully into, as downstream work becomes more efficient. In the most advanced self-healing software factories, usability and accessibility audits are almost entirely handled by agents. That opens an orchestration layer of judgment at the intersection of design systems, evals, systems thinking, and journey management.

  • Evidence at each step. Delivering more doesn't mean creating more value. As the cost of building collapses, the bottleneck moves to deciding what to build and judging whether it is good. As distribution shifts to AI surfaces like Claude and ChatGPT, teams design for agents as well as screens. Investments follow: a design system that makes AI output trustworthy, so anyone can build and machines can read it; brand and legal skills to streamline approvals; semantic layers built with the data team; and evals.

  • Making the easiest thing the best thing. In large enterprises with many tools and processes, teams can now bake their thinking, languages, tools, and diagrams into the company knowledge base as a shared starting point. Rather than debating trade-offs, they can build the right thing into capabilities that get picked up automatically, while staying alert that the wrong thing can spread just as easily at scale.
"We're actually talking about the way LLMs and neural networks work, which in some ways is how designers have always worked."  Heather Winkle, Delta Air Lines
"The investment starts to follow the capability that's needed to reach the outcome, and it doesn't really matter where that sits anymore." Andy Vitale, Taxwell

The big questions that remain

Looking ahead to 2027, the leaders are still wrestling with where to focus, how to prove value, and how to build teams that can thrive when no one has the future of work figured out.

  • Choosing where to focus. How quickly, and with what level of quality and certainty, can teams infuse experience into the fabric of their ecosystem? With so much to play with, design has to make better choices internally about where to invest, what level of energy to give, and what is fine to outsource to an agent, another team, or the greater ecosystem.

  • Candor and shared learning. Rather than only presenting what worked, leaders can open a safe space to examine what didn't, such as a number they expected to move that didn't. That means shifting from automating everything toward a responsive understanding that is collective and shared, something the leaders see as underserved.

  • Resilient teams. Some expect teams to become more senior, with everyone managing agents. Some smaller companies are hiring early-in-career talent, because AI can upskill them faster and that workforce is more cost-effective. There is no one-size-fits-all model, and tools change as soon as they are codified. What leaders can offer is candor, a safe-enough-to-try environment, and room for play, creativity, and joy.

  • Proving the value of capacity. Building software was always a team sport, and now that anyone can build, the need for communication has grown exponentially. Experiences are shaped as much by priority and scope as by what is built. Leaders need to be as rigorous about the value of the work they add as about the time they save. That means not rewarding volume for its own sake, not reporting only efficiency (which turns functions into cost levers), and not claiming outcomes they don't control. One practice: pair every speed metric with a decision metric that captures what was learned or what changed.
"Candor isn't a cost to your credibility. It's the currency that gives you the ability to build going forward." Matthew Menz, formerly Amazon Web Services
"We don't know where it's going to go, and we should find joy and excitement in that instead of fear." Catherine Winfield, Autodesk

Path forward

Across the conversation, the leaders kept touching on speed, cost, and quality, and on how to deliver all three at once. Their closing advice pointed to where design leaders can create that value next.

  • Tie strategy to governance and outcomes. For the first time, teams can build the rules they want to live by into the strategy and see them cascade through the tooling choices that generate outcomes, rather than acting as the creative police. Software factories still need a design component and a strategy component, and the open question is whether they are spec-driven, strategy-driven, or outcome-driven.

  • Make the invisible visible. Storytelling lets leaders show the connections behind the work so people can hear and understand them widely and quickly.

  • Work the seams. As seams between functions collapse, the seams themselves are where design can add the most value: keeping things holistically connected and seamless for customers, with seamless knowledge transfer and collaboration.

  • Stay resilient and iterative. No one knows yet what being effective at the business level will look like in 2027. Staying focused on the outcomes you drive, building resilient teams, and pursuing what you love will carry leaders through a period when everyone is learning together.


DXC is hosting many more of these conversations internally, and is planning more external webinars heading into 2027. DXC now serves senior executives as well as rising design executives.

Explore the Council Explore the Forum

Explore the premier membership network for design executives

DXC provides design executives a trusted network to create impact alongside their peers, access agenda-shaping research, and amplify the strategic role and value of design leadership at the C-Suite and Board-level of the world’s largest companies.

Express interest

Download the report

Thank you! Download the report here:
Download PDF
Oops! Something went wrong while submitting the form.