This is what it’s like to work with
Jesse James Garrett.

Jesse co-founded product strategy and design consultancy Adaptive Path, where he served as President and Chief Creative Officer.

Adaptive Path became one of the most influential digital consulting firms ever, defining core practices that would shape how all digital products get made. In addition to its consulting business, the company influenced thousands of tech professionals around the world through its standalone events business.

As a founder, Jesse was involved in every aspect of running the company, from finding office space and managing cash flow to pitching clients and mentoring teams. A few specific areas of focus include:

• Sales and account oversight: Direct involvement in and accountability for every aspect of the client sale, from initial contact through product scoping and contract negotiation to final signing. Account executive responsible for the ongoing client relationship. Direct reporting oversight of sales team.
• Strategy practice oversight: Responsible for developing shared approaches and best practices for strategy engagements with clients.
• Marketing communications and brand identity: Oversight for editorial copy for website and promotional materials, brand personality and principles, visual brand style guides, and marketing and communications campaign plans. Direct reporting oversight of marketing managers, contractors, and agencies.
• Team mentorship and creative direction: Guidance to project teams and their leads on methodology, best practices, client relationship management, design philosophy.
• Thought leadership publishing: Developing and managing channels and platforms to amplify creative voices from the team and bring their ideas into the public discourse.
• Events programming: Responsible for creating conference and workshop offerings at small and large scale, including identifying topics, recruiting speakers, planning the event program, and overseeing in-house event production team.
• Research and development: Accountability for strategy, budget, and managing dedicated and contract resources for public-facing projects exploring new ideas. Included strategic partnerships with UC Berkeley‘s Haas School of Business, Mozilla Labs, and Glide Memorial.

The company became known for its high caliber of talent, many of whom became thought leaders and company founders in their own right. After 13 years, Adaptive Path was acquired by Capital One to help them build their centralized digital design team.

Jesse’s consulting career features dozens of high-impact projects for companies such as Disney, Apple, CNN, Allstate, and Nike.

Strategy consulting was the backbone of Adaptive Path’s practice, enabling client organizations to evolve to embrace new technologies and approaches. The analytical methods of this work are much closer to management consulting than to traditional design work—more spreadsheets than sketches.

As lead consultant, Jesse’s hands-on engagements focused on delivering robust, business-grounded strategies for clients. Facets of this work included:

• Rapid immersion in new problem spaces: Quickly getting a broad perspective on a client’s history, business model, competitive challenges, market opportunities, and relevant stakeholder constituencies.
• Thinking in systems and journeys: Taking a holistic view of organizations to diagnose challenges and find opportunities. Mapping processes and workflows to identify high-value use cases. Creating system blueprints for future states.
• Bringing structure to ambiguity: Applying analytical problem-solving methods that create shared clarity. Adapting to changing conditions and shifting understanding by reframing problems.
• Driving organizational alignment: Bridging divergent agendas among stakeholders. Facilitating internal client negotiations in requirements definition.
• Translating strategy into tactical implications: Defining budgetary, resourcing, governance, and technology considerations of strategic decisions. Facilitating analysis of tactical tradeoffs. Roadmapping future states.
• Articulating vision for executives: Personally speaking to a strong point of view in front of C-suite and board-level stakeholders. Explaining complex ideas to non-expert audiences.

As a team leader, Jesse also provided direct oversight of complex, cross-functional client-facing teams across multiple projects and initiatives in multi-year client relationships.

Capital One acquired Adaptive Path to provide the seeds of methodology and culture that would grow into an enterprise-scale digital design organization.

As a member of the senior leadership team, Jesse was a key contributor to organizational strategy decisions. His primary focus was identifying opportunities for new centralized functions to support this widely distributed team, and stand up those new teams before handing them off.

Teams Jesse personally built and led included:

• Responsible AI: Policy and governance team orchestrating cross-functional alignment and creating guidelines for ethical application of AI technology in financial services.
• Events: Multiple teams (D.C. and San Francisco) producing dozens of internal and external conferences and workshops, including the Humanity.AI conference series on human-centered AI practices.
• Publishing: Editorial team responsible for content development, solicitation and curation of contributions from team members, and planning and maintenance of multiple internal and external content channels.

Other initiatives for which Jesse advised on strategic direction included design operations, design system governance, and launching the company’s AI chatbot assistant Eno.

Seeking a new leverage point for driving organizational change, Jesse shifted focus to the individual scale to support leaders in advancing their own practices.

Having seen many common and recurring challenges among the many leaders he had worked with, and seeing an opportunity to level up entire organizations by leveling up their leaders, Jesse built a private coaching practice.

Working directly with dozens of leaders in countries around the world, Jesse helped them develop organizational strategies, manage teams through times of change, and align their own roles as leaders with their personal strengths and capabilities. This work required deep understanding of organizational dynamics, team structure and process considerations, and what it takes to persuade people above and below you in the hierarchical chain to advance your own agenda.

This experience working with clients at the executive level has further deepened and broadened Jesse’s perspective on the challenges facing leaders and teams in the modern environment. This work required Jesse to adapt to a diverse range of contexts, from a C-level leader in a startup to a VP trying to create change in a giant enterprise. Working with leaders in the AI tooling space, he was able to get a perspective on the rising technological tide years before it arrived.

In addition to his hundreds of hours of real-world coaching experience, Jesse has also invested hundreds of hours in training in interpersonal coaching methodologies. This work informs how he engages with all his clients, even beyond coaching.

With the rise of generative AI, leaders turned to Jesse for strategic guidance, prompting him to create a new practice helping teams navigate AI transformation.

Having actively followed the development of AI technology for more than a decade before Claude and ChatGPT, Jesse brought a deeply informed perspective to his strategic consultations with leaders. As those leaders began to formalize their transformation initiatives, they asked Jesse to step in.

Jesse’s AI transformation work has included activities such as:

• Internal discovery: Creating a comprehensive view of the current state of AI practices in the client organization. Aligning stakeholder perspectives and agendas.
• Organizational and operational strategy: Defining team structures and processes for dedicated AI transformation initiatives. Analyzing workflows and processes to define high-value use cases.
• Tooling and technology assessment: Evaluating available tools and technology stacks for use case alignment. Making strategic recommendations on technology investments and deployment.
• Fractional leadership: Directly orchestrating AI transformation programs. Defining and leading team engagement, communications, research and governance activities.

This work brings together Jesse’s entire skillset and breadth of experience in new ways. Helping organizations make sense and take action when faced with new technologies and evolving competitive landscapes has been core to Jesse’s work throughout his career, from his consulting work through his time as an in-house leader to today’s AI transformation challenges.

By putting his thoughts out in public throughout his career, Jesse has been responsible for some of the most influential ideas in the history of digital technology.

Jesse’s five-plane Elements of User Experience model has been embraced by a global community of tens of thousands of designers. His book of the same name has been translated into numerous foreign languages and is a common textbook in digital design programs.

Ajax is a technical approach to creating dynamic web applications that Jesse defined in a landmark essay. Ajax dramatically altered the landscape of web development, leading directly to the modern JavaScript-derived frameworks used today.

As a public speaker, Jesse has keynoted dozens of conferences around the world. His recent talks cover issues of organizational strategy, cross-functional collaboration, and AI transformation.

Jesse is co-host of the design leadership podcast Finding Our Way, which has produced more than 70 episodes and counting.