AI Workflow and Systems Design Lead - Remote

CSAA Insurance Group, a AAA Insurer • Washington, NV

8d • $144,450 - $192,550 • Remote

About The Position

CSAA Insurance Group is hiring a senior individual contributor to partner across business and technology teams in redesigning complex workflows and creating AI-ready systems of work. The role leads discovery, defines how people and AI work together, translates business needs into implementation-ready designs, and helps establish repeatable Enterprise Systems Design practices.

The lead partners with business leaders and multidisciplinary teams to understand goals, pain points, and customer or employee needs; assess current-state workflows; and design future-state systems spanning teams, applications, channels, data, decisions, and controls. The role identifies where AI can add value, defines human and AI responsibilities, and designs appropriate oversight, exceptions, approval paths, and feedback loops.

The position creates visual, actionable design artifacts that make complex work clear, surface dependencies and unresolved decisions, and connect business intent to technology delivery. It collaborates with business divisions, BRMs, Architecture, Data, Engineering, and Governance teams, supports implementation and design assurance, and encourages reuse of enterprise patterns and capabilities. The lead also helps develop the Enterprise Systems Design practice, measures the impact of engagements, and communicates results through case studies and executive storytelling.

This is a remote-first role available in the United States, excluding Hawaii and Alaska. Travel may be needed for divisional, team, and other in-person meetings. Applicants must be authorized to work indefinitely in the United States; visa sponsorship is not available.

Requirements

• Bachelor's degree or equivalent practical experience.
• At least 10 years of dynamic experience in systems design, service design, workflow or process transformation, design strategy, digital transformation, product or service innovation, management consulting, or product management.
• Deep expertise in systems thinking, service design, and workflow design, with experience translating complex business problems into coherent future-state systems.
• Experience leading complex multidisciplinary engagements involving multiple business units, systems, collaborators, or technology platforms.
• Ability to work across front-stage experiences and backstage systems.
• Ability to create and communicate design artifacts such as systems-of-work blueprints, service blueprints, workflow maps, dependency maps, role and handoff models, decision models, and operating-model designs.
• Strong AI fluency, including practical knowledge of generative AI, agents, automation, retrieval, decision support, and AI-enabled workflow patterns.
• Understanding of human-AI interaction and human-in-the-loop design.
• Ability to decompose complex workflows into tasks, decisions, context, data, knowledge, tools, controls, and exceptions.
• Strong business insight and ability to connect design decisions to measurable business value.
• Experience facilitating senior-level and multidisciplinary workshops with participants who have differing objectives or ownership.
• Strong visual communication and storytelling skills, including the ability to explain complex systems clearly.
• Comfort with ambiguity and initiatives where no single function leads the entire outcome.
• Ability to influence without formal authority and move groups toward decisions and commitments.
• Ability to work independently on high-profile engagements while collaborating effectively within a small, senior team.

Nice To Haves

• Master's degree in Design Strategy, Human-Computer Interaction, Service Design, Business, Organizational Design, Technology, or a related discipline.
• Relevant training or certification in Systems Thinking, Service Design, Human-Centered Design, Lean Six Sigma, Process Design, Change Management, or AI-related disciplines.
• Experience in insurance, financial services, or another regulated industry.
• Experience redesigning workflows specifically for AI, intelligent automation, or agentic systems.
• Experience in service design, business-process transformation, or operating-model redesign.
• Experience working with enterprise architecture and engineering organizations on cross-system initiatives.
• Experience identifying and creating reusable enterprise patterns, methods, components, or services.
• Familiarity with design systems and design-to-code practices.
• Experience applying human-centered design, Lean, Lean Six Sigma, or related transformation methodologies.
• Experience with prototyping, experimentation, pilot design, or testing future-state workflows before implementation.
• Experience coaching other designers or transformation practitioners.
• Actively shapes company culture, such as supporting employee resource groups, mentoring employees, volunteering, or joining cross-functional projects.
• Champions company cultural norms, including using cameras when appropriate to onboard colleagues and build relationships.
• Demonstrates a company-ownership attitude and thinks beyond the boundaries of their own area.
• Able to travel as needed for divisional, team, and other in-person meetings.
• Able to meet business needs that may include investing extra time or helping other teams.

Responsibilities

• Partner with business leaders and multidisciplinary teams to understand strategic goals, pain points, customer or employee needs, and workflow-reinvention opportunities.
• Assess current workflows and lead future-state design for complex work spanning teams, applications, channels, data sources, decisions, and controls.
• Design end-to-end systems of work connecting experiences with the people, processes, technology, data, decisions, controls, AI agents, and support capabilities needed to deliver outcomes.
• Facilitate workshops that move multidisciplinary teams from ambiguity to aligned future-state decisions.
• Create clear, visual, implementation-ready design artifacts and document future-state workflows, operating-model implications, and reusable patterns.
• Identify appropriate uses of AI, automation, augmentation, recommendations, decision support, orchestration, and autonomous action within workflows.
• Decompose workflows into tasks, decisions, context, data and knowledge, tools and actions, business rules, controls, exceptions, and critical issue paths.
• Define the division of work among employees, customers, partners, AI agents, automation, and traditional systems.
• Design human-in-the-loop approaches, including intervention triggers, confidence thresholds, approvals, exception handling, overrides, feedback loops, and explainability requirements.
• Surface cross-system requirements, dependencies, ownership questions, handoffs, risks, and unresolved decisions early enough to inform architecture and delivery.
• Collaborate with business divisions, BRMs, Architecture, Data, Engineering, and Governance teams to connect business intent with technology delivery.
• Participate in feasibility discussions and support implementation teams in understanding design intent; take part in design-assurance checkpoints when appropriate.
• Identify existing enterprise patterns, components, services, agent skills, and other reusable capabilities, and contribute useful patterns, methods, requirements, and lessons back to the enterprise asset ecosystem.
• Help business leaders articulate desired outcomes, assess tradeoffs, visualize future ways of working, and understand systems-design concepts in business-friendly language.
• Partner with the Senior Director to develop Enterprise Systems Design methods, standards, templates, quality expectations, and repeatable approaches.
• Define success measures with project teams, establish baselines where practical, gather lessons, and communicate the value of workflow reinvention through case studies and executive storytelling.

Benefits

• Total compensation package
• Annual bonus eligibility for most roles
• 401(k) with company match
• Career growth support, including leaders and mentors who help align interests and development opportunities
• Remote-first flexible workplace, with flexibility to work from various locations including CSAA offices

What This Job Offers

• Job Type: Full-time
• Career Level: Senior