[Hiring] AI Workflow and Systems Design Lead @CSAA Insurance Group, a AAA Insurer

Role Description

The AI Workflow & Systems Designer is a senior individual contributor who partners across business and technology to redesign complex workflows and create 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 build repeatable Enterprise Systems Design practices.

Your Work

• Lead AI Workflow Reinvention and Systems-of-Work Design
  • Partner directly with business leaders and multi-functional teams to understand strategic goals, pain points, customer or employee needs, and opportunities for workflow reinvention.
  • Lead current-state assessment and lead future-state design for sophisticated workflows spanning multiple teams, applications, channels, data sources, decisions, and controls.
  • Design end-to-end systems of work that connect front-stage experiences with the backstage people, processes, technology, data, decisions, controls, AI agents, and support capabilities required to deliver the outcome.
  • Move teams beyond application-level optimization by identifying how the complete outcome must work across organizational and system boundaries.
  • Facilitate workshops and working sessions that move multi-functional teams from ambiguity to aligned future-state decisions.
  • Translate sophisticated workflows into clear, visual, implementation-ready design artifacts.
• Design Human + AI Ways of Working
  • Identify where AI can create meaningful value within a workflow through automation, augmentation, recommendations, decision support, orchestration, or autonomous action.
  • Decompose workflows into the elements needed for AI design, including tasks, decisions, required context, data and knowledge, tools and actions, business rules and controls, and exceptions and critical issue paths.
  • Define the appropriate division of work between employees, customers, partners, AI agents, automation, and traditional systems.
  • Design human-in-the-loop approaches that preserve appropriate judgment, accountability, oversight, and trust.
  • Define intervention triggers, confidence thresholds, approval paths, critical issue logic, exception handling, overrides, feedback loops, and explain-ability requirements.
  • Ensure AI-enabled workflow designs reflect both business value and operational realities rather than applying AI for its own sake.
• Create Implementation-Ready Systems Design Artifacts
  • Lead the development of systems design outputs that make sophisticated work visible, align multi-functional teams, and enable confident downstream decisions.
  • Translate business outcomes and future-state concepts into clear, actionable representations of how work should operate across people, AI, processes, decisions, data, controls, and technology.
  • Surface key cross-system requirements, dependencies, ownership questions, handoffs, risks, and unresolved decisions early enough to influence architecture and delivery.
  • Clarify human and AI roles, decision points, exceptions, controls, and opportunities for automation or augmentation where relevant.
  • Document future-state workflows, operating-model implications, and reusable patterns at the level of detail appropriate for the engagement.
  • Adapt the format and depth of work to the complexity, maturity, and needs of each initiative rather than applying a one-size-fits-all approach.
• Connect Business Intent to Technology Delivery
  • Serve as a connective design partner between business goals and downstream technology implementation.
  • Work closely with business divisions, BRMs, Architecture, Data, Engineering, and Governance teams during discovery and design.
  • Surface cross-system requirements, dependencies, design choices, and unresolved decisions early enough to influence architecture and delivery.
  • Translate business and experience needs into clear system-of-work requirements without prescribing technical architecture that belongs to Architecture or Engineering.
  • Participate in feasibility discussions to ensure future-state designs are realistic, executable, and aligned with enterprise standards.
  • Support implementation teams in understanding the design intent as work moves into build and delivery.
  • Participate in design-assurance checkpoints when appropriate to ensure the implemented solution remains consistent with the intended system of work.
• Design for Reuse, Not Just the Current Project
  • Begin each engagement by identifying relevant existing enterprise patterns, components, services, agent skills, and other reusable capabilities.
  • Look across projects for recurring workflows, decisions, interactions, controls, and human-AI patterns that should be solved once and reused.
  • At the end of engagements, ensure useful patterns, methods, requirements, and lessons are collected and contributed back into the enterprise reusable asset ecosystem.
  • Help shift teams from project-by-project invention toward design and reuse by default.
  • Balance enterprise consistency with appropriate flexibility for different business domains and platforms.
• Partner Closely with Business Leaders
  • Act as a trusted design and transformation partner to business leaders working on strategic modernization, workflow reinvention, and AI initiatives.
  • Help leaders articulate the desired business outcome before jumping to a technology solution.
  • Translate business pain points into opportunities for workflow, operating-model, experience, and AI redesign.
  • Facilitate tradeoffs across experience, operational efficiency, risk, technical feasibility, and value.
  • Help teams visualize and understand future ways of working before investment and implementation decisions are finalized.
  • Communicate sophisticated systems-design concepts in simple, business-friendly language.
  • Build confidence that Enterprise Systems Design strengthens business ownership rather than taking it away.
• Help Build the Enterprise Systems Design Practice
  • Partner with the Senior Director to develop and refine CSAA's Enterprise Systems Design methods, standards, templates, and quality bar.
  • Help establish repeatable approaches for systems-of-work design, workflow reinvention, human-AI design, and AI workflow decomposition.
  • Contribute examples, templates, case studies, and reusable methods based on real project engagements.
• Measure the Impact of Systems Design
  • Partner with project teams to define success measures at the beginning of major engagements.
  • Help establish baseline measures where practical.
  • Gather qualitative and quantitative lessons that can improve future engagements.
  • Help demonstrate the value of workflow reinvention and Systems Design through clear case studies and executive storytelling.

Qualifications

• Bachelor's degree or equivalent practical experience.
• 10+ years of dynamic experience in systems design, service design, workflow/process transformation, design strategy, digital transformation, product/service innovation, management consulting, or product management.
• Deep expertise in systems thinking, service design, and workflow design, with demonstrated experience translating sophisticated business problems into coherent future-state systems.
• Demonstrated experience leading sophisticated multi-functional engagements involving multiple business units, systems, collaborators, or technology platforms.
• Solid ability to move between front-stage and backstage systems.
• Solid 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.
• Solid understanding of human-AI interaction and human-in-the-loop design.
• Ability to decompose sophisticated 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 multi-functional workshops where participants have differing objectives or ownership.
• Strong visual communication and storytelling skills; able to simplify sophisticated systems into clear, compelling representations.
• High comfort with ambiguity and initiatives where no single function leads the entire outcome.
• Demonstrated 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.

Requirements

• 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 our company culture (e.g., supporting employee resource groups, mentoring employees, volunteering, joining cross-functional projects).
• Champions our cultural norms (e.g., willing to have cameras when it matters: helping onboard new team members, building relationships, etc.).
• Demonstrates a company ownership attitude, thinking beyond boundaries of their own area.
• Travels as needed for role, including divisional/team meetings and other in-person meetings.
• Fulfills business needs, which may include investing extra time, helping other teams, etc.

Benefits

• Total compensation package, annual bonus eligibility for most roles, 401(k) with a company match.
• Flexible Workplace: Remote-first culture with Home-Flex roles.
• Career Growth: Opportunities for development and long-term success.
• Inclusion and Belonging: A welcoming workplace fostering innovation.
• Sustainability: Commitment to building resilient communities and reducing environmental impact.