AI Workflow and Systems Design Lead - Remote

CSAA Insurance Group; Mississippi; Remote; USD 120,000 - 170,000; Full time

Benefits offered by this job

Annual bonus up to 12%

Remote-friendly

401(k) with match

Job summary

CSAA Insurance Group seeks an AI Workflow and Systems Design Lead to design and implement AI-enabled workflows across multiple business units. The role requires deep systems thinking, human-in-the-loop strategies, and the ability to translate complex business needs into implementable design artifacts.

Remote anywhere in the United States. You will partner with executives to drive workflow reinvention, define future-state designs, and ensure alignment with enterprise design standards and

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.
• Experience leading sophisticated multi-functional engagements involving multiple business units, systems, collaborators, or technology platforms.
• 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.
• Strong 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.
• Master's degree in Design Strategy, Human-Computer Interaction, Service Design, Business, Organizational Design, Technology, or a related discipline.

Responsibilities

• Lead AI Workflow Reinvention and Systems-of-Work Design.
• Partner with business leaders and multi-functional teams to understand strategic goals, pain points, needs, and opportunities for workflow reinvention.
• Lead current-state assessment and future-state design for workflows across teams, apps, channels, data sources, decisions, and controls.
• Design end-to-end systems of work connecting front-stage with backstage people, processes, technology, data, decisions, and AI agents.
• Move teams beyond application-level optimization by addressing cross-boundary outcomes.
• Translate workflows into clear, visual, implementation-ready design artifacts.
• Design Human + AI Ways of Working.
• Identify where AI adds value through automation, augmentation, recommendations, decision support, orchestration, or autonomous action.
• Decompose workflows into tasks, decisions, context, data, knowledge, tools, rules, and exceptions.
• Define division of work between employees, customers, partners, AI agents, automation, and traditional systems.
• Design human-in-the-loop approaches ensuring judgment, accountability, oversight, and trust.
• Ensure AI-enabled designs reflect value and operational reality, not AI for its own sake.
• Create Implementation-Ready Systems Design Artifacts.
• Lead development of design outputs that make work visible and enable downstream decisions.
• Translate outcomes into clear representations of work across people, AI, processes, data, controls, and technology.
• Surface cross-system requirements, dependencies, ownership questions, handoffs, risks early to influence architecture.
• Clarify human and AI roles, decision points, and opportunities for automation where relevant.
• Document future-state workflows and reusable patterns at engagement level."
• Connect Business Intent to Technology Delivery.
• Serve as a connective design partner between business goals and tech implementation.
• Work with divisions, BRMs, Architecture, Data, Engineering, and Governance during discovery and design.
• Surface cross-system requirements early to influence architecture and delivery.
• Translate business needs into system-of-work requirements without prescribing architecture.
• Support implementation teams in understanding design intent during build and delivery.
• Participate in design-assurance checkpoints to ensure alignment with intended system of work.
• Design for Reuse, Not Just the Current Project.
• Look across projects for recurring workflows and patterns to reuse.
• Ensure patterns and lessons are captured in reusable assets.
• Balance enterprise consistency with flexibility across domains.
• Partner Closely with Business Leaders.
• Act as trusted design partner to modernization and AI initiatives.
• Help leaders articulate desired outcomes before tech solutions.
• Translate pain points into opportunities for redesign across workflow and AI.
• Facilitate tradeoffs across experience, efficiency, risk, feasibility, and value.
• Help teams visualize future ways of working before investment decisions.
• Communicate complex design concepts in business-friendly language.
• Build confidence that enterprise design strengthens ownership.
• Help Build the Enterprise Systems Design Practice.
• Develop and refine CSAA's design methods, standards, templates, quality bar.
• Establish repeatable approaches for systems-of-work design and AI workflow decomposition.
• Contribute templates, case studies, and reusable methods from real projects.
• Measure the Impact of Systems Design.
• Define success measures with project teams at start.
• Establish baseline metrics where practical.
• Demonstrate value through case studies and executive storytelling.

Skills

AI fluency

Systems thinking

Design artifacts

Visual storytelling

Education

Bachelor's degree or equivalent practical experience

Job description

AI Workflow and Systems Design Lead - Remote Requisition Number

R8029 AI Workflow and Systems Design Lead - Remote (Open) Location

CSAA Insurance Group (CSAA IG), a AAA insurer, is one of the leading personal lines property and casualty insurance groups in the United States. We build innovative, human-centered solutions that help AAA members prevent, prepare for, and recover from life's uncertainties. We are actively hiring for an AI Workflow and Systems Design Lead - Remote

Your Role: 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.

Responsibilities

• 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.
• 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.
• 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.
• 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.
• 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
• 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.
• Help demonstrates 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 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.
• ~ Strong visual communication and storytelling skills; 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.
• 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.
• supporting employee resource groups, mentoring employees, volunteering, joining cross-functional projects)
• willing to have cameras when it matters: helping onboard new team members, building relationships, etc.)
• 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

Location and Working Conditions

Remote anywhere in the United States

Travels as needed for role, including divisional / team meetings and other in‑person meetings

Benefits and Compensation

• We offer a total compensation package, annual bonus eligibility for most roles, 401(k) with a company match, and so much more!
• Flexible Workplace: We embrace a remote-first culture through our Flexible Workplace.
• Most employees hold Home‑Flex roles, working primarily from home, often with the flexibility to work from various locations including CSAA offices.
• Our flexible workplace empowers you to balance remote work with intentional in‑person moments that deepen connection and collaboration.
• However, we have a location-based compensation structure.
• This role also includes an opportunity for a company-wide annual discretionary bonus, through our Annual Incentive Plan (AIP), of up to 12% of eligible pay.

Equal Opportunity and Inclusion

CSAA is committed to providing reasonable accommodations to qualified applicants and employees with disabilities or other limitations.

At CSAA IG, we are a mission-driven organization proudly committed to empowering our members, our employees, and our communities to thrive.

An inclusive and welcoming workplace is the cornerstone of our success.

Sustainability: As climate change leads to more frequent and severe weather events, we are taking bold action to build more resilient communities and reduce our environmental impact.

Immigration and Sponsorship

Please do not apply for this role if at any time (now or in the future) you will need immigration support (i.e., H-1B, TN, STEM OPT Training Plans, etc.).