AI Workflow and Systems Design Lead - Remote

CSAA Insurance Group, a AAA Insurer • Remote (Hartford, Connecticut, United States) • $0 / year • 4h ago

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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. 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. 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 Please note we are hiring for this role remote anywhere in the United States with the following exceptions: At CSAA IG, we are a mission-driven organization proudly committed to empowering our members, our employees, and our communities to thrive

. 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. Inclusion and Belonging:

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. Submit your application to be considered. CSAA is committed to providing reasonable accommodations to qualified applicants and employees with disabilities or other limitations. If you would like to request an accommodation to participate in the job application or interview process, please contact [email protected] you apply and are selected to continue in the recruiting process, we will schedule a preliminary call with you to discuss the role and will disclose during that call the available salary/hourly rate range based on your location. 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.). 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.

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