AI Strategy Lead - Remote

CSAA Insurance Group, a AAA Insurer • Washington, DC

1d • Remote

About The Position

CSAA Insurance Group (CSAA IG), a AAA insurer, is one of the leading personal lines property and casualty insurance groups in the United States. Here, every employee shapes our mission. We build innovative, human-centered solutions that help AAA members prevent, prepare for, and recover from life's uncertainties. You will join a collaborative, inclusive culture where your strengths have room to grow and your ideas can drive real impact. Step into a role where you can contribute to our shared success through meaningful work. We are actively hiring for a AI Strategy Lead - Remote Your Role: The AI Strategy Lead is a senior individual contributor within a centralized AI Strategy team, responsible for advancing enterprise‑aligned AI strategies across business units. This role partners closely with business leaders, initiative owners, and cross‑functional teams to bring structure, rigor, and strategic insight to AI prioritization and planning. By applying a consistent enterprise strategy approach, the AI Strategy Lead helps business units clarify their AI vision, identify AI‑enabled business value, and build prioritized use‑case portfolios, operating with high autonomy, executive presence, and comfort navigating ambiguity to deliver decision-ready strategic outcomes. Your Work: Business Unit AI Strategy Partner with business unit leaders and initiative owners to support the development of AI strategies aligned to enterprise strategy, principles, and guardrails. Support articulation of business unit AI vision, AI-enabled value propositions, and strategic objectives. Apply AI strategy frameworks to guide consistent, high-quality strategy development across business units. Strategy Development & Opportunity Structuring Support identification and sizing of AI-enabled business value, including value pools and priority business outcomes. Facilitate value-chain analysis to identify where AI can drive impact. Develop structured AI use case portfolios, including value hypotheses, feasibility considerations, risks, and prioritization recommendations. Contribute to clear investment horizon view Enterprise Alignment & Synthesis Synthesize insights across business unit engagements to identify cross-business unit themes, dependencies, and opportunities for reuse or scale. Support enterprise-level views of AI opportunity pipelines, capability needs, and investment considerations. Ensure business unit strategies remain aligned to enterprise direction, shared capabilities, and responsible AI principles. Strategic Analysis & Decision Support Lead structured problem solving in ambiguous contexts, framing complex questions into clear analyses and recommendations. Conduct market, competitive, and capability analysis to inform business unit and enterprise AI strategy decisions. Develop executive-read materials that clearly communicate insights, trade-offs, and recommendations. Business Partnership & Influence Engage confidently with senior business leaders, initiative owners, and cross-functional partners as a strategic thought partner. Influence decisions through structured logic, data-driven insights, and clear storytelling Support governance routines, prioritization discussions, and value-tracking efforts to ensure disciplined progression of AI initiatives.

Requirements

• Bachelor’s degree in business, engineering, or related field; advance degree preferred
• 5-7 years of experience in management consulting, corporate strategy, or enterprise technology strategy
• Experience working directly with senior business stakeholders.
• Solid understanding of AI concepts, capabilities, and real-world business applications.
• Experience in regulated or complex ente

Responsibilities

• Business Unit AI Strategy Partner with business unit leaders and initiative owners to support the development of AI strategies aligned to enterprise strategy, principles, and guardrails.
• Support articulation of business unit AI vision, AI-enabled value propositions, and strategic objectives.
• Apply AI strategy frameworks to guide consistent, high-quality strategy development across business units.
• Support identification and sizing of AI-enabled business value, including value pools and priority business outcomes.
• Facilitate value-chain analysis to identify where AI can drive impact.
• Develop structured AI use case portfolios, including value hypotheses, feasibility considerations, risks, and prioritization recommendations.
• Contribute to clear investment horizon view
• Synthesize insights across business unit engagements to identify cross-business unit themes, dependencies, and opportunities for reuse or scale.
• Support enterprise-level views of AI opportunity pipelines, capability needs, and investment considerations.
• Ensure business unit strategies remain aligned to enterprise direction, shared capabilities, and responsible AI principles.
• Lead structured problem solving in ambiguous contexts, framing complex questions into clear analyses and recommendations.
• Conduct market, competitive, and capability analysis to inform business unit and enterprise AI strategy decisions.
• Develop executive-read materials that clearly communicate insights, trade-offs, and recommendations.
• Engage confidently with senior business leaders, initiative owners, and cross-functional partners as a strategic thought partner.
• Influence decisions through structured logic, data-driven insights, and clear storytelling
• Support governance routines, prioritization discussions, and value-tracking efforts to ensure disciplined progression of AI initiatives.
• 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 mindset, 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

• We offer a total compensation package, annual bonus eligibility for most roles, 401(k) with a company match, and so much more!
• We believe in growth for everyone. Here at CSAA IG, leaders and mentors partner with employees to align interests, unlock development opportunities, and support long‑term success.
• 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.
• An inclusive and welcoming workplace is the cornerstone of our success. By fostering an environment where people feel valued and heard, we deepen our ability to understand and meet the unique needs of our members. This strengthens innovation and enhances our products and services, giving us a competitive edge in the market.

What This Job Offers

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