Senior Legal Innovation Strategist - Remote

CSAA Insurance Group, a AAA Insurer • Washington, DC

2d • 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 Legal Innovation Strategist - Remote! Your Role: The Senior Legal Innovation Strategist drives the identification, evaluation, and adoption of AI- and technology-enabled solutions across the Legal Division. This role translates Legal business needs into practical, compliant solutions and ensures responsible, scalable adoption through structured experimentation, deployment, training, and sustained use. Success is defined by measurable improvements in efficiency, quality, cycle time, and user adoption. The role partners closely with Legal departments (including corporate law teams and staff counsel) along with IT, Data and Security teams to accelerate value realization from AI while maintaining strong governance and user confidence. Success is defined by measurable improvements in efficiency, insight generation, and decision-making across Legal teams.

Requirements

• Bachelor’s degree in Business, Law, Technology, Innovation, or a related field; or equivalent practical experience.
• 8+ years of experience in innovation, technology enablement, legal operations, consulting, or related roles.
• Demonstrated ability to support or lead early-stage innovation efforts across multiple initiatives.
• Practical experience with generative AI tools and AI-enabled workflows.
• Experience implementing or supporting business-facing technology solutions.
• Strong ability to influence cross-functional stakeholders without direct authority.
• Excellent communication skills, including translating technical concepts for non-technical audiences.

Nice To Haves

• Advanced coursework or certifications in analytics, AI, automation, legal transformation, or change management.
• Practical fluency with generative AI tools, including prompt design; experience shaping AI-enabled workflows and collaborating on data structure and solution architecture decisions.
• Demonstrated ability to drive adoption of new tools within professional or expert-driven environments and integrate solutions into existing workflows.
• Experience working within or closely with a corporate legal department, staff counsel organization, and/or law firm environment.
• Familiarity with legal workflows such as matter management, outside counsel engagement, litigation, or advisory practices.
• Experience partnering with IT, data, security, or risk teams in a regulated environment.
• Experience leading initiatives from pilot through deployment and sustained adoption, including defining measurable success criteria and tracking operational impact.
• Experience supporting senior leaders with analysis, recommendations, and decision-making.
• 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

Responsibilities

• Identify and prioritize high-impact innovation and AI opportunities across Legal practice groups.
• Conducts and synthesizes business process analysis, user research, and technology assessments to inform AI use cases and prioritization.
• Partner with attorneys and Legal Operations to translate workflows and pain points into testable use cases.
• Design hypotheses, pilots, and experimentation plans with clearly defined success metrics.
• Lead initiatives from pilot through deployment and sustained adoption, including change management and training.
• Shape AI-enabled workflows, including prompt design, data structure, and solution architecture decisions.
• Design solutions within regulatory and compliance-sensitive environments, establishing guardrails, documentation, and accountability.
• Provides ongoing support, troubleshooting, and continuous improvement for Legal AI tools.
• Evaluate technology vendors using structured criteria such as proof-of-value testing, integration feasibility, scalability, and risk.
• Advise on buy-versus-build decisions aligned with Legal risk posture and long-term strategy.
• Track outcomes such as time savings, cycle-time reduction, quality indicators, and adoption rates.
• Act as the primary AI champion and subject-matter resource for Finance teams.
• Prepare executive-ready updates, insights, and recommendations for Legal leadership.

Benefits

• We offer a total compensation package, annual bonus eligibility for most roles, 401(k) with a company match, and so much more!
• Career Growth: 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.
• 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. 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
• Number of Employees: 1-10 employees