Director, AI Delivery – Onboarding & Enrollment

This is a fully remote position, open to applicants in Oregon.

📋 Description

• Lead and cultivate a high-performing global team through recruitment, coaching, performance management, succession planning, and team engagement.

• Take ownership of the complete delivery of onboarding and enrollment AI products.

• Ensure that business outcomes, quality, compliance, and stakeholder commitments are met.

• Provide operational leadership for production systems, focusing on support, reliability, performance metrics, cost management, and continuous improvement.

• Collaborate with the SGS counterpart to lead a cohesive global organization.

• Align priorities, talent strategy, operating standards, and long-term capability development.

• Oversee vendor and contractor partnerships, including commercial performance, workforce planning, contract governance, and third-party risk management.

• Define and promote the long-term product vision, operating model, investment strategy, and roadmap for AI-driven onboarding and enrollment capabilities.

• Act as the primary technology leader for the value stream.

• Communicate strategy, progress, risks, and outcomes to executives and business stakeholders.

• Utilize hands-on technical coding skills.

⛳️ Requirements

• Bachelor’s degree required; Master’s preferred or equivalent experience.

• Over 10 years in technology delivery, engineering, data science, or AI.

• More than 4 years of experience leading technical teams.

• Proven track record of owning a product or portfolio end-to-end in a regulated enterprise environment, including production operations.

• Experience in leading globally distributed teams, including direct collaboration with an offshore delivery organization.

• Background in managing vendors, contractors, and statements of work, including discussions on commercial performance.

• Technical proficiency in cloud platforms, data engineering, CI/CD, APIs, and modern AI application patterns such as retrieval augmented generation, evaluation, orchestration, and agentic workflows.

• Required hands-on technical experience with Azure, Databricks, and enterprise integration patterns.

• Demonstrated ability to develop and advocate for a multi-year technical strategy to senior business stakeholders.

• Experience in Insurance, group benefits, employee benefits onboarding, enrollment, or policy administration is highly preferred.

• Experience operating in or leading from a global capability center or equivalent offshore organization is highly preferred.

• Familiarity with AI governance, model risk management, and regulatory expectations for AI in insurance is highly preferred.

• A criminal background check and verification of employment, education, and licensing are required as a condition of employment.

• Must be bondable.

🏝️ Benefits

• Medical, dental, and vision insurance.

• 401(k) plan with matching company contributions.

• Annual incentive bonus plan.

• 11 holidays annually.

• 2 wellness days annually.

• 8 volunteer hours annually.

• PTO increases with tenure.

• Opportunities for career growth and advancement.

• Paid parental leave.

• Adoption/surrogacy assistance.

• Employee giving program that double matches donations to eligible nonprofits and schools.