Director, AI Delivery - Onboarding & Enrollment

Accountabilities: Lead and develop a high-performing global technology organization through hiring, coaching, performance management, succession planning, engagement, and capability development. Own end-to-end delivery of AI-enabled onboarding and enrollment products, ensuring business outcomes, quality, compliance, reliability, and stakeholder commitments are achieved. Provide operational leadership for production systems, including support, reliability, performance monitoring, cost management, and continuous improvement. Partner with the global delivery counterpart to establish aligned priorities, talent strategies, operating standards, and long-term capability development across distributed teams. Manage vendors, suppliers, contractors, and statements of work, including workforce planning, commercial performance, contract governance, and third-party risk. Define and advance the long-term product vision, operating model, investment strategy, maturity plan, and roadmap for AI-enabled onboarding and enrollment capabilities. Build and communicate multi-year technology strategies and investment cases, securing alignment and support from senior business and technology stakeholders. Serve as the primary technology leader for the value stream, communicating strategy, progress, risks, dependencies, and outcomes to executive audiences. Apply hands-on technical expertise where needed, particularly across cloud platforms, data engineering, APIs, CI/CD, enterprise integrations, and modern AI application architectures. Maintain a strong focus on operational stability and team health while driving innovation, continuous improvement, and the evolution of AI capabilities. Requirements Bachelor’s degree required; a master’s degree or equivalent professional experience is preferred. 10+ years of experience across technology delivery, engineering, data science, AI, or related disciplines, including at least 4 years leading technical teams. Proven experience owning a product, portfolio, or technology value stream end to end within a regulated enterprise environment, including responsibility for production operations. Demonstrated experience leading globally distributed teams and partnering directly with offshore delivery organizations or global capability centers. Experience managing vendors, contractors, statements of work, commercial performance, workforce planning, and third-party relationships. Strong technical fluency across cloud platforms, data engineering, CI/CD, APIs, and modern AI application patterns, including retrieval-augmented generation, evaluation, orchestration, and agentic workflows. Hands-on experience with Azure, Databricks, and enterprise integration patterns is required. Demonstrated ability to develop, communicate, and secure support for multi-year technical strategies with senior business stakeholders. Experience in insurance, group benefits, employee benefits onboarding, enrollment, or policy administration is highly preferred. Experience with AI governance, model risk management, and regulatory expectations for AI in insurance is highly preferred. Strong strategic thinking, executive communication, stakeholder management, and organizational leadership skills. Ability to create a shared team identity, build momentum around a common purpose, and develop individuals through meaningful feedback and coaching. Comfortable balancing long-term strategic planning with day-to-day delivery, operational reliability, and evolving business priorities. Benefits Annual salary range of $147,750–$280,750 , with actual compensation determined by factors including education, experience, skills, internal equity, position budget, and market data. Annual incentive bonus opportunity, subject to applicable plan rules and individual and organizational performance. Medical, dental, and vision coverage. 401(k) retirement plan with matching company contributions. Generous paid time off, including 11 holidays, 2 wellness days, and 8 volunteer hours annually , with PTO increasing based on tenure. Paid parental leave and adoption/surrogacy assistance. Employee giving program with donation matching for eligible nonprofits and schools. Supportive management and opportunities for professional growth, career development, and advancement. Remote work opportunity within the United States, with the role listed for both remote and Portland, Oregon locations.