Director, AI Delivery - Onboarding & Enrollment in New York at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director, AI Delivery - Onboarding & Enrollment based in United States.

This is a senior global technology leadership role responsible for the delivery and evolution of AI-enabled onboarding and enrollment capabilities.
You will own the full value stream, spanning product strategy, engineering delivery, production operations, and long-term maturity.
The role combines executive-level strategic leadership with hands-on technical fluency across modern AI and cloud technologies.
You’ll lead globally distributed teams while partnering closely with an offshore delivery organization to build a unified operating model.
You’ll also oversee vendors, contractors, commercial relationships, and third-party risks that support the value stream.
Success requires balancing innovation and investment with operational stability, reliability, compliance, and team health.
The role offers significant influence over multi-year technology strategy within a regulated enterprise environment.

• 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.

• 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.

• 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.