# Ladders — Director, AI Delivery - Onboarding & Enrollment

- Generated: 2026-09-28 09:17:06 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4470854557/
- Provider: LinkedIn
- Posting time: Approximately September 28, 2026 at 7:12 AM ET (LinkedIn: 2 hours ago at fetch)
- Applicants: Be among the first 25 applicants
- Work model/location: Remote — United States
- Compensation: $147,750-$280,750 annually
- Travel: Not disclosed
- Positioning track: Technical manager
- Fit outcome: FAIL — 78%

## Evidence map and direct-match strengths

AI product delivery, global engineering leadership, regulated systems, cloud platforms, data engineering, APIs, CI/CD, reliability, compliance, and roadmaps.

## Hard or material gaps

Hands-on Azure and Databricks experience is explicitly required. Keith's source-supported cloud record is AWS-led with Google Vertex AI exposure and does not establish Azure or Databricks experience, creating a hard required-stack gap.

## Full normalized job description

For our client, we are seeking a Director, AI Delivery - Onboarding & Enrollment to join the team of a leader in the Finance & Insurance space.
This leader will guide the delivery of AI-enabled solutions that improve onboarding and enrollment experiences while maintaining strong quality, compliance, and operational performance. The role combines product strategy, technical execution, and cross-functional leadership across global teams and external partners. You will help shape multi-year direction for modern AI applications and ensure reliable delivery in a regulated environment.
In this position, you will partner closely with executives, technology leaders, and offshore delivery teams to align priorities, manage risk, and drive measurable outcomes.
Location: Remote - US based candidates only, no visa sponsorship available
Compensation: $147,750 – $280,750 annually
Responsibilities
Lead and develop a high-performing global team through hiring and performance management
Own end-to-end delivery of AI products for onboarding and enrollment, ensuring quality and compliance
Provide operational leadership, ensuring reliability and performance of production systems
Collaborate with global counterparts to align strategies and standards across operations
Manage vendor and contractor partnerships, overseeing commercial performance and risk management
Advance product strategy and roadmap for AI-enabled solutions
Engage with executives to communicate strategy, progress, and outcomes
Qualifications
Bachelor’s degree required; Master’s preferred, or equivalent experience
10+ years in technology delivery, engineering, data science, or AI; 4+ years in technical team leadership
Proven track record of managing product or portfolio end to end in a regulated environment
Experience leading global distributed teams and collaborating with offshore delivery organizations
Technical fluency in cloud platforms, data engineering, CI/CD, APIs, and modern AI application patterns; hands-on experience with Azure and Databricks is required
Ability to develop and advocate for multi-year technical strategies to senior stakeholders
Preferred experience in insurance or employee benefits onboarding and enrollment
Benefits
Rich benefits package including medical, dental, vision, and a 401(k) with company matching contributions
Annual incentive bonus plan and generous paid time off including holidays and wellness days
Opportunities for career growth and a supportive management approach
Paid parental leave and adoption/surrogacy assistance
Employee giving program that matches donations to eligible nonprofits and schools
Our client is an equal opportunity employer. We encourage you to apply even if you don’t meet every qualification—your background could be exactly what this team needs.