Director, AI Delivery - Onboarding & Enrollment

The Standard; Portland (OR); On-site; USD 148,000 - 281,000; Full time

Benefits offered by this job

Medical, dental, vision insurance

401(k) plan with company matching

Annual incentive bonus

Generous PTO and holidays

Parental leave

Volunteer time

Job summary

The Standard is seeking a Director of AI Delivery for Onboarding & Enrollment to lead a global AI value stream, owning product strategy and cross-border operations. You will manage vendor partnerships, drive unified global standards, and ensure production readiness while guiding maturation and investment roadmaps.

You will combine senior leadership with hands-on technical delivery, shaping the future of AI-enabled onboarding and enrollment capabilities in a regulated insurance context.

Qualifications

• 10+ years in technology delivery, engineering, data science, or AI, including 4+ years leading technical teams.
• Experience owning a product or portfolio end to end in a regulated enterprise environment, including production operations.
• Experience leading globally distributed teams, including direct partnership with an off-shore delivery organization.
• Experience managing vendors, contractors, and statements of work, including commercial performance discussions.
• Technical fluency across cloud platforms, data engineering, CI/CD, APIs, and modern AI application patterns incl. retrieval augmented generation, evaluation, orchestration, and agentic workflows.
• Hands-on technical experience with Azure, Databricks, and enterprise integration patterns is required.
• Experience in Insurance, group benefits onboarding, enrollment, or policy administration is highly preferred.

Responsibilities

• Lead end-to-end delivery of onboarding and enrollment AI products, ensuring business outcomes, quality, compliance, and stakeholder commitments are achieved.
• Provide operational leadership for production systems, including support, reliability, performance metrics, cost management, and continuous improvement.
• Partner with SGS counterpart to lead a unified global organization, aligning priorities, talent strategy, operating standards, and long-term capability growth.
• Oversee vendor and contractor partnerships, including commercial performance, workforce planning, contract governance, and third-party risk management.
• Define and advance the long-term product vision, operating model, investment strategy, and roadmap for AI-enabled onboarding and enrollment capabilities.
• Serve as the primary technology leader for the value stream, communicating strategy, progress, risks, and outcomes to executives and business stakeholders.

Skills

People Leadership

Product strategy

Global delivery

Vendor management

AI governance

Regulated industry experience

Education

Bachelor’s degree

Master’s degree

Tools

Azure

Databricks

Enterprise integration patterns

Job description

The next part of your journey is right around the corner — with The Standard.

A genuine desire to make a difference in the lives of others is the foundation for everything we do. With a customer-first mindset and an intentional focus on building strong teams, we’ve been able to uphold our legacy of financial stability while investing in new, innovative technologies that support the needs of our customers. Our high-performance culture focused on operational excellence thrives thanks to remarkable people united by compassion and a customer-first commitment. Are you ready to make a difference?

Job Summary

The Director of AI Delivery for Onboarding & Enrollment is the senior global leader of that AI value stream. The role carries the full management and delivery accountability of a value stream lead, and adds three things on top: ownership of the product strategy, accountability for the global operation across the United States and India, and responsibility for vendor, supplier, and contractor management.

This role is expected to push beyond day-to-day delivery. The Director is accountable for where the onboarding and enrollment products go next: the maturity plan, the investment case, and the influence needed to get there. Team health and sustained operations remain the priority; strategy that costs the team its stability is not strategy.

• In addition to the above, your hands-on technical coding skill will be highly sought after.

Key Responsibilities

• People Leadership and Team Management
• Lead and develop a high-performing global team through hiring, coaching, performance management, succession planning, and team engagement.
• Delivery Accountability
• Own end-to-end delivery of onboarding and enrollment AI products, ensuring business outcomes, quality, compliance, and stakeholder commitments are achieved.
• Production Support and Operational Ownership
• Provide operational leadership for production systems, including support, reliability, performance metrics, cost management, and continuous improvement.
• Global Operations Leadership (Two-in-a-Box)
• Partner with the SGS counterpart to lead a unified global organization, aligning priorities, talent strategy, operating standards, and long-term capability growth.
• Vendor, Supplier, and Contractor Management
• Oversee vendor and contractor partnerships, including commercial performance, workforce planning, contract governance, and third-party risk management.
• Product Strategy and Maturity
• Define and advance the long-term product vision, operating model, investment strategy, and roadmap for AI-enabled onboarding and enrollment capabilities.
• Executive Engagement and Communication
• Serve as the primary technology leader for the value stream, communicating strategy, progress, risks, and outcomes to executives and business stakeholders.

Skills And Background You’ll Need

Education

Bachelor’s required, Master’s preferred, or equivalent experience.

Experience

• 10+ years in technology delivery, engineering, data science, or AI, including 4+ years leading technical teams.
• Demonstrated record of owning a product or portfolio end to end in a regulated enterprise environment, including production operations.
• Experience leading globally distributed teams, including direct partnership with an off-shore delivery organization.
• Experience managing vendors, contractors, and statements of work, including commercial performance discussions.
• 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 technical experience with Azure, Databricks, and enterprise integration patterns is required.
• Demonstrated ability to build and sell 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 off-shore organization is highly preferred.
• Experience with AI governance, model risk management, and regulatory expectations for AI in insurance is highly preferred.

Key Behaviors of a Successful Candidate

• Engaging Hearts & Minds: Creates a team identity and builds momentum toward a shared purpose.
• Strategic Visioning: Considers different future scenarios, opportunities and risks to generate operational plans that align with the business unit/function’s strategic vision.
• Developing People: Delivers both individual and group feedback to support ongoing development and overall department performance.

Why Join The Standard?

We have built an enduring legacy of stability, financial strength and exceptional customer service through the contributions of the service-oriented people who choose to work at The Standard. To ensure we can attract and retain the best talent, when you join The Standard you can expect:

• A rich benefits package including medical, dental, vision and a 401(k) plan with matching company contributions
• An annual incentive bonus plan
• Generous paid time off including 11 holidays, 2 wellness days, and 8 volunteer hours annually — PTO increases with tenure
• A supportive, responsive management approach and opportunities for career growth and advancement
• Paid parental leave and adoption/surrogacy assistance
• An employee giving program that double matches your donations to eligible nonprofits and schools

In addition to the competitive salary range below, our employee-focused benefits support work-life balance. Learn more about working at The Standard.

• Eligibility to participate in an incentive program is subject to the rules governing the program and plan. Any award depends on a variety of factors including individual and organizational performance.

The actual compensation for this role will be based on a combination of education and experience, knowledge and skills, position budget, internal equity, and market data.

Salary Range

$147,750.00 - $280,750.00

Positions will be posted for at least 5 days from original posting date.

Standard Insurance Company, The Standard Life Insurance Company of New York, Standard Retirement Services, Inc., StanCorp Mortgage Investors, LLC, StanCorp Investment Advisers, Inc., and American Heritage Life Insurance Company and American Heritage Service Company, marketed as The Standard, are Affidative Action/Equal Opportunity employers. All qualified applicants will receive consideration for employment without regard to race, religion, color, sex, national origin, gender identity, sexual orientation, age, disability or veteran status or any other condition protected by federal, state or local law. Except where precluded by state or federal law, The Standard will consider for employment qualified applicants with arrest and conviction records pursuant to the San Francisco Fair Chance Ordinance. The Standard offers a drug- and alcohol-free work environment where possession, manufacture, transfer, offer, use of or being impaired by an illegal substance while on The Standard's property, or in other cases which the company believes might affect operations, safety or reputation of the company is prohibited. The Standard requires a criminal background investigation and employment, education and licensing verification as a condition of employment. After any conditional offer of employment is made, the background check will include an individualized assessment based on the applicant’s specific record and the duties and requirements of the specific job. Applicants will be provided an opportunity to explain and correct background information. All employees of The Standard must be bondable.