The Standard

Director, AI Delivery - Onboarding & Enrollment

The Standard • $147K — $280K *
US-AnywhereRemote in Portland, OR
Enterprise Technology
8 - 10 years of experience
Job Overview by Ladders

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 off-shore 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.

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.

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.
Full Job Description
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:

1. People Leadership and Team Management
  • Lead and develop a high-performing global team through hiring, coaching, performance management, succession planning, and team engagement.


2. Delivery Accountability
  • Own end-to-end delivery of onboarding and enrollment AI products, ensuring business outcomes, quality, compliance, and stakeholder commitments are achieved.


3. Production Support and Operational Ownership
  • Provide operational leadership for production systems, including support, reliability, performance metrics, cost management, and continuous improvement.


4. 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.


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


6. 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.


7. 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.


#LI-Remote

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.

About The Standard

The Standard is a financial services company that provides insurance, retirement, and investment products to individuals and businesses. The company's insurance products include life, disability, and dental insurance. The Standard also offers retirement plans, such as 401(k) and pension plans, and investment products, including mutual funds and annuities. The company was founded in 1906 and is headquartered in Portland, Oregon. The Standard has over 3,000 employees and serves customers across the United States.
Learn more about The Standard
Size
3,000 employees
Industry
Founded
1998

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