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About the Role

The GTO AI Delivery Lead is responsible for the delivery strategy that transforms strategic priorities into executable plans and achieves business outcomes. This role manages complex, high-impact programs involving multiple workstreams across IT, product, underwriting, claims, and external vendors, acting as a liaison between governance and execution. The individual will serve as a strategic delivery advisor to senior leadership.

Responsibilities

Own the development and execution of integrated delivery strategies for complex, cross-functional programs.
Establish execution priorities, governance approaches, and delivery roadmaps aligned with business objectives.
Drive execution of technology initiatives from kickoff through implementation and post-launch stabilization.
Ensure technical delivery and business readiness are synchronized.
Accountable for the successful delivery of complex technology programs and achievement of associated operational outcomes.
Lead complex, high-impact technology programs involving multiple business functions, technology platforms, external vendors, and interdependent delivery teams.
Establish program-level resource plans, financial forecasts, and delivery priorities.
Influence resource allocation decisions to achieve program objectives.
Synthesize and normalize status updates into a consistent delivery narrative for the PMO and executive stakeholders.
Translate team-level detail into decision-ready insight.
Operate within the PMO’s delivery framework, acting as the PMO’s representative for insurance-specific technology programs.
Act as the primary translator and liaison between technology delivery teams and business units.
Ensure technical constraints are understood in business terms and business requirements are understood in technical terms.
Proactively identify delivery risks and drive resolution paths.
Exercise independent judgment and decision-making authority over program execution priorities, dependencies, trade-offs, and risk mitigation.
Resolve complex delivery challenges affecting multiple business and technology functions.
Build realistic, technically-grounded delivery schedules.
Define milestones accounting for IT release cycles and business operational readiness.
Track velocity and KPIs across concurrent initiatives.
Serve as a strategic delivery advisor to senior leadership.
Provide recommendations on program investment priorities, execution alternatives, delivery risks, and operational impacts.
Influence senior stakeholders to adopt decisions that improve program outcomes.

Requirements

10+ years in project/program/delivery leadership.
Demonstrated experience leading complex, cross-functional technology initiatives.
3–5 years specifically in Insurance or Group Insurance.
Strong understanding of the Group insurance policy lifecycle, product filings, underwriting workflows, claims processing, or group benefits administration.
Comfortable working alongside engineering, QA, and architecture teams.
Understands SDLC concepts, release management, and integration dependencies.
Bachelor’s degree in Business Administration, Information Systems, Risk Management, Project Management, or related field.
Fluent in Agile/Scrum with the judgment to know which framework or blend fits a given initiative.
Exceptional stakeholder management across technical and business audiences.
Influencing and negotiating with senior leaders.
Independent decision-making.
Structured risk/issue escalation.
Financial forecasting and resource planning.
Synthesis and reporting.
Ability to decide on and drive solutions under time pressure.

Skills

Stakeholder management
Influencing
Negotiating
Decision-making
Risk/issue escalation
Financial forecasting
Resource planning
Synthesis
Reporting
Problem-solving
Agile/Scrum methodologies

Location

Hybrid
New York, NY
Chattanooga, TN
Des Moines, IA
Philadelphia, PA
Remote (for candidates in Iowa)

Work Type

Hybrid
Remote

Experience Level

10+ years in project/program/delivery leadership
3-5 years in Insurance or Group Insurance

Education Level

Bachelor’s degree in Business Administration, Information Systems, Risk Management, Project Management, or related field.
PMP (Preferred)
CSM/SAFe (Preferred)
Insurance-specific designations (FLMI, CEBS) (Preferred)

Salary/Compensations

$119,000 - $185,000 (New York City, Philadelphia)
$119,000 - $165,000 (Chattanooga, Iowa)

Benefits

Comprehensive insurance and absence management solutions
Leave programs
Adoption assistance
Student loan repayment programs

About the Company

Group Benefit Solutions delivers comprehensive insurance and absence management solutions for mid-sized and large companies.
Our work fosters a healthier, happier, and more secure workforce.
We provide financial security and peace of mind through absence, accident, disability, voluntary benefits, and life insurance solutions.
New York Life is recognized as one of Fortune’s World’s Most Admired Companies.
Committed to improving local communities through employee giving and volunteerism.
Operates in the best interests of policy owners due to its mutuality.

Equal Opportunity

We believe in a diverse workforce because it is our mission to advocate for the financial security and success of people in every community.
Diversity, equity, and inclusion (DEI) are guiding principles embedded in our brand and our culture.