Job Description

Location Designation: Hybrid - 3 days per week

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, contributing to New York Life’s legacy of being there when we’re needed most. Here, you'll design, implement, and support these solutions directly impacting employees’ lives. At our core, we provide financial security and peace of mind to people through our absence, accident, disability, voluntary benefits, and life insurance solutions. Click here to learn more about Group Benefits solutions.

Alternate locations: New York, NY (New York); Chattanooga, TN (Tennessee); Des Moines, IA (Iowa); Philadelphia, PA (Pennsylvania)

** We are open for a fully remote schedule for candidates located in Iowa. **

Role Overview:

The GTO (Group Transformation Office) AI Delivery Lead sits at the intersection of the Group Benefit Solutions technology and operational teams, owning the delivery strategy that turns strategic priorities into executable plans, and is accountable for the business outcomes those plans achieve. This role does not own a single linear project — it leads complex, high-impact programs that orchestrate multiple concurrent workstreams spanning IT delivery teams, product owners, underwriters, claims, product, and external vendors, while operating as the connective tissue between the PMO’s governance model and the day-to-day realities of execution. This person is who both IT and business stakeholders come to when something is off track — and who proactively surfaces what’s about to go off track before it does, and who has the authority to decide how to get it back on track. This person also serves as a strategic delivery advisor to senior GTO and group insurance leadership teams.

What You’ll Do:

• Strategic Program Ownership: Own the development and execution of integrated delivery strategies for complex, cross-functional programs, establishing execution priorities, governance approaches, and delivery roadmaps aligned with business objectives and GTO strategic priorities.
• End-to-End Delivery Ownership & Business Outcomes: Drive execution of insurance and group benefits technology initiatives from kickoff through implementation and post-launch stabilization, ensuring technical delivery and business readiness move in lockstep. Accountable for the successful delivery of complex technology programs and achievement of associated operational outcomes, including implementation readiness, risk reduction, process improvements, delivery effectiveness, and realization of defined business benefits.
• Complex Program & Resource Management: 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, and influence resource allocation decisions to achieve program objectives.
• Status Rollup & Reporting: Collect, synthesize, and normalize status updates from individual workstream leads (engineering, QA, business analysis, underwriting, claims ops) into a single, consistent delivery narrative that flows into the PMO and executive stakeholders — translating raw team-level detail into decision-ready insight.
• PMO Partnership & Governance: Operate within the PMO’s delivery framework — RAID logs, gate reviews, reporting cadences, portfolio prioritization — while acting as the PMO’s eyes and ears on the ground for insurance-specific technology programs.
• Cross-Functional Bridge (IT ↔ Business): Act as the primary translator and liaison between technology delivery teams and business units (Service, Underwriting, Claims, Distribution etc.), ensuring technical constraints are understood in business terms and business requirements are understood in technical terms. This person will work in partnership with the IT Technical Delivery lead.
• Risk & Impediment Mitigation: Proactively identify delivery risks — technical dependencies, integration gaps, regulatory/compliance constraints, resourcing shortfalls, scope creep — and don’t just flag them: bring forward concrete, evaluate mitigation options, and decide on and drive the resolution path.
• Decision-Making Authority: Exercise independent judgment and decision-making authority over program execution priorities, cross-functional dependencies, delivery trade-offs, and risk mitigation strategies. Resolve complex delivery challenges that affect multiple business and technology functions, escalating only decisions requiring executive sponsorship or changes to approved business strategy.
• Roadmap & Milestone Management: Build realistic, technically-grounded delivery schedules; define milestones that account for both IT release cycles and business operational readiness; track velocity and KPIs across concurrent initiatives in partnership with the PMO.
• Senior Leadership Influence: Serve as a strategic delivery advisor to senior GTO and group insurance leadership teams, providing recommendations on program investment priorities, execution alternatives, delivery risks, and operational impacts. Influence senior stakeholders to adopt decisions that improve program outcomes and address emerging business challenges.

What You’ll Bring:

• Experience: 10+ years in project/program/delivery leadership, including demonstrated experience leading complex, cross-functional technology initiatives (not purely business-process projects), with 3–5 years specifically in Insurance or Group Insurance.
• Domain Knowledge: Strong understanding of the Group insurance policy lifecycle, product filings, underwriting workflows, claims processing, or group benefits administration — enough to hold a credible conversation with both a business SME and a solution architect, and to advise senior leaders on trade-offs.
• Technology Fluency: Comfortable working alongside engineering, QA, and architecture teams; understands SDLC concepts, release management, and integration dependencies well enough to identify risk before it surfaces in a status report.
• Education: Bachelor’s degree in Business Administration, Information Systems, Risk Management, Project Management, or related field.
• Methodologies: Fluent in Agile/Scrum with the judgment to know which framework — or blend — fits a given initiative.
• Certifications (Preferred): PMP, CSM/SAFe, or insurance-specific designations (FLMI, CEBS).
• Skills: Exceptional stakeholder management across technical and business audiences, including influencing and negotiating with senior leaders, independent decision-making, structured risk/issue escalation, financial forecasting and resource planning, synthesis and reporting (status rollups that are accurate but not noise), and the ability to decide on and drive solutions — not just problems — under time pressure.

Strategic program ownership

From translating priorities into plans to owning the integrated delivery strategy.

Decision-making authority

From recommending mitigations to deciding on priorities, trade-offs, and dependencies.

Accountability for outcomes

From keeping delivery and readiness in sync to owning measurable business results.

Program and resource management

Adds program-level resource plans, forecasts, and influence over allocation.

Senior leadership influence

From executive reporting to advising and influencing senior leaders.

Location & Work Model:

Hybrid setup with flexibility to work remotely with occasional travel to New York, Philadelphia, or other key collaboration locations.

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Pay Transparency

Salary range: $119,000 - $185,000 (New York City, Philadelphia) // $119,000 - $165,000 (Chattanooga, Iowa)

Overtime eligible: Exempt

Discretionary bonus eligible: Yes

Sales bonus eligible: No

Actual base salary will be determined based on several factors but not limited to individual’s experience, skills, qualifications, and job location. Additionally, employees are eligible for an annual discretionary bonus. In addition to base salary, employees may also be eligible to participate in an incentive program.

Actual base salary within that range will be determined by several components including but not limited to the individual's experience, skills, qualifications, and job location. In addition to base salary, employees may also be eligible to participate in an incentive program.

Our Benefits

We provide a full package of benefits for employees – and have unique offerings for a modern workforce, including leave programs, adoption assistance, and student loan repayment programs. Based on feedback from our employees, we continue to refine and add benefits to our offering, so that you can flourish both inside and outside of work. Click here to discover more about our comprehensive benefit options or visit our NYL Benefits Site.

Our Diversity Promise

We believe in a diverse workforce because it is our mission to advocate for the financial security and success of people in every community. This is why diversity, equity, and inclusion (DEI) are guiding principles that are embedded in our brand and our culture. Click here to learn more about how we have been recognized for our leadership.

Recognized as one of Fortune’s World’s Most Admired Companies, New York Life is committed to improving local communities through a culture of employee giving and volunteerism, supported by the Foundation. We're proud that due to our mutuality, we operate in the best interests of our policy owners. To learn more about career opportunities at New York Life, please visit the Careers page of www.NewYorkLife.com.

​Job Requisition ID: 95214

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