Location Designation: Hybrid - 3 days per week
We are seeking a Senior Scrum Master to drive Agile execution within a Scaled Agile (SAFe) environment, operating at both team and program (ART) levels. This role is critical in enabling predictable, high-quality delivery through strong facilitation of Program Increment (PI) planning, cross-team alignment, and data-driven execution. The ideal candidate brings deep experience in complex, matrixed organizations, effectively navigating competing priorities, multiple stakeholders, and cross-functional dependencies. This role requires strong orientation toward Value Stream delivery, OKRs, and measurable business outcomes, including experience supporting AI/ML-driven initiatives.
Scaled Agile & Value Stream Leadership • Lead Agile execution across teams within a SAFe / Scaled Agile framework aligned to a Value Stream • Ensure alignment of team execution with PI objectives, Value Stream priorities, and enterprise OKRs • Contribute to ART events and coordinate delivery across teams to optimize end-to-end value flow
PI Planning, OKRs & Program Execution • Facilitate and support Program Increment (PI) Planning, ensuring alignment to OKRs and business outcomes • Translate strategic objectives and OKRs into actionable team-level execution plans • Track and drive accountability for PI objectives, OKR progress, and delivery commitments • Manage cross-team and cross-functional dependencies across a complex delivery ecosystem • Lead participation in Inspect & Adapt sessions with a focus on improving outcomes tied to OKRs
Delivery Excellence, Metrics & Flow Optimization • Own and drive improvement of Agile, flow, and outcome-based metrics, including velocity, predictability, throughput, cycle time, lead time, flow efficiency, PI objective achievement, and OKR progress • Define and track Value Stream-level KPIs aligned to business impact • Use data to identify bottlenecks, inform trade-offs, and improve end-to-end delivery performance • Build transparency through dashboards and reporting tied to OKRs and Value Stream metrics
AI / Data Product Delivery • Support delivery of AI/ML and data-driven products, aligning execution to measurable business outcomes (OKRs) • Enable teams to operate within iterative experimentation cycles including hypothesis-driven development, experiment tracking, success metrics, and model validation loops • Balance experimentation versus committed delivery while ensuring visibility into progress and impact • Align data science, engineering, and product workflows to ensure seamless value delivery
Team Coaching & Enablement • Coach teams on aligning day-to-day execution with OKRs and customer outcomes • Enable teams to adopt a metrics-driven mindset focused on impact over activity • Guide Product Owners on prioritization based on business value and OKR alignment • Mentor Scrum Masters and contribute to scaling Agile and outcome-driven practices
Stakeholder Engagement & Influence • Operate effectively within a complex organization with cross-functional priorities • Partner with business and product leaders to ensure alignment between strategy (OKRs) and execution • Communicate progress, risks, and trade-offs in terms of business outcomes • Influence stakeholders to adopt data-driven decision-making and outcome orientation
Required Qualifications • 6+ years of experience in Agile environments, including Scrum Master experience in a scaled enterprise setting • Strong experience with SAFe or equivalent Scaled Agile frameworks • Proven experience supporting PI Planning and program-level execution • Demonstrated experience working within Value Streams and complex, matrixed organizations • Experience aligning delivery to OKRs and measurable business outcomes • Strong understanding of flow metrics, Agile metrics, and outcome-based measurement • Experience supporting AI/ML or data-driven product delivery • SAFe Practitioner (SP) or Release Train Engineer (RTE) certification required • Excellent facilitation, coaching, and stakeholder management skills
Preferred Qualifications • SAFe Advanced Scrum Master (SASM) or additional Agile certifications • Experience in financial services or regulated environments • Familiarity with Jira, Rally, or Azure DevOps • Experience supporting large-scale digital transformation or platform programs
• Strong alignment between team execution, PI objectives, and enterprise OKRs • Improved Value Stream performance and flow efficiency • Measurable progress against business outcomes, not just delivery milestones • Effective navigation of complex stakeholder environments and competing priorities • Increased organizational maturity in metrics-driven, outcome-focused Agile delivery
Pay Transparency
Salary Range: $147,500-$211,000
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.
At New York Life, our 180-year legacy of purpose and integrity fuels our future. As we evolve into a more technology-, data-, and AI-enabled organization, we remain grounded in the values that drive lasting impact.
Our diverse business portfolio creates opportunities to make a difference across industries and communities—inviting bold thinking, collaborative problem-solving, and purpose-driven innovation. Here, you’ll find the rare balance of long-standing stability and forward momentum, supported by an inclusive team that honors tradition while embracing progress.
As a Fortune 100 mutual company, we offer a place to grow your skills, contribute to meaningful work, and deliver solutions that matter. Your ideas drive what’s next, and your growth powers it.
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 Commitment to Inclusion
At New York Life, fostering an inclusive workplace is fundamental to who we are and how we serve our communities. We have a longstanding commitment to creating an environment where individuals can contribute their best and succeed together. This foundation is rooted in our core values of humanity and integrity, ensuring that every employee feels valued and supported. By embracing a broad range of perspectives and experiences, we achieve greater success and fulfill our promise of providing financial security and peace of mind to families across all communities. Click here to learn more about New York Life’s leadership in this space.
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.
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Job Requisition ID: 93934
