Corporate Vice President - Senior Scrum Master

New York Life Insurance Co•New York, NY

3d•Hybrid

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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
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
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
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
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
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