Senior Scrum Master – Scaled Agile, AI/ML

Job Description

Corporate Vice President – Senior Scrum Master | New York Life Insurance Company

The Tone:
This is a full-time role at New York Life Insurance Company, located in a hybrid capacity (3 days per week) in New York, NY. New York Life, a Fortune 100 mutual company with a 180-year legacy, is evolving into a more technology-, data-, and AI-enabled organization. This role is critical for driving Agile execution within a Scaled Agile (SAFe) environment, enabling predictable and high-quality delivery across both team and program levels. The position helps ensure alignment between strategic objectives and measurable business outcomes, contributing to the company’s mission of providing financial security.

The TL;DR
• Role: Full Time
• Location: Hybrid, New York, NY
• Pay: $147500–$211000 yearly
• Mission: Drive Agile execution within a Scaled Agile (SAFe) environment, operating at team and program levels to enable predictable, high-quality delivery.
• Tech Stack: Jira, Rally, Azure DevOps

What You’ll Actually Do
• Lead Scaled Agile: Lead Agile execution across teams within a SAFe framework, ensuring alignment with PI objectives, Value Stream priorities, and enterprise OKRs.
• Facilitate Program Execution: Facilitate Program Increment (PI) Planning, track accountability for PI objectives and OKR progress, and manage complex cross-team dependencies.
• Optimize Delivery Flow: Own and improve Agile, flow, and outcome-based metrics, using data to identify bottlenecks and enhance end-to-end delivery performance.
• Support AI/ML Delivery: Support the delivery of AI/ML and data-driven products, aligning execution to measurable business outcomes and balancing experimentation with committed delivery.
• Coach Teams: Coach teams on aligning day-to-day execution with OKRs and customer outcomes, guiding Product Owners on prioritization and mentoring Scrum Masters.

The Must-Haves
• Background: Senior-level professional with SAFe or equivalent Scaled Agile framework experience, including SAFe Practitioner (SP) or Release Train Engineer (RTE) certification.
• Experience: 6+ years in Agile environments, including Scrum Master experience in a scaled enterprise setting, proven experience supporting PI Planning and program-level execution, and experience supporting AI/ML or data-driven product delivery.
• Skills: Excellent facilitation, coaching, and stakeholder management skills; strong understanding of flow metrics, Agile metrics, and outcome-based measurement; demonstrated ability to align delivery to OKRs and measurable business outcomes.
• Bonus: 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.