Sr Scrum Master

Title: Senior Scrum Master

Location Designation: Hybrid – 3 days per week onsite in New York City

Hours: 7.5 hours/day, 37.5 hours/week

Duration: 6-month (Potential extension/hire)

MUST HAVES (Non-Negotiable Requirements)

·        8+ years of relevant experience as a Scrum Master, preferably within the insurance or financial services industry.

·        Well-versed in leading scrum team events and PI Planning.

·        Strong technical background with hands-on experience in Scrum team competencies (e.g., programming, testing, requirements gathering) prior to assuming Scrum Master or Project Management roles.

·        Technical expertise to mentor Scrum teams across all competencies, including Development, Testing, Business Analysis (BA), DevOps, User Acceptance Testing (UAT), and Integrations, with the ability to effectively coach in agility best practices.

·        Sufficient technical depth to analyze risks and process gaps, propose solutions, and actively assist with remediation activities.

·        Proficiency with Agile and work management tools, including JIRA, Confluence, and Ativo.

·        Demonstrated capability to mentor teams on AI usage to improve productivity and delivery outcomes.

Role Overview

We are seeking an experienced Senior Scrum Master to support our Field Experience value stream. This role is responsible for driving projects from inception through delivery while promoting Agile excellence across technology and business teams.

The Senior Scrum Master will:

·        Lead project facilitation across the Technology portfolio using Agile methodologies and tools

·        Serve as a hands-on mentor and coach to Scrum teams

·        Partner closely with Product Owners, value stream delivery leads, technology teams, and business partners

·        Report directly to the Release Train Engineer (RTE)

What You''ll Do

Agile Coaching & Team Development

·        Provide training, coaching, and facilitation to help teams reach a high-performance state

·        Guide and mentor teams in Scrum and Agile principles to maximize delivery effectiveness

·        Help teams meet sprint and Program Increment (PI) goals

·        Support Product Owners in developing, refining, and maintaining product backlogs

·        Represent teams in Scrum of Scrums and other cross-team planning and coordination forums

·        Support adoption and proficiency of Agile tools such as JIRA and Confluence

·        Mentor teams in the use of AI tools to streamline documentation, planning, and execution

·        Ensure transparency and accuracy of progress reporting to stakeholders

·        Monitor and optimize team velocity and delivery metrics

·        Identify and remove impediments to team progress

·        Proactively resolve conflicts and delivery issues

·        Coach teams toward stronger collaboration, self-management, and accountability

·        Foster healthy interactions within teams and with external stakeholders

·        Bring energy, focus, and resilience to drive sustainable Agile transformation

·        Ensure continuous improvement through retrospectives and process inspection

·        Contribute to Agile maturity through participation in the Community of Practice

·        Track and report Agile performance metrics such as velocity, burndown, and predictability

Facilitate all Scrum events:

·        Daily stand-ups

·        Sprint planning

·        Sprint reviews

·        Retrospectives

·        Monitor Scrum team compliance with Agile frameworks within JIRA

·        Help build and sustain self-organizing, high-performing teams

What You’ll Bring

·        Bachelor’s degree in Computer Science or a related field (required)

·        Scrum Master certification preferred

·        Proficiency with AI-enabled tools, particularly in JIRA, Confluence, Ativo, and Microsoft Copilot

·        Proven technical mentoring experience across software development and delivery disciplines

·        Experience managing projects that leverage service-oriented architecture (SOA)

·        Strong understanding of Agile methodologies and a proven delivery track record

·        Deep understanding of the Software Development Life Cycle (SDLC)

·        Strong familiarity with life insurance or financial services environments

·        Experience facilitating or moderating large-scale workshops or cross-functional sessions

·        Ability to manage multiple complex system projects simultaneously

·        Excellent analytical skills, independent thinking, and sound judgment