Senior Scrum Master (AI-Enabled, Azure DevOps)

Assurant

1d•Remote

About The Position

We are seeking a seasoned Scrum Master who goes beyond facilitating ceremonies and actively enables teams to deliver measurable business value. This role is ideal for someone who thrives in modern Agile environments, partners closely with Product and Engineering leadership, and leverages AI tools such as Microsoft Copilot and GitHub Copilot to improve team effectiveness, flow, and quality. You will coach cross-functional teams to take ownership, continuously improve, and align day-to-day execution with strategic outcomes. What will be my duties and responsibilities in this job? Agile Leadership & Team Enablement Serve as a servant leader and coach to one or more Scrum teams Enable teams to self-organize, take ownership, and continuously improve delivery outcomes Facilitate Scrum ceremonies (Sprint Planning, Daily Scrum, Reviews, Retrospectives) with a strong focus on outcomes vs. activities Identify and remove impediments, escalating when necessary while encouraging team accountability Business Value & Product Partnership Partner closely with Product Owners, Business Analysts, and Engineering Leaders to ensure backlog items are: Well-defined Outcome-focused Aligned to business priorities Coach teams on breaking down work into valuable, testable increments Help teams understand the “why” behind the work, not just the “what” Azure DevOps & Metrics Deep hands-on experience using Azure DevOps for: Backlog management Sprint planning and tracking Dashboards and reporting Leverage metrics such as flow, predictability, cycle time, and throughput to guide improvement (not to micromanage) Help teams and leaders make data-informed decisions AI-Enabled Ways of Working Champion the use of AI tools to increase productivity and quality, including: Microsoft Copilot (documentation, requirements clarity, analysis) GitHub Copilot (engineering efficiency, code quality support) Coach teams on responsible and effective AI usage within Agile workflows Experiment with and promote AI-assisted practices for planning, refinement, and retrospectives Coaching & Continuous Improvement Coach teams on Agile, Scrum, and Lean principles Identify systemic issues across teams and work with leadership to address them Foster a culture of learning, curiosity, psychological safety, and accountability What Success Looks Like? Teams consistently deliver valuable, high-quality increments Teams are engaged, empowered, and accountable Stakeholders trust delivery and see clear alignment to business outcomes AI tools are thoughtfully integrated into team workflows Continuous improvement is visible, measurable, and sustainable

Requirements

7+ years of experience as a Scrum Master or Agile Coach
2+ years of proven experience working with Azure DevOps in a delivery environment
Experience working with AI tools such as Microsoft Copilot and GitHub Copilot
Strong understanding of Scrum, Kanban, and Agile delivery metrics
Experience working with cross-functional teams (engineering, product, QA, business)
Demonstrated ability to drive business value, not just delivery velocity
Excellent facilitation, coaching, and communication skills

Nice To Haves

Background in software development, engineering, or technical product delivery
Experience coaching teams in enterprise or regulated environments
Agile certifications (CSM, PSM, SAFe, ICP-ACC, etc.)

Responsibilities

Serve as a servant leader and coach to one or more Scrum teams
Enable teams to self-organize, take ownership, and continuously improve delivery outcomes
Facilitate Scrum ceremonies (Sprint Planning, Daily Scrum, Reviews, Retrospectives) with a strong focus on outcomes vs. activities
Identify and remove impediments, escalating when necessary while encouraging team accountability
Partner closely with Product Owners, Business Analysts, and Engineering Leaders to ensure backlog items are: Well-defined Outcome-focused Aligned to business priorities
Coach teams on breaking down work into valuable, testable increments
Help teams understand the “why” behind the work, not just the “what”
Deep hands-on experience using Azure DevOps for: Backlog management Sprint planning and tracking Dashboards and reporting
Leverage metrics such as flow, predictability, cycle time, and throughput to guide improvement (not to micromanage)
Help teams and leaders make data-informed decisions
Champion the use of AI tools to increase productivity and quality, including: Microsoft Copilot (documentation, requirements clarity, analysis) GitHub Copilot (engineering efficiency, code quality support)
Coach teams on responsible and effective AI usage within Agile workflows
Experiment with and promote AI-assisted practices for planning, refinement, and retrospectives
Coach teams on Agile, Scrum, and Lean principles
Identify systemic issues across teams and work with leadership to address them
Foster a culture of learning, curiosity, psychological safety, and accountability