Senior Scrum Master (AI-Enabled, Azure DevOps)

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

What are the requirements needed for this position? 

• 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

What other skills/experience would be helpful to have?

• 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.)

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Pay Range:

Any posted pay range considers a wide range of compensation factors, including candidate background, experience and work location, while also allowing for salary growth within the position.

If there is no posting end date listed then this is a pipeline requisition, and we will continue to collect applications on an ongoing basis.

Helping People Thrive in a Connected World
Connect with us. Bring us your best work and your brightest ideas. And we’ll bring you a place where you can thrive. Learn more at jobs.assurant.com.

For U.S. benefit information, visit myassurantbenefits.com. For benefit information outside the U.S., please speak with your recruiter.

What’s the culture like at Assurant?
Our unique culture is a big reason why talented people choose Assurant. Named a Best/Great Place to Work in 15 countries and awarded the Fortune America’s Most Innovative Companies recognition, we bring together top talent around the world. Although we have a wide variety of skills and experiences, we share common characteristics that are uniquely Assurant. A passion for service. An ability to innovate in practical ways. And a willingness to take chances. We call our culture The Assurant Way.

Company Overview
Assurant is a leading global business services company that supports, protects, and connects major consumer purchases. A Fortune 500 company with a presence in 21 countries, Assurant supports the advancement of the connected world by partnering with the world’s leading brands to develop innovative solutions and deliver an enhanced customer experience through mobile device solutions, extended service contracts, vehicle protection services, renters insurance, lender-placed insurance products, and other specialty products.

Equal Opportunity Statement
Assurant is an Equal Employment Opportunity employer and does not use or consider race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other characteristic protected by federal, state, or local law in employment decisions.

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