Senior Scrum Master

Who Are We?

Taking care of our customers, our communities and each other. That’s the Travelers Promise. By honoring this commitment, we have maintained our reputation as one of the best property casualty insurers in the industry for over 170 years. Join us to discover a culture that is rooted in innovation and thrives on collaboration. Imagine loving what you do and where you do it.

Technology

Compensation Overview

The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.

Salary Range

$109,300.00 - $180,200.00

1

Travelers is seeking a Senior Scrum Master to elevate product delivery excellence and Agile maturity across a complex, evolving technology and business ecosystem. In this role, you’ll go beyond facilitating Scrum for your teams — you’ll be a strategic partner who unites Product, Engineering, UX, and Business stakeholders to discover, deliver, and continuously improve customer and business outcomes. You will leverage deep product understanding and systems thinking to connect business strategy with execution, guiding multiple teams through ambiguity and change. You’ll coach toward outcome-oriented delivery, foster empirical decision-making, and build psychological safety so teams can learn, adapt, and thrive.

What Will You Do?

• Practice and model an Agile mindset and behaviors; coach, inspire, and mentor teams on Agile principles, values, and practices while exemplifying Travelers’ leadership behaviors.
• Independently lead Agile practices across multiple teams — including Scrum, Kanban, and hybrid models — ensuring clarity of flow, limiting work in progress, and improving predictability.
• Facilitate discovery and experimentation sessions that help teams frame problems, co-create hypotheses, and validate solutions before execution.
• Partner with Product, Engineering, and Business stakeholders to ensure shared understanding of priorities, value, and technical complexity.
• Enable teams to focus on outcomes (value realized, customer problems solved) rather than outputs (features delivered).
• Guide teams and leaders in setting measurable objectives and using flow metrics (lead time, cycle time, throughput, WIP) to inform improvement and decision-making.
• Identify patterns in team impediments and collaborate with leadership to design systemic improvements that benefit multiple teams.
• Remove obstacles, resolve conflicts, and coach teams through ambiguity, ensuring sustainable pace and delivery consistency.
• Build and sustain psychologically safe environments where teams can experiment, learn, and continuously improve.
• Lead and contribute to the Agile Delivery Practices Chapter and Scrum Master Community of Practice, sharing knowledge and accelerating organizational learning.
• Partner with Circle Leadership (cross-team leaders) on planning activities, including program increments, cross-team synchronization, and portfolio alignment.
• Mentor developing Scrum Masters and Agile practitioners, modeling advanced coaching and facilitation techniques.
• Perform other duties as assigned.

What Will Our Ideal Candidate Have?

• Bachelor’s degree preferred.
• Three or more years' experience as a Scrum Master or similar Agile leadership role, with proven success applying Agile principles and practices across multiple teams.
• Experience leading Agile delivery for complex products or platforms with a deep understanding of product discovery and delivery dynamics, bridging business and technical perspectives.
• Hands-on experience facilitating product discovery practices such as design sprints, user story mapping workshops, and rapid test-and-learn experiments to validate assumptions and accelerate learning.
• Proven ability to coach teams toward higher levels of maturity and performance using flow metrics and empirical data.
• Programming/development experience preferred.
• Experience implementing best practices and standards related to Agile product development.
• Leads through influence, earning trust and challenging teams and leaders to improve and grow beyond their comfort zones.
• Embodies and models Scrum core values of openness, courage, respect, focus, and commitment.
• Fosters environments where individuals thrive as empowered, equal members of a team.
• Facilitates effectively through thoughtful inquiry and discussion, guiding diverse groups toward alignment and decisions.
• Demonstrates commitment to learning, experimentation, and continuous evolution of practices and culture.
• Excels at cross-functional teamwork, building trust across disciplines and levels of the organization.
• Communicates concepts and data effectively at all levels, tailoring messages to technical and non-technical audiences.

What is a Must Have?

• 3 years of project management or related experience required.