Senior Scrum Master – AI/MLOps Product Delivery

Role Overview

• Practice and encourage Agile mindset and behaviors; coach, inspire and mentor teams on Agile principles, values and practices while role modeling Travelers' leadership behaviors.
• Own delivery outcomes across multiple teams by ensuring predictable achievement of commitments, maintaining quality standards, and driving sustainable throughput; analyze system health and guide teams through complex delivery challenges to successful completion.
• Roll up your sleeves and actively partner with engineering teams in the flow of work—unblock issues, navigate technical dependencies, facilitate decision-making, and drive work to completion; be an active participant in delivery, not just an observer of process.
• Independently lead the application of Agile practices for multiple teams. Practices may be Scrum and/or Kanban based. Actions often visualizing work, limiting work in progress, managing work flow, planning and guidance for daily stand ups, sprint planning, short, mid, and long range planning, backlog refinement, and retrospective meetings.
• Ensure progress toward objectives, KPIs and commitments; guide assigned Agile teams to deliver the required product increments and outcomes.
• Leverage delivery metrics (cycle time, throughput, lead time, quality indicators, PR review times, defect rates) to identify constraints, inefficiencies, and improvement opportunities; work with leadership to remove systemic impediments and optimize flow.
• Partner with key stakeholders (i.e. Agile Coach and Team Lead) in backlog prioritization as well as tracking and reporting metrics, providing visibility to the team and stakeholders, ensuring a data-driven approach to decision-making.
• Utilize data to diagnose system health and spot behavioral patterns; bring evidence-based insights that drive meaningful changes in how teams deliver and prioritize their work.
• Identify opportunities to improve team-level Agile performance; focus teams on customer value, quality and continuous improvement activities.
• Remove team-level impediments and resolve conflicts; anticipate challenges, identify risks, and recommend mitigations and solutions.
• Lead and coach other Scrum Masters (direct reports) in developing a delivery-focused mindset; upskill the team in metrics analysis, constraint identification, and systems thinking approaches to achieving outcomes.
• Utilize learnings and best practices in furthering the effective use of Agile practices at Travelers.
• Facilitate open communication among team members and stakeholders; promote positive team dynamics to ensure members collaborate and work effectively.
• Build and leverage effective alliances across other teams and the technical and business communities.
• Partner with Circle Leadership on PI planning activities, organizing and leading PI ceremonies.
• Participate and actively contribute to the Agile Community, partnering closely with Agile Coaches and Leadership to Evolve the Way We Work.
• Increase the overall Agile maturity for teams, and support higher complexity work towards successful outcomes. Supports Agile team(s) that have various levels of agile maturity; actively works to upskill those teams in agile practices and increases their overall agile maturity. Demonstrates ability to lead and influence by enhancing Circle-wide agile practices.
• May also play a scrum-of-scrum role, managing the flow of work through an entire Circle rather than on an individual team or teams.
• Perform other duties as assigned.

Requirements

• Bachelor's degree.
• Three years experience in a Scrum Master or similar Agile role applying Agile principles and practices including delivery of several epics, releases and versions and application of a wide variety of patterns and techniques (i.e. leveraging burndown, facilitating retrospectives, refining user stories, etc.).
• Experience as a Project Manager, Program Manager, or Delivery Consultant also applicable; demonstrated ability to drive teams to 85%+ predictability while maintaining quality through establishing healthy backlogs, managing WIP, and navigating technical/organizational impediments.
• Hands-on experience using delivery metrics (cycle time, lead time, throughput, WIP, volatility) to diagnose performance issues and drive measurable improvements; comfortable translating data into specific process changes that improved team predictability and flow.
• Experience managing and coaching other Scrum Masters or delivery professionals; demonstrated ability to develop team members' capabilities in systems thinking, metrics analysis, and delivery accountability with demonstrated impact on team performance.
• Programming/development experience.
• Technical fluency across the software delivery lifecycle including CI/CD pipelines, DevOps practices, automated testing, version control (GitHub), cloud computing, and QA processes; understand how engineering practices impact delivery outcomes and can coach teams on technical improvement opportunities.
• Experience implementing best practices and standards related to Agile product development.
• Demonstrated ability to establish and enforce delivery standards including Definition of Ready/Done, epic exit criteria, and refinement practices that create sustainable, predictable delivery patterns across multiple teams.
• Experience leading others with the ability to earn trust while still challenging the team to improve and operate outside its comfort zone in an Agile environment.
• Experience guiding teams through organizational change using change management principles; ability to help teams understand the "why" behind changes, build their capability to adopt new practices, and reinforce changes until they become embedded in team behavior.
• Track record of partnering with Product Owners to maintain product vision alignment, drive product discovery activities, and ensure backlogs reflect customer needs and business objectives; understand how to balance discovery with delivery commitments.
• Experience applying AI tools and emerging technologies to optimize delivery practices; comfortable experimenting with new tools to improve team efficiency and exploring responsible AI adoption strategies.
• Active participant in Agile/engineering communities, CoPs, or industry networks where you've contributed insights, learned from peers, and brought best practices back to your organization.
• Agile Mindset: Embody Agile core values of openness, courage, respect, focus, and commitment.
• Delivery Mindset: Focused on outcomes, predictability, and building healthy delivery systems that consistently achieve commitments.
• Systems Thinking: Ability to analyze delivery systems holistically, identify constraints and bottlenecks, and work across organizational boundaries to remove impediments.
• Infuse Agile principles, practices and methodologies to achieve team success.
• Project Management: Ability to initiate, plan, execute, and guide the work of a team to achieve specific goals and meet specific success criteria within a specified time.
• Influence: Ability to influence leaders at all levels and without traditional hierarchy; skilled at building data-driven cases for systemic changes and successfully removing impediments that span multiple teams or organizational boundaries.
• Servant Leadership: Foster an environment where individuals thrive as empowered and equal members of a team.
• Communication: Ability to communicate thoughts, concepts and practices effectively at all levels, adjusting as needed to a target audience.
• Collaboration: Expertise working with others in a cross-functional multi-team environment.
• Continuous Improvement: Demonstrate a commitment to continually improve, share learning with others and encourage team development.

Tech Stack

• Cloud

Benefits

• Health Insurance : Employees and their eligible family members – including spouses, domestic partners, and children – are eligible for coverage from the first day of employment.
• Retirement: Travelers matches your 401(k) contributions dollar-for-dollar up to your first 5% of eligible pay, subject to an annual maximum. If you have student loan debt, you can enroll in the Paying it Forward Savings Program. When you make a payment toward your student loan, Travelers will make an annual contribution into your 401(k) account. You are also eligible for a Pension Plan that is 100% funded by Travelers.
• Paid Time Off: Start your career at Travelers with a minimum of 20 days Paid Time Off annually, plus nine paid company Holidays.
• Wellness Program: The Travelers wellness program is comprised of tools, discounts and resources that empower you to achieve your wellness goals and caregiving needs. In addition, our mental health program provides access to free professional counseling services, health coaching and other resources to support your daily life needs.
• Volunteer Encouragement: We have a deep commitment to the communities we serve and encourage our employees to get involved. Travelers has a Matching Gift and Volunteer Rewards program that enables you to give back to the charity of your choice.