Scrum Master

Hagerty

19d•Hybrid

About The Position

Say hello to Hagerty Hagerty is a company built by drivers for drivers. We put our members at the center of everything we do and are dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. We’re proud to be the world’s largest insurer of collectible and enthusiast vehicles and are home to the Hagerty Drivers Club, the world’s largest car club. Our Marketplace business presents live and digital sales across the U.S. and Europe, we host a number of driving events and concours, and our award-winning automotive journalists produce the most popular car magazine globally, alongside internationally awarded videos. We’re committed to Never Stop Driving. Ready to get in the driver’s seat? Join us! As a Scrum Master you will be a delivery leader responsible for enabling effective execution, collaboration, and continuous improvement within a value stream or domain-aligned team. This role partners closely with Product, Engineering, Architecture, and IT Portfolio Management to help teams deliver value predictably and sustainably. Reporting to the Manager of IT Portfolio Operations, the Scrum Master focuses on how work gets done — facilitating team effectiveness, improving flow, surfacing impediments, and fostering a culture of accountability, learning, and transparency. This role goes beyond facilitating ceremonies to actively coach teams and stakeholders in agile and lean practices that fit the complexity of our environment.

Requirements

Hands-on experience as a Scrum Master in a software delivery environment
Strong facilitation and coaching skills
Systems thinker who understands dependencies and flow beyond a single team
Comfortable influencing without authority
Clear communicator across technical and non-technical audiences
Pragmatic and outcomes-focused, not dogmatic about frameworks
Curious, empathetic, and committed to continuous improvement

Nice To Haves

Experience working in complex or enterprise environments preferred
Financial Technology Industry Experience.
Experience working with Data Engineering Scrum Teams.
Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable. For SOX compliant roles, responsible for designing, executing, and documenting internal controls where they have been identified as owners to prevent errors in financial reporting, processes, and business operations. Including attestation to the completeness, accuracy, and compliance of all financial reporting data, where applicable.

Responsibilities

Facilitate Scrum ceremonies and team-level planning activities in a way that drives clarity, alignment, and outcomes.
Help teams plan, sequence, and execute work effectively while balancing quality, predictability, and flow.
Coach teams on backlog readiness, estimation, and commitment practices.
Support teams in managing dependencies, risks, and impediments, escalating as needed through appropriate channels.
Encourage ownership, accountability, and collaboration within the team.
Promote transparency into delivery progress, risks, and dependencies using agreed tooling and practices (e.g., Azure DevOps).
Help teams understand and use delivery metrics (e.g., flow, predictability, throughput) to inform continuous improvement.
Ensure work items are well-maintained and accurately represented to support portfolio-level visibility.
Partner with IT Portfolio Managers to provide reliable insights into team delivery status and capacity.
Coach team members and stakeholders on Agile and Lean principles and practices.
Facilitate retrospectives that lead to actionable improvement experiments.
Help teams evolve from reactive execution to proactive problem-solving and systems thinking.
Foster a psychologically safe environment that supports learning, experimentation, and honest feedback.
Collaborate with other Scrum Masters to align practices and manage cross-team dependencies.
Partner with Technical Product Managers, Engineering Leaders, and Architects to improve engagement, planning, and delivery outcomes.
Participate in Communities of Practice to share learnings and promote consistent delivery practices.
Support organizational initiatives related to delivery maturity and operational excellence.
Apply and reinforce agreed delivery standards, readiness expectations, and tooling practices.
Use frameworks pragmatically (Scrum, Kanban, Scrumban) based on team context and maturity.
Contribute feedback to resources, templates, and guidance to improve their effectiveness and relevance.