Scrum Master

Role Overview

As a Scrum Master at Hagerty, you will be a delivery leader responsible for enabling effective execution, collaboration, and continuous improvement within a value stream or domain-aligned team. You will partner closely with Product, Engineering, Architecture, and IT Portfolio Management to help teams deliver value predictably and sustainably.

Responsibilities

Team Delivery Enablement

• Facilitate Scrum ceremonies and team-level planning to drive clarity, alignment, and outcomes.
• Help teams plan, sequence, and execute work while balancing quality, predictability, and flow.
• Coach teams on backlog readiness, estimation, and commitment practices.
• Support dependency, risk, and impediment management; escalate appropriately.
• Encourage ownership, accountability, and collaboration.

Flow, Visibility & Metrics

• Promote transparency into delivery progress, risks, and dependencies using agreed tooling and practices (e.g., Azure DevOps).
• Help teams use delivery metrics such as flow, predictability, and throughput for continuous improvement.
• Ensure work items are well-maintained to support portfolio-level visibility.
• Partner with IT Portfolio Managers to provide reliable insights into delivery status and capacity.

Coaching & Continuous Improvement

• Coach teams and stakeholders on Agile and Lean principles and practices.
• Facilitate retrospectives that produce actionable improvement experiments.
• Support evolution from reactive execution to proactive problem-solving and systems thinking.
• Foster psychological safety to enable learning, experimentation, and honest feedback.

Cross-Team & Ecosystem Collaboration

• 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 and delivery outcomes.
• Participate in Communities of Practice and support organizational delivery-maturity initiatives.

Standards, Tools & Ways of Working

• Apply and reinforce delivery standards, readiness expectations, and tooling practices.
• Use frameworks pragmatically (Scrum, Kanban, Scrumban) based on team context and maturity.
• Contribute feedback to improve resources, templates, and guidance.

Reporting / Context

• Reports to the Manager of IT Portfolio Operations.
• Supports one or more teams aligned to a value stream or domain.
• Works with IT Portfolio Managers, Engineering, Product, and Architecture.
• Uses Azure DevOps (ADO) and collaboration platforms (e.g., Lucid or equivalents).