Remote Scrum Master: Agile Delivery Leader

Hagerty; United States; On-site; USD 100,000 - 150,000; Full time

Benefits offered by this job

Remote work options

Hybrid near Traverse City

Job summary

Hagerty is seeking a Scrum Master to serve as a delivery leader, enabling effective execution and continuous improvement within value streams. You will coach teams, facilitate ceremonies, and collaborate with Product, Engineering, Architecture, and IT Portfolio Management to help deliver value predictably.

Reporting to the Manager of IT Portfolio Operations, you will focus on how work gets done, surface impediments, and promote a culture of accountability and learning.

Qualifications

• 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.
• Experience working in complex or enterprise environments preferred.
• Financial Technology Industry Experience.
• Experience working with Data Engineering Scrum Teams.

Responsibilities

• Facilitate Scrum ceremonies and team-level planning activities.
• 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.
• Encourage ownership, accountability, and collaboration within the team.
• Promote transparency into delivery progress, risks, and dependencies using tooling (e.g., Azure DevOps).
• 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.

Skills

Scrum Master

Facilitation

Coaching

Systems thinking

Influencing without authority

Clear communication

Pragmatic

Curiosity & empathy

FinTech experience

Data engineering scrum teams

Tools

Azure DevOps

Lucid

Job description

Hagerty is seeking a Scrum Master to serve as a delivery leader, enabling effective execution and continuous improvement within value streams. You will coach teams, facilitate ceremonies, and collaborate with Product, Engineering, Architecture, and IT Portfolio Management to help deliver value predictably.

Reporting to the Manager of IT Portfolio Operations, you will focus on how work gets done, surface impediments, and promote a culture of accountability and learning.