Hagerty

Scrum Master

Hagerty$90K — $110K *
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years of experience as a Scrum Master in software delivery environments
  • Proficient in facilitating Scrum ceremonies and Agile practices
  • Deep understanding of systems thinking and team dependencies
  • Ability to communicate effectively with technical and non-technical stakeholders
  • Flexible in applying various Agile frameworks based on team needs
  • Curiosity and empathy for continuous improvement in team dynamics
  • Experience in Financial Technology and Data Engineering Scrum Teams is preferred

Responsibilities

  • Facilitate Scrum ceremonies and ensure clarity in planning activities
  • Coach teams on backlog management and effective work execution
  • Promote transparency through delivery metrics and management of risks
  • Foster a culture of ownership and collaboration within teams
  • Encourage continuous improvement through retrospectives and actionable insights
  • Collaborate across teams for alignment and dependency management
  • Reinforce delivery standards and utilize relevant tooling for project management

Benefits

  • Remote work flexibility for U.S. residents
  • Hybrid schedule for local employees
  • Potential travel for quarterly team events
  • Engagement in Communities of Practice for continuous learning and sharing
  • Support for organizational initiatives aimed at improving delivery maturity
Full Job Description
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.

What you'll do

Team Delivery Enablement
  • 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.


Flow, Visibility & Metrics
  • 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.


Coaching & Continuous Improvement
  • 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.


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, 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.


Standards, Tools & Ways of Working
  • 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.


Reporting & Role Context
  • Reports to the Manager of IT Portfolio Operations
  • Supports one or more teams aligned to a value stream or domain
  • Partners closely with IT Portfolio Managers, Engineering, Product, and Architecture
  • Leverages tools including Azure DevOps (ADO) and collaboration platforms (e.g., Lucid or equivalents)


How This Role Fits in the Ecosystem
  • IT Portfolio Managers focus on what is delivered and how value flows across the portfolio.
  • Managers of IT Portfolio Operations enable delivery by developing and supporting Scrum Masters.
  • Scrum Masters focus on how teams work to deliver, acting as facilitators, coaches, and delivery leaders within value streams.


This might describe you
  • 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.


Other things to note
  • This position is open to U.S. remote work. However, team members who reside within 20 miles of the Traverse City headquarters will follow a hybrid schedule, working from the office three days per week.
  • May require travel for quarterly events.
  • 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.

About Hagerty

Hagerty is an insurance company that specializes in classic car insurance. The company was founded in 1984 and is headquartered in Traverse City, Michigan. Hagerty offers insurance policies for classic cars, trucks, motorcycles, boats, and other vehicles. The company also provides valuation tools, educational resources, and other services for classic car enthusiasts. Hagerty has a team of experienced agents who are knowledgeable about classic cars and can help customers find the right insurance coverage for their needs. The company is committed to preserving and promoting the classic car hobby.
Learn more about Hagerty
Size
1,000 employees
Market Cap
$2.6 billion
Industry
NASDAQ

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