Hagerty · 1 hour ago
Scrum Master
United States
Full-time
Remote
Mid LevelHagerty is an automotive enthusiast brand and the world’s largest membership organization, dedicated to preserving car culture for future generations. The Scrum Master will be responsible for enabling effective execution and collaboration within teams, coaching them in agile practices, and promoting continuous improvement.
Auto InsuranceInsuranceInsurTech
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
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)
Qualification
Required
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
Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable
Preferred
Experience working in complex or enterprise environments
Financial Technology Industry Experience
Experience working with Data Engineering Scrum Teams
Benefits
Compensation
Comprehensive benefits
The perks that set us apart
Company
Hagerty
We're Hagerty, and we help enthusiast drivers insure, buy/sell and enjoy their rides. #NeverStopDriving
Founded in 1983
1001-5000 employees
H1B Sponsorship
Hagerty has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2023 (3)
2022 (2)
2021 (1)
2020 (2)
Funding
Current Stage
Public CompanyTotal Funding
$195.6M2025-08-07Post Ipo Secondary· $90.6M
2023-06-23Post Ipo Equity· $80M
2023-06-23Post Ipo Debt· $25M
Leadership Team
Arjun Chowdri
Senior Vice President, Membership & Retention
Gary Chard
Senior Vice President, Operations - Marketplace
Recent News
Broad Arrow Auctions
2025-07-22
Company data provided by crunchbase