Scrum Master

Hagerty Insurance Agency; Northern (KY); Hybrid; USD 90,000 - 120,000; Full time

Job summary

Hagerty seeks a Scrum Master to lead delivery across value streams for our software delivery teams. You will coach teams, facilitate ceremonies, and partner with Product, Engineering, Architecture, and IT Portfolio Management to enable value delivery with transparency and accountability.

The role emphasizes Agile and Lean practices, flow optimization, and cross-team collaboration, with a flexible remote option for eligible U.S. remote staff and hybrid in certain locations.

Qualifications

• Hands-on Scrum Master with software delivery experience.
• Strong facilitation and coaching skills.
• Clear communicator across technical and non-technical audiences.
• Experience operating in complex or enterprise environments preferred.

Responsibilities

• Facilitate Scrum ceremonies and team-level planning to drive clarity and outcomes.
• Coach teams on backlog readiness, estimation, and commitment practices.
• Support teams in managing dependencies, risks, and impediments and escalate as needed.
• Promote transparency into delivery progress and metrics to inform improvements.
• Lead retrospectives and drive actionable improvement experiments.
• Collaborate with Product, Engineering, and Architecture to improve delivery outcomes.

Skills

Facilitation

Coaching

Agile/Lean

Cross-team collaboration

Systems thinking

Communication

Enterprise context

Tools

Azure DevOps

Lucid

Job description

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.

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.

At Hagerty, we share the road. We are an inclusive automotive community where all are welcomed, valued and belong regardless of race, gender, age, or car preference. We are united by our shared passion for driving, our commitment to preserve car culture for future generations and our desire to make a positive impact in the world. #LI-Remote EEO/AA US Benefits Overview Canada Benefits Overview UK Benefits Overview

If you like wild growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us! Hagerty is an automotive enthusiast brand committed to saving driving and to fueling car culture for future generations. We are a leading provider of specialty vehicle insurance, expert car valuation data and insights, live and digital car auction services, immersive events and automotive entertainment custom made for the 67 million Americans who self-describe as car enthusiasts. Hagerty also operates in Canada and the U.K. and is home to Hagerty Drivers Club, a community of over 800,000 who can’t get enough of cars. We are a rapidly growing company that values a winning, values-driven culture. We provide meaningful work for, and invest in, every single team member.