Lead Business Systems Engineer - Jira & Product Tooling

Root is on a mission to unbreak insurance by creating experiences people love at prices they can’t believe. We believe that investing in world-class technology will facilitate a new class of insurance products, driving a massive positive impact on the hundreds of millions of drivers who carry auto insurance in the US. Root’s Engineering team is committed to building a flexible platform on which our product designers and quantitative scientists can quickly test ideas, deploy them into production, and iterate, with the ultimate objective of a delightful customer experience coupled with effective risk management.

The Opportunity

We are seeking a Lead Business Systems Engineer to provide strategic ownership and technical leadership of our Jira product suite, including Jira Software and Jira Product Discovery, as we migrate from Shortcut and Productboard. This role operates with a high degree of autonomy and influence, owning system architecture decisions, platform strategy, and long-term scalability for product development tooling.

As a senior individual contributor, this role partners closely with Product, Engineering, Program Management, and Leadership to ensure Jira enables efficient product discovery, planning, execution, and insight across the organization.

Salary Range: $108,000-$132,000 (Also eligible for competitive bonus and equity offering)
Root is a “work where it works best” company. This means we will support you working in whatever location that works best for you across the US. While this role is remote-friendly, candidates must be located in the U.S. and some travel for interviews or meetings may be required.

How You Will Make an Impact

Strategic Jira Platform Ownership

• Serve as the principal owner and architect for Jira Software and Jira Product Discovery.
• Define and evolve Jira platform strategy, architecture, and standards aligned with company growth.
• Design and maintain complex Jira configurations including workflows, issue hierarchies, custom fields, automations, permissions, and schemas.
• Evaluate and manage Atlassian Marketplace apps and integrations to extend Jira capabilities.

Migration & Transformation Leadership

• Lead the end-to-end migration from Shortcut and Productboard to Jira Software and Jira Product Discovery.
• Drive discovery and decision-making on future-state workflows, data models, and governance.
• Partner with senior Product and Engineering leaders to align Jira design with operating models.
• Own migration planning, execution, risk management, and post-migration optimization.

Jira Product Discovery Enablement

• Architect Jira Product Discovery to support scalable idea intake, discovery workflows, prioritization frameworks, and roadmapping.
• Ensure strong alignment and traceability between discovery, delivery, and outcomes.
• Enable executive-level visibility into product priorities and progress through Jira configurations and reporting.

Cross-Functional Leadership & Influence

• Act as a trusted advisor to senior stakeholders on Jira capabilities, tradeoffs, and best practices.
• Translate ambiguous or evolving business needs into durable system designs.
• Influence teams toward standardized, scalable solutions while balancing flexibility.
• Mentor junior Business Systems Engineers and Jira administrators through design guidance and best practices.

Governance, Risk & Optimization

• Establish and enforce governance models for Jira configuration changes, access, and data quality.
• Proactively identify and remediate system risks, performance issues, and configuration debt.
• Continuously evaluate platform usage and drive simplification and optimization initiatives.
• Ensure Jira remains secure, performant, and compliant with internal standards.

What You Will Need to Succeed

• 7+ years of experience in Business Systems Engineering, Systems Administration, or a related field.
• Deep expertise administering and architecting Jira Software in large-scale, multi-team environments.
• Proven experience leading complex tooling migrations or platform transformations.
• Strong understanding of Agile, Scrum, Kanban, and modern product development practices.
• Demonstrated ability to operate independently and lead initiatives with broad organizational impact.
• Excellent stakeholder management, communication, and influence skills

Nice to Have

• Hands-on experience with Jira Product Discovery.
• Experience designing product discovery and delivery ecosystems.
• Advanced experience with Jira automation, APIs, scripting, or integrations.
• Familiarity with the broader Atlassian ecosystem (Confluence, Jira Service Management).
• Experience in SaaS or high-growth technology organizations.

As part of Root's interview process, we kindly ask that all candidates be on camera for virtual interviews. This helps us create a more personal and engaging experience for both you and our interviewers. Being on camera is a standard requirement for our process and part of how we assess fit and communication style, so we do require it to move forward with any applicant's candidacy. If you have any concerns, feel free to let us know once you are contacted. We’re happy to talk it through.

Please see our Privacy Notice available HERE for more information on how we process your personal data.

Consistent with the Americans with Disabilities Act (ADA) and the Civil Rights Act of 1964, it is the policy of Root to provide reasonable accommodation when requested by a qualified applicant or candidate with a disability, unless such accommodation would cause an undue hardship for Root. The policy regarding requests for reasonable accommodation applies to all aspects of the hiring process. If reasonable accommodation is needed, please contact [email protected]