Technical Project Manager (Release Engineering, Jira, Agile)

About TRUE

TRUE Property Insurance is a reciprocal insurer founded in 2020 to serve homeowners in storm-prone regions across Florida and other coastal markets throughout the United States. The company is actively writing HO3 business in Florida, Georgia, Texas, and South Carolina, in addition to program business with partners in Arizona and California. TRUE plans to continue expanding into additional states in 2026 and beyond as it grows its national footprint. Through a partnership-driven distribution model, TRUE collaborates with both new and existing partners to deliver tailored homeowners insurance solutions while continuing to scale its product offerings, underwriting capabilities, and team.

Job Overview

We are seeking a skilled Technical Project Manager with deep expertise in release engineering, Jira, and Agile methodologies. This role will be responsible for leading cross-functional teams in planning, executing, and delivering high-quality software products on schedule. The ideal candidate will act as a bridge between development, quality assurance, and operations teams, ensuring seamless integration of releases into production while continuously improving processes.

The ideal candidate will also serve as a Jira Subject Matter Expert (SME), with advanced experience in Jira administration, enterprise dashboard creation, executive reporting, plugin management, automation, and multi-project workflow optimization.

Key Responsibilities

• Project Management: Lead end-to-end management of software development projects, from planning and scheduling to execution and release.
• Release Management: Coordinate and manage the release of software, ensuring that releases are on time and meet quality standards. Develop, maintain, and automate release processes.
• Agile Process Management: Oversee Agile ceremonies (stand-ups, retrospectives, planning, etc.) and ensure the team follows Agile best practices. Facilitate sprints, backlog grooming, and sprint reviews.
• Jira Expertise: Manage Jira workflows, boards, and reporting tools. Configure Jira for optimal team performance and use it to track project progress, identify bottlenecks, and report on key metrics.
• Jira Administration & Dashboarding: Administer Jira environments, manage permissions and configurations, support plugins and integrations, and create complex multi-project and executive dashboards that provide actionable insights for leadership and delivery teams.
• Cross-Functional Collaboration: Work closely with development, QA, DevOps, and product teams to align on project goals, ensure resource availability, and mitigate risks.
• Stakeholder Communication: Act as the main point of contact for stakeholders, ensuring timely communication of project updates, risks, and timelines. Provide detailed reports and dashboards to senior management.
• Risk & Issue Management: Identify, track, and resolve project risks and issues in a proactive and timely manner.
• Continuous Improvement: Drive process improvements in release management, Agile processes, support operations, and tool configurations to increase efficiency and scalability.
• Documentation: Ensure that all project documentation, release notes, and Agile artifacts are properly maintained and up to date.

Qualifications

• Bachelor’s degree in computer science, Information Technology, or a related field (or equivalent work experience).
• 5+ years of experience in technical project management, with a focus on software release engineering.
• Proven experience managing projects using Agile methodologies (Scrum, Kanban, etc.).
• Extensive expertise in Jira administration, including setting up workflows, dashboards, and metrics reporting.
• Advanced Jira SME experience, including workflow design, dashboard development, automation rules, plugin/integration management, and enterprise reporting.
• Strong understanding of CI/CD pipelines and release automation.
• Excellent problem-solving skills with the ability to navigate and resolve complex technical challenges.
• Strong communication and interpersonal skills, with the ability to collaborate effectively across teams and with senior management.
• Experience with tools like Confluence, Git, and Jenkins (or other CI/CD platforms) is a plus.

Key Competencies

• Agile Leadership: Ability to lead Agile teams, mentor team members, and foster an Agile culture.
• Technical Acumen: Strong understanding of software development lifecycle, release management, and DevOps practices.
• Detail-Oriented: Ability to manage multiple projects simultaneously with a high degree of accuracy and attention to detail.
• Collaboration: Excellent team player with a focus on achieving project objectives through collaboration and teamwork.
• Adaptability: Comfortable working in fast-paced, dynamic environments with shifting priorities.

Preferred Qualifications

• Certified Scrum Master (CSM) or PMI Agile Certified Practitioner (PMI-ACP).
• Experience managing Kanban-based production defect tracking, application support workflows, and issue resolution processes in fast-paced technology environments.
• Prior experience with cloud platforms (AWS, Azure, GCP) and their release management processes.
• Familiarity with scripting languages for automation (e.g., Python, Bash).
• Experience with Jira plugins and marketplace applications such as Structure, ScriptRunner, Advanced Roadmaps, EazyBI, Tempo, or similar enterprise Jira tools is highly preferred.

*** 

TRUE offers a competitive compensation package with comprehensive benefits. The role is remote, but we offer an opportunity to work in an office environment in Boston, MA and St. Petersburg, FL.