Technical Project Manager (Release Engineering, Jira, Agile) - TRUE Property Insurance

About TRUE:

Trusted Resource Underwriters Exchange (“TRUE”) is a reciprocal insurer established in 2020 to serve homeowners in storm-prone regions of Florida and other parts of the country. At the end of 2023, Gallatin Point Capital acquired a majority stake in the attorney-in-fact for TRUE and raised over $1.25 billion of committed capital, enabling TRUE to not only provide more underwriting capacity in Florida, but also allow it to strategically expand its homeowner’s product offering and footprint nationally. TRUE utilizes a partnership distribution model through new and existing partnerships as it enters a new phase of exciting growth.

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.

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.
• 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, 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.
• 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 in release engineering or DevOps for large-scale distributed systems.
• Prior experience with cloud platforms (AWS, Azure, GCP) and their release management processes.
• Familiarity with scripting languages for automation (e.g., Python, Bash).

Compensation and benefits:

True offers 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.