Project Manager (Optional Work from Home)

Windward Risk Managers is seeking a detail-oriented Project Manager to support the planning, execution, and delivery of projects in an Agile environment. This role is accountable for coordinating project activities, managing timelines and deliverables, and leading Scrum-based delivery activities to ensure alignment with business objectives.

Responsibilities:

• Develop and maintain project plans, schedules, milestones, dependencies, and deliverables
• Actively track each team member’s planned and completed work, including commitments made during daily stand-ups and sprint planning
• Develop a working understanding of the systems, applications, and business processes the team supports in order to effectively track progress, ask informed questions, and identify delivery risks or bottlenecks
• Assist in defining project scope, managing changes, and coordinating resources across cross-functional teams to meet delivery commitments
• Lead Scrum ceremonies including sprint planning, daily stand-ups, sprint reviews, and retrospectives as part of the project execution framework
• Serve as a primary point of contact for project communications
• Provide regular status updates on progress, risks, issues, and dependencies to business and technical stakeholders
• Identify, document, and track project risks, issues, and dependencies
• Support mitigation plans and escalate concerns as needed to minimize delivery impacts
• Maintain project documentation, schedules, and status reports
• Ensure project information is accurate, current, and accessible
• Support adherence to project management standards, processes, and governance requirements while ensuring alignment with Agile delivery practices
• Capture lessons learned and contribute to process improvements to enhance project execution and delivery outcomes

Requirements:

• Bachelor's degree in business, IT, or a related field; or an equivalent combination of relevant work experience and education
• Minimum of two (2) years of experience managing projects within the homeowner's insurance domain, including coordination of cross-functional teams and delivery of business or system initiatives
• Project management certification (PMP, CAPM)
• Strong foundational understanding of project management principles (scope, schedule, cost, risk)
• Working knowledge of Agile/Scrum delivery within a project-managed environment
• Clear and professional communication skills with both technical and business stakeholders
• Strong organizational and time management skills with attention to detail
• Ability to manage multiple tasks and priorities in a structured, deadline-driven environment
• Proficiency in tools like JIRA, Trello, Miro, Smartsheet, or MS Project