Project Manager - Onsite/Hybrid or Remote

Windward Risk Managers•Boca Raton, FL

2d•$70,000 - $85,000•Hybrid

About The Position

We are 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, tracking risks and dependencies, and communicating status to stakeholders. The Project Manager will lead Scrum-based delivery activities as part of the overall project execution, ensuring work is planned, monitored, and delivered in alignment with business objectives.

Requirements

Bachelor’s degree in business, IT, or a related field.
Project management certification (PMP, CAPM)
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.
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.

Nice To Haves

Proficiency in tools like JIRA, Trello, Miro, Smartsheet, or MS Project

Responsibilities

Project Planning & Execution: Develop and maintain project plans, schedules, milestones, dependencies, and deliverables. Track progress against plans and support on-time, on-scope delivery.
Individual Work & Progress Tracking: Actively track each team member’s planned and completed work, including commitments made during daily stand-ups and sprint planning. Retain and follow up on prior-day and sprint-level commitments to ensure transparency, accountability, and forward momentum.
Delivery Awareness & System Understanding: 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.
Scope, Schedule & Resource Coordination: Assist in defining project scope, managing changes, and coordinating resources across cross-functional teams to meet delivery commitments.
Agile & Scrum Delivery Oversight: Lead Scrum ceremonies including sprint planning, daily stand-ups, sprint reviews, and retrospectives as part of the project execution framework. Ensure Agile practices are applied to support delivery predictability and transparency.
Stakeholder Management & Communication: 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.
Risk, Issue & Dependency Management: Identify, document, and track project risks, issues, and dependencies. Support mitigation plans and escalate concerns as needed to minimize delivery impacts.
Reporting & Documentation: Maintain project documentation, schedules, and status reports. Ensure project information is accurate, current, and accessible.
Delivery Governance & Controls: Support adherence to project management standards, processes, and governance requirements while ensuring alignment with Agile delivery practices.
Continuous Improvement: Capture lessons learned and contribute to process improvements to enhance project execution and delivery outcomes.