Retail Operations Project Manager Jobs in Boca Raton, FL

Position Summary:

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.

Essential Functions:

• 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.

Why Windward Risk Managers:

• Windward Risk Managers is proud to be recognized on Fortune's 2026 Best Medium Workplaces list, ranking #28 among the Top 100 companies
• 100% employer paid health insurance for employees
• Up to 6% 401(k) match with immediate vesting
• Long-term and short-term disability insurance
• 3 weeks PTO to start + generous paid holidays
• Tuition reimbursement and continuing education support
• Collaborative and growth focused culture

Required Education and Experience:

• 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.

Preferred Qualifications:

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

Essential Skills:

• 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.
   

Due to current business and operational considerations, we currently hire employees residing in the following states at this time: AL, AR, CA, CT, FL, GA, KY, MO, NC, NV, OH, SC, TN, TX, VA, and WI.
Candidates must be authorized to work for any employer in the U.S. without requiring visa sponsorship now or in the future.
WRM is committed to providing equal employment opportunities to all employees and applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, disability, or veteran status. We take affirmative action to ensure that all employment decisions are based on merit, qualifications, and abilities.
Notice to Third Party Agencies: WRM does not accept unsolicited resumes from third party recruiting firms. Absent a signed Service Agreement by WRM’s Human Resources Department, WRM reserves the right to pursue and hire these candidates without financial obligation to recruiters or agencies.