JOB OVERVIEW

As the Project Manager, you will oversee end-to-end execution, sprint planning, and workflow governance across all six pillars of our Digital department: Software Development, Product Management, Design, Business Intelligence, Digital Marketing, and IT. Working directly under the Director of Technology, you will translate strategic directives into structured execution roadmaps, optimize cross-functional intake processes, and keep multi-disciplinary projects moving on deadline.

You will serve as the central operational engine—eliminating execution bottlenecks, aligning internal teams and contractors, and providing transparent reporting to executive leadership to ensure our technology stack scales predictably and efficiently.

This is an independent contractor position, offering the flexibility to work from anywhere within the United States.

Contract consists of a competitive hourly rate with approximately 120-160 hours available per month, depending on the agreed-upon hourly rate.

RESPONSIBILITIES

● Project Management & Process Optimization: Oversee and continuously improve project management processes across Software Development, Product, Design, BI, Digital Marketing, and IT. Manage ClickUp governance, workflows, and reporting.

● Sprint & Workflow Management: Lead sprint planning, backlog refinement, task allocation, and cross-functional handoffs to maintain project momentum and delivery.

● Timeline & Risk Management: Develop project schedules, track milestones and dependencies, identify risks, and proactively address roadblocks to keep initiatives on schedule.

● Stakeholder Communication: Serve as the operational link between teams, contractors, and leadership, providing clear updates on project health, priorities, risks, and milestones.

● Intake & Priority Management: Manage incoming requests, align priorities with business goals and team capacity, and prevent scope creep.

● Documentation & Resource Coordination: Maintain project documentation, decision and risk logs, SOPs, budgets, contractor resources, and vendor deliverables.

● Quality & Launch Readiness: Coordinate QA, UAT, approvals, and cross-functional launch readiness for digital initiatives and system enhancements.

● Team Facilitation: Lead standups, planning sessions, sprint reviews, and retrospectives while driving accountability and effective collaboration.

● Continuous Improvement: Monitor project and operational metrics, evaluate outcomes, and implement Agile, Lean, and AI-assisted practices to improve efficiency and execution.

QUALIFICATIONS

● 3+ years of professional project management experience directly leading cross-functional teams in a digital, software development, or technology-focused environment.

● Demonstrated command of project management frameworks and tooling, with deep hands-on expertise in ClickUp (or equivalent platforms like Jira/Asana) for backlog, sprint, and dashboard management.

● Proven track record managing multi-disciplinary projects spanning software development, product backlogs, UI/UX design systems, BI analytics, digital marketing campaigns, and IT operations.

● Strong understanding of Agile/Scrum methodologies, sprint planning, roadmap development, and technical requirement intake.

● Exceptional stakeholder management and communication skills, with experience synthesizing technical details into clear executive updates.

● Strong documentation discipline, with proven capability crafting project plans, decision logs, SOPs, and workflow diagrams.

● Must be proactive, detail-oriented, and resourceful, capable of bringing order to complex initiatives in a fast-paced environment.

Preferred

● Project Management Professional (PMP), Certified ScrumMaster (CSM), or equivalent certification.

● Prior experience in real estate platforms, multi-brand digital environments, e-commerce, or SaaS technology operations.

● Experience managing a blended bench of full-time employees and remote contractors across multiple U.S. time zones.

● Familiarity with modern technology stack workflows, data warehousing, CRM integrations (e.g., HubSpot), and AI-assisted workflow tooling.

Pay: $42.00 - $45.00 per hour

Expected hours: 32.0 – 38.0 per week

Work Location: Remote

Whitetail Properties Real Estate

Latest Jobs

Project Manager