Head of Project Management (Remote)

Project Manager

About The Project Manager Role:

WIN is looking for a proactive and execution-focused Project Manager who can drive projects end-to-end, remove blockers quickly, manage timelines efficiently, and ensure strong collaboration across teams.

We are looking for someone who can lead from the front, a structured thinker who understands technology well enough to hold teams accountable, provide meaningful feedback, and ensure smooth execution without unnecessary process overhead.

Organize and manage end-to-end execution of multiple SaaS-based projects and priorities with strong ownership.

Define project scope, timelines, deliverables, dependencies, and responsibilities across teams.

Define and manage project roadmaps in coordination with stakeholders and development teams.

Drive day-to-day project execution and ensure timely delivery across all phases.

Identify blockers, risks, and operational gaps proactively and ensure timely resolution.

Maintain and manage release sheets, sprint trackers, project documentation, and status reports.

Communicate project progress, timelines, dependencies, and risks clearly to stakeholders and leadership.

Lead project planning meetings, sprint reviews, stand-ups, and delivery discussions.

Ensure accountability across teams through regular follow-ups and structured execution processes.

Review workflows, suggest process improvements, and implement best practices in project planning and execution.

Ensure teams follow quality standards, security practices, and scalable execution methodologies.

Balance execution speed with quality and operational efficiency.

5+ years of experience in Project Management, Program Management, or Delivery Management roles.

• Strong expertise in utilizing project management and collaboration tools such as Jira, Confluence, Asana, Trello, and similar platforms for sprint tracking, release management, documentation, and execution planning.
• Experience managing SaaS-based, cloud-driven, and AI-powered products/projects.
• Strong understanding of software development lifecycle and agile execution processes.
• Hands-on experience managing teams working on AI-driven products, integrations, or intelligent automation workflows.
• Strong problem-solving, planning, and organizational abilities.
• Ability to manage multiple projects, teams, and shifting priorities simultaneously.
• Structured thinker with strong process orientation and execution mindset.
• Ability to maintain structure while enabling teams to move fast.

Strong emphasis on personal and professional development

Flexibility to work remotely

Founded in 1993, WIN is a highly innovative Proptech company, building new disruptive software platforms and products for the massive real estate industry. We have the stability and brand recognition as a 30-year old company along with the curiosity and energy of a start-up. We are an Entrepreneur 500 company, Entrepreneur Fastest Growing company, and recognized as the Most Innovative Home Services Company.

They enjoy a culture of high energy and collaboration where we listen to each other with empathy, experience personal and professional growth, and celebrate small victories and big accomplishments.