Project Manager/Scrum Master

ABOUT THE PRODUCT 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. KEY RESPONSIBILITIES: 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. Collaborate closely with product, engineering, design, QA, and business teams to ensure smooth execution. 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. Facilitate effective collaboration and alignment between cross-functional teams. 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. Take a hands-on approach when required by diving deep into solutions. Ensure teams follow quality standards, security practices, and scalable execution methodologies. Balance execution speed with quality and operational efficiency. REQUIRED QUALIFICATIONS: 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. Excellent stakeholder communication and coordination skills. 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. Ownership mentality with high accountability and bias for action. Strong work ethic, integrity, and collaborative mindset. Willingness to learn and adapt to evolving technologies and workflows. GOOD TO HAVE: Lead teams from the front with ownership and accountability. Do not need to be an expert in every technology but should understand systems and workflows well enough to ask the right questions and provide detailed feedback. Ability to maintain structure while enabling teams to move fast. Strong communicator who can work effectively across technical and non-technical teams. Someone who naturally solves problems instead of escalating everything. WHY JOIN US? High-energy team enthusiastic about disrupting a massive industry Highly inclusive and collaborative culture built on mutual respect Focus on core values, initiative, leadership, and adaptability Strong emphasis on personal and professional development Opportunity to build AI-first products that create real business leverage Flexibility to work remotely About WIN 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.

Our Culture

Our colleagues are driven by curiosity and tinkering and a desire to make an impact. 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. Click here to learn more about our company and culture: https://www.linkedin.com/company/winhomeinspection/life Apply To This Job