About Simplify Healthcare: Simplify Healthcare, a Simplify Group company, is a leading healthcare technology company focused on transforming how U.S. health plans (Payers) operate across benefits, provider, and claims functions. We build cloud-based, AI-driven SaaS platforms that modernize core payer workflows and enable scalable, compliant, and efficient operations. Our flagship platform, Simplify Health Cloud™, brings together enterprise-grade solutions for product configuration, benefits administration, provider lifecycle management, claims operations, and experience orchestration. Designed specifically for the U.S. health insurance ecosystem, our platforms are built to support real-world regulatory complexity, operational scale, and continuous change. Headquartered in Chicago, with a Global Development & Delivery Center in Pune and a global workforce of 900+ professionals, Simplify Healthcare supports more than 70 U.S. health plans. We are a bootstrapped, debt-free organization with over 18 years of profitable growth, combining long-term stability with a strong execution culture. Our work has been consistently recognized by Deloitte (Technology Fast 500™), Inc. (Inc. 5000), FORTUNE, IDC, and Gartner. As we enter our next phase of growth, we continue to invest in applied AI, platform modernization, and leadership talent to shape the future of payer technology. About the Role: We are looking for a driven and experienced Senior Project Manager to lead complex, high-impact technology initiatives across our organization. In this role, you will be at the center of our digital transformation — including spearheading the company-wide adoption of AI tools and processes. You will work cross-functionally to align teams, manage stakeholders, and deliver results on time and at scale. Key Responsibilities: Project Leadership & Delivery Own end-to-end delivery of multiple concurrent software and technology projects, from initiation through closeout. Define project scope, goals, milestones, and success metrics in collaboration with executive sponsors and technical leads. Proactively identify risks and dependencies, developing mitigation plans to keep projects on track. AI Transformation & Change Management Lead change management efforts for the company-wide rollout of AI tools and workflows, ensuring smooth adoption across departments. Develop and execute change management plans including stakeholder impact assessments, communications strategies, and training programs. Serve as a bridge between technical teams building/deploying AI solutions and the business units adopting them. Monitor adoption metrics post-launch and iterate on enablement strategies to drive sustained change. Agile / Scrum Practice Champion Agile methodologies across project teams, facilitating sprint planning, retrospectives, standups, and backlog grooming sessions. Coach team members and stakeholders on Agile best practices and continuously improve team velocity and delivery quality. Adapt Agile frameworks pragmatically to fit the needs of each project and team. Utilize burndown and burnup charts to track team progress, forecast project completion dates, and surface risks early — communicating trends and course-correction plans to stakeholders in a clear, data-driven way. Stakeholder Communication Build and maintain strong relationships with senior leadership, business stakeholders, and external partners. Deliver clear, concise, and audience-appropriate project updates — including executive-level status reports and dashboards. Facilitate alignment across competing priorities and manage stakeholder expectations with transparency and confidence. Team Leadership Lead and inspire cross-functional project teams, fostering a culture of accountability, collaboration, and continuous improvement. Mentor junior project managers and contribute to the development of PM standards and practices across the organization. Act as a servant leader — removing blockers and creating the conditions for teams to do their best work. Qualifications: Required 12+ years of project management experience, with at least 6+ years in a tech or software environment. Demonstrated experience leading organizational change management initiatives, ideally involving technology adoption. Strong working knowledge of Agile/Scrum methodologies including burndown/up charts; experience as a Scrum Master is a plus. Exceptional communication and presentation skills, with a proven ability to influence at all levels of an organization. Experience managing cross-functional teams and navigating complex stakeholder landscapes. Hands-on experience managing AI, automation, or digital transformation projects. Proficiency with project management tools (e.g., Jira, Asana, , Confluence). Preferred PMP, PMI-ACP, CSM, or equivalent certification. Familiarity with change management frameworks such as Prosci/ADKAR. Experience working in a fast-paced, high-growth tech environment.
Job Title
Senior Project Manager