Senior Principal Program Manager

At PlanSource, a leading cloud-based provider of benefits administration technology and services, we are on a mission to simplify how people choose, use, and manage benefits through cutting-edge, AI-powered experiences. This is an incredible time to launch your career with us!

We are seeking a strategic and experienced Sr. Principal Program Manager to lead the planning, coordination, and execution of cross-functional programs across our Benefits Administration platform. This high-impact role offers a unique opportunity to shape how we deliver value to clients, influence executive decision-making, and lead initiatives that define the future of our platform. You will serve as a thought partner and coach for project management best practices across the Product & Technology organization, while also driving operational excellence, change management, and program execution. You will be instrumental in standing up our Release Management function, optimizing operational processes, and driving change management initiatives. You will collaborate with Product, Engineering, Client Operations, Marketing, and Sales to ensure seamless delivery, communication, and adoption of new features and enhancements.

Responsibilities:

• Strategic Program Leadership: Drive the execution of complex, cross-functional programs that align with organizational goals and deliver measurable impact.
• Project Management Fluency: Champion project management best practices across Product & Technology, fostering consistency, scalability, and operational excellence.
• Cross-Functional Collaboration: Collaborate with Product Management, Engineering, Client Operations, Marketing, and Sales to ensure initiatives are well-communicated, commercialized, and operationalized.
• Release Management: Support the development and coordination of release planning and readiness activities, including timelines, documentation, enablement, and phased rollout strategies.
• Change Management Leadership: Lead organizational change initiatives and oversee training programs and documentation to facilitate adoption.
• Process Optimization: Develop, implement, and continuously improve processes and procedures to ensure efficiency and transparency.
• Performance Metrics and Reporting: Develop performance metrics and provide regular updates to executive stakeholders.
• Risk Management: Identify and mitigate risks and troubleshoot complex problems as they arise.
• Continuous Improvement: Champion continuous improvement in program and project management processes and tools.

Qualifications:

• 10+ years of experience in Benefits Administration, with a strong background in program and project management.
• PMP certification required; additional certifications such as Agile Practitioner or Scrum Master are a plus.
• Proven experience coordinating complex releases and programs across cross-functional teams.
• Strong understanding of Agile methodologies and tools such as Jira and Confluence.
• Excellent communication, organizational, and stakeholder management skills.
• Experience in a technology-driven, SaaS environment with a deep understanding of product development cycles.
• Strong analytical and problem-solving skills with a focus on process improvement and operational efficiency.
• Experience with change management and leading teams through transformation initiatives.
• Ability to thrive in a fast-paced, remote-first environment.

What we Offer:

• Great benefits package, including a full suite of health benefits, a generous 401(k) Plan, unlimited PTO, paid parental leave, a strong rewards and recognition program, and a focus on mental health and well-being.
• An inclusive environment with Employee Resource Groups to join, volunteering days and the ability to donate to organizations of your choice through our recognition platform.
• The opportunity to work for a growing, established technology company, but work side-by-side with a small, dynamic team of talented professionals.
• Fast-paced environment with big goals and the opportunity to make a big impact.

Top five reasons to come to PlanSource:

#5: Join the Vista Family. In March 2019, Vista Equity Partners acquired PlanSource, marking a new phase of growth. Vista’s portfolio of technology and software companies collectively make up the 4th largest software ecosystem in the world.

#4: PlanSource is highly rated with our customers. Be proud of our sophisticated cloud-based technology that meets the needs of even the most complex benefit programs.

#3: Success is rewarded. With more than just a pat on the back, your success is recognized and rewarded. We take care of our employees in every way we can, with comprehensive benefits, employee recognitions, and a commitment to wellbeing.

#2: You can grow and develop professionally. PlanSource has a great track record of internal promotions within the company and offering development plans and tracks to pursue your personal and professional goals.

#1: Share our values. Be part of a team that values diversity and representation in all levels of the organization. Be part of a team that gives back to local communities and is actively aware of their social and environmental impact.

PlanSource is committed to fostering, cultivating, and preserving a culture of diversity and inclusion. Our employees are the most valuable asset we have. The collective sum of the individual differences, life experiences, knowledge, inventiveness, innovation, self-expression, unique capabilities and talent that our employees invest in their work represents a significant part of not only our culture, but our reputation and company’s achievement as well.

We celebrate and support our employees’ diversity in age, color, disability, ethnicity, cultural beliefs, family or marital status, gender identity or expression, language, national origin, physical and mental ability, political affiliation, race, religion, sexual orientation, socio-economic status, veteran status and other characteristics that make our employees unique.

NOTE: We will consider a remote employee for approved cities PlanSource can accommodate.

If you’re selected, you’ll receive your offer and be asked to complete a background check. This will include a drug screen, criminal record search and verification of previous employment and/or education.

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