Director, Benefits Planning and Strategy - Remote

For our client, we are seeking a Director, Benefits Planning and Strategy to join the team of a leader in the Healthcare space. This role will lead benefits planning and strategy efforts that shape how complex healthcare offerings are designed, governed, and delivered. The director will translate regulatory requirements into practical business guidance while partnering with senior leaders and cross-functional stakeholders to align client needs, operating processes, and business outcomes. This position will also help modernize operating models, support annual readiness cycles, and contribute to the thoughtful use of AI to improve productivity and decision-making. Location: Remote - US based candidates only, no visa sponsorship available Compensation: $134,600 – $230,800 annually Responsibilities Serve as a thought leader on benefit administration and CMS guidance Translate complex CMS regulations into actionable business guidance Own governance for product strategy and execution Support annual sales and readiness cycles as a subject matter expert Ensure alignment between benefit designs, client needs, and operational processes Influence senior leaders to adopt customer outcome solutions Lead efforts to embed AI solutions and modernize operating models Qualifications 8+ years of experience in Medicare Advantage, Medicaid, benefits administration, and/or healthcare strategy Experience developing governance and operational processes in healthcare or financial services Expertise interpreting CMS guidance and translating regulations into business strategy Proven ability to influence senior leadership on complex decisions Strong executive presence and capability to simplify complex concepts for varied audiences Success in addressing ambiguous, enterprise-level business challenges Comfortable using AI tools to enhance productivity and decision-making Benefits Comprehensive benefits package Incentive and recognition programs Equity stock purchase options 401k contribution Flexible remote work opportunity from anywhere in the U.S. Our client is an equal opportunity employer. We encourage you to apply even if you don’t meet every qualification—your background could be exactly what this team needs.