Greenway Health is seeking a high-impact Director of Product Operations to establish and lead the operating model for the Product & Technology organization. This leader is accountable for making product delivery predictable, measurable, and value-driven at enterprise scale.

Reporting to the CPTO, the Director defines and institutionalizes the operating mechanisms and decision frameworks that govern Product & Technology investment, prioritization, and execution. This role owns portfolio governance, performance management, operating rhythms, and value realization, ensuring product investments translate corporate priorities into disciplined execution and measurable business outcomes.

Success in this role means delivering transparent portfolio economics, reliable roadmap commitments, and clear ROI from product initiatives. The ideal candidate is a systems-oriented operator and change leader who thrives in complex SaaS environments and is passionate about modernizing product development through data, automation, and AI-enabled workflows.

Essential Duties & Responsibilities

Product Operations, Planning & Portfolio Governance

• Own the enterprise product planning process, ensuring capacity-based prioritization, explicit tradeoff decisions, and alignment to financial and value-creation targets.
• Own portfolio performance and health, including investment allocation, ROI visibility, capacity utilization, customer impact, and technical debt balance.
• Establish and track leading and lagging indicators for roadmap predictability (e.g., plan vs. actual delivery, scope volatility, cycle time, throughput).
• Deliver standardized, data-driven executive reporting on roadmap predictability, value realization, portfolio ROI, and organizational productivity.

Strategic Execution & Enterprise Initiatives

• Serve as accountable executive operator for high-priority, cross-functional initiatives ensuring clear ownership, measurable milestones, disciplined execution, and transparent reporting.
• Identify, assess, and mitigate risks that could impact delivery, value realization, or organizational alignment.
• Drive accountability and execution rigor across initiatives with multiple stakeholders and dependencies.
• Drive post-launch value realization reviews to confirm expected business and customer outcomes are achieved.

Product & Technology Leadership Enablement

• Provide structured analytical insight and performance transparency that enables Product and Technology leaders to make faster, higher-quality investment and execution decisions
• Establish and standardize operating rhythms (OKRs, QBRs, roadmap reviews, capacity reviews) to ensure alignment, accountability, and outcome visibility.

Champion AI-Enabled Productivity & Operational Excellence

• Lead the evaluation, pilot, and scaled adoption of AI-powered tools across Product Management, UX Design, and Engineering.
• Identify opportunities for automation and process optimization to improve productivity, quality, and speed to market.
• Define governance and success metrics to ensure responsible, measurable impact from AI-enabled initiatives.
• Define baseline productivity metrics and quantify measurable improvements resulting from AI-enabled tools and process automation.

Build and Lead a High-Performing Team

• Build a lean, high-leverage team focused on analytics, portfolio governance, and execution excellence.
• Foster a culture of accountability, continuous improvement, and results-driven execution.
• Coach team members to effectively partner with senior leaders and cross-functional stakeholders.