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.

Education and Experience

• Bachelor’s degree in Business, Economics, Healthcare Management, or a related field required.
• MBA or advanced degree (or equivalent experience) preferred.
• Eight (8) to twelve (12)+ years of relevant professional experience in product operations or senior operational leadership roles.
• Proven track record of leading complex, cross-functional initiatives from strategy through execution.
• Experience in B2B SaaS, healthcare technology, or regulated technology environments strongly preferred.
• Experience in private-equity-backed or value-creation-focused organizations is a plus.
• Demonstrated experience partnering with executive leadership and influencing at the C-suite level.\

Skills, Knowledge, and Abilities

• Ability to translate strategy into executable plans and measurable outcomes.
• Ability to design and institutionalize operating mechanisms that scale predictability and performance.
• Trusted communicator who can influence, align, and challenge leaders at all levels.
• Skilled at managing complex initiatives, dependencies, and tradeoffs.
• Effective at building alignment and momentum in evolving environments.
• Comfortable using metrics, financial analysis, and insights to guide decisions.
• Builds trust and navigates ambiguity with confidence.
• Maintains rigor while operating across strategic and tactical levels.
• Ability to travel up to 20%

Work Environment/Physical Demands

• While at work, this position is primarily a sedentary job and requires that the associate be able to work in an environment where they will consistently be seated for the majority of the workday
• This role requires that one can sit and regularly type on a keyboard for the majority of the workday
• This position requires the ability to observe a computer screen for long periods of time to observe their own and others’ work, as well as incoming and outgoing communications via the computer and/or mobile devices
• Must be able to work remotely, manage workload efficiently, prioritize projects with minimal supervision, and maintain a quiet setting while working with customers
• The role necessitates the ability to listen and speak clearly to customers and other associates
• This role requires up to 20% travel

Here’s what we can offer you in exchange for your amazing work:

• Competitive pay and incentive plan
• Medical, dental and vision benefits
• Matching 401(k) 
• Open paid time-off programs
• Education reimbursement
• Growth potential for your career
• Corporate discounts

At Greenway, we strive to imagine, empower, engage, and inspire. Join us!

To learn more about Greenway, take a video tour of our office, and meet our employees, visit us at www.GreenwayHealth.com/careers.

Disclaimer: This Job Summary indicates the general nature and level of work expected of the incumbent(s). It is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities required of the incumbent. Incumbent(s) may be asked to perform other duties as requested. Greenway Health, LLC is an Equal Opportunity Employer. We do not discriminate on the basis of race, religion, age, gender, national origin, sexual orientation, disability, or veteran status. 

While this position is primarily remote, please note that if you reside within a 26-mile radius of our corporate office, you will be required to work in a hybrid capacity. This means you will be expected to work on-site at the corporate office for part of the week and remotely for the remainder. This hybrid arrangement is designed to foster team collaboration and engagement. Our corporate office is located at 4301 Boy Scout Blvd, Tampa, FL 33607. Please consider your proximity to this location when applying.

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