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Bring your best and truest self. We celebrate what makes us different and what brings us all together. At Greenway Health, we are committed to an inclusive environment and a culture of belonging as we pursue our purpose of healthier communities, successful providers, and empowered patients. We are united in our goal to build the future of healthcare technology. Join us.

As a Program Manager (AI Native), you will drive delivery across a multi-product program—owning cross-functional outcomes for a product line, anticipating problems before they surface, forcing timely decisions, removing blockers across teams, and holding product, engineering, and partner teams to their commitments. You are a driver and a doer: you act without waiting to be asked, you own the outcome, and you never confuse reporting on delivery with delivering. Status reporting is an output of this role, not the job itself.

You will operate in an environment with multiple products, many cross-functional stakeholders, and competing priorities. You will manage program scope, schedule, resources, communications, risks, issues, cross-product dependencies, roadmap capacity, and release readiness, and ensure that Wrike, Agility (or Jira or other ALM), Smartsheet, Domo, and related planning systems accurately reflect reality so they can be used to act, not just to report.

AI gives you leverage. You bring judgment. You remain accountable for validating AI-assisted outputs, protecting sensitive information, and making delivery decisions that are accurate, transparent, and aligned to business needs.

Key Outcomes

• Drive program, release, and roadmap commitments across multiple products and teams to completion, with predictable, on-time delivery.

• Get ahead of cross-product risks, dependencies, and slippage—act on them and drive them to resolution before they become delivery problems.

• Force clarity on competing priorities: bring executives and stakeholders the decisions, trade-offs, and escalations needed to keep the program on track, not just status updates.

• Keep program delivery data in Wrike, Agility (or Jira or other ALM), Smartsheet, and Domo accurate, current, and traceable across products so it can be used to make decisions and trigger action.

• Ground program and release commitments in real team and roadmap capacity across the product line.

• Ensure every release is ready across product, engineering, and cross-functional teams.

• Use AI, analytics, and approved agentic AI tools responsibly to anticipate risks, forecast capacity, and accelerate delivery decisions.

Success Measures / Accountable Outcomes

• Program and release commitments across the product line are met with strong say/do, predictability, and minimal spillover.

• Project Managers assigned to the product line’s delivery teams, whether direct or dotted-line reports, consistently meet their delivery commitments and keep their project data accurate and current.

• Cross-product risks, issues, dependencies, and slippage are anticipated early and driven to resolution, not just surfaced.

• Competing priorities are resolved through timely, well-framed decisions; stalled decisions are escalated before they put delivery at risk.

• Wrike, Agility (or Jira or other ALM), Smartsheet, and Domo data is accurate, current, and traceable, with the program RAID log updated at least weekly.

• Program and release commitments reflect real team and roadmap capacity.

• Releases are ready on time across all cross-functional teams.

• Agentic software development KPIs are tracked, understood, and acted on, so AI-agent contributions improve delivery speed and quality without adding hidden rework or risk.

• Executives and cross-functional stakeholders get timely decisions, trade-offs, and escalations that keep delivery on track, backed by transparent reporting on actual program health and progress.

• AI-assisted work is reviewed, validated, and used responsibly.

Essential Duties & Responsibilities

• Serve as the accountable program manager for a product line; own end-to-end program delivery outcomes across multiple products, teams, and releases.
• Hold the Project Managers assigned to the product line’s delivery teams accountable for their delivery commitments, whether they report directly to this role or on a dotted-line basis; set clear expectations, review their plans, RAID logs, and delivery data, intervene early when commitments are at risk, and escalate performance concerns to their line manager as needed.
• Plan and drive cross-organization programs using Agile and traditional program management practices; translate roadmap and portfolio priorities into integrated program plans, milestones, and release commitments.
• Personally drive the work forward: anticipate obstacles, identify cross-product trends before they become delivery problems, take early corrective action, and escalate when appropriate—without waiting to be asked.
• Navigate competing priorities across products and stakeholders; surface conflicts early, frame options and trade-offs, drive decisions to closure, and hold owners accountable for follow-through.
• Manage program scope, schedule, budget, resources, communications, cross-product and cross-team dependencies, and delivery progress.
• Regularly communicate with and manage expectations of executive stakeholders; represent the product line’s programs, plans, timelines, risks, and required decisions in a concise, action-oriented way.
• Serve on the product leadership team alongside development and product management; foster effective communication and alignment across product areas and cross-functional partners.
• Maintain accurate, current program information in Wrike, including release milestones and a program-level RAID log updated at least weekly; ensure risks, assumptions, issues, and dependencies across products are visible, owned, actively managed, and escalated as needed.
• Keep Smartsheet program plans, trackers, and status reporting updated so they accurately reflect current milestones, progress, risks, and dependencies, and use them to drive follow-through on actions and owners.
• Ensure Agility, Jira, or other ALM data is accurate and traceable across the product line, including correct release/project tagging, accurate capability and feature mapping, and alignment from roadmap and PRD capabilities through FDDs and execution artifacts.
• Partner with product, engineering, and leadership to manage roadmap and release capacity across multiple teams, including realistic commitments, sequencing, cross-team dependency impacts, and trade-off visibility; challenge commitments that are not grounded in real capacity.
• Drive risk management and impediment removal across products; distinguish risks from issues, assign owners and due dates, document decisions and actions, and escalate early with clear options and a recommendation.
• Use Domo and other approved reporting to monitor agile and delivery metrics across teams, including churn, say/do, quality, feature progress, spillover, and delivery health, along with agentic software development KPIs such as the share of work completed by AI agents, agent task success and acceptance rates, human review and rework rates, defect escape on AI-generated code, and cycle-time impact, to decide where to intervene; turn insights into specific actions with owners and dates rather than simply reporting status.
• Coordinate with cross-functional teams (product, engineering, quality, implementation, support, training, and go-to-market) to ensure release readiness; drive readiness gaps to closure before release.
• Coordinate and facilitate user-feedback sessions throughout the development life cycle, and ensure feedback is converted into actionable decisions.
• Keep the broader organization aware of the product line’s activities, upcoming releases, and impacts.
• Serve as a subject matter expert in work item tracking and project tracking software.
• Manage vendor contracts and relationships for the product line.
• Ensure compliance with regulatory requirements and maintain documentation for audit readiness.
• Follow established PMO and product delivery processes; evaluate and optimize processes within the PMO and product line, and lead improvements when a process is not achieving its intended outcome.
• Support development and implementation of agentic AI-enabled PMO workflows, including requirements input, workflow design, validation, adoption support, and ongoing performance monitoring.
• Mentor Project Managers and Agile Project Managers on proactive delivery practices and responsible AI use; may serve as a direct line manager for Project Managers.
• Model and foster a culture of ownership, accountability, innovation, transparency, continuous improvement, and learning.

AI Usage and Accountability Requirements

• Use approved AI-enabled and agentic AI tools to anticipate risks, forecast capacity, monitor team health across products, and accelerate planning and delivery decisions; use AI to reduce time spent compiling status so more time goes to driving outcomes.
• Review and validate AI-generated summaries, status reports, forecasts, risk assessments, and recommendations before use.
• Ensure underlying data quality, traceability, and governance support reliable AI-enabled insights.
• Do not expose confidential, customer, production, proprietary, credential, or restricted data through AI tools unless explicitly approved.
• Escalate inaccurate, incomplete, biased, insecure, or unclear AI outputs.
• Maintain human ownership of delivery decisions, commitments, escalations, and final deliverables.

Skills, Knowledge, and Abilities

• Expertise in the software development life cycle, preferably agile lifecycle management, including iterative development and continuous delivery within a scaled Agile model (SAFe, LeSS, Scrum at Scale, Disciplined Agile, etc.).
• Driver and doer: proactive, action-oriented, and accountable; anticipates problems, drives decisions to closure, and follows through personally without waiting to be asked.
• Comfortable operating in a multi-product environment, balancing many cross-functional stakeholders and competing priorities while keeping delivery on track.
• High expertise in program management practices, with emphasis on estimating, planning, dependency management, risk management, and servant leadership.
• Strong capacity planning, roadmap planning, and release management across multiple teams.
• Working proficiency with Wrike, Agility (or Jira or other ALM), Smartsheet, Domo, and Microsoft Office.
• Ability to maintain accurate, traceable program and execution data, including release milestones, RAID logs, capabilities, features, cross-product dependencies, and delivery commitments.
• Knowledge of team health and delivery metrics, including churn, say/do, quality, feature progress, spillover, capacity, and predictability indicators, as well as agentic software development KPIs (agent throughput, acceptance and rework rates, quality of AI-generated code, and cycle-time impact).
• Excellent written and verbal communication skills at all levels of the organization, including executive audiences.
• Strong interpersonal, facilitation, negotiation, critical thinking, and problem-solving skills.
• Experience in a matrixed resource environment and the ability to influence without direct authority.
• Knowledge of healthcare IT is extremely helpful.
• Experience as a people manager, leveraging a growth mindset approach, is a plus.
• Responsible use of approved AI-enabled tools to improve productivity, quality, and clarity.
• Work on issues requiring the analysis of data and relevant factors across multiple products and teams, and resolve problems.
• Exercise judgment and interpretation to help define procedures and policies and determine appropriate action.
• Make and drive timely decisions amid competing priorities and incomplete information; know when to decide and when to escalate.
• Work independently with minimal oversight on day-to-day work and new assignments, taking ownership without waiting for direction.
• Align and influence cross-functional stakeholders who do not report to the role.
• Communicate risks, issues, options, and trade-offs clearly, with a recommended course of action.
• Wrike, Agility (or Jira or other ALM), Smartsheet, Domo, Microsoft Office, agile collaboration tools, reporting and analytics tools, and approved AI-enabled and agentic AI productivity tools.

Work Environment/Physical Demands

• While at work, this position is primarily a sedentary job and requires that the associate can 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 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 in-coming and out-going communications via the computer and/or mobile devices
• The role necessitates the ability to listen and speak clearly to customers and other associates

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

• Competitive pay
• Medical, dental and vision benefits
• Matching 401(k)
• Generous 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.

If you are a resident of a state that requires pay transparency, please email us at recruiting@greenwayhealth.com to receive compensation and benefits information for this role. Be sure to include the Job ID in the subject line of your email.