Project Manager

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 an Agile Project Manager (AI Native), you will drive delivery for assigned product and development teams—anticipating problems, forcing timely decisions, removing blockers, and holding teams to their commitments using Agile and project management best practices. Status reporting is an output of this role, not the job itself. You will manage scope, schedule, resources, communications, risks, issues, dependencies, roadmap capacity, and release readiness, and ensure that Wrike, Agility, 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 project, release, and roadmap commitments to completion for assigned teams, with predictable, on-time delivery.
• Get ahead of delivery trends, risks, and slippage—act on them and drive them to resolution before they become delivery problems.
• Keep delivery data in Wrike, Agility, Smartsheet, and Domo accurate, current, and traceable so it can be used to make decisions and trigger action.
• Ground sprint and release commitments in real team and roadmap capacity.
• Bring stakeholders the decisions, trade-offs, and escalations needed to keep delivery on track, not just status updates.
• Use AI, analytics, and approved agentic AI tools responsibly to anticipate risks, forecast capacity, and accelerate delivery decisions.

Success Measures / Accountable Outcomes

• Delivery commitments are met with strong say/do, predictability, and minimal spillover.
• Wrike, Agility, Smartsheet, and Domo data is accurate, current, and traceable, with the RAID log updated at least weekly.
• Risks, issues, dependencies, and slippage are anticipated early and driven to resolution, not just surfaced.
• Sprint and release commitments reflect real team and roadmap capacity.
• Stakeholders get timely decisions, trade-offs, and escalations that keep delivery on track, backed by transparent reporting on actual team health and progress.
• AI-assisted work is reviewed, validated, and used responsibly.

Essential Duties & Responsibilities

• Plan and drive delivery of project, release, and roadmap outcomes for assigned product and development teams using Agile and traditional project management practices.
• Own delivery outcomes for assigned teams; understand commitments, anticipate obstacles, identify trends before they become delivery problems, take early corrective action, and escalate when appropriate.
• Manage scope, schedule, budget, resources, communications, dependencies, and delivery progress for assigned projects, products, teams, and releases.
• Maintain accurate, current delivery information in Wrike, including release milestones and a RAID log updated at least weekly; ensure risks, assumptions, issues, and dependencies are visible, actively managed, and escalated as needed.
• Keep Smartsheet project 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 data is accurate and traceable, 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 development team and roadmap capacity, including sprint capacity, release capacity, realistic commitments, sequencing, dependency impacts, and trade-off visibility.
• Ground sprint planning in real capacity, including proper sizing, available team capacity, planned time away, support load, and realistic commitments; help protect committed sprint work from unnecessary mid-sprint priority churn.
• Drive capability and feature commitments throughout the sprint and release lifecycle; anticipate and remove blockers, challenge unplanned scope changes, and intervene early on missed commitments, spillover risk, and delivery slippage.
• Use Domo and other approved reporting regularly for assigned teams, including churn, say/do, quality, feature progress, spillover, and delivery health, to decide where to intervene; turn insights into specific actions with owners and dates rather than simply reporting status.
• Actively mitigate risks and drive issues to resolution using standard project management practices; distinguish risks from issues, assign owners and due dates, document decisions and actions, and escalate early with clear options and a recommendation.
• Drive stakeholder decisions and trade-offs through clear communication, expectation-setting, decision tracking, and feedback loops; escalate when stalled decisions put delivery at risk.
• Support Agile ceremonies and team communications as appropriate, while remaining actively informed on team activity, blockers, commitments, and progress without unnecessarily duplicating Scrum Master responsibilities.
• Manage vendor contracts and relationships for the assigned product area.
• Ensure compliance with regulatory requirements and maintain documentation for audit readiness.
• Follow established PMO and product delivery processes; educate teams and stakeholders on expected practices and collaborate on process 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.
• Use approved AI-enabled and agentic AI tools to anticipate risks, forecast capacity, monitor team health, 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.
• Protect sensitive information; 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.
• Foster a culture of accountability, innovation, autonomy, transparency, continuous improvement, and learning within the team
  
  

Education and Experience

• Bachelor’s degree, preferably in Project Management, Software Development, IT, Cybersecurity, or a similar field; relevant experience may substitute for the degree requirement
• Project management certification desirable
• Experience using AI or analytics to forecast capacity, identify delivery risks, or monitor team health metrics.
• Two (2)+ years of experience in a project management role and six (6)+ years of overall work experience

Skills, Knowledge, and Abilities

• Working knowledge of Agile/Scrum and the software development life cycle, preferably agile lifecycle management
• Proactive, action-oriented delivery mindset: anticipates problems, drives decisions, and follows through without waiting to be asked
• Project management capability across scope, schedule, resources, communications, risks, issues, and dependencies
• Understanding of capacity planning, roadmap planning, and release management
• Working proficiency with Wrike, Agility, Smartsheet, Domo, and Microsoft Office, as well as agile collaboration tools, reporting and analytics tools, and approved AI-enabled and agentic AI productivity tools
• Ability to maintain accurate, traceable planning and execution data, including release milestones, RAID logs, capabilities, features, dependencies, and delivery commitments
• Knowledge of team health and delivery metrics, including churn, say/do, quality, feature progress, spillover, capacity, and predictability indicators
• Excellent written and verbal communication skills at all levels of the organization
• Strong interpersonal, facilitation, critical thinking, and problem-solving skills
• Experience in a matrixed resource environment
• Knowledge of healthcare IT is extremely helpful
• Responsible use of approved AI-enabled tools to improve productivity, quality, and clarity
• Ability to work on problems of moderate scope that are often varied and routine
• Ability to review situations or data across a variety of factors and determine appropriate action
• Ability to exercise judgment within defined procedures and practices
• Ability to apply learned techniques and contribute to analysis and investigation to solve problems
• Ability to work with little instruction on day-to-day work and general instructions on new assignments
• Ability to communicate risks, issues, options, and trade-offs clearly, with a recommended course of action

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 [email protected] to receive compensation and benefits information for this role. Be sure to include the Job ID in the subject line of your email.

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