Director of Program Management, PayIt

• 8–12+ years of program or project management experience, including managing multiple concurrent, complex, client-facing implementations simultaneously
• Demonstrated ability to operate credibly with C-suite/executive stakeholders and with day-to-day project teams – you can run a steering committee and a stand-up in the same day
• A track record of building (not just following) delivery governance: reporting structures, status cadences, escalation frameworks, and portfolio-level visibility
• Experience working across product and engineering organizations, with enough technical fluency to understand delivery risk without needing it translated
• Excellent written and verbal communication; you can turn a messy delivery reality into a clear, confidence-building narrative for a client executive or a PayIt SVP
• A bias toward organization and follow-through – things don't fall through the cracks on your accounts
• Bachelor's degree or equivalent experience; PMP, PgMP, or similar certification required

Desirable

• The Director, Program Management is the connective tissue between PayIt's executive leadership, client executives, and the implementation, product, and engineering teams delivering for PayIt Outdoors clients
• This person keeps the delivery engine running: an organized, predictable, and transparent way of shipping commitments across a portfolio of concurrent state agency engagements
• They are equally comfortable in a steering committee with a state agency director and in a working session with an implementation lead debugging a launch blocker – and they know when each posture is needed
• This is a hands-on leadership role, not a purely strategic one
• The right person builds and runs the cadences, reporting, and governance that make a multi-client delivery portfolio predictable, while personally stepping in on the accounts and escalations that need it most
• Serve as a senior escalation point and trusted advisor for PayIt Outdoors clients, building relationships with state agency executives and program sponsors
• Represent delivery status, risk, and roadmap in executive business reviews – both with clients and with PayIt's leadership team
• Translate between client priorities and internal delivery capacity, setting realistic expectations and holding the line on scope, timeline, and quality
• Own end-to-end coordination across implementation, product, and engineering teams for every active PayIt Outdoors client engagement
• Identify dependencies and conflicts across the client portfolio early – shared engineering capacity, competing launch dates, overlapping resources – and resolve or escalate them before they become blockers
• Partner with product and engineering leadership to align the delivery roadmap with what has been committed to clients, and flag gaps in both directions
• Design and run the operating cadence for the Outdoors delivery organization: status cycles, steering committees, risk reviews, and launch readiness gates
• Build and maintain a consistent, repeatable program management framework (RAID logs, status taxonomy, escalation paths, definitions of "on track," "at risk," and "red") so every account is tracked the same way
• Continuously improve the delivery process based on what breaks – turning one-off fire drills into permanent process fixes
• Develop a project reporting framework suitable for hybrid SaaS solutions that can be efficiently replicated across projects
• Produce client-facing status reports and executive readouts that are accurate, timely, and honest about risk
• Build and maintain internal reporting (portfolio dashboards, delivery scorecards) that gives PayIt executives a real-time, trustworthy view of the entire Outdoors book of business
• Ensure reporting flows both ways: client-facing commitments are visible internally, and internal capacity/risk is reflected in what clients are told
• Maintain a live view of risk across the portfolio and drive mitigation plans, not just risk logs
• Lead root-cause reviews after missed dates or escalations, and ensure fixes stick
• Mentor and, as the portfolio grows, manage a team of program and project managers; set the standard for how they run their accounts
• Hire, coach, and develop program management talent to keep pace with the growth of the Outdoors business