[Hiring] Director, Program Management @PayIt

Role Description

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.

What You'll Do

• Executive & Client Relationship Management
  • 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.
• Cross-Functional Delivery Orchestration
  • 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.
• Program Governance & the Delivery Engine
  • 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.
• Reporting & Communication
  • 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.
• Risk & Issue Management
  • 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.
• Team Leadership
  • 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.

Qualifications

• 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.

Nice to Have

• Experience with state or local government clients, GovTech, or regulated public-sector procurement and delivery environments.
• Experience with outdoor recreation, licensing, permitting, DMV, or similar agency systems.
• Experience scaling a PMO or delivery function through a period of client/portfolio growth.
• Familiarity with delivery and reporting tooling such as Jira, Smartsheet, Monday.com, Confluence, and BI/dashboarding tools (e.g., Power BI, Tableau).

Benefits

• Our mission matters. Your work will make life better for our government agency clients and the millions of residents they serve.
• You’ll do some of the best work of your career here. We tackle complex challenges that are interesting to solve, and you’ll grow a ton working at PayIt.
• People are our most important resource. Everyone has a voice. Collaboration is our default setting. And we have fun together.
• We #payitforward with our corporate volunteer program, serving the communities where we work and live.
• Competitive salaries, excellent benefits, flexible working arrangements, and all the resources you will need to do your best work.

Commitment to Equal Opportunity

PayIt is committed to diversity in its workforce and is proud to be an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, creed, gender, national origin, age, disability, veteran status, sex, gender expression or identity, sexual orientation or any other basis protected by applicable law.