Director, Program Management

This is a fully remote position, open to applicants in United States, +1 more country.

📋 Description

• Act as a senior escalation contact and trusted advisor for clients of PayIt Outdoors.

• Foster relationships with executives from state agencies and program sponsors.

• Present delivery status, risks, and project roadmaps during executive business reviews.

• Convert client priorities into realistic expectations concerning scope, timeline, and quality.

• Oversee end-to-end delivery by coordinating implementation, product, and engineering teams.

• Identify, resolve, or escalate any portfolio dependencies and conflicts.

• Align delivery roadmaps with client commitments effectively.

• Design and facilitate status cycles, steering committees, risk reviews, and launch readiness gates.

• Create and maintain program management frameworks, including RAID logs, status taxonomies, escalation paths, and definitions of delivery health.

• Enhance delivery processes and transform recurring issues into permanent solutions.

• Develop standardized project reporting frameworks for hybrid SaaS solutions.

• Generate client-facing status reports and executive summaries.

• Maintain dashboards for portfolio status and delivery scorecards.

• Drive plans for portfolio risk mitigation.

• Conduct root-cause analyses following missed deadlines or escalations.

• Mentor and manage program and project managers as the portfolio expands.

• Recruit, coach, and develop talent in program management.

⛳️ Requirements

• 8–12+ years of experience in program or project management, including the simultaneous management of multiple complex, client-facing implementations.

• Ability to work credibly with C-suite/executive stakeholders and daily project teams.

• Proven experience in establishing delivery governance, reporting structures, status cadences, escalation frameworks, and portfolio-level visibility.

• Experience collaborating across product and engineering teams.

• Technical proficiency to comprehend delivery risks.

• Exceptional written and verbal communication skills.

• Strong organizational skills and commitment to follow-through.

• Bachelor’s degree or equivalent experience is required.

• PMP, PgMP, or similar certification is mandatory.

• Experience with state or local government clients, GovTech, or regulated public-sector procurement and delivery environments.

• Familiarity with outdoor recreation, licensing, permitting, DMV, or similar agency systems.

• Experience in scaling a PMO or delivery function.

• Knowledge of tools such as Jira, Smartsheet, Monday.com, Confluence, Power BI, Tableau, or similar delivery/reporting software.

• U.S. citizens and individuals authorized to work for any employer in the U.S. may apply; no U.S. sponsorship is available.

• Canadian citizens and those authorized to work in Canada without sponsorship may apply.

🏝️ Benefits

• Bonus Pay.

• Competitive salaries.

• Excellent benefits.

• Flexible working arrangements.

• Resources necessary for optimal performance.

• Corporate volunteer program.

• Opportunities for professional growth through engaging and challenging work.