Director, Program Manager

PayIt; Kansas City (MO); On-site; USD 150,000 - 190,000; Full time

Benefits offered by this job

Remote-first working arrangements

Job summary

PayIt is seeking a Director of Program Management to lead a multi-client delivery portfolio for PayIt Outdoors. You will establish cadences, governance, and reporting while personally stepping in on critical accounts to unblock blockers and escalations.

This hands-on leadership role drives predictability across initiatives. You will manage executive relationships, coordinate across product and engineering, and align delivery with commitments.

Qualifications

• Bachelor's degree or equivalent; PMP, PgMP or similar certification preferred.
• 8–12+ years of program or project management experience with multiple concurrent client engagements.
• Ability to operate credibly with C-suite and executive stakeholders and with project teams.
• Experience across product and engineering; enough technical fluency to discuss delivery risk.
• Excellent written and verbal communication; ability to turn complex delivery into clear client narratives.

Responsibilities

• Serve as senior escalation point and trusted advisor for PayIt Outdoors clients; build relationships with executives and sponsors.
• Represent delivery status, risk, and roadmap in executive reviews with clients and leadership.
• Translate client priorities into internal capacity and manage scope, timeline, and quality.

Skills

Executive stakeholder management

Delivery governance

Cross-functional leadership

Program management

Communication skills

Portfolio visibility

Education

Bachelor's degree or equivalent

PMP/PgMP certification

Tools

Jira

Smartsheet

Monday.com

Confluence

Power BI/Tableau

Job description

PayIt builds digital government experience and payments technology that helps state and local agencies serve residents the way modern consumers expect to be served – fast, mobile, and simple. Through PayIt Outdoors, the company partners with state wildlife, parks, and natural resources agencies to modernize hunting, fishing, boating, and outdoor recreation licensing, permitting, and e-commerce. As the Outdoors portfolio has grown across multiple state agency clients, the business needs a director‑level program leader to make sure delivery scales without losing quality, transparency, or trust.

Our culture welcomes people who exhibit what we call “PayIt DNA”: High integrity, drive, grit, high aptitude, and team orientation. We are collaborative and passionate about the work we do to improve the lives of our government clients and the end users they serve. We have ambitious scaling goals, and we look for team members who are ready to roll up their sleeves, solve problems, and find new opportunities to win with our clients. And we have a lot of fun together.

About The Role:

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 elevate 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.
• 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.

What You'll Bring:

• 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.

Bonus Points For:

• 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).

Why Work For Us:

• 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, remote‑first working arrangements, and all the resources you will need to do your best work

What We Care About:

We hire high‑aptitude, high‑integrity people who are great communicators and want to be part of a growing team.

We’re about openness, integrity, accessibility and great communication.

We obsess over the usability of our products, sharing ideas with each other, and our commitments to the communities we serve

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.

PayIt is also committed to providing reasonable accommodations to individuals with disabilities. If you need a reasonable accommodation because of a disability for any part of the employment process, please send an email to the People Operations Team and let us know the nature of your request and your contact information.

NOTE: U.S. Citizens and all those authorized to work for any employer in the U.S. are encouraged to apply. We are unable to provide sponsorship in the United States at this time. PayIt participates in E-Verify. To learn more, click here. Canadian Citizens and those authorized to work in Canada without sponsorship are also encouraged to apply.

Within the parameters of this position, ensure the confidentiality, integrity, and availability, and exercise due care of, company, client, and citizen data that is stored, processed, and transmitted by and for PayIt, as outlined in PayIt’s Business Code of Conduct and Information Security Policies.