Director of Program Management

About Us: DailyPay is transforming the way people get paid. As a worktech company and the industry’s leading on demand pay solution, DailyPay uses an award-winning technology platform to help America’s top employers build stronger relationships with their employees. This voluntary employee benefit enables workers everywhere to feel more motivated to work harder and stay longer on the job while supporting their financial well-being outside of the workplace. DailyPay is headquartered in New York City, with operations throughout the United States as well as in Belfast. For more information, visit DailyPay's Press Center.

We are seeking a highly experienced and strategic Director of Program Management to lead our Program Management Office (PMO) and the delivery of the company’s most important and complex enterprise-level initiatives. You will orchestrate project activities, from resource allocation to risk management, while fostering an environment that enables project managers and their teams to excel. This pivotal role will be responsible for defining, implementing, and driving a new product roadmap planning process that ensures accountability, tracks changes, and focuses on the most strategic initiatives across our diverse business units. The ideal candidate will be a true leader and driver of these processes, fostering company-wide adoption and clearly defining the role and responsibilities of the PMO.

Key Responsibilities

Team Leadership and Development - Manage, mentor, and develop a team of seven program managers, fostering a culture of excellence, collaboration, and continuous improvement.

• Establish and champion best practices, technical repositories, and effective mechanics for the Program Management team.

• Build, mentor, and lead a high-performing team of technical program managers, fostering a culture of excellence, accountability, and continuous improvement.

• Recruit, onboard, and retain top talent, contributing to the growth and development of the program management function.

Strategic Product Roadmap Planning - Promulgate and lead the implementation of a new product roadmap planning process that holds leadership accountable to their roadmap commitments.

• Oversee the end-to-end development of the product roadmap and go-to-market program, ensuring on-time, on-budget, and high-quality delivery.

• Develop and implement mechanisms for tracking changes to the product roadmap and ensuring alignment with strategic objectives.

• Highly engaged in, and providing support for, PMO team as they drive the most strategic initiatives within various business units, ensuring timely execution and successful delivery.

Stakeholder Engagement and Accountability - Serve as a key stakeholder to business leadership, ensuring clear understanding, agreement, and appropriate budgeting/staffing for committed work.

• Serve as a primary point of contact for executive stakeholders, providing regular updates on program status, risks, and strategic implications.

• Develop and deliver clear, concise, and compelling presentations to various audiences, including executive leadership, technical teams, and external partners.

• Champion cross-functional collaboration, ensuring alignment and effective communication across all contributing teams.

Process Adoption and Communication - Lead company-wide adoption of new program management processes and methodologies.

• Implement and continuously improve program management methodologies within the PMO team.

• Ensure clarity and accountability across all phases of the product lifecycle, including ideation, design, development, testing, deployment, and post-launch optimization.

• Proactively identify and mitigate technical and operational risks, developing contingency plans to ensure program success.

• Facilitate effective communication and collaboration between technical and non-technical stakeholders, bridging potential gaps.

Qualifications

• Proven experience in a senior program management role, with a strong track record of leading and developing high-performing teams.

• Extensive experience in or working closely with product and engineering teams, especially in relation to product roadmap planning, execution, and change management.

• Demonstrated ability to influence and collaborate with executive leadership and cross-functional teams.

• Strong understanding of budgeting, resource allocation, and project staffing.

• Exceptional communication, presentation, and interpersonal skills.

• A true leader and driver with the ability to inspire and motivate others towards common goals.

• Strong proficiency in program management software and tools, as well as product development tools like JIRA.

• PMP, CDP, CPMP, APO/CSM, or other relevant certifications are a plus.

What You'll Bring

• A strategic mindset with the ability to see the big picture while paying attention to critical details.

• A passion for building efficient processes and driving organizational change & adoption.

• The ability to navigate complex organizational dynamics and build strong relationships.

• A commitment to continuous improvement and fostering a culture of accountability.

What We Offer:

• Exceptional health, vision, and dental care

• Opportunity for equity ownership

• Life and AD&D, short- and long-term disability

• Employee Assistance Program

• Employee Resource Groups

• Fun company outings and events

• Unlimited PTO

• 401K with company match