WorkMoney - Managing Director of Administration
Grossman Solutions
United States
USD 300k-350k / year
Posted on Dec 2, 2025
Reporting to: Managing Director
Location: United States / Remote, ~10–15% travel
Term: Full-Time, Exempt, requires U.S. work authorization
Compensation: $300,000-$350,000 Annually
Deadline: Applications will be considered on a rolling basis; Target start early 2026
About WorkMoney, Inc.
At WorkMoney.org, we are dedicated to enhancing the financial well-being of hardworking Americans. Founded on the belief that everyone deserves a fair shot at the American dream, we provide our members with the tools, resources, and support they need to navigate their financial journeys with confidence.
We don't stop at individual support. At WorkMoney, we believe in systemic change and actively advocate for policies that promote economic fairness and opportunity. By amplifying the voices of our members and engaging policymakers, we strive to create a more just and equitable economic landscape.
We believe that financial stability should be accessible for everyone — and we're here to make that a reality. By offering practical tools, fostering a supportive community, and championing policy changes, we empower our members to take control of their finances and build a more secure future.
Join us at WorkMoney, Inc. and become part of an organization dedicated to making sure all Americans can afford to live a good life.
Why do we need a Director of Administration?
WorkMoney is entering an exciting new phase of growth, expanding our programs, deepening partnerships, and reaching millions more members. To support this momentum, we must strengthen the internal systems, talent, and infrastructure that make our mission possible. As our work grows in reach and complexity, we need a senior operational leader who can ensure our structures, people, and processes evolve in step with our ambitions.
The Managing Director of Administration will serve as the organization’s chief operational steward, providing strategic leadership and operational excellence across finance, legal affairs, people and culture, administration, and organizational infrastructure. This leader will ensure our internal operations are efficient, values-driven, resilient, and designed for scale.
This is a pivotal role for an accomplished executive who excels at turning strategy into action. The ideal candidate brings operational rigor, people-centered leadership, and a systems-oriented mindset. They will help guide WorkMoney’s evolution, ensuring we remain grounded in our mission while equipped to deliver greater impact, sustainably and at scale.
Key Responsibilities
Organizational Leadership & Executive Partnership
Finance & Administration
Legal & Governance
People, Culture & Talent
Organizational Infrastructure, Technology & Systems
Leadership, Supervision, and Team Development
Mission & Values Alignment. You are deeply committed to WorkMoney’s mission to improve the financial well-being of hardworking Americans and bring empathy, integrity, and urgency to this work.
Operational and Financial Leadership. You have demonstrated success overseeing complex operational, financial, and administrative systems. You know how to scale organizations thoughtfully and sustainably, balancing long-term planning with day-to-day execution in a fast-moving environment.
Strategic Judgment & Prioritization. You are skilled at seeing the big picture while sequencing priorities and making trade-offs amid competing demands. You bring focus, foresight, and calm to moments of complexity or change.
People and Culture Expertise. You have significant experience leading HR, people, and talent functions, and believe organizational culture is a strategic asset. You have successfully managed teams with varied professional experiences and worked effectively in unionized environments, including participating in or leading collective bargaining processes.
Leadership & Collaboration. You are an adaptive and inclusive leader who thrives in dynamic, fast-moving environments. You build trust across differences, lead with empathy and equity, and bring steadiness amid change. You partner effectively with senior executives and teams alike—aligning strategy, structure, and execution while fostering clarity, accountability, and shared purpose.
Emotional Intelligence. You navigate complexity with composure, self-awareness, and care. You inspire trust and collaboration across lines of difference and authority.
Preferred Qualifications
Benefits
At WorkMoney, Inc., we’re proud to offer a robust benefits package designed to support your overall well-being and professional growth. In addition to competitive salaries, we invest in your success and create a work environment that’s as dynamic and rewarding as the work we do!
We fully cover premiums for medical, dental, and vision insurance; our retirement plan includes up to a 6% employer match for IRA contributions; and we contribute toward student debt repayment. You’ll enjoy five weeks of paid vacation each year, alongside generous paid family and medical leave. To further enhance your work experience, we offer stipends for remote work expenses, professional development, health & wellness, and cell/internet data usage.
Why Join Our Team?
In our vibrant and ever-evolving work environment, we embrace change and pivot quickly when necessary. Our team is deeply mission-driven, combining hard work with ingenuity and a fearless approach to overcoming complex challenges. Teamwork is integral to our culture — we readily jump in to support each other, celebrate achievements, and learn from our experiences.
At the heart of it all, we are passionate about the innovative projects we undertake, collaborating with exceptional people, and having a great time along the way.
WorkMoney, Inc. believes that embracing diversity enriches our workplace and enhances our ability to achieve our mission and serve our members. We are an equal opportunity employer and welcome applications from all qualified individuals, regardless of age, race, color, religion, gender identity or expression, sexual orientation, national origin, genetics, disability, or veteran status.
We are committed to maintaining an inclusive and accessible environment and provide reasonable accommodations for individuals with disabilities throughout the recruitment and employment process. For accommodations or assistance during the application or interview process, please contact [email protected].
Location: United States / Remote, ~10–15% travel
Term: Full-Time, Exempt, requires U.S. work authorization
Compensation: $300,000-$350,000 Annually
Deadline: Applications will be considered on a rolling basis; Target start early 2026
About WorkMoney, Inc.
At WorkMoney.org, we are dedicated to enhancing the financial well-being of hardworking Americans. Founded on the belief that everyone deserves a fair shot at the American dream, we provide our members with the tools, resources, and support they need to navigate their financial journeys with confidence.
We don't stop at individual support. At WorkMoney, we believe in systemic change and actively advocate for policies that promote economic fairness and opportunity. By amplifying the voices of our members and engaging policymakers, we strive to create a more just and equitable economic landscape.
We believe that financial stability should be accessible for everyone — and we're here to make that a reality. By offering practical tools, fostering a supportive community, and championing policy changes, we empower our members to take control of their finances and build a more secure future.
Join us at WorkMoney, Inc. and become part of an organization dedicated to making sure all Americans can afford to live a good life.
Why do we need a Director of Administration?
WorkMoney is entering an exciting new phase of growth, expanding our programs, deepening partnerships, and reaching millions more members. To support this momentum, we must strengthen the internal systems, talent, and infrastructure that make our mission possible. As our work grows in reach and complexity, we need a senior operational leader who can ensure our structures, people, and processes evolve in step with our ambitions.
The Managing Director of Administration will serve as the organization’s chief operational steward, providing strategic leadership and operational excellence across finance, legal affairs, people and culture, administration, and organizational infrastructure. This leader will ensure our internal operations are efficient, values-driven, resilient, and designed for scale.
This is a pivotal role for an accomplished executive who excels at turning strategy into action. The ideal candidate brings operational rigor, people-centered leadership, and a systems-oriented mindset. They will help guide WorkMoney’s evolution, ensuring we remain grounded in our mission while equipped to deliver greater impact, sustainably and at scale.
Key Responsibilities
Organizational Leadership & Executive Partnership
- Serve as a key member of the WorkMoney Executive Team, partnering with other executives to set and drive organizational strategy, priorities, and performance.
- Translate strategic goals into operational plans and infrastructure that enable WorkMoney’s continued growth and impact.
- Ensure organizational decisions are supported by clear data, strong systems, and cross-team coordination.
Finance & Administration
- Supervise the Chief Financial Officer (CFO) and oversee all aspects of financial management, including budgeting, forecasting, reporting, and long-term financial planning.
- Partner with the CFO to develop sustainable financial strategies that support growth, innovation, and mission impact.
- Partner with the CFO to ensure strong financial controls, compliance, and risk management practices across all departments and entities.
- Partner with the CFO to establish and monitor clear metrics for financial health and organizational accountability.
Legal & Governance
- Supervise the General Counsel, ensuring sound legal advice and oversight across all areas of WorkMoney’s operations, including contracts, compliance, and risk mitigation.
- Ensure WorkMoney’s governance structures are clear, compliant, and aligned with organizational goals.
- Foster a culture of proactive risk management and legal integrity across the organization.
People, Culture & Talent
- Supervise the Senior Vice President of Administration and guide the People team in cultivating a thriving, inclusive, high-performance workplace.
- Partner with executives to align talent strategy with organizational goals, including recruitment, retention, professional development, and performance management.
- Champion an organizational culture grounded in trust, equity, employee wellbeing, and continuous learning.
- Ensure that all people systems, processes, and policies — from onboarding and compensation to development and retention — reflect WorkMoney’s mission and values.
- Build organizational capacity through thoughtful succession planning, leadership development, and culture stewardship.
Organizational Infrastructure, Technology & Systems
- Provide executive oversight of WorkMoney’s operational infrastructure, ensuring systems, processes, and workflows are efficient, coordinated, values-aligned, user-friendly, adaptable and built for scale.
- Lead the organization’s technology and IT strategy, ensuring platforms, tools, and data systems effectively support collaboration, security, and performance.
- Partner with senior leaders to strengthen cross-functional coordination through improved systems, documentation, and communication channels.
- Ensure policies and procedures are current, accessible, and consistently applied across the organization.
Leadership, Supervision, and Team Development
- Accountable for the Legal Affairs, Finance, and Administration departments, overseeing a total team of 12. Manage and mentor the General Counsel, CFO, and SVP of Administration to foster clarity, collaboration, and accountability.
- Build and sustain strong cross-functional relationships across the organization, ensuring operational excellence supports programmatic impact.
- Inspire, empower, and develop staff at all levels, ensuring strong alignment to WorkMoney’s mission, values, and culture.
Mission & Values Alignment. You are deeply committed to WorkMoney’s mission to improve the financial well-being of hardworking Americans and bring empathy, integrity, and urgency to this work.
Operational and Financial Leadership. You have demonstrated success overseeing complex operational, financial, and administrative systems. You know how to scale organizations thoughtfully and sustainably, balancing long-term planning with day-to-day execution in a fast-moving environment.
Strategic Judgment & Prioritization. You are skilled at seeing the big picture while sequencing priorities and making trade-offs amid competing demands. You bring focus, foresight, and calm to moments of complexity or change.
People and Culture Expertise. You have significant experience leading HR, people, and talent functions, and believe organizational culture is a strategic asset. You have successfully managed teams with varied professional experiences and worked effectively in unionized environments, including participating in or leading collective bargaining processes.
Leadership & Collaboration. You are an adaptive and inclusive leader who thrives in dynamic, fast-moving environments. You build trust across differences, lead with empathy and equity, and bring steadiness amid change. You partner effectively with senior executives and teams alike—aligning strategy, structure, and execution while fostering clarity, accountability, and shared purpose.
Emotional Intelligence. You navigate complexity with composure, self-awareness, and care. You inspire trust and collaboration across lines of difference and authority.
Preferred Qualifications
- 12+ years of senior leadership experience, including management of finance, legal, and people functions.
- Experience in mission-driven, high-growth, or multi-entity organizations.
Benefits
At WorkMoney, Inc., we’re proud to offer a robust benefits package designed to support your overall well-being and professional growth. In addition to competitive salaries, we invest in your success and create a work environment that’s as dynamic and rewarding as the work we do!
We fully cover premiums for medical, dental, and vision insurance; our retirement plan includes up to a 6% employer match for IRA contributions; and we contribute toward student debt repayment. You’ll enjoy five weeks of paid vacation each year, alongside generous paid family and medical leave. To further enhance your work experience, we offer stipends for remote work expenses, professional development, health & wellness, and cell/internet data usage.
Why Join Our Team?
In our vibrant and ever-evolving work environment, we embrace change and pivot quickly when necessary. Our team is deeply mission-driven, combining hard work with ingenuity and a fearless approach to overcoming complex challenges. Teamwork is integral to our culture — we readily jump in to support each other, celebrate achievements, and learn from our experiences.
At the heart of it all, we are passionate about the innovative projects we undertake, collaborating with exceptional people, and having a great time along the way.
WorkMoney, Inc. believes that embracing diversity enriches our workplace and enhances our ability to achieve our mission and serve our members. We are an equal opportunity employer and welcome applications from all qualified individuals, regardless of age, race, color, religion, gender identity or expression, sexual orientation, national origin, genetics, disability, or veteran status.
We are committed to maintaining an inclusive and accessible environment and provide reasonable accommodations for individuals with disabilities throughout the recruitment and employment process. For accommodations or assistance during the application or interview process, please contact [email protected].