About WorkMoney, Inc.

At WorkMoney.org, we are dedicated to enhancing the financial well-being of hardworking Americans. Founded on the belief of the American dream, we strive to 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, Inc., we believe in systemic change and actively advocate for policies that promote economic fairness and opportunity. By amplifying the voices of our members, and partnering with 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 Chief of Staff to the Executive Director?

WorkMoney's nonprofit is at an exciting and demanding moment — growing in reach, deepening its programs, and taking on greater complexity across teams and initiatives. As the organization expands, the Executive Director needs a trusted partner who can help her stay focused on what matters most, ensure nothing falls through the cracks, and keep the whole organization moving in the same direction.

The Chief of Staff will serve as an organizational integrator and force multiplier — someone who brings clarity to ambiguity, structure to competing priorities, and follow-through to big ideas. This is a senior role that requires equal parts strategic thinking and operational discipline. The right person will be someone who earns trust quickly, communicates with precision and care, and finds genuine satisfaction in making a leader and an organization more effective. If you thrive behind the scenes, love solving hard problems, and are energized by mission-driven work, this role is for you.

Key Responsibilities

Strategic Advisor, Thought Partner & Proxy

● Partner with the Executive Director to think through organizational priorities, program strategy, and team direction.

● Help the ED stay ahead of challenges and needs, offering perspective that keeps both near-term needs and longer-term goals in view.

● Be a trusted thought partner on decisions that are sensitive, complex, or high-stakes — bringing candor, good judgment, and discretion.

● Serve as a proxy for the ED in meetings, conversations, and decision points as needed, representing her perspective and priorities with credibility and care.

● Ensure the ED and CEO are aligned and supporting one another in both short- and long-term goals and strategies.

Execution & Operational Leadership

● Help turn the ED's input and directives into concrete plans, ensuring teams understand what's expected and work stays on track.

● Serve as a smart filter for the ED— surfacing what needs her attention and handling or redirecting what doesn't.

● Support the ED's ability to lead effectively day-to-day — preparing agendas, talking points, and materials for meetings she leads, and coordinating logistics and follow-through for key convenings.

● Keep a close eye on organizational commitments, flagging when things are slipping and helping remove obstacles.

● Build and maintain high-trust relationships across teams, ensuring open communication and shared understanding of goals.

● Partner with the senior leaders to move organizational priorities forward and strengthen cross-team collaboration.

● Look for ways to make the organization operate a little smarter, faster, and more effectively.

Project Management 

● Own and drive cross-organizational projects and initiatives at the direction of the ED — from scoping and planning through execution and follow-through.

● Step in during transitions or pivots to keep work moving while permanent solutions are found.

● Pilot new ideas and initiatives that fall outside the purview of existing teams, defining success and shaping the path to implementation.

● Address cross-team opportunities or challenges that don't sit neatly within existing portfolios or structures.

● Among the kinds of projects this role will own: tracking progress on organizational goals; reviewing Board materials; designing staff retreats; tracking efforts to align budget to programming.

Essential Qualifications

Mission & Values Alignment. You are inspired by WorkMoney’s mission to improve the financial well-being of hardworking Americans and bring empathy, rigor, and determination to achieving measurable impact.

Strategic Judgment. You know how to assess a situation quickly, weigh competing considerations, and offer sound guidance — even when the answer isn't obvious. You're comfortable operating in gray areas and don't need perfect information to move forward. You know when to decide, when to escalate, and when to slow down and ask better questions.

Trust-Building & Emotional Intelligence. You know how to build genuine relationships at every level of an organization — and people trust you to represent them and their work fairly. You read people and rooms well. You know when to push, when to listen, and how to navigate sensitive situations with grace.

Leadership & Influence. You get things done through relationships and trust, not title. You know how to bring people along, build consensus, and move work forward even when you don't have formal authority — and people genuinely want to work with you.

Nonprofit or Mission-Driven Experience. You have meaningful experience working in nonprofit, advocacy, or other mission-driven settings — and it shows in how you operate. You understand the particular dynamics of purpose-driven organizations: navigating resource constraints, balancing urgency with sustainability, and keeping the mission front and center even when the work gets complex. 

Operational Excellence. You have a knack for taking something messy or undefined and turning it into a clear plan with owners and deadlines. Things don't fall through the cracks on your watch. You're the person who notices what's missing, follows up without being asked, and brings the same rigor to a small task as a big one. You have a proven ability to wrangle complexity, align stakeholders, and deliver results even when priorities are shifting.

Communication. You write and speak clearly and adapt your style to your audience. You can represent someone else's voice and priorities faithfully and well. Whether you're drafting a memo, running a meeting, or delivering a difficult message, you communicate with clarity, intention, and care.

Discretion & Confidentiality. You handle sensitive information with care and know how to hold confidence. People feel safe bringing you into sensitive conversations. You understand that trust is foundational to this role — and you treat it accordingly.

Entrepreneurial Drive. You're proactive and resourceful — you spot gaps and fill them without waiting to be asked, while staying anchored to the ED's priorities. You're energized by figuring things out in real time and don't need a playbook to get started.

Work Ethic & Adaptability. You bring energy and steadiness in equal measure, and you don't rattle easily when priorities shift or things get hard. You can hold a lot at once, pivot when needed, and still show up with good judgment and good humor.

Preferred Qualifications

● 7+ years of experience, with at least some of that time in a role that required supporting, advising, or partnering closely with a senior leader.

● Demonstrated experience as a programmatic leader in a nonprofit, advocacy, or mission-driven organization.

● Preference may be given to candidates on the East Coast.

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 401K 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. 

The salary range for this role is $210,000.00 - $230,000.00 annually and, as part of our commitment to pay transparency and equity in our organization, the salary for this position is not negotiable.

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, and 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.

To Apply

To apply for this position, submit a cover letter and resume at https://grossmansolutions.applytojob.com/apply. Your cover letter should be compelling, concise and include an example of how you have served as a thought partner to a senior leader. Applications will be reviewed on a rolling basis.

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] and include “WorkMoney Application Assistance” in the subject line.