WorkMoney - Chief of Staff
Grossman Solutions
People & HR, Operations
Remote
USD 260k-300k / year
Posted on Nov 15, 2025
Chief of Staff to the Founder & CEO
Reporting to: Founder & CEO
Location: United States / Remote, preference for West Coast, ~10–20% travel
Term: Full-Time, Exempt, requires U.S. work authorization
Compensation: $260,000-$300,000 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 Chief of Staff?
WorkMoney is growing rapidly — in scale, complexity, and ambition. Our Founder & CEO leads an organization that spans multiple entities, partnerships, and initiatives designed to deliver tangible impact for millions of Americans. To meet the demands of this moment, we are seeking a Chief of Staff who can act as a strategic partner and extension of the Founder & CEO — ensuring clarity, focus, and execution across a fast-moving portfolio of priorities.The Chief of Staff will be a trusted advisor and integrator, ensuring that the Founder & CEO’s time, decisions, and relationships have maximum impact. This is a senior-level role for someone with exceptional judgment, emotional intelligence, and the ability to bring order to complexity. The right candidate will balance strategic insight with operational discipline, handle sensitive matters with discretion, and thrive in a dynamic, fast-paced, high-trust environment alongside a visionary leader.
Key Responsibilities
Strategic Advisor & Thought Partner
- Serve as a trusted advisor to the Founder & CEO on strategy, priorities, and organizational direction.
- Synthesize perspectives and data into clear insights and actionable recommendations.
- Anticipate challenges and emerging opportunities, providing counsel that balances urgency, judgment, and long-term vision.
- Act as a sounding board on sensitive or high-impact decisions, ensuring choices reflect both strategic intent and organizational reality.
Execution & Operational Leadership
- Translate the Founder’s vision into clear, actionable priorities and ensure consistent progress across multiple entities.
- Sequence decisions, meetings, and communications to ensure the right conversations happen at the right time with the right people.
- Manage the flow of information to and from the Founder—distilling what requires her engagement and empowering others to act decisively.
- Track progress and surface risks or bottlenecks early, clearing obstacles and ensuring commitments are met.
- Continuously refine systems and processes to improve the quality, speed, and impact of decision-making.
Executive Office Leadership & Supervision
- Lead and develop the Executive Office team as a strategic extension of the CEO.
- Supervise and coach Executive Office staff, setting clear standards for performance while modeling organizational values and advancing a positive team culture.
- Inspire calm and integrity for the team, especially when under pressure or operating within ambiguity.
Strategic Relationships & Bridge-Building
- Build and nurture high-trust relationships across teams, ensuring open communication and shared understanding of goals.
- Serve as a bridge between the Founder & CEO and relevant staff, fostering alignment, clarity, and accountability.
- Partner with the senior leadership team to move organizational priorities forward
- Strengthen collaboration across entities so work moves fluidly and decisions are well-informed.
- Represent the Founder & CEO with internal and external stakeholders, embodying her leadership values and strategic intent.
Special Projects
- Pilot new ideas and initiatives that fall outside the purview of existing teams, defining success and shaping the path to implementation.
- Address cross-entity challenges or opportunities that don’t sit neatly within existing portfolios or structures.
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 have the maturity, judgment, and analytical ability to navigate complex situations, make sound recommendations, and act with confidence and discretion.
Leadership & Influence. You are comfortable managing up, down and across through influence rather than authority. You know how to build high-trust relationships, shape direction, and move work forward in partnership with staff and other stakeholders.
Operational Excellence. You are highly organized, disciplined, and systems-oriented, able to turn broad ideas into concrete plans and deliverables. You have a track record of successfully driving highly complex initiatives with evolving priorities and goals.
Communication & Relationship Management. You are a clear, direct communicator who can represent the Founder & CEO with credibility and care. You know how to build and nurture enduring relationships.
Emotional Intelligence. You bring self-awareness, humility, and empathy to your work. You understand how to read a room, manage complex interpersonal and power dynamics, and build trust while holding others accountable.
Entrepreneurial Drive. You thrive in a fast-paced, mission-driven environment. You’re resourceful, proactive, and thrive amid ambiguity and change.
Work Ethic & Adaptability. You bring stamina, professionalism, and composure under pressure. You’re comfortable working outside of standard hours and traveling as needed to stay in sync with the Founder’s pace.
Preferred Qualifications
- 10+ years of professional experience, including at least 3 years in a senior advisory, strategy, or executive office role.
- Demonstrated experience supporting or partnering with a founder, CEO, or principal.
- Background in mission-driven, entrepreneurial, or multi-entity organizations preferred.
- Track record of driving organizational alignment, problem-solving complex issues, and delivering results in high-stakes contexts.
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.
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].