Director, People Operations

Title: Director, People Operations

Organization: WorkMoney, Inc.

Reporting to: VP, People Operations

Location: United States / Remote, <10% travel

Term: Full-Time, Exempt, requires U.S. work authorization

Compensation: $125,000.00 - $145,000.00 Annually

To Apply: LINK

Deadline: Applications will be considered on a rolling basis; Target start October 2025

About WorkMoney, Inc.

At WorkMoney.org, we are dedicated to enhancing the financial well-being of hard working 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, 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 financial tools and resources, fostering a supportive environment 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.

About the Director of People Operations Role

At WorkMoney, we know that people are the heart of what we do, and a strong People Operations team is essential to a thriving organization. As Director of People Operations, you’ll play a pivotal role in fostering a supportive, compliant, and people-centric workplace. You’ll be a trusted expert for ensuring employees feel valued and supported, policies are clear and consistently applied, smooth and efficient processes, and much more! 

Reporting to the VP of People Operations, the Director of People Operations is a trusted partner and collaborative leader in supporting key HR functions that fortify our organization, enrich our culture, and enhance both engagement and operational excellence. With a blend of big-picture strategy and hands-on execution, you’ll manage critical functions such as labor relations, compliance, benefits administration, performance management, and employee development. Success in this role hinges on strong cross-functional collaboration, as you’ll work alongside leaders, managers, and employees.

The Director of People Operations will take the lead on employee and labor relations, serving as a key point of contact for navigating workplace concerns, conducting fair and timely investigations, resolving conflicts, and advising leadership on effective, compliant, and inclusive people practices. You’ll play a critical role in building trust and fostering an equitable workplace culture.

This role will also manage daily and routine people operations functions such as onboarding new employees and offboarding exiting employees, maintaining employee information and files, providing employee support regarding benefits and policies, processing and managing LOAs, and other similar duties within the scope of the role and department. 

If you’re a seasoned and accomplished HR professional, specifically in labor and employee relations, who is a solutions-oriented individual that can also prioritize the employee experience and ensure a safe work environment, we would love to meet you! 

A typical day might include:

• Employee & Labor Relations
• Serving as a first point of contact for employee and labor relations matters, ensuring fair and consistent resolutions while upholding our Collective Bargaining Agreement (CBA).
• Conducting thorough, impartial investigations delivering timely resolutions that reflect our organizational values and compliance standards.
• Guiding managers and employees through complex workplace situations with empathy, professionalism, and discretion, ensuring policies are applied fairly and consistently.
• Policy & Compliance Leadership
• Developing, interpreting and implementing People Operations policies that balance compliance, consistency, and employee experience.
• Ensuring compliance with federal, state, and local employment laws, as well as our CBA.
• Maintaining a pulse on employment law trends and proactively offering recommendations to ensure our policies and processes are compliant and future-ready.
• Onboarding, Offboarding & Employee Support
• Managing and continuously improving onboarding and offboarding, creating  seamless and engaging transitions for new hires and departing employees.
• Overseeing employee status changes, including job transfers, promotions, compensation adjustments, while ensuring transparency and fairness.
• Identifying opportunities to streamline workflows and enhance efficiency, compliance, and employee satisfaction.
• Benefits & Leave Management
• Managing benefits programs and serving as a go-to resource for benefits-related inquiries and policy interpretations.
• Managing leave administration, ensuring employees have the support they need while maintaining regulatory compliance.
• Analyzing benefits utilization trends and recommending improvements that align with employee needs and organizational goals.
• HR Systems & Data Optimization
• Managing our Professional Employer Organization (PEO) and HR technologies, optimizing systems for efficiency, accuracy, and user experience.
• Leveraging People Operations data and trends to inform strategic decisions and proactively address workplace challenges.
• Partnering with leadership to streamline processes, automate manual tasks and drive continuous improvement in People Operations.

• Performance Management & Strategic Support
• Manage and oversee performance review processes, ensuring they’re fair, transparent and designed to help employees thrive. Lead performance improvement plans and corrective actions with clarity, consistency and respect, creating opportunities for growth while maintaining compliance.
• Supporting and guiding managers in coaching, feedback, and performance management, including performance improvement plans (PIPs) and corrective actions with fairness, compliance, and clarity.
• Partnering with leadership to analyze employee climate trends and develop proactive solutions that enhance workplace culture.
• Organizational Development & Project Leadership
• Driving change management initiatives that help employees navigate new processes, policies and programs with clarity, support and engagement.
• Leading role-related People Operations projects from concept to completion, ensuring goals are clear, timelines are met and outcomes create meaningful impact across the organization.
• Creating and maintaining standard operating procedures (SOPs) to keep People Operations practices consistent, efficient and ready for growth.
• Team Leadership & Development
• Leading and empowering your People Operations team, setting clear goals and priorities that align with organizational objectives
• Building a team culture rooted in accountability, collaboration and continuous learning.

Essential Qualifications

• Mission & Values Alignment. You are inspired by the WorkMoney mission and are passionate about advancing economic fairness and opportunity. You are deeply committed to meaningfully improving the financial well-being of everyday Americans and fostering a fair, inclusive, and supportive workplace where employees can thrive. You believe that policies should empower, not just enforce, and you’re committed to balancing compliance with compassion.
• HR Expertise & Compliance Mastery. You have 10+ years of progressive and applicable experience in People Operations or Human Resources, with a deep knowledge of employment laws, policies, and best practices. You have a strong background in employee and labor relations, with experience managing employee complaints.
• Strategic Problem-Solving & Investigations. You have a proven ability to conduct thorough, fair, and compliant investigations, including gathering evidence, interviewing relevant parties, and preparing well-documented summaries and recommendations. You have strong risk assessment skills, with the ability to identify workplace trends, track employee relations patterns, and provide proactive recommendations that enhance workplace culture and compliance.
• Performance & Change Management. You are experienced in guiding managers through performance reviews, PIPs, disciplinary actions, and employee development, ensuring fair and strategic decision-making. You have a talent for successfully navigating and implementing organizational change, helping teams adapt while maintaining stability and engagement.
• Process Optimization & HR Systems Knowledge. You are experienced in managing HRIS systems, PEOs, and other HR technologies, with a knack for optimizing workflows and driving process improvements. You have a data-driven approach, using analytics and reporting to assess trends, identify risks, and recommend proactive solutions.
• Communication & Leadership. You have exceptional written, verbal, and interpersonal communication skills, with the ability to translate complex People Operations concepts into clear, actionable guidance. You are a natural relationship builder, able to earn trust across all levels of the organization and act as a confidant, strategist, and problem solver.

Preferred Qualifications 

• HR certification(s): PHR, SPHR, SHRM-CP, or SHRM-SCP
• Experience working within unionized environments, including navigating and maintaining collective bargaining agreements
• In-depth understanding and ensuring adherence to compliance requirements across multiple states
• Proven experience working with PEOs (e.g., TriNet) and performance management systems such as Lattice

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 the premiums for medical, dental, and vision insurance, our retirement plan includes up to a 6% employer match for IRA contributions and we contribute toward your student debt repayment. You'll enjoy five weeks of paid vacation each year, alongside generous paid family and medical leaves. To further enhance your work experience, we offer stipends for remote work expenses, professional development, health & wellness, and cell/internet data usage.

As part of our commitment to pay transparency and equity in our organization, the starting annual salary for this position

is $125,000 - $145,000 and is non-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, celebrating achievements and learning from our experiences. At the heart of it all, we are passionate about the innovative projects we undertake, collaborating with exceptional people, and are having a great time along the way.

How to Apply and What to Expect

Follow the link to complete a brief application and upload your resume. We review applications on a rolling basis and encourage you to apply early. 

What to expect after you apply:

• Applicant Review: We review applicants continuously and will reach out if your experience aligns with the role.
• Interview Process: You’ll participate in four rounds of interviews with the hiring manager and other team members. Before the final round, we’ll invite you to share a work sample that reflects your skills and experience.
• Timeline: Our goal is to finalize our hiring decision by early fall, with a planned start date in early October.
• Communication: We value your time and effort and will keep you informed throughout the process. All applicants will receive updates on the status of their candidacy.
  
  

**Please do not reach out directly to any team members. If you'd like more information or to check the status of your application, email [email protected]