Payroll And Benefits Specialist (Pt And Mt Preferred)

Diversity, equity, inclusion, and belonging at Two Chairs

Two Chairs is committed to building a culture of inclusivity, belonging, and safety. We center these efforts around open dialogue, employee support, education and advocacy, and culturally-responsive care.

Diversity, equity, and inclusion are more than just words to us; they're the principles guiding how we build our business and teams. We encourage interested candidates from diverse backgrounds to apply even if they don't think they meet every criterion of the role. Achieving our mission of building a world where everyone has access to exceptional mental health care starts with creating a workplace that represents people from all identities, backgrounds, experiences, abilities, and perspectives.

About Us

Two Chairs is building a world where everyone has access to exceptional mental health care. We’re building a system that’s far easier to navigate and creating experiences for therapists and clients that are centered in relationships, backed by research, and powered by thoughtful technology. We’ve brought together an exceptional team at the intersection of clinical care, technology, and design to revolutionize how people connect with and receive care. We’re united by our collective personal experiences with the mental health care system and a desire to build a better one for everyone.

About The Role

We’re looking for an exceptional People teammate to join the Two Chairs People Operations Team! As a Payroll & Benefits Specialist, primarily focused on payroll transformation, leave administration, compliance and data and analytics, you will play a key role in helping to accelerate our growth and scale by enhancing recurring current processes, managing sensitive people information, and supporting cross-functional projects. If you thrive on ownership, working in the details and collaborating with teammates to curate processes that enable a great employee experience, this is the role for you!

You'll be responsible for

• In partnership with our leave administrator and People Partner team, coordinating and supporting employee leave cases.
• Using data and analytics to share updates on key people team insights.
• Ensuring Two Chairs meets all People regulatory compliance requirements and submissions.
• In partnership with the People Ops Manager, supporting open enrollment and ongoing benefits administration for all employees.
• Managing bi-monthly payroll company-wide, ensuring accuracy and compliance with appropriate documentation and system entry.
• In partnership with the People Ops Manager, enhancing Two Chairs’ current payroll procedures for increased scalability and accuracy as we expand into new, more complex markets.

Core Areas of Responsibility

Payroll 35%

• End-to-end ownership of Two Chairs’ bi-monthly payroll company-wide.
• Answer ad-hoc requests and questions from employees and or their managers
• Optimize Two Chairs’ current payroll procedures for increased scalability and accuracy
• Manage state registration and employment taxes.

Leave Administration 20% Coordinate and support Two Chairs leave cases, ensuring employees are supported throughout the process while also maintaining compliance.

• Enhance Two Chairs leave tracking processes
• Answer ad-hoc requests and questions from employees and or their managers

Benefits Administration 20% Support benefit plan research and open enrollment company-wide.

• Enable employees with benefits resources and tools
• Answer ad-hoc requests and questions from employees and or their managers

Compliance 15%

• Build an annual compliance roadmap
• Manage federal and state compliance requirements and reporting submissions.
• Proactively share new requirements with People team leadership and recommend scalable solutions for compliance

Data & Analytics 10%

• Build a quarterly People Team dashboard that summarizes People key metrics and highlights strengths and areas for improvement

Impact and Success Indicators:

Where you’ll make an impact in the first 90 days:

• Support open enrollment planning and communications
• Execute on additional day-to-day HR operations and tasks as needed
• Own Two Chairs bi-monthly payroll, learning current processes and ensuring accuracy
• Support Two chairs leaves cases, ensuring employee support and coordination

Where you’ll make an impact in the first year:

• Manage state registrations and employment taxes, as well as annual reporting
• Develop and maintain Two Chairs compliance dashboard, communicating and tracking all compliance-related tasks from employee training to company filing requirements
• Develop a People team dashboard, analyzing and providing insights on key people team metrics
• Maintain and protect confidential data with great discretion, judgment, and professionalism
• Enhancing Two Chairs payroll processes for increased scalability and accuracy
• Support Two Chairs open enrollment, ensuring a positive and fluid experience for employees
• Support the broader company in educating employees on company policies while also answering individual questions
• Collect, track, and maintain employee data between a multitude of systems and outside partners

You’ll be successful if you have:

• A collaborative approach and thrive in a team setting
• A solid HR foundation in a startup or fast-paced company environment
• Impeccable personal integrity and sound judgment
• Passionate about mental health
• Ability to thrive and live by operational excellence - you’re able to prioritize across many stakeholders without dropping the ball
• Strong analytical, written, and verbal communication skills
• An understanding of federal and state labor laws
• A pragmatic approach and are committed to delivering exceptional quality work
• Experience supporting leave requests and working within an established leave framework
• A prevalence for thinking on your feet but exhibit the ability and humility to ask questions
• A certificate in HR, payroll, compensation, or benefits is preferred but not required
• Experience supporting payroll and affiliated state taxes a plus
• Strong attention to detail with a desire to enhance processes for scalability and are able to work independently and multitask
• A low ego, are deeply empathetic and outcome-oriented

Compensation & Benefits

We offer perks and benefits that support the health and well-being of our teams, including:

• Equity in a high-growth start-up

PTO program, including a Winter Office Closing: Christmas Day (Observed) through New Year's Day

• Annual $500 professional development stipend to support your professional development
• Comprehensive medical, dental, and vision coverage
• Annual $500 wellness stipend to encourage and support a well-rounded and healthy lifestyle
• Paid parental leave
• One-time $200 Work from Home reimbursement
• Annual $500 subsidized company contribution to your healthcare FSA