Senior Total Rewards Analyst (Sr. Pay & Tax Analyst)

Why Workit: Workit Health is an industry-leading provider of on-demand, evidence-based telemedicine care. Our programs are based in harm reduction, and bring together licensed clinicians who really listen, FDA-approved medication, online recovery groups and community, interactive therapeutic courses, and care for co-existing conditions. Workit Health's patient-centered telemedicine model is improving clinical outcomes and eliminating barriers to treatment, making long-term recovery accessible to individuals who need it, without disrupting their daily lives. We’re excited to expand our team as our impact and coverage areas continue to grow. Our team members are dedicated and passionate about our mission of making exceptional, judgment-free care for addiction more accessible. We believe everyone deserves respectful, effective treatment for substance use disorder at the moment they're ready for it. We're looking for driven and compassionate individuals who share this goal. Join us in reducing stigma, saving lives, and changing the way addiction is treated in America. Job Summary: Workit Health is seeking a remote Senior Total Rewards Analyst (Sr. Pay & Tax Analyst) to join the HR team. This role will report to the Sr. Manager, People Services (People Operations) and will own and optimize day-to-day payroll and employee tax operations for a company of 150-200 employees and contractors. In addition, the Senior Total Rewards Analyst will work closely with Accounting & Operations to lead pay and tax strategy for new state expansion efforts, own end-to-end leave administration, and serve as a senior escalation point to assist with employee benefits programs. The successful candidate will have owned payroll operations and leave administration for a company of a similar size, be an expert in federal, state and local pay and leave laws (FMLA/ADA/PFL) in the US, have worked previously with complex tax operations common to a dispersed (remote) workforce, and have experience supporting total rewards and benefits programs. Core Responsibilities: Own and optimize full-cycle payroll, tax, and leave administration operations Create and execute on pay and leave processes, in tandem with the employee’s manager, that adhere to the highest levels of compliance Provide excellent customer service to Workit’s employees in all matters and all communication formats (Slack, email, verbal, Jira, etc.) Drive strategy and resolution for complex multi-state pay and tax compliance issues Monitor and process department mail digitally sent from our physical offices Lead special pay, tax, and registration projects related to new state expansion efforts Own equity administration in Carta and serve as a senior point of contact to assist with employee benefits programs as needed Other pay, tax, and people services duties as assigned Qualifications: 4+ years of experience working in a People Operations, People Services, or Payroll capacity (HR/payroll) 2+ years of experience being the primary payroll point of contact 1+ years owning or administering employee leaves Proven ability to own start-to-finish projects Demonstrated expertise in payroll, employee taxes, pay laws, and leave compliance (FMLA, ADA, multi-state PFL) Ability to assist with employee benefits programs, vendor management, and employee escalations as needed Proactive and curious approach to problem-solving Excellent verbal and written communication skills Strong organizational skills, and attention to detail The ability and willingness to complete several concurrent tasks with attention to time constraints, quality and sufficient detail Expertise with Google Suite products and experience creating documents and presentations for a professional audience Passion for learning about behavioral health Desire to become certified in HR/Payroll Preferred Qualifications: 4 years of experience working in a People Operations, People Services, or Payroll capacity 1+ years of experience using Rippling Interest in pay and benefits technology HR/Payroll certification SEO : You may also be looking for Sr. Payroll Specialist, Sr. Payroll Coordinator, Total Rewards Coordinator #LI-MM1 Pay range $69,000 — $84,000 USD Benefits & Rewards: Fully remote work 5 weeks PTO (includes your birthday, 2 mental health days, and 2 floating holidays!) 11 paid holidays Comprehensive health, dental, pharmacy, and vision insurance with options to fit your family's needs 12 weeks paid Parental Leave after 1 year of employment (includes maternity, paternity, adoption, and all ways in which our people build modern families) 401k + 4% matching Healthcare & dependent care Flexible Spending Accounts (FSA & DCFSA) Health Savings Accounts (HSA) Employee assistance program, complete with financial coaching and counseling sessions Professional development allowance for Providers and Behavioral Health team Opportunities for internal mobility and growth at a Company with a proven track record of really promoting internally Vibrant, democratized culture with clubs and multiple ERG groups Colleagues who care deeply about closing health disparity gaps within the addiction space for underserved populations Equal Opportunities for Everyone, including Folks in Recovery: As we are an addiction recovery company founded by people in recovery, those in addiction recovery themselves are encouraged to apply. Workit Health is proud to be an Equal Employment Opportunity and Affirmative Action employer. We do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. AI Interview Policy: At Workit Health, we value authenticity, curiosity, and personal insight during our hiring process. To ensure a fair and genuine experience for all candidates, we ask that you refrain from using AI tools or external assistance during interviews or assessments. We’re most interested in your unique ideas, problem-solving approach, and communication style—qualities that help us understand how you’ll contribute to our team. Demonstrating your own thinking and creativity gives both you and us the best sense of fit and potential. Privacy Policy: Applicant personal information is collected and used in accordance with Workit Health’s Privacy Policy , which includes disclosures and rights under applicable U.S. privacy laws.