Business Compliance & Payroll Specialist

About Rugiet Rugiet is an Inc 5000 direct-to-consumer telemedicine company reinventing men's health. We combine clinical rigor, luxury service, and a modern digital experience to deliver personalized, compounded treatments at scale. We're not here to blend in. We're building the future of healthcare and we move fast. About the Role We are a fully remote company of approximately 100 people. Our legal structure is more complex than our headcount suggests: six entities comprising a holding company, an operating company, and four professional corporations that conduct consultations and collect revenue on a state-by-state basis. That structure carries a substantial compliance burden — at least fifty state registrations across the professional corporations, combined with a workforce distributed across the country — and we need one person who owns the full picture. At present, we do not have a single reliable view of where each entity is registered, what remains active, what has lapsed, and what is coming due. Establishing that baseline is the first and most important objective of this role. From there, this becomes the person who knows which states each entity is registered in, when annual reports are due, why a state unemployment rate changed, whether a new hire in Ohio has a withholding account established, and where a 401(k) distribution stands. This is not a financial reporting role. It does not involve closing the books or preparing financial statements. It suits someone who takes genuine satisfaction in closing loops, building systems that prevent problems, and being the person others trust to handle things correctly. You would not be doing this alone or from scratch. Rippling is our system of record for payroll, benefits, onboarding, expenses, and corporate cards. CT Corporation acts as registered agent across the entity group, and we engage outside tax advisors and counsel on specialized matters. This role owns the whole picture: knowing what each provider is responsible for, holding them to it, catching what falls between them, and maintaining the single source of truth none of them can maintain on our behalf. What You Will Own Payroll Administration (25%): Prepare semi-monthly and bi-weekly payroll for Controller review. Process off-cycle runs, final pay, retroactive adjustments, and corrections. Maintain employee records including new hires, terminations, compensation changes, and direct deposit updates. Administer garnishments and wage orders and respond to related agency requests. Review each payroll register against expected changes prior to submission and escalate discrepancies. Benefits and Retirement Administration (20%): Administer benefits enrollment, changes, and terminations including annual open enrollment. Serve as day-to-day administrator of the company 401(k) plan covering enrollments, deferral changes, loans, distributions, and termination processing. Manage ACA reporting and coordinate with brokers and carriers. Reconcile benefit invoices against payroll deductions and resolve variances. State Accounts and Entity Compliance (30%): Establish and maintain a complete, current inventory of state registrations across all six entities, distinguishing active, lapsed, and pending. Register for new state withholding, unemployment, and business accounts as hiring and clinical operations expand. File or coordinate quarterly and annual payroll tax returns, resolve agency notices, and pursue penalty abatements. Own the entity compliance calendar across the group covering Secretary of State annual reports, foreign qualifications, registered agent renewals, franchise tax filings, and business licenses, coordinating filings through CT Corporation and verifying completion. Monitor nexus exposure as the company footprint shifts and escalate newly triggered obligations. Triage incoming corporate mail for all six entities, logging each item, routing it to the appropriate owner, and tracking it through to resolution. HR Administration (15%): Manage onboarding and offboarding logistics including offer letter execution, I-9 verification, system provisioning coordination, and exit documentation. Respond to employment and income verifications, unemployment claims, and agency requests. Administer PTO tracking, leave-of-absence logistics, and supporting documentation. Maintain the employee handbook, policy acknowledgments, and required state and federal notices. Finance Administration (10%): Administer employee expense reimbursements and corporate card documentation in Rippling, including receipt follow-up, consistent policy application, and moving submissions through approval. Produce reports and supporting documentation from Rippling for the finance team at month-end. Assemble backup materials for audit, diligence, and outside advisor requests. What We Are Looking For Required: Two (2) or more years in an administrative, operations, compliance, or coordinator capacity with direct ownership of recurring deadlines. Real exposure to corporate compliance or business administration including state filings, registrations, licensing, payroll and benefits paperwork, or agency correspondence. Comfort working with government agencies including portals, forms, notices, and the follow-up they require. Excel skills and the ability to learn new cloud systems quickly. A demonstrated record of working through long lists of detail-oriented tasks to completion without close supervision. Sound judgment and discretion handling confidential compensation, medical, and personal information. Preferred: Experience managing outside service providers such as registered agents, payroll platforms, brokers, or tax advisors. Experience with multistate payroll or state tax account registration. Experience with Rippling or a comparable HRIS platform as a primary user. Experience in a multi-entity environment, particularly professional corporation or MSO structures. Exposure to 401(k) plan administration. Startup or high-growth company background. Working Style We are looking for someone who closes loops and does not let open items linger, who documents processes rather than relying on memory, and who escalates early when something appears wrong. Much of this work is repetitive, procedural, and invisible when done well. The people who thrive in roles like this take genuine satisfaction in a clean queue rather than in novelty. The position carries considerable autonomy — this is the only person doing this job, in a fully remote company. How the Role Evolves The opening months are the heaviest. There is a backlog to work through, a compliance calendar to build from scratch, and a considerable amount of process that currently lives in individual heads and needs to be documented. Once that foundation is established, the work shifts from catch-up to rhythmic — filings run on a known schedule, payroll cycles proceed without incident, and notices are handled as they arrive. Building systems robust enough that the role becomes steadier is precisely what we are hiring for. This position does not own employee relations, performance management, hiring decisions, compensation strategy, workplace investigations, or financial statement preparation. It partners with the people who do. To Apply If you are someone who finds genuine satisfaction in owning a complex system and making it run cleanly, we want to hear from you. Please submit your resume and a brief note on the compliance or payroll challenge you are most proud of solving.