Business Compliance & Payroll Specialist

About the Role

We are a fully remote company of approximately 100 people with a complex legal structure: 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. This structure carries a substantial compliance burden, including at least fifty state registrations across the professional corporations and a distributed workforce. We need one person to own the full compliance picture.

The first objective is establishing a reliable baseline of where each entity is registered, what remains active, what has lapsed, and what is coming due. From there, this role becomes the go-to person for compliance details, such as state registrations, annual report deadlines, unemployment rate changes, withholding accounts, and 401(k) distributions.

This is not a financial reporting role and does not involve closing the books or preparing financial statements. It suits someone who takes satisfaction in closing loops, building preventive systems, and being the trusted person others rely on for accuracy.

You will not work alone or from scratch. Rippling is our system of record for payroll, benefits, onboarding, expenses, and corporate cards. CT Corporation acts as our registered agent, and we engage outside tax advisors and counsel for specialized matters. This role owns the whole picture: knowing provider responsibilities, holding them accountable, catching gaps, and maintaining the single source of truth.

Responsibilities

• 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; 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 covering Secretary of State annual reports, foreign qualifications, registered agent renewals, franchise tax filings, and business licenses; coordinate filings through CT Corporation and verify completion.
  • Monitor nexus exposure as the company footprint shifts and escalate newly triggered obligations.
  • Triage incoming corporate mail for all six entities, log each item, route it to the appropriate owner, and track 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.

Requirements

• 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 Qualifications

• 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 considerable process documentation needed. 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.