Business Compliance & Payroll Specialist

Overview

This role supports a multi-entity, multistate telemedicine organization operating through six entities (a holding company, an operating company, and four professional corporations). The organization requires a single owner who can establish and maintain a reliable, current view of entity registrations and compliance obligations across states.

Key objectives include:

• Building an accurate baseline inventory of where each entity is registered, what is active vs. lapsed vs. pending, and what is coming due.
• Maintaining the single source of truth for compliance timelines and operational follow-through across the entity group.

This is not a financial reporting role.

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 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.
• 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 ability to learn new cloud systems quickly.
• 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.

Compensation & Benefits

• Not specified in the job description.

Location

• Fully remote.