Tax Compliance & Regulatory Filings Specialist

Position Summary The Tax Compliance & Regulatory Filings Specialist owns end-to-end execution of all federal, state, and healthcare-related tax and regulatory filings. This role is accountable for timely, accurate, and auditable submission of statutory filings without reliance on external vendors or consultants. The position serves as the internal authority for tax compliance, ACA reporting, RxDC submissions, and related regulatory obligations, ensuring filing readiness, deadline management, and regulator-facing accountability in a highly regulated health-tech environment. This role is focused on regulatory execution and filing accountability and does not include strategic tax planning, payroll tax operations. Provides regulatory input into system design and data remediation efforts but does not own system development or upstream data correction. Key ResponsibilitiesTax & Information Reporting (Federal & State) - Own preparation, submission, and confirmation of federal information returns, including IRS AIR filings and Form 1095-B. - Manage applicable 1099 series filings and other required federal information returns. - Maintain IRS credentials, TCCs, authorized users, and official contact information. - Submit and manage filing extensions, corrections, and amended returns. - Track acknowledgements, submission receipts, and maintain auditable evidence. - Serve as the primary internal contact for tax filing inquiries and notices. - Own execution of complex federal and state information reporting obligations across healthcare, benefits, and multi-jurisdictional entity structures. State Tax & Statutory Filings - Own state-level tax and regulatory filings, including all applicable jurisdictions. - Manage state tax portal access and credentials (e.g., MassTaxConnect). - Track state-specific filing and furnishing requirements and deadlines. - Submit state extensions, corrections, and responses to state inquiries. - Maintain documentation and proof of submission. Healthcare Regulatory Reporting - Own execution of healthcare-specific regulatory reporting and attestations required for group health plans and related entities. - Coordinate data intake, validation, submission, and evidence retention across internal systems, delegated partners, and regulatory portals. - Coordinate and manage RxDC reporting, including data intake, submission workflows, attestations, and evidence retention. - Manage CMS annual and mid-year disclosures and Medicare Part D Creditable Coverage reporting. - Monitor regulatory changes impacting healthcare reporting obligations. Furnishing Compliance & Controls - Ensure compliant furnishing of required forms to members and recipients. - Oversee electronic opt-in compliance, auditability, and reporting. - Define and enforce mail fallback requirements where electronic consent is not present. - Partner with Systems to validate furnishing workflows and reporting accuracy. - Maintain documentation supporting furnishing compliance decisions. Regulatory Calendar & Readiness - Own and maintain the enterprise tax and regulatory filing calendar. - Identify dependencies, risks, and readiness gaps well in advance of deadlines. - Maintain readiness across overlapping regulatory cycles with varying deadlines, dependencies, and regulator expectations. - Conduct pre-filing readiness checks and post-filing reviews. - Proactively escalate risks related to data quality, access, or vendor delays. Audit & Regulator Support - Serve as the primary contact for regulator and auditor inquiries related to filings. - Serve as the internal authority for regulator and auditor inquiries related to statutory filings, attestations, and plan- or entity-level reporting. - Coordinate responses to notices, penalties, and information requests. - Maintain organized evidence to support audits and examinations. - Partner with Legal on risk assessments and formal responses as required. Required Skills & QualificationsEducation & Experience - Bachelor’s degree in Accounting, Finance, Compliance, or related field. - 7+ years of hands-on experience in tax compliance, regulatory reporting, or information reporting. - Direct experience filing federal and state information returns using IRS AIR and state tax portals. - Experience managing extensions, corrections, and penalty response. - Hands-on experience owning ACA information reporting and related healthcare regulatory reporting cycles; RxDC, plan-level attestations, or similar healthcare reporting strongly preferred. - Experience in healthcare, insurance, financial services, or other highly regulated environments. - Certification (preferred): CPA and/or EA (Enrolled Agent). - Demonstrated hands-on ownership of ACA AIR (1094/1095, including 1095-B) and multi-state filing obligations required; RxDC and gag clause attestation experience strongly preferred. - Experience preparing, reviewing, or coordinating partnership tax reporting deliverables, including Schedule K-1s, and managing timelines, data collection, and reconciliation with internal stakeholders and/or external preparers. - Experience owning multi-state entity license registrations and renewals (as applicable), including portal access, attestations, fee payments, proof of filing, and audit-ready record retention. Technical Proficiency - Prior experience in health plans, insurers, benefits administration, or regulatory consulting - Experience coordinating reporting across multiple vendors and distributors - Familiarity with CMS submissions and healthcare compliance frameworks - Experience operating as an individual contributor with independent ownership Leadership & Communication - Demonstrated ability to lead cross-functional initiatives, influence without direct authority, and communicate effectively with technical teams, executives, and auditors. Key Attributes - Regulatory execution and accountability - Deadline and dependency management - Cross-functional coordination - Attention to detail under regulatory scrutiny - Clear written and verbal communication with regulators and executives - Comfort operating independently with high accountability - Collaborative and approachable, fostering trust across departments. Job Type: Full-time Pay: $95,000-$120,000 Benefits: 401(k), 401(k) matching, Dental insurance, Employee assistance program, Health insurance, Health savings account, Life insurance, Paid time off, Vision insurance