Payroll and Benefits Analyst
About Reserv
Reserv is an insurtech innovator building AI and automation solutions to simplify claims. Founded by industry veterans with deep experience in SaaS and insurance, we're backed by leading investors like Bain Capital and Altai Ventures. We're scaling fast — currently ~600 people — and we’re building the systems, infrastructure, and processes to support hyper growth.
About the Role
As a Payroll and Benefits Analyst, you’ll be a linchpin on our Finance & HR teams, ensuring accurate, timely, and compliant payroll processing across multiple jurisdictions. You’ll handle the end-to-end payroll lifecycle, from data collection and verification to reporting, reconciliation, and audits. The ideal candidate is detail-oriented, technically savvy, and comfortable working in a fast-paced, scaling environment. A disproportionate amount of the manual work revolves around benefits administration – specifically, understanding deeply our employee benefits and the resulting payroll deductions; the Benefits portion of your role will revolve around reconciliations on this front, as well as explaining benefits and deductions to our employee base
You’ll report to the Controller and interact with cross-functional teams, including HR, Benefits, Accounting, and Legal.
What You’ll Do
- Process payroll for multiple business units, including exempt and non-exempt employees, contractors.
- Validate payroll data inputs (time sheets, deductions, bonuses, reimbursements) and resolve discrepancies.
- Coordinate with HR and finance to ensure correct tax withholdings, benefit deductions, garnishments, etc.
- Explain, answer questions, and provide guidance to the employee base on how deductions for those benefits will be reflected in their payroll, and help reconcile any issues that arise.
- Address questions related to paystubs (e.g., 401k, FSA, etc.) in collaboration with People Ops, and ensure any necessary corrections are promptly addressed.
- Complete state filings and ensure deadlines are met.
- Maintain compliance with federal, state, and local regulations (tax, labor laws, wage & hour, reporting).
- Prepare and file payroll tax returns, quarterly reports (Form 941, state filings), and year-end documents (W-2s, 1099s).
- Reconcile payroll accounts (liability accounts, general ledger) and investigate variances.
- Support audits and inquiries (internal, external) and provide necessary documentation.
- Analyze payroll data for trends, anomalies, and opportunities to improve efficiency.
- Assist in payroll process improvements, system implementation or upgrades, and policy updates.
What We Need (Qualifications)
- 7+ years of experience in payroll processing in a multi-state / multi-entity organization.
- Strong knowledge of U.S. payroll tax rules, labor laws, and reporting requirements.
- Experience with payroll systems (specifically Rippling) and Excel / data tools.
- Detail-oriented with strong analytical and reconciliation skills.
- Ability to adapt, troubleshoot, and resolve issues quickly in a fast-changing environment.
- Strong communication and organization skills.
- Bachelor’s degree in Accounting, Finance, or related field (preferred).
Nice-to-Haves
- Experience in insurtech, SaaS, or startups.
- Exposure to international payroll or global compliance.
- Experience implementing payroll systems or integrations.
- CPP Certification
What We Offer
- Competitive salary + equity package.
- Medical, dental, and vision insurance.
- 401(k) with matching.
- Generous PTO and flexible work arrangements.
- High-end laptop, second monitor, and quality-of-life tools to do your job well.
- Opportunity to grow in a rapidly scaling fintech / insurtech environment.
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