Benefits Analyst

Company: Hillpointe
Location: Winter Park
Posted on: April 1, 2026

Job Description:

WHY HILLPOINTE? Hillpointe is a fully integrated real estate development and investment management firm focused on developing market-rate workforce housing across the Sun Belt. Ranked at the top of NMHC's list of Builders and Developers, our team ensures best-in-class execution. Built on its long and proven track record of real estate development, the firm’s investment approach is centered around its in-house general contracting expertise, enabling direct control of cost and delivery timeframe. For each project, Hillpointe directly controls land acquisition, land development, construction, procurement of building materials, asset management, and capital markets. This is more than just a job - it's a career-defining opportunity! At Hillpointe, you'll be part of a dynamic, innovative team that has tangible impacts on day-to-day operations and contributes directly to overall success. Benefits Analyst Hillpointe is hiring a Benefits Analyst to lead the performance and oversight of our self-funded health plan and related benefit programs. This role emphasizes financial stewardship, compliance, and data transparency—aligning benefit strategies with organizational financial goals and operational efficiency. Essential Responsibilities: Benefit Plan Analytics & Financial Oversight Collaborate with UMR and Broker of Record to monitor claims activity, reserve positions, and stop-loss reimbursements. Ensure accurate benefit deduction mapping between UKG and payroll systems. Manage the reconciliation workflow from benefits through payroll and into the general ledger. Analyze cost allocation across business units and EINs to support internal financial modeling. Performance Dashboards & Reporting Infrastructure Develop foundational reporting tools for: Claims vs. budget performance Wellness program impact measurement Program-level return on investment (ROI) Provide leadership with actionable insights that inform benefit plan adjustments and budget forecasts. Regulatory Compliance & Accounting Alignment Maintain adherence to regulatory standards including ACA, HIPAA, SPD disclosures, and 1095-C reporting. Partner with Accounting on health account bank reconciliations and ensure timely submission of benefit filings. Strategic Program Deployment & Governance Support the implementation and rollout of financially driven initiatives such as: 401(k) plan launch UKG Wallet deployment Travel and entertainment policy ramp-up Expense reimbursement guardrails (in coordination with Payroll) Requirements: Bachelor’s degree in Business, Finance, HR, or related field preferred. 2–3 years of experience in benefits administration or financial operations. Strong quantitative skills with demonstrated ability to manage and synthesize large datasets. Familiarity with health plan reporting, regulatory compliance, and payroll systems (UKG experience a plus). NOTE: This document outlines the general nature and level of work expected from individuals in this role. It's important to understand that this is not an exhaustive list of responsibilities, duties, and skills. Additional tasks or job functions that can be safely performed may be required as necessary by supervisory personnel. This flexibility in additional duties showcases the company's adaptability and encourages employees to be versatile. The employee is expected to adhere to all work rules, procedures, and policies established by the company, including, but not limited to, those contained in the employee handbook.

Keywords: Hillpointe, Lakeland , Benefits Analyst, Accounting, Auditing , Winter Park, Florida