Hillpointe · 11 hours ago
Benefits Analyst
Winter Park, FL
Full-time
Onsite
Entry, Mid Level
2+ years expHillpointe is a fully integrated real estate development and investment management firm focused on developing market-rate workforce housing. They are seeking a Benefits Analyst to lead the performance and oversight of their self-funded health plan and related benefit programs, emphasizing financial stewardship, compliance, and data transparency.
LeasingProperty DevelopmentReal Estate
Responsibilities
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
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
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
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)
Qualification
Required
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
Preferred
Bachelor's degree in Business, Finance, HR, or related field preferred
UKG experience a plus
Benefits
401(k) plan launch
UKG Wallet deployment
Travel and entertainment policy ramp-up
Expense reimbursement guardrails (in coordination with Payroll)
Company
Hillpointe
Hillpointe is a real estate development and investment management firm that controls land acquisition, land development, and construction.
201-500 employees
Funding
Current Stage
Growth StageLeadership Team
Steven Campisi, CFA
Co-Founder and Managing Partner
Recent News
Crowdfund Insider
2026-01-23
2025-12-15
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