Senior Benefits Manager

Juniper Square

. Serve as the front-line owner for employee benefits inquiries, including medical, dental, vision, FSA/HSA mechanics, dependent coverage, and qualifying life events .

Posted 11/5/2026full-timeRemote • United States, CanadaSenior💰 $120,000 - $150,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive expertise in Benefits Administration, Leave Management, and Benefits Compliance, including ACA and Form 5500 filings. Proven ability to manage carrier relationships, project manage benefits enrollment, and implement AI-powered workflow automation.

Highest-signal resume keywords

Benefits AdministrationLeave ManagementBenefits ComplianceProject ManagementCarrier Relationship Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Benefits AdministrationLeave ManagementBenefits ComplianceProject ManagementPre-Payroll PreparationCarrier Relationship ManagementEDI File ManagementEnrollment Platforms401(k) Plan AdministrationAI-Powered Tools

Soft Skills

Relationship BuildingCross-Functional CollaborationAttention to DetailAdaptabilityOperational Rigor

Tools & Technologies

SparrowClaudeEnrollment PlatformsAI-Powered Tools

Industry Keywords

SaaSNon-Discrimination TestingForm 5500Employee PerksRecognition Programs

About the role

Key responsibilities & impact

Serve as the front-line owner for employee benefits inquiries, including medical, dental, vision, FSA/HSA mechanics, dependent coverage, and qualifying life events
Own benefits enrollment across regions, including new-hire enrollment, qualifying life event processing, and annual open enrollment coordination
Manage carrier and EDI relationships, investigating file errors and coordinating eligibility changes, cancellations, and reinstatements
Partner with the benefits broker on carrier issues, plan design, renewals, and employee communications
Project-manage renewals, open enrollment, and plan changes end to end
Own leave administration through Sparrow, including communications, paystub coordination, return-to-work logistics, and fitness-for-duty documentation
Ensure accurate leave and benefits deductions and supporting documentation each pay cycle
Own benefits compliance cycles, including ACA, Form 5500 filings, and non-discrimination testing
Prepare and validate benefits- and leave-related pre-payroll inputs
Own the employee anniversary program across the U.S., Canada, and India
Own year-end gifting and swag, including vendor selection, budget, and fulfillment
Administer the Regional Culture Ambassadors Program budget across North America and India
Maintain ambassador records, program guidelines, and trackers
Report on program spend and participation and improve program operations
Serve as backup for compensation and equity operations
Identify and implement AI-powered workflow automation opportunities for benefits, leave, perks, and recognition

Requirements

What you’ll need

7+ years of benefits experience, ideally within a SaaS or technology company operating across multiple geographies
Deep expertise in benefits administration, leave management, and benefits compliance (ACA, 5500, non-discrimination testing)
Hands-on experience managing carrier and broker relationships, EDI files, and enrollment platforms
Strong project management skills, with a track record of running your own projects end to end and delivering on deadline
Strong operational rigor and attention to detail, with a track record of delivering clean, audit-ready data under recurring deadlines
Familiarity with pre-payroll preparation and the interface between benefits, leave, and payroll
Experience administering employee perks or recognition programs, including managing budgets across locations, is a plus
Exposure to 401(k) plan administration, such as recordkeeper and TPA partnership, deferral reconciliation, nondiscrimination testing, or Form 5500, is a plus
Exposure to compensation is a plus
Exposure to equity operations is a plus
Hands-on experience with, or genuine curiosity about, AI-powered tools; comfort experimenting with and deploying new tooling, including platforms such as Claude, is a strong plus
Exceptional relationship-building and cross-functional collaboration skills, especially with Finance, Payroll, and People Business Partners
Ability to work in a fast-paced, dynamic environment and adapt to changing priorities