Senior Benefits Manager

Juniper Square•,

1d•$120,000 - $150,000

About The Position

The Senior Benefits Manager owns the end-to-end benefits and leave experience for Juniper Square’s global, distributed workforce and serves as the operational backbone of the Total Rewards function. The role also owns employee perks and recognition programs, including anniversary awards, year-end gifting and swag, and the Regional Culture Ambassadors Program. The manager partners with Finance, Payroll, People Business Partners, brokers, and carriers to operate programs accurately, compliantly, and at scale. The position reports to the VP of Total Rewards & People Operations. It also serves as a key backup for compensation and equity operations and is expected to identify opportunities to automate recurring benefits, leave, and recognition workflows, including through AI-powered tools.

Requirements

At least 7 years of benefits experience.
Deep expertise in benefits administration, leave management, and benefits compliance, including ACA, Form 5500, and non-discrimination testing.
Hands-on experience managing carrier and broker relationships, EDI files, and enrollment platforms.
Strong project management skills and a record of managing projects end to end and delivering on time.
Strong operational rigor and attention to detail, with a record of delivering clean, audit-ready data under recurring deadlines.
Familiarity with pre-payroll preparation and the relationship between benefits, leave, and payroll.
Exceptional relationship-building and cross-functional collaboration skills, particularly with Finance, Payroll, and People Business Partners.
Ability to work in a fast-paced, dynamic environment and adapt to changing priorities.

Nice To Haves

Benefits experience in a SaaS or technology company operating across multiple geographies.
Experience administering employee perks or recognition programs, including managing budgets across locations.
Exposure to 401(k) plan administration, such as recordkeeper and TPA partnership, deferral reconciliation, non-discrimination testing, or Form 5500.
Exposure to compensation.
Exposure to equity operations.
Hands-on experience with or genuine curiosity about AI-powered tools, and comfort experimenting with and deploying new tooling such as Claude.

Responsibilities

Serve as the primary point of contact for employee benefits inquiries, including medical, dental, vision, FSA/HSA, dependent coverage, and qualifying life events, escalating urgent coverage or eligibility issues promptly.
Own benefits enrollment across regions, including new-hire enrollment, qualifying life event processing, and annual open enrollment.
Manage carrier and EDI relationships; investigate and resolve file errors, coordinate eligibility changes, and track cancellations and reinstatements.
Partner with the benefits broker on carrier issues, plan design, renewals, and employee communications.
Project-manage benefits work end to end, including renewals, open enrollment, and plan changes.
Administer leaves through Sparrow, including communications, paystub coordination, return-to-work logistics, and fitness-for-duty documentation follow-up.
Ensure leave and benefits deductions are accurate and supported by appropriate documentation each pay cycle.
Manage benefits compliance cycles, including ACA, Form 5500 filings, and non-discrimination testing.
Prepare and validate benefits- and leave-related pre-payroll inputs and provide clean, audit-ready data to the Payroll Manager before each cycle cutoff.
Manage the employee anniversary program across the U.S., Canada, and India, including milestone awards, payroll inputs for cash awards, swag fulfillment, and announcements.
Manage year-end gifting and swag, including vendor selection, budget, and fulfillment.
Administer the Regional Culture Ambassadors Program budget across North America and India, including regional budget modeling, spend tracking with Finance, and annual budget proposals.
Support volunteer ambassadors, add regions and ambassadors, and maintain program guidelines and trackers.
Report on program spend and participation and use the data to improve program operations.
Provide backup support for compensation and equity operations.
Identify opportunities to automate benefits, leave, and perks and recognition workflows, and partner with the team to implement AI-powered tools while maintaining accuracy and compliance.
Contribute to a continuous-improvement culture by surfacing automation opportunities.