Senior Benefits Manager

Posted 4hrs ago

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Job Description

Senior Benefits Manager owning benefits, leave, and employee programs at Juniper Square. Supporting a distributed workforce through compliance, payroll coordination, and automation.

Responsibilities:

  • 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:

  • 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

Benefits:

  • Health, dental, and vision care for you and your family
  • Life insurance and disability coverage
  • Mental wellness coverage
  • Fertility and growing family support
  • Unlimited vacation in addition to company paid holidays
  • Paid family leave, medical leave, and bereavement leave policies
  • 401k retirement savings plan
  • Healthcare FSA and commuter benefits programs
  • Allowance to customize your work and technology setup at home
  • Annual professional development stipend
  • Equity
  • Employee anniversary awards
  • Year-end gifting and swag
  • Regional Culture Ambassadors Program
  • Flexible remote-to-office work options