[Hiring] Senior Benefits Manager @Juniper Square

Role Description

As the Senior Benefits Manager, you'll own the benefits and leave experience end to end for a global, distributed workforce, and serve as the operational backbone of our Total Rewards function. You'll also own the employee perks and recognition programs that sit alongside our benefits, from anniversary awards to the budget for our Regional Culture Ambassadors Program. Reporting directly to the VP of Total Rewards & People Operations, you'll partner cross-functionally with Finance, Payroll, People Business Partners, and our benefits brokers and carriers to ensure our programs run flawlessly, stay compliant, and scale with the company.

What You'll Do

• Serve as the front-line owner for all employee benefits inquiries, including medical, dental, vision, FSA/HSA mechanics, dependent coverage, and qualifying life events, acknowledging and escalating urgent coverage or eligibility issues immediately.
• Own benefits enrollment across regions, including new-hire enrollment within eligibility windows, QLE processing, and annual open enrollment coordination.
• Manage carrier and EDI relationships, investigating and resolving file errors, coordinating eligibility changes, and tracking cancellations and reinstatements.
• Partner with our benefits broker on carrier issues, plan design, renewals, and employee communications.
• Project manage your own benefits work end to end, including renewals, open enrollment, and plan changes, setting timelines, coordinating partners, and delivering on deadline.
• Own leave administration end to end through Sparrow, including employee, manager, and People Business Partner communications, paystub coordination, return-to-work logistics, and fitness-for-duty documentation follow-up.
• Ensure leave and benefits deductions are accurate and supported with the right documentation each pay cycle.
• Own benefits compliance cycles, including ACA, Form 5500 filings, and non-discrimination testing.
• Prepare and validate all benefits- and leave-related pre-payroll inputs, delivering clean, audit-ready data to the Payroll Manager ahead of each cycle cutoff.
• Own the employee anniversary program across the U.S., Canada, and India, including milestone awards by level and tenure, cash award inputs to payroll, swag fulfillment, and employee announcements.
• Own year-end gifting and swag, managing vendor selection, budget, and fulfillment so every employee has a great experience, wherever they're located.
• Administer the Regional Culture Ambassadors Program budget across North America and India, including modeling and setting each region's annual budget, tracking spend with Finance, and preparing the annual budget proposal.
• Serve as the point of contact for our volunteer ambassadors, adding new regions and ambassadors, and keeping program guidelines and trackers current.
• Report on program spend and participation, and use the data to improve how the programs run.
• Serve as a key backup on compensation and equity operations, supporting the Total Rewards function.
• Identify opportunities to automate high-repetition benefits, leave, and perks and recognition workflows, partnering with the team to embed AI-powered tooling that reduces manual lift without sacrificing accuracy or compliance.
• Contribute to a continuous-improvement culture where surfacing automation opportunities is an expected part of the role.

Qualifications

• 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.

Compensation

Compensation for this position includes a base salary, equity, and a variety of benefits. The U.S. base salary range for this role is $120,000 – 150,000 USD. Actual base salaries will be based on candidate-specific factors, including experience, skillset, and location, and local minimum pay requirements as applicable. Your recruiter can provide further details.

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