Senior Benefits Manager

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🔥 1 minute ago

🌐 United States, Canada – Remote

🇺🇸 United States – Remote 🇨🇦 Canada – Remote

💵 $120k - $150k / year

⏰ Full Time

🟠 Senior

👔 Manager

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Juniper Square

WebsiteLinkedInAll Job Openings

201 - 500 employees

💸 Finance

🏠 Real Estate

☁️ SaaS

💰 $75M Series C on 2019-11

Finance • Real Estate • SaaS

Juniper Square is a company that provides a comprehensive platform and solutions tailored for private investment partnerships. Founded in 2014, the company focuses on enabling seamless connection and communication between General Partners (GPs) and Limited Partners (LPs) throughout the entire investment lifecycle. Juniper Square's technology is purpose-built to support commercial real estate, private equity, and venture capital firms of all sizes. The platform offers services such as fund administration, fundraising, investor management, compliance, and investor reporting, all aimed at enhancing transparency, data governance, and the overall investor experience.

📋 Description

• 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

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