Sr. Benefits Specialist

Immigration / Work Authorization Notice: Applicants must be currently authorized to work in the United States. iSpot is not able to sponsor or take over sponsorship of an employment visa for this position at this time. iSpot competes for the best talent. Our compensation packages consist of salary and equity in one of Seattle’s hottest start-ups, as well as other standard benefits. Most importantly, we provide a really interesting working experience, and the chance to contribute to the success of something great. What You'll Be Part Of At iSpot, we are the pioneers of real-time TV ad measurement and attribution. We know that behind every cutting-edge data point is a human being driving that innovation. That’s why our People Team treats employee care with the same precision and dedication we bring to our analytics. As our Senior Benefits Specialist, you will sit at the intersection of empathy and data, overseeing both our comprehensive benefits and our Leave of Absence (LOA) programs. We are looking for someone who loves the analytical challenge of negotiating plans, diving into data‑driven audits, and mastering complex multi‑state regulations, but who never loses sight of the “why”—supporting our people through life’s big moments. Whether you are auditing a Form 5500 or guiding an employee through the nuances of parental or medical leave, your work ensures our team feels secure and valued. You will directly impact our culture of care, helping us support and retain the brilliant minds who are revolutionizing the future of media analytics. Responsibilities Plan Management & Administration: Oversee the day‑to‑day administration of iSpot’s comprehensive benefits portfolio, including medical, dental, vision, retirement (401k), wellness initiatives, and supplemental plans. Leave of Absence (LOA) Management: End‑to‑end management of all leave programs (FMLA, short‑term/long‑term disability, parental leave, state‑mandated leaves, and ADA accommodations) from initial request and compliance tracking to successful return‑to‑work. Onboarding & New Hire Experience: Lead the benefits onboarding experience for all new hires, ensuring a welcoming, clear, and comprehensive introduction to iSpot’s total rewards from day one. Employee Benefits Support: Serve as the primary, empathetic point of contact for daily employee inquiries, providing high‑touch support for claims resolution, coverage details, and life event changes. Benefit & Payroll Reconciliation: Partner closely with the Payroll team to perform monthly premium reconciliations, ensure accurate benefit deductions, resolve billing discrepancies, and maintain clean data between HRIS and carriers. Compensation Planning Support: Provide analytical support during annual compensation review cycles, assisting with market data benchmarking, internal equity reviews, and salary band analysis. Vendor Relations & Negotiation: Partner with brokers, insurance carriers, and third‑party leave administrators to manage, review, and negotiate annual plan renewals and service agreements. Compliance & Auditing: Lead annual benefit audits, non‑discrimination testing, and the preparation/filing of Form 5500s to ensure strict compliance with ERISA, ACA, DOL, IRS, and state leave regulations. Multi‑State Operations: Manage benefits compliance and varied leave‑of‑absence laws tailored to a diverse, multi‑state workforce. HRIS Management: Utilize ADP Workforce Now to manage benefit enrollments, life events, deductions, leave tracking, and accurate data synchronization with carriers. Open Enrollment & Education: Lead the strategy, communication, and execution of the annual Open Enrollment process, creating clear, educational materials regarding benefits and leave policies. Equity administration: Process new hire and termination equity in Carta to ensure a smooth onboarding/offboarding process. Qualifications and Education Requirements Experience: 3–5 years of dedicated benefits administration experience, including direct experience managing, reviewing, and auditing plans, as well as hands‑on management of Leave of Absence (LOA) programs. Technical Skills: Strong proficiency and hands‑on experience with ADP (specifically Workforce Now) for benefits administration, leave tracking, and reporting. Compliance Mastery: Solid understanding of Form 5500 filings, benefits auditing processes, and federal/state regulations (ERISA, COBRA, HIPAA, FMLA, ADA, and state‑paid family leave laws). Geographic Scope: Experience managing benefits and varied leave compliance for employees spread across multiple states. Education: Bachelor's degree in Human Resources, Business Administration, or a related field (or equivalent practical experience). Preferred Skills Professional certifications such as CEBS (Certified Employee Benefit Specialist), CLMS (Certified Leave Management Specialist), PHR, or SHRM-CP. Advanced Excel & Data Analytics: Strong capability with data analysis, pivot tables, audit reconciliation, and leave tracking to drive insights. Strong communication and presentation skills, with the ability to explain complex benefit and leave concepts in simple, empathetic terms. Experience working in a fast‑paced tech or SaaS environment. Additional Notes: This role is a fantastic opportunity for a detail‑oriented, analytical professional who loves data and compliance but is equally passionate about employee wellness and advocacy during critical life events. This position operates on a hybrid schedule out of our corporate headquarters in Bellevue, WA, where you will collaborate closely with the broader HR, Legal, and Payroll teams. Hybrid & Flexible Workplace Policy iSpot supports a hybrid and flexible workplace. Depending on location and work responsibilities, employees may be designated as full‑time or part‑time office‑based or a fully remote employee. A hybrid work schedule indicates that you work in the office some days and work from home other days. The best hybrid workplaces allow for flexibility while also encouraging consistency. Those local or living in surrounding areas to one of our offices (Bellevue, WA or New York, NY) will work a hybrid schedule, coming into their local office 1-3 days a week. While those in a role, not office‑based and located further away from our offices, will work a fully remote schedule. If you have questions regarding exact details of our hybrid & flexible workplace policy, please let your recruiter know and they will discuss with you further. iSpot is an equal opportunity employer. All applicants will receive consideration for employment without regard to race, ethnicity, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status. If you need assistance and/or a reasonable accommodation due to a disability during the application or the recruiting process, please contact our HR team. California Residents applying for positions at iSpot can access our California Consumer Privacy Act here. Target cash compensation range: $87,930‑108,160 USD Annually We are committed to providing competitive, market-informed compensation. The cash compensation above includes base salary, variable commission for employees in eligible roles, and annual bonus targets for eligible roles. In addition to cash compensation, all full time iSpotters are eligible to participate in iSpot’s equity plan to receive stock options. Non‑exempt roles will also be eligible for (pre‑approved) overtime pay. Individual compensation packages are influenced by different factors unique to each candidate, including their skills, experience, qualifications and other job‑related reasons. For more information on total rewards package, go HERE. #J-18808-Ljbffr Madrona Venture Labs