Senior Benefits Manager

Zūm•Redwood City, CA

11d•$193,000 - $215,000•Hybrid

About The Position

Zūm is revolutionizing mass mobility with its Connected Mobility Experience (Zūm CMX™) system that connects and coordinates people, vehicles, and operations in real time. In the $50 billion student mobility market – the largest segment of the mass mobility industry – Zūm CMX is transforming a daily source of anxiety and disruption into a reliable, transparent, and efficient mobility experience for students and families. Today, more than 4,500 schools rely on Zūm CMX. Recognized globally for its innovative approach and operational execution, Zūm has been named to Fast Company’s World’s Most Innovative Companies, CNBC Disruptor 50 and Changemakers, the World Economic Forum, and the Financial Times’ Fastest Growing Companies lists. Zūm is backed by leading investors including Sequoia Capital, GIC, TPG, and Softbank. We're looking for a Senior Benefits Manager to own Zūm's benefits function end-to-end, covering strategy, administration, compliance, and continuous improvement across health, welfare, retirement, and leave programs for approximately 5,000 employees in 15+ states. The role is genuinely complex: programs span PEO and direct-employer structures, unionized and non-union populations, CDL-licensed drivers and corporate staff, and multiple administration platforms. You'll partner with brokers, carriers, payroll, legal, and finance, and report to the VP of People Operations as a strategic thought partner on total rewards. You thrive where answers aren't obvious, documentation doesn't exist yet, and you build the fix before anyone has to ask. You're equally comfortable presenting a renewal strategy to the CPO and walking a field employee through enrollment. You catch the off-by-a-dollar deduction, the compliance deadline no one else is tracking, and the employee who needs help navigating a claim. And you understand that what you build today must scale with a company preparing for its most visible chapter yet. This is a hybrid position based out of our headquarters in Redwood City, CA. You will be required to be onsite 3 days per week (Monday, Tuesday, and Thursday). We will only consider candidates already located in the Bay Area.

Requirements

8–12+ years of progressive experience in people operations, benefits management, administration, and strategy, with at least 3 years at a senior or lead level.
Deep expertise in health & welfare plan design, 401(k)/retirement plan administration, and leave management.
Thorough working knowledge of ERISA, ACA, COBRA, HIPAA, FMLA, Section 125, and state/local benefits regulations.
Proven experience managing benefits for a large, distributed, multi-state workforce (1,000+ employees), including hourly and non-exempt populations.
Strong vendor management skills: experience leading broker relationships, carrier negotiations, renewals, and RFPs.
Exceptional analytical skills: you can model plan costs, interpret utilization data, and build executive-level reporting.
Strong project management capabilities with the ability to drive multiple complex initiatives simultaneously and hold vendors accountable to timelines.
Excellent written and verbal communication skills, with the ability to translate complex benefits concepts for employees at all levels.
Proficiency in HRIS platforms, benefits administration systems, and advanced Excel/Google Sheets.

Nice To Haves

Experience in a high-growth, venture-backed company, ideally through a liquidity event.
Experience managing benefits across both PEO-administered and direct-employer plan structures.
Experience with Compensation, including market benchmarking (e.g Radford, Pave), job architecture, and end-to-end merit review cycle management.
Familiarity with unionized workforce benefits, including CBA interpretation and compliance with collectively bargained benefit obligations.
Experience with ADP platforms, Employee Navigator, Charles Schwab retirement services, or Sequoia consulting.
Knowledge of self-funded and level-funded health plan structures, including stop-loss and claims analysis.
CEBS, CBP, PHR/SPHR, or SHRM-CP/SHRM-SCP certification.

Responsibilities

Be the go-to expert on all things benefits -- designing and managing programs that are competitive, compliant, and aligned with Zūm’s business goals and employee value proposition.
Lead benefits strategy across multiple plan structures, including PEO-administered plans, direct-employer plans, MERP, union/CBA-governed benefits, and state-mandated programs (e.g., Washington SEBB).
Conduct benchmarking and market analysis to ensure our offerings are competitive and cost-effective across both corporate and field employee populations.
Partner with the leadership and brokers to evaluate funding models (fully insured, self-funded, level-funded) and make data-driven recommendations on plan design.
Drive the design and modeling of new benefit constructs, including field employee medical reimbursement plans and deductible-exposure analysis.
Continuously evaluate and improve benefits offerings to enhance employee satisfaction and retention while managing cost trends.
Serve as the day-to-day operational owner of Zūm’s 401(k) program, including contribution remittance, eligibility management, loan administration, and participant support.
Partner with plan advisors on fiduciary governance, investment menu reviews, plan design changes, and 401(k) committee meeting preparation.
Manage annual nondiscrimination testing (ADP/ACP, top-heavy, coverage) and coordinate corrective actions, including QNEC distributions and HCE refunds.
Oversee compliance filings (Form 5500, annual audits) and ensure adherence to ERISA fiduciary standards.
Ensure full compliance with federal, state, and local benefits regulations, including ERISA, ACA, COBRA, HIPAA, FMLA, CFRA, and city-specific health care ordinances (e.g., SF HCSO).
Own ACA compliance end-to-end: eligibility tracking across variable-hour field employees, 1095-C reporting, and IRS penalty response and abatement processes.
Manage Wrap Plan and SPD documentation, Section 125 (POP) Plan administration, and Section 105(h) MERP nondiscrimination testing.
Partner with inside and outside counsel on benefits-related legal matters, due diligence requests, and regulatory filings.
Support the development of sophisticated operational workstreams: benefits disclosures, plan documentation for legal due diligence, and ERISA loan covenant review.
Manage relationships with compliance consultants and ensure timely and accurate regulatory filings across all benefit plans.
Manage the full lifecycle of benefits administration: new hire enrollment, qualifying life events, open enrollment, COBRA, and offboarding.
Own vendor and broker relationships across medical carriers, ancillary providers, retirement recordkeepers, benefits administration platforms, and leave management partners.
Oversee carrier invoice reconciliation, premium billing, and payroll deduction accuracy across multiple payroll systems, identifying and resolving discrepancies promptly.
Manage and improve leave of absence programs (FMLA, CFRA, ADA interactive process, state-specific leaves, parental leave) in coordination with the broader People Ops team.
Establish and standardize policies, processes, and documentation across the benefits function, building scalable infrastructure for continued growth.
Support the implementation of ben admin systems that can handle multi-thousand enrollments nationally.
Lead annual open enrollment planning and execution, including vendor coordination, employee education materials, and system configuration.
Develop clear, accessible benefits communications for a diverse workforce -- from corporate employees to CDL drivers and attendants across 15+ states.
Serve as the senior escalation point for complex benefits questions, ensuring timely and empathetic resolution.
Partner with field operations to ensure benefits information is accurately communicated at the local level.
Collaborate with Finance on benefits budgeting, forecasting, renewal cost modeling, and accounts payable coordination for vendor payments.
Build and maintain dashboards and reports on benefits utilization, cost trends, enrollment metrics, and program effectiveness.
Partner with HRIS and Payroll teams during system implementations and integrations, ensuring benefits data flows cleanly across platforms.
Support compensation-adjacent projects as needed, including total rewards statements and offer benchmarking inputs.