Benefits Specialist - Lifecycle

RemotePass; Boston; Remote; PHP 4,383,000 - 6,888,000; Full time

Benefits offered by this job

Profitability & growth

Global scale

Ambitious roadmap

Remote-first culture

Inclusive culture

Job summary

RemotePass is hiring a Benefits Specialist to join our Lifecycle team and own the global employee benefits experience across multiple countries. You’ll run renewals, scope and launch new plans, and keep enrolment and administration accurate with Payroll, Finance and Legal.

Health insurance is at the core of the role, and you’ll work with brokers, insurers, and local partners to ensure plans are well priced and compliant.

Qualifications

• 3+ years in employee benefits, benefits administration, insurance, or HR operations.
• Strong knowledge of health insurance; life, disability, pension, wellness benefits is a plus.
• Hands-on experience managing renewals or new plan implementations.
• Experience reviewing plan proposals and comparing coverage and pricing with brokers or insurers.
• Benefits experience across multiple countries, with understanding of jurisdiction variations.
• Background in EOR/PEO/global mobility/HR tech/international payroll or insurance brokerage is a strong advantage.
• Analytical skills to assess pricing, plan structures, and commercial proposals.
• Highly organised and detail-oriented, able to run multiple renewals and projects at once.
• Fluent written and spoken English.

Responsibilities

• Own global benefits renewals; manage renewal calendar and ensure on-time completions.
• Scope and launch new plans; research local requirements and compare proposals.
• Keep enrolment and administration accurate; coordinate with Payroll, Finance and Legal.
• Be the go-to for benefits questions; guide internal teams on statutory vs supplemental benefits.
• Manage brokers, insurers, and partners; be main contact for complex issues.
• Stay ahead of market changes; flag implications for plans at scale.
• Standardise workflows; document global benefits processes to support growth.

Skills

Benefits admin

Health insurance

Renewals

Plan comparison

Global benefits

EOR/PEO

Data analysis

Organization

English

Job description

About RemotePass

RemotePass is a leading global platform transforming the way businesses access and manage top talent. Recognised as one of G2's Top 100 Fastest Growing Software Products, we're on a mission to break down geographical barriers and create a world where exceptional talent can thrive anywhere.

By streamlining global hiring, onboarding, payroll, and compliance, RemotePass empowers organisations to build high-performing remote teams. Our platform is designed to improve the lives of millions of workers worldwide by giving them unprecedented opportunities to connect with global employers and reach their full potential.

We're backed by world-class investors: Endeavor Catalyst, Khwarizmi Ventures, Oraseya Capital, Flyer One Ventures, Access Bridge Ventures, A15, Swiss Founders Fund, and Plug & Play.

About the Role

When a company hires through RemotePass in a new country, its employees expect benefits that are competitive, compliant, and in place from day one. We're hiring a Benefits Specialist to join our Lifecycle team and own that experience across our global EOR workforce.

You'll run annual renewals across multiple countries, scope and launch new plans where clients need them, and keep enrolment and administration accurate. Health insurance is at the core of the role, and you'll work with brokers, insurers, local partners, clients, and internal teams to make sure every plan is well priced and compliant.

This isn't a single-market benefits role. Every country has its own statutory requirements, market norms, and providers, and you'll navigate all of them.

What You'll Do

• Own benefits renewals. Run the global renewal calendar and see every renewal through on time. Review terms, pricing, and coverage, flag cost increases and gaps, and support negotiations with brokers and providers.
• Scope and launch new plans. Research local market practice and statutory requirements wherever clients need new or enhanced benefits. Compare proposals on coverage, pricing, exclusions, and limits, then take the chosen plan from scoping through launch.
• Keep enrolment and administration accurate. Oversee enrolments, changes, and terminations. Work with Payroll, Finance, and Legal so billing is right, and reconcile invoices, employee data, and plan costs when discrepancies appear.
• Be the go-to for benefits questions. Handle employee and client queries and escalations. Give internal teams clear guidance on statutory vs supplemental benefits in each market.
• Manage brokers, insurers, and partners. Build strong relationships with providers and local partners, and act as the main point of contact when complex issues need resolving.
• Stay ahead of market changes. Track shifts in local requirements, market practice, and insurance offerings, and flag what they mean for our plans.
• Standardise how we work. Improve and document global benefits processes so they scale as our workforce grows.

What We're Looking For

• 3+ years in employee benefits, benefits administration, insurance, or HR operations.
• Strong knowledge of health insurance. Familiarity with life, disability, pension, and wellness benefits is a plus.
• Hands-on experience managing benefits renewals or new plan implementations.
• Experience reviewing plan proposals and comparing coverage and pricing with brokers or insurers.
• Benefits experience across multiple countries, with a clear understanding of how requirements vary by jurisdiction.
• A background in EOR, PEO, global mobility, HR tech, international payroll, or insurance brokerage is a strong advantage.
• The analytical skills to assess pricing, plan structures, and commercial proposals.
• Highly organised and detail-oriented, able to run multiple renewals and projects at once.
• Fluent written and spoken English.

Nice to Have

• Benefits experience across EMEA, GCC, APAC, or LATAM.
• Experience with benefits benchmarking and market analysis.
• Exposure to benefits audits, compliance reviews, or due diligence.
• Familiarity with HRIS or benefits administration platforms.

You'll Thrive in This Role If

• You take ownership and catch problems before an employee or client does.
• You enjoy the puzzle of making benefits work across very different markets.
• You can explain a complex plan clearly to an employee, a client, and a finance team alike.
• You like building processes, not just following them.

Why Join RemotePass?

• Profitable, and scaling fast. We reached profitability in 2025 and just raised a $17.4M Series B led by EBRD, with 500 Global joining. You get the pace of a scale-up with the stability of a business that works.
• Real global scale. We support 35,000+ workers in 150+ countries and have processed over $800M in cross-border payroll for companies like Logitech, Tata Group, and Careem.
• Big bets ahead. We're expanding across Europe and the US, building financial products for distributed teams, and investing heavily in AI. There's a lot to build, and room to grow with it.
• Remote-first, for real. We don't just sell remote work, we live it. Work from anywhere.
• Inclusion matters. We value different perspectives and empower everyone to bring their authentic self to work.