People Operations Generalist

About Bennie

Bennie ( www.bennie.com

) is an employee benefits services and technology firm that helps companies create a healthier workplace. Bennie provides services and technology that are beyond what growing companies typically receive, yet exactly what they need.

Bennie has built the ultimate benefits platform that connects disparate systems across the benefits supply chain to deliver a complete experience for employees, employers, and partners. Bennie’s technology, benefit plans, and service model are designed to enable employers and their employees to experience best-in-class outcomes that reduce overall health plan costs. Bennie’s team members use the platform and its data to supplement their market knowledge and bring innovative solutions to Bennie’s customers.

Bennie is headquartered in Stamford, CT, and is a remote-first company with employees across the U.S.

• Core Values at Bennie
• As an organization, we value our team members who are
• Optimistic, Accountable, Thoughtful

, and

Healthy

. We believe these values, known as our O.A.T.H.

, are essential for our collective success. The ideal candidate for this role will embody these values by:

Maintaining a positive attitude throughout our journey of building our company.

Being responsible for the quality of their work and for meeting their goals.

Respecting our differences and looking out for one another.

Believing in living complete lives that balance our work and personal time.

About the role:

As our first dedicated

People Operations Generalist

, you will serve as the engine of Bennie’s employee experience and operational foundation. Because our platform and services directly empower HR leaders every day, our internal People team sets the standard for what modern, empathetic, and tech-driven People Operations should look like.

In this role, you will balance operational execution with high emotional intelligence (EQ). You will combine data, facts, and AI-driven workflows with a deeply human-centric approach to support our team across the entire employee lifecycle. Reporting directly to the VP of People

, you’ll help build, scale, and refine the programs that keep Bennie an exceptional place to work.

Reporting to:

VP, People

Responsibilities include:

• Employee Lifecycle & Onboarding Operations
• Manage HRIS data integrity, maintaining accurate employee records and lifecycle status changes
• Map, document, and maintain clear standard operating procedures and employee handbooks across all People Operations
• Identify operational bottlenecks and and implement modern automations and AI workflows to help streamline daily operational HR tasks
• Support the administration of Bennie’s total rewards, policies, and wellness initiatives in alignment with our remote first culture
• Ensure strict operational compliance with federal, state, and local employment laws, multi-state remote work guidelines, and documentation standards
• Embody Bennie’s O.A.T.H. values by helping champion internal culture initiatives, peer recognition programs, and remote team connection

Requirements:

• 3-5 years of equivalent practical experience in a multi-state, remote environment
• Technical Skills: Hands on experience managing modern HR tech stacks such as Rippling and Lattice. Comfortable using modern AI productivity tools (e.g. Gemini) to automate workflows, draft communications, and optimize operational workflows.
• Multi-State Compliance & Labor Laws: Practical knowledge of federal, state, and local employment laws (FMLA, ADA, FLSA) and multi-state compliance considerations for a remote workforce.
• Soft Skills: Clear and thoughtful communication skills, strong problem-solving abilities, ability to work independently and as part of a remote team, adaptability and solution-building, data-informed decision-making.
• Location: Ability to work remotely from anywhere within the United States.
• Nice to Have: HR Industry or Benefits Knowledge: prior experience within an HR-tech, employee benefits, or SaaS platform environment (bonus points for understanding benefits brokerages)
• HR Certification SHRM-SP, PHR, or equivalent
• Project Management Experience: Familiarity with lightweight project management tools (e.g., Jira, Monday.com)

Flexible Time Off:

We have a flexible vacation policy and offer paid company holidays

Remote-first environment:

Bennie is 100% remote (must be based in the US)

Comprehensive Medical Benefits

Stock Options:

All full-time employees are granted stock options

Remote Work Stipend:

• A $1,000 WFH Stipend
• Paid Parental & Bonding Leave
• Employee Referral Bonus Program
• Bennie is an Equal Opportunity Employer