HR Generalist

About the Role

Lakeside Software is seeking a highly organized and proactive HR Generalist to join our People & Culture team in Boston. This hybrid position requires being in the office 2–3 days per week to support collaboration, connection, and on-site projects.

This role is ideal for someone who enjoys working across a wide range of HR functions, thrives in a collaborative environment, and has a strong sense of ownership for both process and detail. The HR Generalist will serve as the operational backbone of our People team—supporting projects, programs, and day-to-day administrative excellence across the employee lifecycle. From onboarding and benefits coordination to data integrity, compliance, and process improvement, this person will help build a thoughtful, efficient, and high-trust HR function that scales with Lakeside’s growth.

Key Responsibilities

People Operations & Administration

• Maintain employee records, data accuracy, and reporting within HRIS and supporting systems.
• Manage documentation for new hires, terminations, promotions, and policy changes; ensure compliance with state and federal regulations.
• Partner with Payroll and Finance to ensure accuracy of pay, bonuses, and benefits deductions.
• Oversee employment verification, background checks, and compliance filings.
• Coordinate benefits administration and open enrollment, partnering with brokers and vendors to support employees.

Programs & Projects

Employee Experience & Communication

Requirements

Benefits

Why Join Lakeside

At Lakeside, we combine technical excellence with a human-centered culture. You’ll be joining a team that values integrity, thoughtful growth, and connection. The HR Generalist will play a vital role in shaping how we operate day-to-day and how we scale our people practices for the future. Our Boston office offers a welcoming, collaborative environment that encourages in-person teamwork while supporting flexibility through our hybrid schedule (2–3 days per week in office).

Benefits