Lakeside Software is hiring: HR Generalist in Boston

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

• Support the VP of People & Culture in executing HR projects such as job leveling, compensation reviews, and engagement initiatives.
• Lead process documentation and project tracking for recurring HR cycles (open enrollment, performance reviews, compliance training).
• Partner with leadership on new HR programs related to wellness, professional development, and recognition.
• Collaborate with global HR counterparts and cross-functional teams (Finance, IT, Legal) to ensure consistent practices and data integrity.

Employee Experience & Communication

• Serve as a first point of contact for HR questions, providing clear and timely guidance to employees.
• Support new hire onboarding logistics, communication, and employee documentation.
• Draft and distribute internal HR communications, alerts, and process updates.
• Uphold a positive, approachable, and professional tone in every interaction, helping maintain Lakeside’s culture of respect and accountability.

Requirements

• 3–5 years of experience in HR, People Operations, or HR Administration; experience in a SaaS or technology environment preferred.
• Strong project management skills—able to handle multiple priorities with precision and follow-through.
• Demonstrated success managing confidential employee data and sensitive communications.
• Excellent written and verbal communication; strong attention to accuracy and detail.
• Proficiency with HRIS systems (ADP Workforce Now preferred) and Microsoft Office or Google Workspace.
• Familiarity with U.S. employment laws and HR best practices.
• Collaborative mindset with the ability to partner across levels and functions.

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

• Medical, Dental & Vision Insurance
• Flexible Spending Accounts
• Short & Long-Term Disability Insurance
• Company Paid & Voluntary Life Insurance
• 401(k) with Matching
• 11 Company Holidays
• 20 Days PTO + 5 Paid Sick Days
• Professional Development Opportunities
• Collaborative, inclusive culture