HR Generalist, Lakeside Software
2-3 days a week in office
AI-driven DEX platform
Be an early applicant
AI-driven DEX platform
201-500 employees
Be an early applicant
2-3 days a week in office
201-500 employees
Company mission
To give IT architects and EUC engineers the data they need to understand the hidden issues, fix problems faster, and make informed decisions.
Role
Who you are
- 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
What the job involves
- 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
- 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
- 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 take
It’s often difficult for large companies to gain an overview of their IT systems and environments. Siloed systems and processes can lead to a waste of resources and mean companies miss opportunities to make and save money. Lakeside Software is an AI-driven digital employee experience company that is helping businesses gain more control over their digital environments.
It achieves this through a savvy use of AI systems. Lakeside Software’s SysTrack platform provides analytics, dashboards and applications that augment and optimize digital landscapes through data collection. With a reported 10,000 data points collected every 15 seconds, Lakeside Software has amassed an impressive customer base that includes Fortune 500 companies. Ultimately, SysTrack provides end-to-end digital visibility, error fixes and data analysis, increasing company value through the power of data.
With consistent industry recognition throughout 2024, Lakeside Software is capitalizing on its awards by growing its leadership team and expanding its product capabilities.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Company
Company benefits
- Medical, Dental & Vision Insurance
- Flexible Spending
- Short & Long Term Disability Insurance
- Company Paid Life & Voluntary Life & AD&D Insurance
- 401(k) matching
- 11 Days Observed Holidays
- 20 Days PTO
- 5 Days Paid Sick Time
- Opportunities for career development and growth
- A collaborative and supportive team culture
Company HQ
Financial District, Boston, MA
Leadership
Mike Schumacher
(Founder & CEO)Studied at the University of Michigan before working on the Research Staff for the Industrial Technology Institute. Also previously a Director of Software Development at Paradata Computer Networks, a Director of Software Engineering at the Telebit Corporation and the Cubix Corporation.
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