People Operations Manager

MassMutual Ventures; Boston (MA); Hybrid; USD 115,000 - 135,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

401k with company match

Equity awards

Flexible PTO

Parental leave

Life and disability insurance

Job summary

LinkSquares, a Boston-based AI-powered CLM SaaS company, is hiring a People Operations Manager to own both the operational backbone and strategic programs of the People function. You’ll lead onboarding, benefits, HRIS data integrity, and compliance while advising managers on employee relations and performance development.

This hybrid role requires 3–5+ years in People Operations, strong analytical skills, and discretion.

Qualifications

• 3–5+ years in People Operations, HR Generalist, or related role in SaaS/high-growth.
• Experience administering benefits and owning HRIS data.
• Knowledge of employment law, leave requirements, and compliance basics.
• Experience supporting compensation programs and benchmarking is a plus.

Responsibilities

• Benefits administration: open enrollment and broker partnerships.
• Compliance & audits: employment laws, leaves, compensation regulations.
• HRIS data integrity: maintain accurate, confidential records.
• Cross-functional collaboration on headcount, onboarding, and offboarding.
• People analytics: reporting for quarterly metrics.
• Support compensation programs with leaders on pay decisions.
• Manage Performance Management processes and systems.
• Employee relations: investigations and exits.
• Trusted advisor to managers on people matters.

Skills

Excel

Data analysis

HRIS data management

Employment law knowledge

Confidentiality

Organization & multitasking

Tools

HRIS systems

Job description

About the company

LinkSquares is a Boston-based, AI-powered CLM SaaS leader trusted by organizations like DraftKings, Manscaped, and Vivid Seats. We automate the contracting process for legal, finance, and HR teams, helping them save time, cut costs, and improve business outcomes. For more information, visit linksquares.com.

About the team:

Come join our People team! From the moment someone accepts an offer through every stage of their time here, our People team is essential to creating a world-class employee experience. We partner with the business on programs like onboarding, performance management, total rewards, and ongoing culture initiatives that keep employees engaged and supported. We're a hands-on, detail-driven team that partners closely to support every department at LinkSquares.

About the role:

The People Operations Manager is a detail-oriented, highly organized professional who thrives on owning both the operational backbone and the strategic programs of a People function. You'll be the go-to resource for onboarding, benefits, HRIS data integrity, and compliance, while also acting as a trusted advisor to managers on employee relations, performance management, and development. This role is a strong fit for someone who wants to innovate and improve People programs utilizing AI and new technology.

Responsibilities:

• Benefits Administration: Manage annual open enrollment and serve as the primary point of contact for employee benefits questions; partner with our brokers to continuously improve our offerings.
• Compliance & Audits: Maintain compliance with employment law, leave of absence requirements, benefits, and compensation regulations, including recurring audits with our vendors.
• HRIS & Data Integrity: Own our HRIS system — timely, accurate data entry and administration, with the strictest confidentiality for sensitive employee information.
• Cross-Functional Collaboration: Partner across the People team and other departments on operational processes like headcount management, new hire logistics, and offboarding.
• People Analytics: Own People analytics and reporting, compiling and analyzing data for quarterly metrics reports that inform business decisions.
• Compensation Program Support: Support LinkSquares' compensation program through job evaluations, job leveling, and benchmarking, partnering with business leaders and Talent Acquisition on new hire pay decisions.
• Performance Management: Maintain and evolve LinkSquares’ Performance Management processes by managing applicable systems, training and feedback.
• Employee Relations: Partner with the organization to navigate challenging employee matters, conduct exit conversations and investigations.
• Trusted Advisor: Act as a go-to resource for managers and executives on people matters — performance management, leaves of absence, employee development, and employee relations.

Requirements:

• 3–5+ years of experience in People Operations, HR Generalist, or a related People/HR role, ideally in a SaaS or high-growth environment.
• Hands-on experience administering employee benefits programs and owning HRIS data.
• Working knowledge of employment law, leave of absence requirements, and compliance fundamentals.
• Experience supporting compensation programs (job evaluations, leveling, benchmarking) is a plus.
• Strong Excel and analytical skills and comfort turning People data into clear reports and insights.
• Excellent judgment and discretion. You'll regularly manage highly confidential information.
• Highly organized and proactive, with the ability to manage multiple priorities and deadlines.
• Based in or able to work from our Boston office Tuesday and Thursday each week (hybrid).

Compensation for this role includes an annual base salary between $115,000 to $135,000. LinkSquares takes into consideration a number of factors when determining an employee's starting salary, including work location, job-related skills, and relevant education, experience, and training.

Candidates are eligible to participate in the company's benefit programs. LinkSquares' benefits include but are not limited to medical, dental, and vision insurance, 401k retirement plan with a company match, equity awards (a new hire grant, along with opportunities for additional awards throughout your tenure), flexible paid time off, generous parental leave, life and disability insurances, and more.

LinkSquares is an Equal Opportunity Employer and does not discriminate based on any legally protected characteristics.