Vice President, Benefits

Firm Overview

PSG Equity is a growth equity firm that partners with software and technology-enabled services companies to help them navigate transformational growth, capitalize on strategic opportunities, and build strong teams. Having backed more than 160 companies and facilitated over 530 add-on acquisitions, PSG Equity brings extensive investment experience, deep expertise in software and technology, and a firm commitment to collaborating with management teams. Founded in 2014, PSG Equity has since raised over $30 billion in capital and operates out of offices in Boston, Kansas City, London, Paris, Madrid and Tel-Aviv.

Applicants must be authorized to work for an employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa for this position.

Position Overview

The Vice President, Benefits will report to the Director, Head of Human Capital Management and serve as the senior benefits leader responsible for the strategy, design, administration, and compliance of all North America employee benefit programs. This includes medical, dental, vision, life and disability insurance, flexible spending accounts, commuter benefits, family planning and parenthood support, employee assistance programs, and wellness offerings.

This role requires a seasoned benefits professional who can operate both strategically and tactically owning vendor relationships, ensuring regulatory compliance across multiple jurisdictions (with particular depth in Massachusetts), driving benefits optimization and cost management, and serving as the primary benefits subject-matter expert for the firm’s employees and leadership team. The VP, Benefits will also oversee benefits-related HRIS transactions and reporting within Workday and partner closely with external benefits consultants, legal counsel, and finance.

The pay range for this position is $135,000 to $155,000 annually. The estimated salary range reflects an anticipated range for this position. The actual base salary offered may depend on a variety of factors, including the qualifications of the applicant for the position, years of relevant experience, specific and unique skills, level of education attained, and certifications or other professional qualifications

Responsibilities

Benefits Strategy & Administration

• Own the end-to-end administration of all North America benefit programs including but not limited to medical, dental, vision, life/AD&D and disability, FSA/commuter accounts, EAP, family planning, and One Medical
• Lead the annual benefit renewal; evaluate plan design, carrier performance, cost trends, and employee utilization data to recommend enhancements that balance competitiveness with fiscal responsibility
• Manage the annual open enrollment process end-to-end, including employee communications, enrollment verification, and carrier file feed quality control
• Oversee new hire benefits onboarding, life event processing, and COBRA administration; ensure all enrollment timelines and documentation requirements are met

Compliance & Regulatory

• Ensure compliance with all applicable federal, state, and local benefits laws and regulations including ERISA, ACA, COBRA, HIPAA, Section 125, FMLA, etc.
• Monitor and respond to legislative and regulatory changes impacting benefits across all jurisdictions where PSG operates
• Oversee preparation and timely filing of all required government reports and filings including Form 5500, Summary Plan Descriptions (SPDs), Summary of Benefits and Coverage (SBCs), and annual notices
• Manage non-discrimination testing for Section 125 cafeteria plan and other applicable plans
• Partner with legal counsel on benefits-related matters including plan document amendments, policy updates, and interpretation of multi-state compliance obligations

Vendor & Consultant Management

• Serve as the primary relationship owner for all benefits carriers, brokers, and third-party administrators
• Lead RFP processes and contract negotiations for benefits renewals and new vendor selection; hold vendors accountable to service-level standards and escalate issues as needed
• Manage broker and consultant engagements to ensure PSG receives timely market intelligence, benchmarking data, and compliance guidance

Financial Management

• Develop and manage the annual benefits budget; forecast costs, track actual spend against projections, and report variances to leadership
• Review and approve carrier invoices, reconcile premium billing, and resolve discrepancies
• Analyze claims experience data and utilization trends to identify opportunities for cost containment without compromising plan quality

Employee Communication & Support

• Serve as the firm’s primary subject-matter expert on all benefits matters; handle escalated employee inquiries, resolve complex claims issues, and ensure timely and accurate responses
• Develop and maintain benefits communications including the annual Employee Benefits Guide, enrollment materials, new hire orientation content, and ongoing employee education
• Partner with the HCM team on benefits-related aspects of employee life events, leaves of absence, return-to-work coordination, and separations

Systems & Process

• Own benefits module transactions and maintenance within Workday including plan setup, enrollment events, and benefits-related reporting
• Continuously evaluate and improve benefits administration processes for efficiency, accuracy, and employee experience
• Maintain accurate benefits records and documentation; ensure data integrity across all systems and carrier platforms

Ideal Experience and Competencies

• Minimum 6–10 years of progressive experience in benefits administration, with demonstrated ownership of multi-state benefits programs; experience in financial services or private equity environments strongly preferred
• Deep working knowledge of ERISA, ACA, COBRA, HIPAA, Section 125, FMLA, and related federal and state benefits regulations
• Hands-on experience with Workday Benefits module (open enrollment, reporting, carrier integrations) strongly preferred
• Proven track record managing carrier and broker relationships, leading RFPs, and negotiating renewals
• Strong financial acumen including experience with benefits budgeting, cost analysis, and claims data interpretation
• Excellent communication and interpersonal skills with the ability to translate complex benefits concepts for a non-technical audience and interact confidently across all levels of the organization
• Strong analytical skills and proficiency in Excel, HRIS reporting, and data-driven decision making
• High degree of discretion and professionalism in handling sensitive employee information
• Self-directed, detail-oriented, and able to manage competing priorities in a fast-paced, growing environment

Benefits and Perks

At PSG, we are committed to providing excellent benefits that show our deep appreciation for the hard work of our team. Our current benefits offerings include:

• Comprehensive medical, dental, and vision insurance, paid for 100% by PSG
• Retirement savings plan with PSG match contribution and discretionary profit sharing
• Short- and long-term disability and life insurance policies
• Flexible spending accounts for health, commuting, and dependent care
• Competitive paid vacation and paid holidays
• Paid parental leave
• Tuition reimbursement program
• Employee Assistance Program
• Partnership with Maven for family planning and parenthood support, support including fertility & family building, maternity & newborn care, and parenting & pediatrics
• Personal training sessions with our Director of Health & Fitness
• Beautiful office space in the Fenway area with a state-of-the-art gym
• Lunch 3x/week, snacks, coffee, and other beverages available to all employees

PSG Equity L.L.C. (the “Firm”) is an equal opportunity employer and complies with all applicable federal, state, and local fair employment practice laws. The Firm strictly prohibits and will not tolerate, condone or allow discrimination or harassment with respect to any employee or applicant for employment in matters of hiring, promotion, transfer, disciplinary action, termination, compensation, fringe benefits or other terms and conditions of employment on the basis of race, color, religion, creed, age, national origin, ancestry, alienage or citizenship status, sex (including pregnancy, childbirth, breastfeeding or other related medical conditions), gender (including sex stereotyping, gender identity, gender dysphoria, gender expression, or transgender status), sexual orientation, disability (including physical disability or mental disability), military or veteran status, familial status, partnership status, or marital status, or any other status protected by relevant federal, state and local laws. All employees are prohibited from engaging in unlawful discrimination.