Vice President, Benefits

PSG•Boston, MA

1d•$135,000 - $155,000

About The Position

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

Requirements

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

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
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
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
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
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
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

Benefits

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