Senior Strategy Consulting Associate

Hilb Group

Strategy Consulting Senior Associate designing complex employee benefit programs for Hilb Group brokerage clients. Leading renewals, funding strategies, analytics, compliance, and client engagements.

Posted 8/9/2026full-timeCanton • Massachusetts, Rhode Island • 🇺🇸 United StatesSenior💰 $200,000 - $220,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in developing and executing comprehensive benefit strategies for large clients, with a strong focus on self-funded plans, compliance, and financial analysis. Proven ability to manage complex client relationships and lead strategic discussions while mentoring junior staff.

Highest-signal resume keywords

Employee Benefits ExperienceSelf-Funded Medical PlansProject Management SkillsNegotiation SkillsLeadership and Mentoring

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Financial AnalysisContract ReviewBenefit ComplianceData InterpretationPharmacy BenefitsStop-Loss CoverageUtilization AnalysisRFP ManagementPlan DesignFunding Arrangements

Soft Skills

Interpersonal CommunicationProblem-SolvingAttention to DetailResourcefulnessTeam Collaboration

Tools & Technologies

Microsoft ExcelMicrosoft PowerPointMicrosoft OutlookMicrosoft Teams

Certifications & Qualifications

L&H License

Industry Keywords

BrokerageConsultingTPAPBMACA ReportingERISA RequirementsDOL AuditsEmployee EngagementVendor SolutionsMarket Trends

About the role

Key responsibilities & impact

Develop and execute comprehensive, multiyear benefit strategies for large and complex clients
Own and manage the client Roadmap and coordinate the stewardship, pre-renewal, marketing, renewal, open enrollment, implementation, and post-renewal cycle
Lead client strategy discussions and provide recommendations on funding arrangements, plan design, contribution strategy, employee engagement, vendor solutions, compliance, and cost management
Manage annual renewal and marketing processes, including RFPs, proposal analysis, carrier and vendor negotiations, and client recommendations
Provide strategic consulting for self-funded and complex funding arrangements
Lead provider network analyses and evaluate pharmacy benefit strategies
Advise clients on complex leave and disability programs and review ancillary benefit contracts
Lead stop-loss placement and ongoing management and monitor stop-loss performance
Review utilization, claims, pharmacy, financial, and large claimant reporting to identify trends, risks, and cost drivers
Translate complex financial and clinical data into actionable client recommendations
Partner with Producers on client meetings, executive presentations, finalist meetings, and new client onboarding
Serve as primary strategic contact and escalation point for assigned clients
Build relationships with client executives, HR leaders, finance teams, carriers, TPAs, PBMs, stop-loss carriers, and vendors
Oversee implementation of benefit program changes, vendors, funding arrangements, and administrative solutions
Advise on benefit compliance requirements, including ACA reporting, PCORI fees, ERISA requirements, and DOL audits
Maintain knowledge of market trends, benchmarking, legislation, compliance, analytics, vendor solutions, and industry developments
Provide guidance, technical support, and training to client service team members
Mentor junior consulting staff and support professional development
Delegate responsibilities and provide expectations, oversight, and feedback
Document meeting outcomes, recommendations, decisions, and follow-up
Participate in market meetings, client functions, industry seminars, and professional development programs
Perform additional duties and strategic projects as assigned
Travel as needed, including occasional overnight travel
Conduct meetings outside standard business hours when reasonably required by client needs

Requirements

What you’ll need

Bachelor’s degree in business, finance, healthcare administration, human resources, or a related field preferred
L&H license
Seven or more years of employee benefits experience within a brokerage, consulting, carrier, TPA, PBM, or related environment
Demonstrated experience managing large, complex, and preferably self-funded clients
Strong knowledge of self-funded medical plans, ASO arrangements, provider networks, pharmacy benefits, ancillary benefits, stop-loss coverage, and complex leave programs
Experience leading benefit renewals, carrier and vendor marketing, financial analysis, contract review, negotiation, and implementation
Ability to interpret complex carrier, ASO, PBM, stop-loss, and ancillary contract language and explain financial and operational implications to clients
Understanding of benefit needs and contractual considerations for specialized industries and diverse employee populations
Ability to develop strategic recommendations using claims, utilization, financial, pharmacy, network, and benchmarking data
Strong project management skills, including timeline establishment, stakeholder coordination, prioritization, and accurate execution
Ability to manage multiple complex client relationships in a fast-paced environment
Strong leadership and mentoring skills
Excellent written, verbal, presentation, negotiation, and interpersonal communication skills
Strong judgment, resourcefulness, attention to detail, and problem-solving ability
Ability to work independently, make sound decisions, and perform effectively under pressure
Ability to collaborate effectively as a team member and team leader
Advanced proficiency in Microsoft Office, particularly Excel, PowerPoint, Outlook, and Teams

Benefits

Comp & perks

Company Paid Life Insurance
Long-Term and Short-Term Disability
Medical, Dental, Vision and FSA/HSA plans
401(k) with company match
Additional voluntary benefits including Critical Illness, Accident Insurance, Hospital Indemnity and Supplemental Life Insurance
Legal and Identity Protection
Pet benefits
Generous PTO
Career and professional development
Professional development programs