Grow With Us! At Hilb Group, we recognize that our associates are our greatest asset. We promote a service-driven culture of high performance that encourages career and professional development. The Hilb Group is currently seeking a motivated and ambitious Employee Benefits Consultant (Small Group) to join our team. This position will be located to our agency locations in Canton, MA. The ideal candidate will be motivated to succeed, is well organized, able to prioritize, and able to work well with a team. This is an in-office position.
Responsibilities:
Serve as the primary strategic advisor for an assigned portfolio of employee benefits clients
Build trusted relationships with HR leaders, business owners, and key decision-makers
Conduct ongoing discovery to understand client goals, challenges, workforce dynamics, and business objectives
Create confidence by helping clients evaluate options and make informed decisions
Deliver a proactive service experience focused on long-term partnership and retention
Lead development and execution of annual client service plans and strategic Roadmaps
Facilitate stewardship, pre-renewal, renewal, and strategic planning meetings
Guide discussions around plan design, funding strategies, employee engagement, compliance, and cost management
Monitor progress against client goals and identify opportunities throughout the year
Ensure key initiatives remain on track and stakeholders remain aligned
Analyze benefit plan performance, claims information, benchmarking data, market trends, and workforce demographics
Translate findings into actionable recommendations and strategic guidance
Identify opportunities to improve plan performance, employee experience, and financial outcomes
Lead renewal strategy development and recommendation discussions
Possess a strong understanding of: Fully Insured Plans, Level-Funded Plans, Self-Funded Plans, Consumer-Driven Health Plans HSAs, FSAs, HRAs, and related account-based benefits
Evaluate carrier options, contribution strategies, and funding approaches
Collaborate with internal teams to develop recommendations aligned with client objectives
Partner closely with Account Managers, Benefit Analysts, Compliance Specialists, and Carrier Partners
Delegate and coordinate operational activities while maintaining accountability for client outcomes
Support problem resolution and escalation management
Share knowledge and contribute to a collaborative team culture
Maintain working knowledge of employee benefits regulations and market developments
Advise clients regarding ACA, ERISA, COBRA, HIPAA, Section 125, and related compliance considerations
Monitor legislative and regulatory changes impacting clients
Stay informed on industry trends and emerging benefits solutions
Deliver educational presentations for employer groups and employees
Create and present communications supporting open enrollment and benefit initiatives
Simplify complex concepts into understandable recommendations
Communicate confidently in both virtual and in-person settings
Qualifications:
5+ years of employee benefits consulting, brokerage, account management, or related experience
Strong understanding of medical, dental, vision, life, disability, and voluntary benefit programs
Bachelor's Degree preferred; High school required
Experience with BenefitPoint, ImageRight, AMS360, Employee Navigator, or similar platforms preferred
Experience presenting to executive leaders and business owners preferred
Understanding of self-funded and alternative funding arrangements preferred
Professional benefits designations such as CEBS, GBA, SHRM, PHR, or similar preferred
Experience working with small and mid-sized employer groups
Exceptional communication and presentation skills
Ability to manage multiple priorities in a fast-paced environment
Proven problem-solving and relationship management skills
Active Life and Health insurance license (or ability to obtain)
Benefits:
Compensation: $105,000/yr.
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, and Pet benefits.
Generous PTO.
An awesome team of professionals!
The Hilb Group is an equal opportunity employer, and we actively support and comply with all applicable federal, state, and local laws prohibiting all forms of discrimination in employment. Additionally, we have a zero-tolerance policy for all forms of harassment in violation of federal, state, and local laws.
Skills Required
- 5+ years of employee benefits consulting, brokerage, account management, or related experience
- High school diploma
- Active Life and Health insurance license, or ability to obtain one
- Strong understanding of medical, dental, vision, life, disability, and voluntary benefit programs
- Experience working with small and mid-sized employer groups
- Exceptional communication and presentation skills
- Ability to manage multiple priorities in a fast-paced environment
- Proven problem-solving and relationship management skills
- Bachelor's degree
- Experience with BenefitPoint, ImageRight, AMS360, Employee Navigator, or similar platforms
- Experience presenting to executive leaders and business owners
- Understanding of self-funded and alternative funding arrangements
- Professional benefits designation such as CEBS, GBA, SHRM, PHR, or similar
Hilb Group Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Hilb Group and has not been reviewed or approved by Hilb Group.
-
Strong & Reliable Incentives — Base pay and commission compare favorably to nearby agencies or prior employers in certain markets and roles.
-
Retirement Support — The 401(k) program is frequently praised, with the match described as good.
-
Wellbeing & Lifestyle Benefits — Work-from-home flexibility consistently stands out as a top perk and is often highlighted as part of the overall package.
Hilb Group Insights
What We Do
Partners Together - Endless Possibilities Hilb Group provides the resources of a big insurance broker and the attentive, personal service of a small agency. Our people are our greatest strength. Our values of trust, passion, integrity and growth drive our actions to benefit every client. Managing Risk Your risk profile doesn’t matter – Hilb paints a very wide portrait. We have more than 30 industry specialties, which gives our clients and brokers a unique advantage. We form enduring partnerships to get the best results every time, and work with the top insurers to provide a huge range of high-quality choices, matched exactly to your needs. About Hilb Group Founded in 2009, Hilb Group is a Top 25 middle market independent insurance broker. Hilb Group offers expertise in property & casualty, employee benefits, and retirement services to business and individuals throughout the nation.







