Director of Small to Mid Employee Benefits - New England
Job Description
OVERVIEW
Alera Group is seeking a Director of Small to Mid Employee Benefits to provide leadership, structure, and strategic direction across our Massachusetts and New Hampshire Employee Benefits teams.
This role is ideal for a leader who combines strong employee benefits expertise with a passion for developing people, building high-performing teams, and creating operational excellence
Reporting to the Regional Director, you will serve as a player-coach, overseeing service teams, supporting key client relationships, and helping drive consistency, growth, and innovation across the region. You will have the opportunity to influence team structure, mentor future leaders, and play a key role in shaping the next phase of growth for our New England Employee Benefits practice.
About Alera Group
Alera Group was founded in 2017 and has grown to become one of the nation's leading independent insurance and financial services firms
Through collaboration and shared expertise, we provide clients with national resources while maintaining the local relationships and personalized service that set us apart.
Meaningful Impact: Help clients and employees navigate benefits programs that drive retention, engagement, and satisfaction
Growth & Learning: Opportunities to deepen your expertise and gain exposure to a variety of clients and industries
Collaborative Culture: Work in a team-oriented environment that values accountability, partnership, and the principles of The Collaborative Way
RESPONSIBILITIES
What You'll Do
Leadership & Team Development
- Lead, mentor, and develop Employee Benefits Consultants, Account Managers, and service team colleagues across Massachusetts and New Hampshire.
- Serve as a player-coach, helping elevate team capabilities through coaching, education, and professional development.
- Foster a culture of accountability, collaboration, and continuous improvement.
- Partner with leadership to evaluate team structure, optimize workflows, and support organizational growth.
- Help standardize service delivery models and best practices across offices and market segments.
Client & Business Leadership
- Serve as strategic advisor and executive sponsor for key client relationships.
- Maintain a select portfolio of client accounts and provide guidance on benefits strategy, renewals, funding arrangements, compliance, and market trends.
- Support retention, growth, and profitability goals across the team's book of business.
- Build and maintain strong relationships with carriers, vendor partners, and executive stakeholders.
Strategic & Regional Impact
- Partner with regional leadership to execute key initiatives and growth strategies.
- Support cross-selling opportunities across Employee Benefits, Property & Casualty, Retirement, and specialty practice solutions.
- Participate in finalist meetings, prospect presentations, and business development opportunities.
- Drive consistency, operational excellence, and adoption of Alera resources and capabilities.
QUALIFICATIONS
What We're Looking For
Required Qualifications
- 7+ years of Employee Benefits experience, preferably supporting small to mid-market employer groups.
- Active Life & Health insurance license.
- Strong knowledge of employee benefits strategy, plan design, funding arrangements, renewals, carrier markets, and regulatory requirements.
- Demonstrated ability to build relationships and influence stakeholders at all levels.
- Strong communication, leadership, and problem-solving skills.
Preferred Qualifications
- Prior leadership, management, or supervisory experience.
- Experience coaching, mentoring, and developing Employee Benefits professionals.
- Knowledge of the Massachusetts Employee Benefits marketplace strongly preferred.
- New Hampshire market experience is a plus.
- Experience leading teams through growth, change, process improvement, or organizational transformation.
Why This Opportunity
- Lead and help shape the future structure of the Massachusetts and New Hampshire Employee Benefits teams.
- Partner directly with regional leadership on strategic initiatives, growth, and organizational development.
- Influence team development, operational excellence, and the overall client experience.
- Play a key role in building the next generation of Employee Benefits leaders.
- Bring fresh perspectives and help drive consistency, structure, and best practices across the region.
What Success Looks Like
In this role, you'll help:
- Develop, mentor, and inspire high-performing Employee Benefits professionals.
- Create greater structure, consistency, and accountability across service teams.
- Drive client retention, growth, and overall satisfaction.
- Strengthen collaboration across offices, teams, and market segments.
- Support the continued evolution and standardization of service delivery throughout the New England region.
- Help shape the future of Alera Group's Employee Benefits practice in Massachusetts and New Hampshire.
ADDITIONAL INFORMATION
Compensation
- Salary Range: $150,000 – $180,000 annually
- Eligible for annual performance-based incentive compensation
Benefits: Alera Group offers a comprehensive benefits package including:
- Medical, Dental, and Vision Insurance
- Company-Paid Life and Disability Coverage
- 401(k) with Company Match
- Paid Time Off and Paid Holidays
- Employee Assistance Program
- Additional voluntary benefit offerings
Work Model: Hybrid
This is a hybrid position supporting teams across Massachusetts and New Hampshire
Regular travel to Alera Group offices, client meetings, and regional events throughout Massachusetts and New Hampshire is expected.
Professional Development – Alera Group Academy
At Alera Group, growth isn’t left to chance
Through Alera Group Academy, we provide structured development opportunities designed to help you expand your expertise and build a meaningful career.
You’ll have access to:
Role-specific learning paths
Leadership development programs
Technical and compliance training
Industry certifications and continuing education support
Peer learning and knowledge-sharing communities
Whether you’re deepening technical expertise or preparing for leadership, we’re invested in helping you grow.
Licensure & Certifications
- Active Life & Health Insurance License required
- Additional industry designations such as RHU, REBC, CEBS, or similar are a plus
- Ongoing continuing education required to maintain active licensure
We're an equal opportunity employer
All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status, or any other protected class.
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