Director of to Mid - England

Director Of Small To Mid Employee Benefits

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.

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

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.

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.

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.

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.

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…