Dickerson Group
OVERVIEW
Alera Group is looking for a
Director of Retirement Plan Services
to help lead the next evolution of workplace retirement. This is a highly visible, national leadership role for someone who thrives at the intersection of strategy, data, technology, and client impact. This role is a hybrid reole- preferred location is Boston, Chicago or other major Alera Group office market preferred.
Founded in 2017, Alera Group has grown to become the 14th largest broker of U.S. business, delivering solutions across Employee Benefits, Property & Casualty Insurance, Retirement Plan Services, and Wealth Services. With a national footprint and strong local offices, we combine scale, collaboration, and innovation to better serve clients and advisors.
RESPONSIBILITIES This role leads the strategic, operational, and innovation direction of Alera Group’s national Retirement Plan Services practice. You’ll partner closely with regional leaders and cross-practice teams to scale advisor success, modernize systems, strengthen fiduciary governance, and elevate the client experience. A major focus of this role is using
data, automation, and AI-enabled tools
to drive smarter decisions and more efficient operations across the practice.
Key Responsibilities
Execute the national Retirement Plan Services strategy to drive growth, advisor enablement, and operational excellence
Lead AI-enabled and data-driven initiatives that improve workflows, insights, and client outcomes
Partner across Wealth, Employee Benefits, and Insurance to expand integrated client solutions
Oversee fiduciary governance, compliance, and vendor relationships at a national level
Mentor and develop regional leaders while serving as an escalation point for complex matters
QUALIFICATIONS
Bachelor’s degree in Business, Finance, Economics, or related field; advanced degree or certifications preferred
10+ years of leadership experience in retirement plan consulting or institutional financial services
Deep knowledge of ERISA, fiduciary governance, and retirement plan operations
Strong fluency in data, analytics, and modern CRM/workflow tools (Power BI experience preferred)
Proven ability to lead change, scale operations, and collaborate across a matrixed organization
ADDITIONAL INFORMATION This job is hybrid. Preferred location is Boston, Chicago or other major Alera Group office market is preferred.
Alera Group offers comprehensive benefits to our colleagues, including medical, dental, life and disability insurance, 401k, generous paid time off and much more.
Salary range is $120K to $160K per year.
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.
Alera Group is committed to protecting your privacy. Please review our Privacy Policy to understand what personal information we may collect and use as part of your application process.
#LI-JP1
#LI-Hybrid
Location Type Remote
#J-18808-Ljbffr
Director of Retirement Plan Services
to help lead the next evolution of workplace retirement. This is a highly visible, national leadership role for someone who thrives at the intersection of strategy, data, technology, and client impact. This role is a hybrid reole- preferred location is Boston, Chicago or other major Alera Group office market preferred.
Founded in 2017, Alera Group has grown to become the 14th largest broker of U.S. business, delivering solutions across Employee Benefits, Property & Casualty Insurance, Retirement Plan Services, and Wealth Services. With a national footprint and strong local offices, we combine scale, collaboration, and innovation to better serve clients and advisors.
RESPONSIBILITIES This role leads the strategic, operational, and innovation direction of Alera Group’s national Retirement Plan Services practice. You’ll partner closely with regional leaders and cross-practice teams to scale advisor success, modernize systems, strengthen fiduciary governance, and elevate the client experience. A major focus of this role is using
data, automation, and AI-enabled tools
to drive smarter decisions and more efficient operations across the practice.
Key Responsibilities
Execute the national Retirement Plan Services strategy to drive growth, advisor enablement, and operational excellence
Lead AI-enabled and data-driven initiatives that improve workflows, insights, and client outcomes
Partner across Wealth, Employee Benefits, and Insurance to expand integrated client solutions
Oversee fiduciary governance, compliance, and vendor relationships at a national level
Mentor and develop regional leaders while serving as an escalation point for complex matters
QUALIFICATIONS
Bachelor’s degree in Business, Finance, Economics, or related field; advanced degree or certifications preferred
10+ years of leadership experience in retirement plan consulting or institutional financial services
Deep knowledge of ERISA, fiduciary governance, and retirement plan operations
Strong fluency in data, analytics, and modern CRM/workflow tools (Power BI experience preferred)
Proven ability to lead change, scale operations, and collaborate across a matrixed organization
ADDITIONAL INFORMATION This job is hybrid. Preferred location is Boston, Chicago or other major Alera Group office market is preferred.
Alera Group offers comprehensive benefits to our colleagues, including medical, dental, life and disability insurance, 401k, generous paid time off and much more.
Salary range is $120K to $160K per year.
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.
Alera Group is committed to protecting your privacy. Please review our Privacy Policy to understand what personal information we may collect and use as part of your application process.
#LI-JP1
#LI-Hybrid
Location Type Remote
#J-18808-Ljbffr