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Senior Director - National Captive Practice

Alera Group

Chicago, Illinois

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JOB DETAILS
SKILLS
Best Practices, Business Development, Business Strategy, Channel Strategies, Coaching, Compensation and Benefits, Continuous Improvement, Cross-Functional, Customer Experience, Employee Benefits, Employee Retention, Executive Relationships, Financial Operations, Financial Services, Funding, Health Plan, Insurance, Leadership, Marketing, Mentoring, Multitasking, Onboarding, Operational Improvement, Operational Strategy, Organizational Skills, Partner Sales, Project Development, Project Management Certification, Project Management Professional (PMP), Project Planning, Risk Management, Sales Proposals, Strategic Planning, Team Lead/Manager, Team Player
LOCATION
Chicago, Illinois
POSTED
2 days ago
OVERVIEW

At Alera Group, our National Captive Practice helps organizations evaluate and implement innovative funding strategies that support growth, risk management, and long-term benefit program performance. We're seeking a Senior Director who will serve as a strategic partner to executive leadership, producers, and internal teams by leading strategic initiatives, supporting producer success and business development efforts, and helping scale the practice through operational excellence and disciplined execution.

About Alera Group

Alera Group was founded in 2017 and has grown to become one of the nation's largest independent insurance and financial services firms. Through a collaborative network of offices across the country, we bring together national resources with local expertise to help clients achieve their business goals. Our Employee Benefits teams partner with organizations to develop innovative strategies that attract, retain, and engage employees while delivering exceptional client experiences.
Why Alera Group
  • Strategic Impact: Partner directly with the Practice Leader to help shape the future of Alera Group's growing National Captive Practice.
  • Executive Visibility: Collaborate with executive leadership, producers, consultants, and cross-functional teams while influencing strategic business initiatives.
  • Growth Opportunity: Play a key role in scaling a national practice, supporting business development, and building operational excellence.
  • Leadership: Coach producers, mentor team members, and help develop best practices that drive long-term success.
  • Collaborative Culture: Join an organization that values accountability, innovation, partnership, and The Collaborative Way.
RESPONSIBILITIES

What You'll DoStrategic Partnership
  • Serve as the trusted strategic partner to the National Captive Practice Leader, helping execute business priorities and long-term growth initiatives.
  • Translate strategic objectives into actionable operating plans while ensuring successful execution across the practice.
  • Partner closely with executive leadership to identify opportunities that strengthen organizational performance.
Business Development & Producer Support
  • Support revenue-generating initiatives, including finalist presentations, new business pursuits, producer coaching, and client expansion strategies.
  • Prepare producers for executive-level client engagements, proposals, and strategic presentations.
  • Help identify growth opportunities while supporting execution of business development strategies.
Operational Leadership
  • Lead multiple strategic initiatives simultaneously while maintaining alignment across departments.
  • Develop project plans, timelines, milestones, and accountability measures.
  • Anticipate risks, remove roadblocks, and ensure initiatives are executed successfully.
  • Design scalable processes and workflows that improve operational effectiveness.
Cross-Functional Leadership
  • Partner across Sales, Marketing, Finance, Operations, HR, and Executive Leadership.
  • Support onboarding and development of producers and practice resources.
  • Mentor direct reports while fostering collaboration, accountability, and continuous improvement.
  • Drive initiatives that strengthen organizational execution and overall practice performance.
QUALIFICATIONS

What You BringRequired
  • 10+ years of progressive Employee Benefits leadership experience.
  • Strong knowledge of self-funded health plans, alternative funding strategies, and captive insurance arrangements.
  • Experience partnering with producers, consultants, executive leadership, and business development teams.
  • Demonstrated success leading strategic initiatives across multiple stakeholders.
  • Exceptional communication, executive presence, and relationship-building skills.
  • Highly organized with the ability to manage multiple priorities in a fast-paced environment.
  • Proven ability to influence without direct authority.
Preferred
  • CEBS, GBA, or other Employee Benefits certifications.
  • PMP or other project management certifications are a plus.
  • Experience supporting producer development, sales enablement, proposal strategy, and executive presentations.
  • Previous leadership experience managing and developing teams.
What Success Looks Like
In this role, you'll become a trusted ext

About the Company

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Alera Group