Project Manager – Senior Director

Winged Keel Group-posted 3 days ago
Full-time • Director
Needham, MA
101-250 employees
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The Project Manager, Senior Director is a key leadership role responsible for overseeing and advancing the case management function within Winged Keel Group. The individual will work as a Project Manager ensuring opportunities close in a timely manner, and will be responsible for a team of 5-8 individuals consisting of: 2 Project Managers, Directors: 3-6 Client Relationship Manager (CRM), Associates rotating through the Project Manager function as part of their two-year CRM training and development program. This role requires a seasoned professional with deep technical knowledge of life insurance products, underwriting processes, and case design as well as proven leadership and operational management capabilities. The Senior Director will ensure that all opportunities progress efficiently, accurately, and in alignment with the firm’s commitment to delivering exceptional client service.

  • Provide strategic leadership, direction, and oversight for the Project Management team, including two Directors of Project Management and CRM trainees.
  • Establish and maintain department-wide workflows, standards, and quality control processes.
  • Lead performance management, professional development, and skills training initiatives for Project Managers and trainees.
  • Serve as the primary escalation point for complex case strategy, operational issues, and cross-departmental coordination.
  • Partner with senior leadership to align departmental objectives with firmwide goals and operational priorities.
  • Manage select high-impact or complex life insurance opportunities from inception through placement.
  • Ensure accurate and timely setup and maintenance of all case documentation, including Salesforce entries, case logs, internal drives, and opportunity records.
  • Prepare and/or oversee production of illustrations, in-force reviews, analytical materials, and presentation decks.
  • Draft communications for CRMs, advisors, and clients to support case movement and ensure clarity and accuracy.
  • Guide underwriting strategy, including carrier negotiation, capacity considerations, cover letter positioning, and analysis of offers.
  • Oversee all aspects of the formal application process, including documentation collection, application preparation, and communication with signers and advisors.
  • Provide servicing support for in-force policies and guidance to team members on servicing requirements.
  • 10+ years of experience in life insurance, financial services, or related project management functions.
  • Strong technical knowledge of life insurance products, underwriting processes, carrier guidelines, and case design principles.
  • Demonstrated leadership experience, including managing and developing teams.
  • Exceptional written and verbal communication skills, with the ability to craft precise and professional communications for clients and advisors.
  • High level of organizational skill, attention to detail, and ability to manage multiple priorities in a fast-paced environment.
  • Proficiency with CRM/case management systems (Salesforce preferred), Microsoft Office Suite, and digital workflow tools.
  • Bachelor’s degree required
  • Advanced degree or professional designation (CLU®, ChFC®, CFP®, MBA, etc.) preferred.
  • Attractive annual compensation package is commensurate with experience
  • Comprehensive benefit package includes medical, dental, life, disability, 401(k), Section 125, and other voluntary benefits.
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