Director, Client Engagement & Strategy

Responsible for leading a Manager of Account Management and a team of Strategic Account Executives with planning and direction, talent acquisition, and Employee Benefit Consultant (EBC)/client relationship development with the goal of improving account retention rates and achieving key performance indicator standards. The Director drives improvement in account retention rates, achieves KPI standards, and champions a tech-first, AI-augmented operating model that modernizes service delivery, automates workflows, and elevates the team's capacity to serve clients at scale. This role requires approximately up to 50% travel for client or EBC-facing meetings. Essential Job Responsibilities Include: Develop and manage talent: Identify the skills and performance criteria necessary for success across a variety of roles and manage staff to meet and exceed these standards. In coordination with the VP of Client Engagement and HR, assist in creating career-building development plans for staff. Coach and mentor Strategic Account Executives and Manager of Account Management by observing and providing feedback in order to foster development and success of individuals. Assists Vice President of Client Engagement in yearly strategic planning and execution of the plan. Strategize to develop ways to increase client satisfaction and preserve loyalty and market share. Embedding AI tools into daily workflows — leveraging platforms such as CRM AI copilots, conversation intelligence (e.g., Gong, Chorus), and generative AI tools to reduce administrative burden and accelerate decision-making. Establishing AI-enhanced operating rhythms — replacing manual reporting and status updates with automated dashboards, AI-generated meeting summaries, and real-time KPI visibility. Continuously evaluating emerging AI capabilities to identify adoption opportunities that improve client outcomes, team efficiency, and competitive positioning. Coaching and upskilling the Client Engagement team on effective, responsible use of AI tools in client-facing and internal workflows. Coach and mentor Strategic Account Executives and the Manager of Account Management using conversation intelligence platforms (e.g., call recording/AI coaching tools) to provide objective, data-backed feedback at scale. Leverage AI-powered market intelligence and CRM analytics to identify trends, client risk signals, and growth opportunities that inform strategic priorities. Develop strategies to increase client satisfaction and preserve loyalty using predictive retention modeling to proactively identify and address at-risk accounts. Ensure Client Engagement standards, methods, and procedures are followed, with a focus on digitizing and automating repeatable workflows to reduce manual effort and human error. Identify operational efficiency opportunities and provide business requirements, with a focus on automation feasibility and AI augmentation potential when evaluating proposed solutions. Build Employer Benefit Consultant (EBC) relationships and maintain proactive outreach to identify changing needs and competitor strategies. Partner with Business Development to build EBC relationships. This includes participating in expectations sessions with the EBC and attending finalist meetings as appropriate. Evaluates team’s performance against KPI’s and intervenes with management direction to assist account management team meet and exceed goals. Conduct meetings with account teams and EBC firms to discuss BOB utilization, market updates, obstacles and dynamics. Attend reviews with Strategic Account Executive for development opportunities, at risk clients and new business. Ensure that the Client Engagement department standards, methods, and process and procedures for client service are followed through working with the Manager(s) of Account Management. This includes the delivery of client marketing and messaging programs to meet revenue objectives, budgets, ROI, and client service satisfaction. Directs Manager(s) of Account Management activities and coaches them on handling issues that require escalation. Operational Ease: Participates in new product/service development teams with other functional team leaders to optimize the launch and other revenue driving processes increasing speed to market and ease of using our platform for the teams and our clients. All other assigned duties. Required Skills / Experience: Bachelor’s Degree required Minimum of 6 years of demonstrated proven progressive leadership experience in the PBM or healthcare related service industry; Customer-facing leadership and account relationship strategy experience Demonstrated experience leveraging AI tools, CRM platforms, or digital workflow automation to improve team performance and operational efficiency Capable of interfacing well at all levels within a large organization and client base Project management, planning, and organizational skills Excellent verbal and written communication skills Excellent organization, motivation, leadership and interpersonal skills High energy, with a strong ‘can do’ attitude Thrives in a dynamic, fast paced environment with many simultaneous projects Preferred Skills/Experience: Master’s Degree preferred Minimum of 10 years of work experience preferred experience with tools such as Salesforce (Einstein/AI features), Gong, Chorus, Microsoft Copilot, or comparable platforms strongly preferred