Director of Sales

We are seeking an experienced, results-driven Director of Sales to lead our Account Management team supporting Medicare Secondary Payer (MSP) Compliance and broader casualty solutions. This leader will translate business strategy into disciplined account plans, strengthen executive-level client relationships, and drive retention, expansion, and revenue growth across an assigned territory.

The Director will manage, coach, and develop Account Managers; establish clear expectations and performance measures; maintain reliable forecasting and CRM data; and partner with Account Executives, Product, Marketing, Operations, Services, Finance, and executive leadership to deliver an exceptional client experience and sustainable growth.

The ideal candidate combines strong people leadership with deep understanding of sales resources, the sales process, industry knowledge, and a consultative approach. This role requires a visible leader who can guide complex client engagements, remove barriers for the team, and represent the organization confidently at executive meetings and industry events.

The Director of Sales is accountable for the performance and development of the Account Management team and for the strategic stewardship of the assigned accounts. The role establishes account-management strategy, operating cadence, and performance standards; oversees retention, expansion, pipeline, and forecast execution; and ensures Account Managers build trusted relationships from operational contacts through executive leadership. The Director reports to the Assistant Vice President of Account Management and works closely with Account Managers, Account Executives and cross-functional leaders to achieve customer revenue and growth objectives.

• Lead, coach, and develop the Account Management team by setting clear expectations, conducting regular one-on-ones and performance reviews, supporting career development, and fostering accountability, collaboration, and continuous improvement.

• Own account performance, including client retention, revenue growth, solution adoption, quota attainment, pipeline health, and forecast accuracy.

• Establish and execute account-management strategy, including account assignments, coverage models, territory assignments, stewardship cadence, and strategic growth plans.

• Guide strategic client relationships by supporting Account Managers in developing trusted partnerships with key stakeholders and by serving as an executive sponsor for priority and at-risk accounts.

• Oversee client stewardship and business reviews, ensuring meetings are insight-driven, aligned to client goals, and supported by clear outcomes, owners, and follow-up actions.

• Drive expansion across existing accounts by identifying whitespace, cross-sell, upsell, referral, and adoption opportunities and coordinating qualified opportunities with the appropriate Account Executive.

• Maintain a disciplined operating cadence for pipeline reviews, forecasting, account planning, activity management, and performance reporting.

• Ensure Salesforce accuracy and adoption, including timely documentation of client interactions, opportunities, next steps, risks, and forecast updates.

• Monitor account health and customer risk, proactively addressing service concerns, escalations, competitive threats, and renewal or retention risks in partnership with internal stakeholders.

• Use data and market intelligence to assess team and portfolio performance, identify trends, recommend corrective action, and inform business decisions.

• Partner cross-functionally with Sales, Product, Marketing, Services, Operations, Finance, Business Intelligence, and executive leadership to improve the customer experience and support key priorities.

• Represent the organization at executive client meetings, national and regional conferences, industry events, and public forums as a knowledgeable leader in MSP compliance and casualty solutions.

• Translate client and market feedback into actionable recommendations for product strategy, service delivery, marketing, pricing, and operational improvement.

• Support team capacity and succession planning, including recruiting, onboarding, training, performance management, and development of future leaders.

• Stay current on MSP compliance requirements, casualty market developments, competitive activity, and emerging technology to guide team strategy and client conversations.

• Bachelor’s degree in business, marketing, insurance, or a related field, or equivalent practical experience.

• 7+ years of progressive experience in sales, account management, client success, or relationship management, including at least 3 years leading and developing sales or account-management professionals.

• Demonstrated success achieving retention, revenue, growth, and portfolio objectives in a complex business-to-business environment.

• Experience in insurance, claims, MSP compliance, or a related regulated industry; knowledge of Medicare Set-Asides, Conditional Payments, Section 111 reporting, carriers, TPAs, and self-insured organizations is strongly preferred.

• Strong leadership and coaching capabilities, with experience setting measurable expectations, managing performance, developing talent, and building an accountable team culture.

• Proven ability to build executive-level client relationships, lead strategic business reviews, manage escalations, and influence complex decisions.

• Strong understanding of data and analytical judgment, including experience with account planning, pipeline management, forecasting, performance metrics, and data-informed decision-making.

• Proficiency with Salesforce and Microsoft Office, including Excel, Word, PowerPoint, Outlook, Teams, and PowerBI.

• Exceptional communication, presentation, negotiation, and interpersonal skills, with the ability to tailor messages for clients, team members, and senior leaders.

• High degree of integrity, professionalism, sound judgment, and discretion when handling confidential client and employee matters.

• Excellent organizational and change-management skills, with the ability to prioritize effectively and lead through ambiguity in a fast-paced, collaborative environment.

• Up to 75% travel.