Director, Enterprise Sales

The Director, Enterprise Sales will serve as a key member of the Professional leadership team, responsible for shaping and executing the commercial strategy for the Enterprise segment across North America. Reporting directly to the Executive Vice President and Segment Leader, U.S. Professional Market, Wolters Kluwer Tax & Accounting North America, this executive will serve as the top commercial leader for the Enterprise business – driving growth for the segment.

The Director will lead a team of three high level sellers who serve Tax & Accounting’s largest customers. Operating within a matrixed structure, this leader will collaborate closely with the three North American General Managers, as well as partners across Revenue Operations, Enablement, Marketing, and Product, to align strategy, drive execution, and achieve scalable, predictable growth.

This role represents a pivotal opportunity to lead during a period of accelerated transformation, shifting towards enterprise, value-based customer engagement. The Director will partner with the Vice President, Professional Segment Sales to for modernize the go-to-market strategy, drive adoption of AI-enabled and data-driven solutions, and elevate sales performance standards. They will own end-to-end commercial outcomes including bookings, ARR growth, pipeline health, and forecast accuracy, ensuring alignment with broader divisional and enterprise objectives.

This is a highly visible, field-oriented role requiring a forward-thinking, results-driven leader who combines strategic vision with operational discipline. The Director must be able to translate insight into action, lead through influence in a complex organization, and sustain a culture of accountability and high performance.

Essential Duties and Responsibilities

▪Develop and execute the commercial strategy for the Enterprise segment, aligning with divisional and enterprise growth objectives across retention and new business acquisition.
▪Lead a team of high level sellers who serve our largest customers, fostering collaboration, accountability, and performance excellence.
▪Drive transformation toward an enterprise, value-based, consultative model focused on long-term client partnerships and holistic solutions.

▪Establish a disciplined operating cadence, implementing robust forecasting, pipeline inspection, and performance management processes to improve predictability and ensure consistent achievement of revenue targets.
▪Collaborate cross-functionally with Product, Marketing, and Revenue Operations to strengthen go-to-market execution, refine segmentation models, and enhance commercial enablement and alignment.
▪Champion talent development, building a high-performing, engaged sales culture focused on professional growth, skill-building, and succession readiness.
▪Partner with customer unit General Managers and divisional leadership to ensure cohesive execution across business lines and alignment on customer strategy, pricing, and territory design.
▪Serve as a strategic voice of the customer, relaying market insights, emerging needs, and competitive intelligence to influence product roadmaps, innovation priorities, and service enhancements.
▪Act as a field-oriented leader, maintaining regular engagement with clients and teams to reinforce customer intimacy, coach in-market execution, and ensure delivery of value-based outcomes.
▪Collaborate with Revenue Operations and Enablement to enhance sales readiness, operational efficiency, and the integration of data, analytics, and AI-driven insights into the commercial process.
▪Foster a culture of collaboration and accountability, ensuring sales goals, compensation plans, and performance metrics are tightly aligned with strategic objectives.
▪Lead with transparency and integrity, serving as a visible ambassador of Wolters Kluwer’s values, leadership standards, and commitment to innovation, inclusion, and customer success.

Wolters Kluwer seeks a commercially minded sales executive who can accelerate growth and lead the transformation of its Enterprise segment into a value-based, enterprise-oriented sales organization. The Director, Enterprise Sales will bring a balance of strategic vision, operational discipline, and leadership presence to drive predictable, scalable revenue outcomes.

The ideal candidate will combine deep SaaS sales leadership experience with a proven ability to lead large, hybrid sales organizations through transformation. This executive will be known for building accountability, elevating performance standards, and driving collaboration across a complex, matrixed enterprise.

Experience & Expertise

▪15+ years of progressive sales leadership experience in enterprise software or SaaS environments, managing both field and inside sales teams across multiple segments.
▪Demonstrated success driving revenue growth through value-based, solution selling and SaaS or subscription-based models.
▪Experience leading commercial organizations through sales modernization, including forecasting rigor, pipeline inspection, and metrics-driven process improvement.
▪Proven ability to collaborate cross-functionally with Product, Marketing, and Revenue Operations to align go-to-market plans and improve execution.
▪Expertise in Salesforce (SFDC) and data-driven sales management practices to increase forecast accuracy, pipeline quality, and sales velocity.
▪Track record of building and scaling high-performing teams, fostering accountability, coaching talent, and developing next-generation leaders.
▪Experience operating within a matrixed, global organization, balancing near-term tactical delivery with long-term strategic growth.
▪Strong commercial acumen and understanding of key financial levers including ARR growth, CAC efficiency, and margin optimization.

Our Interview Practices

To maintain a fair and genuine hiring process, we kindly ask that all candidates participate in interviews without the assistance of AI tools or external prompts. Our interview process is designed to assess your individual skills, experiences, and communication style. We value authenticity and want to ensure we’re getting to know you—not a digital assistant. To help maintain this integrity, we ask to remove virtual backgrounds and include in-person interviews in our hiring process. Please note that use of AI-generated responses or third-party support during interviews will be grounds for disqualification from the recruitment process.

Applicants may be required to appear onsite at a Wolters Kluwer office as part of the recruitment process.

Compensation:

$137,900.00 - $246,350.00 USD

Compensation range listed is based on primary location of the position. Actual base salary offer is influenced by a wide array of factors including but not limited to skills, experience and actual hiring location. Your recruiter can share more information about the specific offer for the job location during the hiring process.

Additional Information:

Wolters Kluwer offers a wide variety of competitive benefits and programs to help meet your needs and balance your work and personal life, including but not limited to: Medical, Dental, & Vision Plans, 401(k), FSA/HSA, Commuter Benefits, Tuition Assistance Plan, Vacation and Sick Time, and Paid Parental Leave. Full details of our benefits are available upon request.