Director, Professional Services Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Oversee the commercial operations for Professional Services, which includes managing the pipeline, deal structure, pricing discipline, forecast accuracy, and collaborations across Sales, Account Management, and Delivery.

• Achieve and surpass growth and bookings objectives for Professional Services while ensuring high levels of customer satisfaction.

• Develop strategies to bridge gaps between the committed pipeline and targets, focusing on pursuits, timing, and actionable steps.

• Establish and execute comprehensive forecasting and pipeline rhythms; ensure data integrity, make proactive risk assessments, and deliver leadership insights.

• Communicate sales activities and forecasts to senior executives and guide the team on effective closing strategies.

• Direct the strategy, pricing, and structuring of service engagements in collaboration with Delivery, Operations, Deal Desk, and RevOps.

• Oversee the mechanics of statements of work, risk assessments, scope, assumptions, commercial terms, and margin preservation.

• Collaborate with Delivery leadership to ensure engagements are realistically defined, adequately staffed, commercially sound, and positioned for successful execution.

• Act as the primary commercial point of contact for Professional Services for Sales and Growth leaders, positioning services early in the engagement process.

• Develop a commercial strategy for positioning, pricing, and selling services across various customer segments and market routes.

• Identify service priorities, customer journey touchpoints, offerings, and pricing strategies by segment.

• Lead discussions on value and economics with client executives at key accounts and act as an executive sponsor for critical engagements.

• Maintain an active presence in the field, including travel to customer sites when necessary.

• Guide and nurture the services sales team through recruitment, training, pipeline management, opportunity oversight, deal reviews, performance evaluations, and career development.

• Steer the team through WEX's technology and AI evolution by embracing tools and fostering sales innovation.

• Function as an enterprise leader, proactively identifying commercial risks and opportunities, linking services performance to the Health & Benefits vision and strategy, and influencing cross-functional decisions that shape customer experiences.

⛳️ Requirements

• A minimum of 8 years in professional services sales, consulting, or solution sales, with direct accountability for service revenue and a proven record of consistently exceeding quotas.

• At least 3 years of experience in sales management and consultative selling, demonstrating success in building and developing commercial teams.

• Experience in selling professional services within a technology, software, or platform organization.

• Proven expertise in the services attach motion, including early positioning of services during licensing or subscription cycles, navigating platform and services revenue, understanding how service investments foster platform growth and retention, and gaining the trust of quota-bearing sales personnel.

• Strong commercial insight and knowledge of service delivery dynamics, including statement of work mechanics, project/engagement risk, staffing realities, and margin preservation.

• Successful track record of developing and maintaining C-level relationships as a trusted advisor.

• Ability to excel in uncertain environments and create structure in a dynamic setting.

• Demonstrated capacity for rapid learning and building credibility in a regulated market.

• Highly collaborative, capable of functioning within a complex, matrixed environment across sales and delivery ecosystems.

• Excellent written and verbal communication skills, with the ability to formulate clear commercial narratives.

• Preferred: Background in benefits administration, consumer-directed healthcare, payments, or healthcare technology.

• Preferred: Familiarity with the purchasing processes of employers, health plans, brokers, and third-party administrators; understanding of benefits program regulations; and insights into how annual enrollment cycles affect implementation timing and scope.

• Preferred: Experience in developing or scaling an advisory or consulting offering within a technology or platform business.

• Preferred: Knowledge of services P&L construction, utilization, and margin management.

🏝️ Benefits

• Health insurance

• Dental insurance

• Vision insurance

• Retirement savings plan

• Paid time off

• Health savings account

• Flexible spending accounts

• Life insurance

• Disability insurance

• Tuition reimbursement

• Commission eligibility for most sales roles under an applicable plan

• Quarterly or annual bonus eligibility for non-sales positions based on role and applicable plan

• Comprehensive and competitive benefits designed to enhance personal and professional well-being