Director, Professional Services Sales

WEX; Maine; On-site; USD 170,000 - 205,000; Full time

Job summary

WEX in Maine is seeking a quota-carrying Services Sales leader who drives the commercial engine for Professional Services, overseeing pipeline, pricing discipline, and forecast integrity while partnering with Sales, Account Management, and Delivery.

You will co-lead large pursuits, build commercial rigor, and position services to help employers, health plans, and administrators design, implement, and optimize benefits programs across segments and channels.

Qualifications

• 8+ years in professional services sales, consulting, or solution sales with quota responsibility.
• 3+ years of sales management and team development experience.
• Experience selling professional services inside a technology, software, or platform business.
• Strong commercial acumen with delivery dynamics: SOW, risk, staffing, margins.
• Proven ability to build and maintain C-level relationships.
• Thrives in ambiguity and fast-paced settings.
• Demonstrated learning velocity in regulated markets, credibility with customers.
• Highly collaborative in complex, matrix environments.

Responsibilities

• Exceed Professional Services growth and bookings targets while delivering high customer satisfaction.
• Create and maintain a rigorous forecast and pipeline cadence with data hygiene and early risk calls.
• Lead strategy, pricing, and structuring of services engagements with Delivery, Operations, and RevOps.
• Partner with Delivery leadership to ensure engagements are scoped, staffed, and financially viable.
• Serve as the commercial front door to ProServ for Sales and Growth leaders, ensuring early positioning of services.
• Craft the commercial strategy for segments and channels, including direct employer relationships.
• Lead value and economics conversations with client executives at largest accounts.
• Mentor and develop the services sales team and promote innovation in selling.

Skills

Strategic sales leadership

Pricing & deal structuring

Forecasting & pipeline management

Executive relationship management

Cross-functional collaboration

Healthcare benefits domain

SOW & contract knowledge

Matrix environment navigation

Job description

Position Summary

Benefits are one of the most consequential things an employer offers and one of the hardest to get right. WEX Professional Services ensures our customers realize the full value of the WEX solution: launching well, adopting fully, and continuing to get more out of the platform as their programs and populations change.

This role owns the commercial engine behind that ambition: pipeline, deal construction, pricing discipline, forecast integrity, and the partnership with Sales, Account Management, and Delivery that puts the right services in front of the right customers at the right moment in their journey.

This is a quota-carrying, player-coach role in a highly matrixed environment. You will be a strategic problem solver with outstanding strategic, enterprise, commercial, and cross-functional skills, bringing high energy and real command of commercial management. You will personally co- lead the largest and most complex pursuits, build the commercial rigor and cadence the business runs on, and position Professional Services as the partner that helps employers, health plans, and administrators design, implement, and optimize their benefits programs, including the commercial strategy for how those services reach customers across segments and channels. You will partner with client executives on a regular basis and maintain positive relationships with internal peers across Delivery, Sales, Account Management, Product, Technology, Finance, and Operations to ensure customer needs are met seamlessly from the initial pitch through successful implementation and beyond.

Key Responsibilities

• Commercial Results & Customer Outcomes: Exceed Professional Services growth and bookings targets while delivering high customer satisfaction on the engagements you and your team sells. Own the plan to close any gap between committed pipeline and target, including the specific pursuits, timing, and actions that close it.
• Forecast & Pipeline Discipline: Create and conduct a rigorous forecast and pipeline cadence, maintain data hygiene, early risk calls, and the commentary leadership relies on to run the business. Surface forecast changes early with a recommendation attached. Report clearly on sales activity and forecasts to senior management. Mentor team on strategies to drive closings.
• Deal Construction & Commercial Viability: Lead strategy, pricing, and structuring of services engagements in partnership with Delivery, Operations, Deal Desk, and RevOps. Bring command of statement of work mechanics, engagement risk assessment, and margin preservation. Ensure engagements are priced to their economics and structured with clear scope, assumptions, and commercial terms.
• Delivery Partnership: Partner as a trusted peer with Delivery leadership so that engagements are realistically scoped, properly staffed, and commercially viable before they are signed. Collaborate to bridge the gap between pre-sales vision and successful implementation, safeguarding both project margins and customer success.
• Sales & Account Management Partnership: Serve as the commercial front door to ProServ for Sales and Growth leaders. Build a working cadence with those leaders and teams so that services are positioned early in pursuits.
• Segmentation & Channel Strategy: Craft the commercial strategy for how services are positioned, priced, and sold across customer segments and routes to market, including direct employer relationships and customers who come to WEX through partners. Define which services matter most in each segment, where they attach in the customer journey, and how the offer and pricing should differ across them.
• Executive Customer Engagement / Consulting: Personally lead value and economics conversations with client executives at the largest strategic accounts, and serve as executive sponsor on key engagements. Stay active in the field, including customer-site travel where the relationship warrants it.
• Team Leadership & Development: Mentor and develop the services sales team, including recruiting, hiring, training, pipeline management, opportunity management, deal reviews, performance management, and career planning. Lead the team through WEX's technology and AI journey by demonstrating adoption of the tools yourself and promoting innovation in how the team sells.
• Enterprise Contribution: Operate as an enterprise leader beyond the services number. Anticipate commercial risk and opportunity early, connect services performance to the broader Health & Benefits vision and strategy, and contribute as a peer to cross-functional leaders on the decisions that shape the customer experience.

Required Qualifications

• 8+ years in professional services sales, consulting, or solution sales, including direct accountability for a services number and a track record of consistent quota over-achievement.
• 3+ years of sales management and consultative selling experience, with a track record of building and developing commercial teams.
• Experience selling professional services inside a technology, software, or platform business, with demonstrated command of the services attach motion: positioning services early in a license or subscription cycle, navigating the tension between platform revenue and services revenue, understanding how services investment supports platform growth and retention, and earning the trust of quota-carrying sellers who do not report to you.
• Strong commercial acumen paired with genuine understanding of services delivery dynamics: SOW mechanics, project / engagement risk, staffing realities, and margin preservation.
• Proven ability to develop and maintain C-level relationships where you are recognized as a trusted advisor.
• Thrive operating in ambiguity and building the structure in a fast-paced environment.
• Demonstrated learning velocity. This is a regulated market where credibility with customers depends on understanding their business. Candidates without direct benefits experience should be able to point to a market they learned from scratch, what they did to become credible, and how they knew when they were.
• Highly collaborative and excels in a highly complex, matrix environment working across both sales and delivery ecosystems.
• Strong written and verbal communication skills, with the ability to construct a clear commercial narrative for both customers and senior internal audiences.

Preferred Qualifications

• Demonstrated experience in benefits administration, consumer-directed healthcare, payments, or healthcare technology.
• Working command of how employers, health plans, brokers, and third-party administrators buy, the regulatory environment shaping benefits programs, and how the annual enrollment cycle affects implementation timing and scope.
• Experience building or scaling an advisory or consulting offer within a technology or platform business.
• Exposure to services P&L construction, utilization, and margin management.

Disclaimer

This description may not be exhaustive of all of the possible responsibilities, tasks, duties and/or qualifications of the role and the Company reserves the right to assign other responsibilities, tasks, duties and/or qualifications from time to time in the future in accordance with applicable law.

The base pay range represents the anticipated low and high end of the pay range for this position. Actual pay rates will vary and will be based on various factors, such as your qualifications, skills, competencies, and proficiency for the role. Base pay is one component of WEX's total compensation package. Most sales positions are eligible for commission under the terms of an applicable plan. Non-sales roles are typically eligible for a quarterly or annual bonus based on their role and applicable plan. WEX's comprehensive and market competitive benefits are designed to support your personal and professional well-being. Benefits include health, dental and vision insurances, retirement savings plan, paid time off, health savings account, flexible spending accounts, life insurance, disability insurance, tuition reimbursement, and more. For more information, check out the "About Us" section.

Pay Range: $170,200.00 - $205,300.00