Director, Professional Services Sales

WEXWEXUS•Remote, OH

10d•$170,200 - $205,300

About The Position

This role owns the commercial engine behind the ambition of ensuring 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 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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.
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.
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.
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.
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.
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.
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.
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.
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.