Regional Sales Director (Chicago)

About Team / Role

The Regional Sales Director of WEX Health & Benefits is responsible for driving new business growth and expanding existing relationships across an assigned geographic territory. This role manages relationships across the broker and consultant channel, referral partners, employers, and internal WEX stakeholders to generate new opportunities, increase market share, and achieve annual revenue targets.

We are seeking a highly motivated, relationship-driven sales professional who thrives in a competitive environment and understands how to build long-term partnerships. The ideal candidate is a strategic networker, strong communicator, compelling presenter, skilled negotiator, and disciplined operator who consistently follows through on commitments.

This is an outside sales position, and success requires a strong presence within the assigned territory. The Regional Sales Director is expected to spend a minimum of three of the five working days per standard week in the field networking and meeting with clients, consultants, brokers, partners, and prospects.

How You'll Make an Impact

Territory & Revenue Growth

• Own and execute a comprehensive sales strategy for the assigned territory, with accountability for achieving annual revenue and new business goals.
• Develop and maintain a healthy pipeline of qualified opportunities through strategic prospecting, networking, referrals, and existing relationships.
•  Identify, prioritize, and pursue the highest-value growth opportunities within the territory.
• Increase WEX market share by developing new relationships, expanding existing partnerships, and identifying emerging market opportunities.
• Monitor market trends and competitive activity to inform territory strategy and growth priorities.

Broker, Consultant & Partner Relationships

• Establish and maintain strong relationships with brokers, consultants, referral partners, employers, and other key stakeholders.
• Build trusted-advisor relationships that position WEX as a preferred partner and generate a consistent flow of RFPs and new business opportunities.
• Understand the roles, motivations, and dynamics among consultants, brokers, referral partners, employers, and WEX sales teams.
• Build strong internal equity and advocacy across WEX to ensure stakeholders are aligned around and supportive of territory opportunities.
• Strengthen relationships by delivering on commitments and providing an exceptional client and partner experience.

Sales Execution

• Proactively schedule and conduct meetings with new and existing relationships to generate opportunities and advance sales cycles.
• Lead finalist presentations and communicate WEX’s value proposition effectively to prospects, consultants, brokers, and other stakeholders (in person is preferred).
• Deliver compelling product demonstrations, presentations, and training that educate partners and drive adoption.
• Apply effective consultative selling, negotiation, and closing skills to advance opportunities through the sales process.
• Maintain accurate and timely Salesforce activity, opportunity, pipeline, and forecasting information, using available data and insights to manage territory performance and sales effectiveness.

Territory Management & Travel

• Maintain a strong field presence within the assigned territory, with a minimum expectation of three days per week in the field.
• Independently manage territory travel, including scheduling, transportation, lodging, and meeting coordination.
• Plan and prioritize travel to maximize time with high-value clients, consultants, brokers, partners, and prospects.
• Demonstrate strong time management and organizational skills while effectively managing multiple priorities and opportunities.

Collaboration & Leadership Behaviors

• Demonstrate emotional intelligence, professionalism, self-awareness, sound judgment, and strong communication in interactions with clients, partners, and WEX colleagues.
• Contribute as a collaborative team member and support a high-performance culture.
• Seek and respond positively to feedback and coaching, demonstrating a commitment to continuous improvement.
• Demonstrate a growth mindset, curiosity, resilience, accountability, and competitive spirit.
• Recognize the contributions of others, support teammate success, and provide constructive feedback when appropriate.
• Serve as a role model for professional behavior, customer-centricity, integrity, and accountability.

Compliance & Other Responsibilities

• Adhere to all WEX security, compliance, privacy, and company policies.
• Maintain confidentiality when handling sensitive customer, partner, employee, or company information.
• Complete all other duties and responsibilities as assigned.

Experience You'll Bring

Required Qualifications

• 3+ years of sales experience, preferably in B2B, SaaS, benefits, healthcare, financial services, or a related industry.
• Proven track record of achieving or exceeding sales goals.
• Demonstrated success developing and managing relationships with brokers, consultants, partners, clients, and/or other business stakeholders.
• Strong presentation, negotiation, communication, networking and relationship-building skills.
• Ability to independently manage a geographic territory and travel schedule.
• Strong organizational skills, with the ability to prioritize multiple opportunities and competing demands.
• Proficiency with Salesforce or another CRM platform and standard business technology.
• Ability to work effectively in a fast-paced, performance-driven environment.

Preferred Qualifications

• Bachelor’s degree preferred.
• Experience selling through a broker, consultant, channel, or referral-partner ecosystem.
• Experience in Health & Benefits, employee benefits, SaaS, healthcare technology, or related markets.
• Established network of broker and consultant relationships within the assigned territory.

What Success Looks Like

The successful Health & Benefits Regional Sales Director will:

•  Achieve or exceed assigned annual sales and revenue targets.
• Network daily in the territory.
• Build relationships that create revenue and generate qualified RFP and pipeline opportunities across the full H&B WEX product suite.
• Become a trusted partner to brokers, consultants, employers, clients, partners, and internal WEX stakeholders.
• Maintain a strong and consistent field presence throughout the assigned territory.
• Deliver an exceptional experience to every client and partner.
• Create strong internal advocacy and collaboration around customer and territory opportunities.
• Maintain a disciplined, accurate, and actionable sales pipeline.
• Bring energy, competitiveness, accountability, and a growth mindset to the role.
• Represent WEX with professionalism, integrity, and a strong customer-first mindset.

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: $112,700.00 - $143,000.00