Regional Sales Director - Health & Benefits (Remote/Field)

WEX Inc.; Chicago (IL); Hybrid; USD 113,000 - 143,000; Full time

Benefits offered by this job

Health, dental and vision insurance

Retirement savings plan

Paid time off

Health savings account

Flexible spending accounts

Life insurance

Disability insurance

Tuition reimbursement

Job summary

WEX Health & Benefits is seeking a Regional Sales Director in the Chicago area. You will own the territory, drive new business, and expand relationships with brokers, consultants and employers. The role combines strategic selling with extensive field activity and strong collaboration with internal teams.

The successful candidate will manage a robust pipeline, deliver compelling product demonstrations, and close opportunities while leveraging Salesforce for accurate forecasting and reporting.

Qualifications

• 3+ years of sales experience in B2B/SaaS, preferably health benefits or related industry.
• Proven track record of meeting or exceeding sales goals.
• Strong presentation, negotiation, communication, networking and relationship-building skills.
• Ability to independently manage a geographic territory and travel schedule.
• Proficiency with Salesforce or another CRM platform.

Responsibilities

• Own and execute a comprehensive sales strategy for the territory to achieve revenue goals.
• Develop and maintain a healthy pipeline through prospecting, networking, referrals, and relationships.
• Lead finalist presentations and demonstrate WEX value to brokers, consultants and employers.
• Maintain accurate Salesforce activity, pipeline, and forecasting information.
• Maintain a strong field presence and travel as needed to engage high-value clients.

Skills

Sales

Negotiation

Presentation

Networking

CRM (Salesforce)

Territory management

Education

Bachelor's degree

Tools

Salesforce

Job description

WEX Health & Benefits is seeking a Regional Sales Director in the Chicago area. You will own the territory, drive new business, and expand relationships with brokers, consultants and employers. The role combines strategic selling with extensive field activity and strong collaboration with internal teams.

The successful candidate will manage a robust pipeline, deliver compelling product demonstrations, and close opportunities while leveraging Salesforce for accurate forecasting and reporting.