Regional Sales Director (Chicago)

WEX•Illinois - Remote Office, IL

2d•$112,700 - $143,000

About The Position

The Regional Sales Director of WEX Health & Benefits drives new business growth and expands existing relationships across an assigned geographic territory. The role manages relationships across broker and consultant channels, referral partners, employers, and internal WEX stakeholders to generate opportunities, increase market share, and achieve annual revenue targets. This is an outside sales position requiring a minimum of three of five working days per standard week in the field networking and meeting with clients, consultants, brokers, partners, and prospects. The successful candidate is a motivated, relationship-driven sales professional who can build long-term partnerships in a competitive environment. The role requires strategic networking, strong communication and presentation skills, negotiation ability, and disciplined follow-through. The Regional Sales Director independently manages territory strategy and travel, maintains an accurate sales pipeline, collaborates with internal teams, and represents WEX professionally while delivering a customer-focused experience.

Requirements

At least 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, 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 and 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.

Nice To Haves

Bachelor’s degree.
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.

Responsibilities

Own and execute a comprehensive territory sales strategy, meeting annual revenue and new-business goals.
Develop and maintain a qualified pipeline through prospecting, networking, referrals, and existing relationships.
Identify and pursue high-value growth opportunities, increase market share, and monitor market trends and competitive activity.
Build and maintain relationships with brokers, consultants, referral partners, employers, and other stakeholders.
Position WEX as a preferred partner and generate RFPs and new-business opportunities.
Build internal alignment and advocacy for territory opportunities across WEX.
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 to prospects and stakeholders.
Deliver product demonstrations, presentations, and training to educate partners and drive adoption.
Use consultative selling, negotiation, and closing skills to advance opportunities through the sales process.
Maintain accurate and timely Salesforce or CRM activity, opportunity, pipeline, and forecasting information.
Maintain a strong field presence, with at least three days per week in the field.
Independently manage territory travel, including scheduling, transportation, lodging, and meeting coordination.
Plan and prioritize travel and manage multiple priorities and opportunities effectively.
Collaborate with colleagues, respond positively to feedback and coaching, and contribute to a high-performance culture.
Demonstrate professionalism, sound judgment, accountability, resilience, and customer-centric behavior.
Follow WEX security, compliance, privacy, and company policies; maintain confidentiality of sensitive information.
Complete other duties and responsibilities as assigned.