Director of Sales – Enterprise

This is a fully remote position, open to applicants in Illinois, +5 more states.

📋 Description

• Achieve and surpass annual ARR sales targets through strategic sales initiatives, acquiring new customers, and nurturing long-term partnerships with channel partners.

• Represent and cultivate an in-depth understanding of the company’s employee benefits technology products and services.

• Educate key influencers and employers regarding product and service delivery.

• Engage with brokers, consultants, advisors, carriers, and employers to generate qualified leads.

• Prepare action plans and schedules to identify targets and develop a robust sales pipeline.

• Build and sustain a qualified sales pipeline.

• Monitor activities and opportunities utilizing company tools and procedures.

• Develop territory action plans through data analysis and modify sales techniques based on outcomes.

• Follow up on leads and referrals generated by marketing efforts.

• Implement consultative sales strategies.

• Create and present client proposals while assisting in navigating paths to closing deals.

• Conduct systems demonstrations and product presentations.

• Evaluate the needs of prospects and adhere to the established selling process.

• Collaborate with sales leadership, transition teams, and sales-support resources to strategize deals.

• Promote teamwork and cooperation with sales support, marketing, product, and operations teams.

• Work together with aligned prospect teams to ensure shared understanding and deliverability.

• Perform additional assigned duties.

⛳️ Requirements

• A Bachelor’s degree is preferred but not mandatory.

• Equivalent experience may be accepted in lieu of a Bachelor’s degree in sales, business analytics, management information systems, human resources management, benefits administration, or a related field.

• A minimum of 5 years of experience selling technology and services to enterprise clients (7.5k+).

• Demonstrated ability to create and deliver presentations.

• Proven track record in developing and maintaining a business-development territory, including prospecting efforts.

• Established capability to execute a comprehensive sales discovery process.

• Strong negotiation and closing skills.

• Excellent interpersonal and communication abilities.

• Proven experience in building and nurturing client relationships with brokers, consultants, and employers.

• Experience in relationship-building.

• Preferred experience in channel sales.

• Background in selling HCM, payroll, health and welfare benefits, or benefit administration services.

• Equivalent combinations of education, experience, and training may be considered.

• Willingness to travel up to 50% of the time.

🏝️ Benefits

• Opportunity for remote/virtual work arrangement.

• Potential for up to 50% travel.