Sales Director

Jobtailor; Chicago (IL); On-site; USD 90,000 - 140,000; Full time

Job summary

Jobtailor in Chicago seeks a results-driven sales and recruitment leader with deep healthcare/Medicare knowledge to drive growth, manage agent relationships, and educate partners on value propositions. This role balances strategic planning with hands-on training and compliance oversight.

You will build and execute a year-round strategy, oversee marketing and community engagement, and coordinate with the Producer Support Team to maximize agent satisfaction. Travel up to 75% is expected.

Qualifications

• 3+ years of experience in healthcare or Medicare industry.
• Active Health Insurance License is required.
• Bilingual in English/Spanish preferred.
• Must live in the market area.
• Willingness to travel up to 75% within the assigned market.

Responsibilities

• Build a year-round sales and recruitment strategy.
• Oversee community presence and grassroots lead generation.
• Establish relationships with key partners; educate on value proposition.
• Train on products, services, compliance, and community relations.
• Budget management and market spending oversight.
• Communicate effectively internally and externally.
• Translate data into actionable business recommendations.
• Collaborate with Producer Support Team to ensure agent satisfaction.
• Ensure compliance with CMS, State, and Federal guidelines.
• Recruit agents and agencies; drive RTS growth and agent engagement.
• Establish and retain market relationships; perform other duties as assigned.

Skills

Sales strategy development

Lead generation

Budget management

Data analysis

Compliance knowledge

Agent recruitment

Market spending oversight

Community relationship building

Presentation skills

Time management

Self-motivated

Education

College degree preferred

Tools

Microsoft Office Suite

Job description

Responsibilities

• Build a year-round sales and recruitment strategy while servicing all agents & agencies to ensure all sales objectives are met/exceeded.
• Accountable to oversee our community presence and grassroots lead generation efforts.
• Establish relationships with key partners within each market, educate agents/agencies on Agility Insurance Services’ compelling value proposition, growth initiatives and member retention.
• Responsible for training on products, services, compliance, and building community relationships.
• Responsible for budgeting and market spending.
• Effectively communicate both internally and externally.
• Translate complex data into clear and actionable recommendations to drive business.
• Work hand in hand with our Producer Support Team to ensure utmost agent satisfaction.
• Ensure CMS, State, and Federal regulatory guidelines are communicated to direct reports and other team members as needed to maintain compliance.
• Recruiting agents and agencies.
• Drive RTS (Ready to Sell) growth and agent engagement.
• Establish and retain relationships throughout the market and business.
• Perform other duties as assigned.

Requirements

• Three (3) + years of experience in the healthcare or Medicare industry, with a proven track record of managing insurance agents, agency relationships, and driving business growth.
• Previous broker or agency experience is preferred.
• College degree preferred.
• Active Health Insurance License is required.
• Bilingual in English/Spanish preferred.
• Demonstrated ability to quickly establish, develop, and maintain strong relationships with agent partners.
• Strong presentation, interpersonal, and communication skills.
• Excellent written and verbal communication skills.
• Knowledge of and ability to effectively present ACA, Medicare, Life, and Ancillary insurance products.
• Willingness to travel up to 75% within the assigned market, including overnight travel as needed.
• Proficient in Microsoft Office Suite, particularly Excel, Word, Outlook, and PowerPoint.
• Must have reliable transportation.
• Self‑motivated with excellent time management and organizational skills.
• Innovative, results‑driven, and focused on achieving growth objectives.
• Must live in the market area.

Core Competencies

Demonstrates expertise in building sales and recruitment strategies within the healthcare and Medicare industry, focusing on agent relationship management, compliance, and effective communication. Proven ability to drive business growth through innovative lead generation and community engagement.

Hard Skills

• Sales Strategy Development
• Lead Generation
• Product Training
• Data Analysis
• Budget Management
• Compliance Knowledge
• Insurance Product Presentation
• Agent Recruitment
• Market Spending Oversight
• Community Relationship Building

Soft Skills

• Strong Presentation Skills
• Interpersonal Skills
• Excellent Communication Skills
• Time Management
• Self‑Motivated