Outbound Insurance Jobs in Chicago, IL (NOW HIRING)

Mid Mountain Insurance Agency (MMIA), a Fortegra company, isn’t just another agency — we’re Fortegra’s fast-growing retail arm, built to move quickly, sell smarter, and create real opportunity for top producers.

If you’re competitive, sales-driven, and motivated by building something big, this is your moment. This role is perfect for someone who thrives on outbound prospecting, including cold calling, and is eager to leverage MMIA’s industry strength and support to scale their book of business.

Why MMIA?

• Uncapped Commission – Your effort directly drives your income
• Base + Commission Structure – Stability + upside
• Commission on New Business + Renewals – Build recurring income over time
• 15+ Carrier Options – More solutions = more wins
• Fast-Growth Environment – Get in early and grow with us
• Backed by Fortegra – Strength, scale, and credibility of a carrier with 45+ years of growth
• Comprehensive Training – We set you up to succeed from day one
• Career Growth Opportunities – Build your career alongside a rapidly growing organization
• Work-Life Balance – No nights or weekends
• We Cover Licensing Costs – Reciprocal state licenses, carrier appointments, and continuing education paid for
• Full Benefits Package – Medical, dental, vision, 401(k) match, PTO, and paid holidays
• Free Lunch Daily – Because we take care of our team

Pay Structure: Base + Uncapped Commission + Renewals

• Reliable Base – Competitive hourly starting at $21.75/hour, adjusted based on industry experience
• Growth Potential – Your earning power is in your hands. With commissions on new sales and recurring renewal income, average agents earn $50K–$65K annually
• Top Performers – For those who master the process, $75K+ is well within reach in year one. There is no cap on what you can earn

What You’ll Do

• We’ll give you leads — you’ll build your pipeline through outbound calls, referrals, networking, and proactive follow-up
• Drive new business through outbound prospecting and relationship-building
• Close new business while delivering an excellent customer experience
• Leverage our carrier options to find the right fit for every customer
• Maintain and grow relationships with existing clients and strategic partners
• Track performance and manage activity in CRM systems
• Stay sharp on industry trends, compliance, and product knowledge
• Maintain accurate records and monitor pipeline activity and performance metrics
• Deliver excellent customer service to retain and grow client relationships

What You Bring

• Active Property & Casualty license (multi-state a plus)
• Proven track record of outperforming sales goals, especially in outbound sales environments
• Strong communication, negotiation, and relationship-building skills
• Self-starter mindset with the discipline to own your results
• High energy, enthusiasm, and persuasive sales ability
• Motivated, competitive spirit with strong computer and organizational skills
• 1+ year of sales experience

Bonus Points If You Have

• 4–7 years of insurance sales experience
• Bi-lingual Spanish
• A book of business you can bring with you

The Bottom Line

At MMIA, you’ll have the tools, carriers, and support to scale your income and your career.

If you’re ready to bet on yourself, we’re ready to back you.

About Mid Mountain Insurance Agency

Mid Mountain Insurance Agency (MMIA) is a full-service retail insurance agency committed to helping individuals, families, and businesses secure the protection they need with confidence. Established in 1997 as Pacific Benefits Group in Portland, Oregon, the agency was acquired by Fortegra in 2011 and rebranded as MMIA in 2025 to reflect its expanded capabilities and national footprint. Licensed to offer Life & Health, Property & Casualty, and specialty (E&S) insurance products, MMIA is proudly backed by Fortegra — a global specialty insurer rated A- (Excellent) by AM Best.

Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.

Job Type: Full-time

Benefits:

• 401(k)
• Dental insurance
• Health insurance
• Paid time off
• Vision insurance

Work Location: In person