Sales Representative

At The Liberty Company, we’re not just growing—we’re thriving. Our award-winning company culture is built on positivity, innovation, and collaboration, fueling the success of our entire team. If you’re searching for a place to grow professionally and personally while finding your Joy of Being (JOB), you’ve found it here!

We’re proud to offer competitive pay, exceptional benefits, PTO, paid training, stress management programs, and opportunities to give back to the community—all while fostering an environment where wellness and teamwork come first.

Join our team as a Sales Representative at the Shore Tompkins Office in Chicago, IL! If you’re ready to bring your energy and expertise to a company that values culture above all, let’s connect!

Position Summary:
Shore Tompkins is seeking a dynamic Sales Representative to expand our presence in the investment advisory market. This role involves building strong relationships with advisors, promoting our value proposition, and driving lead generation and conversions within a short sales cycle. The position is based in the Chicagoland area, and candidates must reside locally.

Essential Duties and Responsibilities

• Build and maintain relationships with investment advisors to serve as a trusted resource.
• Promote and articulate the unique value of Shore Tompkins’ services.
• Identify and generate new leads while nurturing existing ones.
• Conduct virtual and in-person meetings with potential referral sources in the Chicagoland area.
• Keep sales team activity logs current to review with manager.
• Complete any other administrative requirements set by the manager.

​​​Compensation:

• Base Salary + Commission
• Commission Structure:
  • Annual commission on retained business, after the first year.
  • Tiered incentives rewarding performance.
  • Higher payouts for exceeding targets (e.g., 25 plans/year).

Training and Support

• Comprehensive onboarding with support from technical managers.
• Training focused on Shore Tompkins’ services and offerings.
• Regular performance reviews and goal setting to drive continuous improvement.

Minimum Qualifications (Education, Experience, Skills)

• Proven sales aptitude with the ability to generate and close leads.
• Self-motivated, money-driven, and results-oriented.
• Strong organizational, time management, and interpersonal skills.
• Adaptable and quick to learn company offerings and market dynamics.
• Prior sales or client-facing experience preferred.
• Familiarity with short sales cycles is advantageous.
• Resides in or near the Chicagoland area.
• No specific educational requirement, but a background in sales, marketing, or business is a plus.

Promoting Peace of Mind for All

At Liberty, we take great care to promote peace of mind for all. We create a safe space to find your Joy of Being as your most authentic self. Being uniquely YOU, with your unique experiences and ideas, we will continue to strengthen our company as we grow together.

HABU has nothing to do with age, gender identity, race, sexual orientation, physical or mental ability, or ethnicity. We pursue people who value: Integrity, excellence, caring, kindness, fairness, teamwork, good feelings, and fun! Liberty empowers our team with tools and knowledge to support the purposeful spread of positive energy, kindness, and good feelings with others.

We recognize that our industry has more work to do in advancing diversity and inclusion. Our dream is to become the north star others can look to for direction as we advance together.

*Qualified applications with arrest or conviction records WILL be considered for employment. For positions in our organization that require a state insurance license to perform the duties described herein, applicants must meet the state licensing requirements as required by the applicable DOI, must not have been disqualified or barred from licensure, and must not have been prohibited from conducting the business of insurance under Title 18 U.S. Code, §§1033 and 1034 to qualify for that role