Demo

Area Sales Representative

Keystone Strategy Partners
Libertyville, IL Full Time
POSTED ON 4/14/2026
AVAILABLE BEFORE 6/10/2026

The Role: Strategic Business Development At Keystone Strategy Partners, we are dedicated to setting our team up for long-term, sustainable success. We are looking for an Area Sales Representative to serve as a Business Development Consultant and the strategic face of our firm within the local business community.

This is a high-impact role that goes far beyond simple prospecting. You are a relationship-builder responsible for identifying local organizations and navigating professional conversations with owners and HR directors. Your mission is to help leadership realize the value of voluntary benefits in attracting and retaining top talent.

Focus on Your Strengths: You manage the most critical phase of the business cycle: initial discovery and securing the strategic partnership. Once you have successfully consulted with the business owner and secured their commitment to partner with us, our dedicated enrollment specialists take over the technical implementation and employee sign-ups. This allows you to stay focused on what you do best—cultivating new opportunities and expanding your local market footprint.

The Keystone Success Model

We provide a high-accountability, high-support structure designed to turn talent into expertise:

  • Strategic Office Days (Monday & Friday): We start and end the week together at our regional headquarters. These days are dedicated to collaborative prospecting, professional development, and sharpening your sales skills with the leadership team while preparing for the week.
  • Local Field Days (Tuesday – Thursday): The middle of the week is yours to own. You will be out in the community meeting face-to-face with decision-makers. Your focus will be on your own town and the surrounding ring of communities, allowing you to build deep, local roots.
  • Mentorship-First Training: We don't believe in "sink or swim." You will have a partner in the field for joint sales calls until you are fully prepared and confident to lead those conversations on your own.

What You’ll Do

  • Strategic Market Development: Identify and engage with key businesses in your local area to introduce Keystone Strategy Partners and the Colonial Life legacy.
  • Consultative Selling: Conduct discovery meetings with decision-makers to understand their current benefit structures and present tailored solutions.
  • Partnership Acquisition: Lead the negotiation and commitment phase to launch new accounts.
  • Territory Stewardship: Act as a long-term ambassador for the brand within your defined community.

What We’re Looking For

  • Professional Persistence: You are comfortable initiating new business relationships and navigating B2B sales cycles.
  • Community Focus: We want partners who live in or have strong ties to Lake, McHenry, or Northern Cook County and want to build a business that serves their immediate local area.
  • Growth Mindset: You value training and want to be part of a team that sharpens your skills weekly.
  • Licensing: A Life, Accident & Health Insurance License is required. For the right candidate, we will sponsor and pay for your pre-licensing course.

Compensation & Partnership

  • Uncapped Potential: This is a 1099 contract role with income driven by sales results, renewal income, and bonuses through Colonial Life.
  • Proven Stability: Benefit from the 80-year legacy of Colonial Life paired with the boutique, hands-on culture of Keystone Strategy Partners.
  • Professional Development: Access to world-class corporate resources and local mentorship to help you build a profitable, long-term business.

Pay: $50,000.00 - $100,000.00 per year

Benefits:

  • Dental insurance
  • Employee assistance program
  • Life insurance
  • Professional development assistance
  • Referral program
  • Retirement plan
  • Vision insurance

Work Location: Hybrid remote in Libertyville, IL 60048

Salary : $50,000 - $100,000

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