Health Benefits Sales Advisor – On-Site (Chicago Loop)

If you’re early in your career and looking for a place where effort, discipline, and consistency create real momentum, this could be the right move.

A nationally recognized health benefits organization is expanding its Chicago team and hiring motivated, coachable individuals ready to step into a structured, high-activity role with strong earning potential and long-term opportunity.

This is a phone-first, performance-driven environment. Expectations are clear. Metrics matter. Consistency matters. At the same time, the support structure is real - leadership is present, coaching happens daily, and improvement is taken seriously. This environment rewards people who are intentional about building their skills and advancing their career.

The Environment

This is a young, energetic sales floor inside Willis Tower. The pace is high, the standards are clear, and the energy is real.

Managers sit with their teams, live-listen, and coach in real time - but it’s not a stiff or corporate atmosphere. It’s competitive in a healthy way. People push each other, celebrate wins, and build momentum together.

There’s a strong sense of team here. Reps lean on each other, share strategies, and develop quickly because they’re surrounded by other motivated peers. It’s common to see teams grabbing lunch together, celebrating milestones, or decompressing after a big week.

If you enjoy being around other ambitious, high-energy people who are building something - you’ll feel it here.

The Role

• Speak with individuals actively exploring health insurance options
• Manage a high-volume call flow (typically 50–100 calls per day)
• Work primarily with inbound and warm follow-up leads
• Follow a structured, proven sales process
• Track daily and weekly activity metrics
• Collaborate within a defined team structure

You won’t be sourcing your own leads. Once trained, and with support, you will be expected to own your preparation, your activity, and your results.

Training & Ramp

New hires receive structured onboarding and licensing support, including classroom-style training on systems and fundamentals before moving fully into production.

There is a supported ramp period - but performance standards remain clear. The goal is steady improvement and long-term development within a results-driven environment.

Compensation & Opportunity

• $20/hour base pay
• $1/hour raise after first performance milestone
• Monthly bonuses typically $1,000–$3,000
• First-year earnings commonly $55K–$75K , with growth from there
• Clear internal mobility based on performance

This role can be a strong foundation - whether someone continues advancing within the sales organization or grows into other areas of the broader company. Success here creates options.

Requirements

• Illinois residency required (licensing compliance).
• Full-time, on-site availability in downtown Chicago (Willis Tower).

If you’re someone who takes growth seriously and wants to build real professional momentum in a structured, high-energy environment - apply below.