Insurance and Financial Services Sales Representative

SD Group

Chicago, IL

JOB DETAILS
SALARY
$40,000–$60,000 Per Year
SKILLS
Coaching, Communication Skills, Continuous Improvement, Customer Support/Service, Financial Services, Follow Through, Insurance, Insurance Sales, Licensing, Marketing Strategy, Mentoring, Organizational Development/Management, Organizational Skills, Process Development, Sales, Sales Pipeline, Sales Prospecting, Sales Strategy, Sales Support, Team Player
LOCATION
Chicago, IL
POSTED
9 days ago

You’re not looking for another commission job where people throw around words like “opportunity” but leave you completely on your own.


You want flexibility, real mentorship, and a chance to build income that can actually grow over time.


You want a team that pushes you to improve, supports your development, and rewards effort with real opportunity.


At Sand Dollar Group, we’re building a performance-driven insurance and financial services team for people who are coachable, motivated, and serious about personal and professional growth.


If you’re competitive, self-driven, and ready to learn fast, keep reading.


Who We Are

Sand Dollar Group is a lighthearted team with a big heart. We care deeply about helping people protect their future while creating meaningful impact in the communities we serve. At the same time, we believe growth should be challenging, rewarding, and supported by the right people.


This is not a “figure it out yourself” environment.


As an Insurance Sales Representative, you’ll join a team built around mentorship, accountability, continuous learning, and long-term opportunity. You’ll work alongside experienced advisors and professionals who want to help you improve, grow your confidence, and build a career with real earning potential.


We move with purpose, support each other, and believe people grow faster when they’re surrounded by high standards and the right culture.


What You'll Be Doing

Your days will be fast-moving, people-focused, and growth-oriented. You’ll spend time building relationships, following up with prospects, learning sales strategies, developing communication skills, and helping clients make smart insurance and financial decisions with professionalism and integrity.


This role blends flexibility with accountability.


One moment you’re sharpening your sales skills through hands-on coaching and mentorship. The next, you’re managing follow-up conversations, staying organized, and taking ownership of your pipeline and results.

You’ll:

  • Connect with clients and build strong relationships
  • Learn insurance and financial service products and solutions
  • Develop communication, follow-up, and sales skills
  • Participate in coaching, mentorship, and ongoing training
  • Manage pipeline organization and client follow-up
  • Work toward activity and performance goals
  • Operate independently while staying connected to team support
  • Continuously improve your confidence, professionalism, and consistency


You’ll work a flexible part-time schedule of 15 to 30 hours per week, with remote flexibility available for the right candidate.

This role matters because consistency creates momentum.

The people who succeed here are the ones who stay coachable, improve every week, follow through, and learn how to turn conversations into long-term relationships and income growth.


The Hiring Process

We move quickly for strong candidates and use a streamlined hiring process designed to identify people with strong communication skills, growth potential, and the right mindset.

Here’s what the process looks like:

  1. Apply online through the job posting
  2. Complete the R.E.G.I. assessment and screening process
  3. Submit a short one-way video interview
  4. Qualified candidates will be invited to an in-person interview with our team

We review every application carefully and aim to move qualified candidates through the process as efficiently as possible.


What You'll Earn

  • Expected earnings: $40,000–$60,000 per year
  • Performance-based bonuses
  • Uncapped earning potential
  • Flexible part-time schedule with growth opportunity
  • Clear path toward full-time advancement as performance grows
  • Long-term commission growth potential
  • Opportunity for licensing support including life/health and 65

This role starts part-time, but the opportunity grows as your skills, consistency, and production increase.

For motivated people who stay coachable and committed, this can become much bigger than a side income.


Why Work With Us

A lot of sales organizations promise support. Very few actually provide mentorship, development, and real investment in people.


That’s where Sand Dollar Group is different.


You won’t get tossed into a sink-or-swim setup and expected to magically succeed overnight.


You’ll have access to experienced mentors, hands-on training, ongoing coaching, and a collaborative team culture that values growth, accountability, and long-term success.


What you’ll find here:

  • Flexible part-time scheduling
  • Remote flexibility for qualified candidates
  • Mentorship from experienced advisors
  • Hands-on training and continuous learning
  • Licensing and advancement pathway opportunities
  • Supportive, collaborative team environment
  • Opportunity to build long-term income through commission growth
  • Personal and professional development opportunities
  • A culture that values consistency, growth, and accountability
  • Marketing support and strategy


This is a strong fit for someone who wants flexibility with real upside and is willing to earn opportunities through performance.


Who We're Looking For

You’ll do well here if you’re motivated, coachable, organized, and hungry to improve.

You communicate well, follow through consistently, and take ownership of your results instead of waiting to be pushed every day.


Experience in sales, insurance, or financial services can help, but mindset matters more than background.


We’re looking for someone who:

  • Is coachable and eager to learn
  • Is self-motivated and performance-driven
  • Communicates confidently and professionally
  • Is comfortable in a commission-based environment
  • Can stay organized and accountable independently
  • Is interested in insurance, sales, or financial services
  • Is open to mentorship, coaching, and feedback
  • Is goal-oriented and motivated by income growth
  • Wants long-term development and advancement opportunities
  • Brings professionalism, consistency, and initiative daily


Not a Fit If

  • You resist feedback or accountability
  • You want guaranteed pay without performance expectations
  • You struggle with consistency and follow-through
  • You need constant hand-holding to stay productive
  • You’re looking for a low-effort or low-standard environment
  • You dislike commission-based earning structures
  • You avoid personal growth, coaching, or competition


Apply Today

If you’re ready to learn fast, grow through coaching, earn through performance, and build something meaningful with a supportive team, apply now.

Strong opportunities with flexibility, mentorship, and real long-term earning potential don’t stay open forever.

About the Company

S

SD Group