Membership Advisor

Simpay; Illinois; On-site; USD 80,000 - 200,000; Full time

Benefits offered by this job

Uncapped commission structure

Paid training and ongoing professional

Career advancement opportunities

Paid time off and company holidays

Medical, dental, and vision insurance

Job summary

Simp ay is seeking a dynamic Membership Advisor to introduce and sell the Exectras Membership program to SMBs. You will rely on warm lists from associations, build relationships with business owners, and guide prospects from initial contact to close.

The role thrives in a high-activity sales environment with uncapped earning potential and ongoing product training. You will be part of a fast-growing fintech team focused on meaningful employee benefits and employer savings.

Qualifications

• 2+ years of sales experience preferred
• Experience selling to small/medium businesses
• Strong communication and relationship-building skills
• Comfortable with high outbound call volume
• Experience with CRM systems like Salesforce or HubSpot

Responsibilities

• Conduct outbound calls to business owners from assigned prospect lists
• Build relationships with decision-makers and educate them on the value of the Exectras Membership program
• Identify customer needs and position the membership as a solution that benefits both employers and employees
• Schedule and conduct virtual or phone presentations
• Guide prospects through the sales process from initial contact through close
• Consistently achieve and exceed monthly sales goals
• Maintain accurate records of customer interactions and pipeline activity within the CRM
• Follow up with prospects through calls, email, and other communication channels
• Participate in sales meetings, coaching sessions, and ongoing product training
• Collaborate with marketing and leadership to maximize opportunities within partner associations

Skills

Outbound calls

Relationship building

Consultative selling

Sales planning

CRM proficiency

Communication skills

Time management

Meeting sales targets

Tools

Salesforce

HubSpot

Job description

At Simpay, we help businesses simplify operations through payment processing, payroll, business solutions, and our exclusive Exectras Membership program. Exectras provides business owners and their employees with valuable savings, access to an affordable healthcare platform, and resources designed to improve employee retention while reducing everyday expenses.

As we continue to grow, we're looking for driven sales professionals who enjoy building relationships, educating business owners, and closing deals that create real value.

Position Summary

The Membership Advisor is responsible for introducing and selling the Exectras Membership program to small and medium-sized businesses. Unlike traditional cold calling, you'll primarily work from warm prospect lists consisting of businesses that belong to associations and organizations with which we have established relationships.

This role is ideal for someone who thrives in a high-activity sales environment, enjoys speaking with business owners, and is motivated by uncapped earning potential.

What You'll Do

• Conduct outbound calls to business owners from assigned prospect lists.
• Build relationships with decision-makers and educate them on the value of the Exectras Membership program.
• Identify customer needs and position the membership as a solution that benefits both employers and employees.
• Schedule and conduct virtual or phone presentations.
• Guide prospects through the sales process from initial contact through close.
• Consistently achieve and exceed monthly sales goals.
• Maintain accurate records of customer interactions and pipeline activity within the CRM.
• Follow up with prospects through calls, email, and other communication channels.
• Participate in sales meetings, coaching sessions, and ongoing product training.
• Collaborate with marketing and leadership to maximize opportunities within partner associations.

What We're Looking For

• 2+ years of sales experience (inside sales, B2B sales, or business development preferred).
• Strong communication and relationship-building skills.
• Comfortable making a high volume of outbound calls each day.
• Excellent listening and consultative selling abilities.
• Self-motivated with a competitive, goal-oriented mindset.
• Strong organizational and time management skills
• Experience using CRM systems such as Salesforce, HubSpot, or similar platforms is preferred.
• Proficiency with Microsoft Office and Google Workspace.

Preferred Qualifications

• Experience selling employee benefits, payroll, HR solutions, insurance, merchant services, SaaS, or other B2B solutions.
• Experience selling to small and medium-sized businesses.
• Proven track record of meeting or exceeding sales quotas.
• Uncapped commission structure
• Paid training and ongoing professional development
• Medical, dental, and vision insurance (if applicable)
• Paid time off and company holidays
• Career advancement opportunities within a growing organization

Earning Potential

Our Membership Advisors are rewarded for performance through a base salary and uncapped commission plan. Advisors who achieve 100% of their sales quota can expect the following On-

Target Earnings (OTE) ranges

• Year 1: $80,000-$95,000
• Year 2: $135,000-$155,000
• Year 3: $180,000-$200,000

These earnings are estimates provided for illustrative purposes and are not guaranteed. Actual compensation will vary based on individual performance and several factors, including quota attainment, average deal size, customer retention, and the timing of closed business. Because commissions are uncapped, top performers who exceed quota have the opportunity to earn substantially more than the estimated OTE.

Why Join Simpay?

At Simpay, you'll join a fast-growing fintech organization where your work has a direct impact on helping businesses provide meaningful benefits to their employees. You'll receive qualified prospect lists, ongoing coaching, and the support needed to build a successful sales career while enjoying unlimited earning potential through commissions.

If you're passionate about helping businesses, enjoy building relationships, and are looking for a sales role with significant income potential, we'd love to hear from you.