Whether they’re building great payment software or collaborating with a client, every CardFlight employee is committed to empowering small businesses to accept electronic payments with ease. Our team works primarily remote in over 25 US states with the ability to work in any US state and is passionate about delivering easy to use software to help small businesses accept payments from their customers. Joining our team means that you will be part of a fast-moving company, work collaboratively with others, and have a direct impact on making payments simpler for small businesses.

We are looking for two motivated and results-driven Sales Associates to join our growing Inside Sales team. In this role, you will be responsible for generating and qualifying leads, driving new business opportunities, and helping small businesses adopt SwipeSimple Connect. This is a great opportunity for a competitive and ambitious sales professional looking to develop their career in fintech and software sales. 

These two positions are related to the growth of the company, as new positions. You will also be part of a new sales team responsible for growing our new business, SwipeSimple Connect. With proven success, there will be opportunities to fast-track your sales career to an Account Executive role quickly. SwipeSimple Connect is a cutting-edge payment solution designed to empower small businesses with seamless and efficient payment processing. As part of CardFlight, we are committed to driving growth through innovative solutions that simplify transactions for merchants across the U.S.

📍 Location: Greater Chicago, IL metro area. Work is primarily remote, but will be expected to work in person alongside colleagues 3-10 days per month on dates determined by the company
💰 Compensation: On Track Earnings (OTE) annualized amount: $70,000-$75,000
🕒 Job Type: Full-Time

What You’ll Do

• Prospect & Qualify Leads – Conduct outbound outreach via calls, emails, and social channels to identify and engage potential small business customers.
• Educate & Consult – Understand customer needs and educate them on how SwipeSimple Connect can streamline their payment processing.
• Manage Sales Pipeline – Maintain and track sales activity in the CRM, ensuring accurate forecasting and reporting.
• Schedule & Conduct Demos – Set up and deliver product demonstrations to potential customers to showcase the value of SwipeSimple Connect.
• Collaborate with Sales & Marketing – Work closely with Account Executives and the marketing team to optimize lead generation efforts.
• Achieve & Exceed Sales Targets – Consistently meet or exceed monthly and quarterly sales quotas.

What You’ll Bring to the Table

• Strong communication and negotiation skills with a customer-first approach.
• A self-starter with a hunter mentality—comfortable making outbound calls and engaging prospects.
• Ability to quickly learn and articulate product benefits in a compelling way.

Bonus Points for:

• 1-2 years of sales, business development, or customer-facing experience (SaaS or fintech experience is a plus).
• Experience using a CRM (e.g., Salesforce, HubSpot) to track sales activities.
  
  

Why You'll Love Being A Part Of Our CardFlight Team

• Flexibility to work from home most days, provided that you are willing and able to work in person with colleagues in River North, Chicago, IL on dates designated by the company
• Home-office equipment stipend
• Flexible paid time off
• Employee Engagement (Lunch & Learns, team building events)
• Learning & Development culture
• Comprehensive health benefits
• Competitive compensation and company ownership/stock options
• And more!!

Our signature product, SwipeSimple, is used by 125,000+ small businesses across the country. SwipeSimple is a software solution that enables small businesses to accept payments seamlessly via phone, tablet or computer. SwipeSimple is sold through a partner network comprising financial institutions, merchant service providers, and independent sales organizations. The solution is also sold directly by CardFlight through SwipeSimple Connect.

In addition to a competitive base salary, this position is also eligible for cash bonus and equity awards based on factors such as experience and performance. At CardFlight, we lead with respect for one another, our customers and business partners, vendors, and prospective employees. Our objective is to ensure CardFlight team members are passionate about the growth of our company, supported in their personal growth and development, and connected to their colleagues. We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.