Account Executive

Love closing deals and making a difference? Are you a driven sales professional ready to empower small businesses to thrive? Do you want to help small businesses grow, compete, and succeed in today‘s fast-moving market? ️ Then this position might be for you.

We‘re currently looking for an Account Executive to join our Inside Sales Team and contribute to the growth of our SwipeSimple Connect product. The ideal candidate for this position will be on the front lines helping local business owners streamline payments, boost revenue, and modernize their customer experience with our cutting-edge CRM and Payment Procession Solution. You‘ll turn everyday transactions into lasting relationships—understanding the needs of small businesses and presenting passionate business owners with our software‘s value.

Location : Greater Chicago, IL metro area. This position is primarily remote, but you will be expected to work in person alongside colleagues up to 10 days per month on dates determined by the company.

The ideal candidate will have cold outbound sales experience, excellent communication skills, and a ‘go-getter‘ attitude–payments experience, other services to small-to-medium size businesses (SMBs), and an understanding of the payments industry is preferred but not required. You will report to the Head of Inside Sales. This is a full-time, non-exempt position and employment is contingent upon a successful background check. Upon hire, you‘ll participate in an in-person onboarding during your first week and receive a set schedule based on business needs. We provide a clear path for advancement, including a structured 3-month ramp-up plan, and offer company equity to reward your success and align your growth with ours.

What You‘ll be Responsible for :

Outreach to Leads : Respond to inbound leads and perform outreach to leads generated by various channels and campaigns including cold calling, email campaigns, social media, and digital advertising.

Customer Engagement : Serve as the initial point of contact for prospective customers, understanding their business needs and effectively communicating how our credit card processing solution can address those needs.

Product Demonstrations : Conduct engaging and informative product demonstrations to prospective clients, showcasing the features and benefits of our software.

Sales Process Management : Manage the entire sales process from lead qualification to closing, ensuring a seamless and positive experience for the customer.

Relationship Building : Develop and maintain strong relationships with potential customers, acting as a trusted advisor and point of contact throughout the sales cycle.

Sales Reporting : Maintain accurate and up-to-date records of sales activities, opportunities, and customer interactions in the CRM system.

Collaboration : Work closely with the marketing and product development teams to align sales strategies with business objectives and customer feedback.

Market Insights : Stay informed about industry trends, competitor activities, and emerging technologies in the payments space to effectively position our software.

What You‘ll Bring To The Table

Education : Bachelor degree or equivalent, preferred but not required

Experience : 1-2+ years of sales experience, preferably in SMB software sales or the payment industry

Preferred Skills :

Proven ability to meet and exceed sales targets.

Excellent communication, negotiation, and presentation skills.

Proficiency with CRM software and sales tools.

Strong organizational skills and attention to detail.

Attributes :

Self-motivated and driven to succeed.

Ability to work independently and as part of a team.

Positive attitude and high energy level.

Ability to quickly learn and adapt to new technologies and sales strategies.

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

Location-neutral work environment

Home-office equipment stipend

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 .

The annualized target cash compensation range for this role is $90,000, consisting of a base salary of $50,000, incentive compensation consisting of commission and bonus with an On-Track-Commission Earnings (OTE) target of $35,000, and a target bonus of $5,000. In addition to competitive cash compensation, this position is also eligible for equity awards. 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.