FiveStars is hiring an

Inside Sales Representative

New York, United States

Fivestars is redefining the way businesses and communities interact by turning every transaction into a relationship. As the leader in the SMB loyalty space, we understand that we belong to a community bigger than ourselves. At Fivestars, we’re helping local businesses come back stronger than ever by turning their payments into a marketing machine. We provide Fortune 500 technology for local businesses, allowing merchants to collect payments and customer contacts seamlessly. Fivestars is redefining the way businesses and communities interact by turning every transaction into a relationship. Over 60 million people use Fivestars to shop at and support the local businesses that make their communities great.

We’ve recently raised $52.5 million in Series D funding for a total of $145.5 million raised from HarbourVest, Menlo Ventures, Lightspeed, DCM, and Y-Combinator. We invite you to join us in creating a Love Local movement across the US and Canada. Visit for more information

We’re looking for an Inside Sales Representative  to bring our product and services to market.

A Day in the Life:

  • You will own the full sales cycle process including utilization of a CRM to track performance and ensure communication and success
  • You customize a solution and then onboard new merchants with best practices to succeed on the Fivestars platform
  • 8 hour workday (M-F), schedule will be set by your manager
  • This is pure outreach;  100+ dials or 2 hour talk time a day. Be able to close 5+ deals a month. We will provide you a qualified leads list
  • Two set appointments & 1 meeting held a day
  • You ensure new merchants are successful by coordinating the installation and on-boarding of the product in their business

This role is for you if:

  • You have the desire to be a part of a fast growing start-up
  • Demonstrated sales experience in a full sales cycle capacity
  • Technical grasp/expertise of multiple B2B solution areas such as payment solutions (or similar other vendor solutions)
  • You are a CLOSER - you have the ability to engage a prospect, demonstrate the value of our products and close the sale
  • History of success at achieving at a quota+ level, month in and month out
  • Embrace coaching and development, treating feedback as a gift while maintaining a positive attitude and a hustle mindset
  • Excellent time management and organization skills
  • Ability to adapt to a fast-paced and demanding environment, with the self discipline to effectively work remotely
  • Demonstrated experience delivering superior customer service and attention to detail
  • You are punctual and have a history of good attendance
  • You have reliable internet connection and a quiet space to work without interruptions
  • You are tech savvy - you are comfortable working on computers (i.e. toggling between screens and using multiple systems) 
  • Point of Sale - merchant services sales experience preferred
  • 0 - 2  years of Inside Sales experience, Associate’s degree preferred


  • Base plus Uncapped Commission; unlimited earning potential
  • Company Equity
  • 4 weeks of annual PTO plus 10 paid holidays per year
  • Medical, Dental, Vision, 401k
  • Industry leading sales development program and PAID training

Fivestars provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability or genetics. In addition to federal law requirements, Fivestars complies with applicable state and local laws governing nondiscrimination in employment in every location in which the company has facilities. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.