Sales Development Representative


Who are we?
Welcome to Chekkit! Chekkit is customer interaction and reputation management software! We give customers the tools to better communicate with their customers. Our mission is to build software that is easy to use and affordable for everyday business owners, and build a great team of people to work with and support our customers!

What is the opportunity?

The Sales Development Representative is responsible for generating new business via outbound phone opportunity qualification. This role will work closely with- and learn from - Chekkit Sales Executives to seek new target accounts, and ultimately grow Chekkit's clientele base. To be successful in this role, you will be a high-performing lead generator making outbound calls to prospective clients, Introducing them to the full scope of technology services offered by Chekkit.

Duties and Responsibilities:

  • Perform outbound calling to generate new sales opportunities and pipeline
  • 300 to 400 phone calls a day
  • Identify the needs of the prospect and generate interest.
  • Schedule and execute demo’s of our software via Zoom
  • Follow-up on sales inquiries to close leads
  • Work in softwares used to input and update vital prospect information.
  • Research target accounts for outbound call campaigns
  • Ability to read off of a script if necessary/create them
  • Participate in weekly Sales Meetings and work with the Sales Team.
  • Performs other related duties as assigned

What you need to succeed:

  • 1-2 years experience
  • Ability to work Monday - Friday, 9:00am - 5:00 pm
  • Ability to work remotely for parts of the year.
  • Ability to reliable commute to our Main office in downtown Winnipeg full time during training, and part time when training is complete


  • Competitive salary: $37,440 a year or $18 an hour
  • Commission: The more customers you sign up, the more you make. Commissions upwards of $2,000-$3,000/month are possible on top of your base salary.
  • Dental and Eye Coverage.
  • Opportunity for growth in the company as we see your skills and abilities.

If you believe you're the perfect candidate for this position, send us your cover letter outlining why you think you're the best fit, as well as your resume so we can see your previous experience.

Interested in applying?
Email us:

Life at Chekkit

Founders Emily and Lee, presenting Chekkit.
Our office is always hosting events!
Myles and Chekkit presenting Chekkit to potential customers.
We love delivering product updates to customers.
Myles in the Chekkit booth.
You'll find us across North America at tech-industry events.
Myles and Dan.
Recognize us from Instragram?
Emily and Lee discussing potential product updates.
Debating who was the best 90s boy-band.
Myles and Dan working by the beach.
Travelling over the winter keeps the winter blues away.
Chekkit office.
Admire our new collaboration room.