Customer Success Manager

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?
In this role you will champion customer support by providing exceptional customer service to our clients as they will interact with us in very different ways; whether it is by phone, email, chat, video, or mobile.

This role will be enticing to people who thrive in a fast-paced goal-orientated team environment, love working with people, and have the flexibility to work on a schedule designed to meet our client’s needs.

If you are passionate about delivering exceptional customer service, providing solutions for clients’ needs, want to contribute to Chekkit’s customer success strategies, and collaborate with internal leaders from multiple departments to deliver consistently excellent customer experiences, then this role is for you!

What will you do?
Provide professional, responsive customer service to incoming client calls, emails, live chat, etc. You will deliver effective root cause analysis, problem diagnosis, and solution recommendation that matches the client's level of technical expertise.

Focus on helping clients by responding empathetically to a variety of questions, resolving client concerns at the first point of contact, and engaging with our development team for assistance when needed.

Provide training of our software via Zoom to customers, ensuring they understand the depths of our software, the daily use best practices for workflow efficiency, and take a consultative approach in helping clients overcome issues and achieve goals.

Deliver Chekkit’s retention strategy which includes weekly, monthly, and yearly follow-ups with current customers to ensure they are using the software to the maximum of its ability.

What do you need to succeed?

  • 1+ years of experience in communications, account management, or customer success.
  • Strong Computer literacy skills as we use a variety of computer software (Mongo, PostMan, etc)  that help us operate far beyond what we would be capable of on our own.
  • Exceptional verbal and written communication skills along with the confidence to relay information, advice, and guidance to customers in a way that computes best to them.
  • Ability to work independently as well as in a team environment. You’ll need the ability to manage your time effectively and efficiently as you will be communicating with multiple customers at once at all times.

What’s in it for you?

  • Full-time employment with the ability to work from home during certain parts of the year
  • Competitive pay at $18 per hour
  • Opportunity for growth in the company as we see your skills and abilities.
  • A fabulous work environment, we believe in working hard and playing hard. Each member of Chekkit dominates their role, and enjoys what they do! This provides an environment that is fun, energetic, lively, and celebrates Fridays!


  • Customer Support & Client Services Managers: 1 year (required)

Work Location: Hybrid remote in Winnipeg, MB

If you believe you are the perfect candidate for this position, send us your coverletter outlining why you think you are the best fit, as well as your resume so we cansee 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.