Head of Sales

  • Burlington, ON, Canada
  • Employees can work remotely
  • Full-time

Company Description

Chit Chats' vision is to help Canadians deliver their goods to the world with postage at unbelievable prices. We are a fast growing entrepreneurial company making a huge impact to Canadian entrepreneurs and businesses. As ecommerce removes borders, we don’t want high Canadian postal rates to be a barrier to world commerce. We aim to remove these physical and financial restraints to create a seamless, borderless and boundless world of opportunity for Canadians.

If you relate with being Caring, Curious and Cheerful; we are looking forward to having you onboard! 

Job Description

The Role

We are looking for a hands-on sales leader to build and lead the sales team at Chit Chats, while gaining and retaining key clientele. This role is for a passionate sales leader, with proven sales acumen, pipeline management skills, great attention to detail, and the ability to effectively prioritize and multi-task.

This leader will focus on executing sales strategies that will exceed aggressive revenue, selection and discoverability goals achieved both by driving sales and working cross-functionally with operations, marketing and finance teams.

Roles & Responsibilities: 

  • Serve as the primary interface with internal teams including Business Development, Operations, Finance, and Member relations teams to align programs and initiatives to drive growth.

  • Implement sales strategies and best practices while developing SOPs for business development.

  • Understand our key clientele and map our current and potential clients by defined metrics.

  • Increase our client portfolio by type and volume; conduct cold calls to generate leads.

  • Work with the Member Experience team to retain and regain our clients.

  • Establish partnerships with internal teams to manage joint selling opportunities.

  • Develop modeling and forecasting business metrics for the purpose of making strategic decisions to grow key Seller accounts.

  • Identify key business opportunities for the territory and manage toward a growth plan.

  • Develop weekly metrics to track critical inputs and outputs and report out in weekly business reviews and regular flash reports to senior management.

  • Analyze territory trends, diagnose the root cause of performance and create actionable plans for operational improvements.


  • 10+ years of successful sales experience, preferably in the eCommerce, retail technology, SaaS, or software industries.

  • BA/BS or other relevant experience.

  • Fluent in English, fluency in French would be an asset.

  • Experience in cold calling, prospecting, and qualifying companies.

  • Demonstrated success in exceeding sales targets using a consultative, solutions-focused approach.

  • Strong analytical skills with the ability to influence others

  • Detail-oriented and focused.

  • Able to work well in a fast-paced environment and prioritize effectively.

  • Proactive, professional, and friendly.

  • Strong verbal and written communication skills and the ability to communicate clearly, effectively, and professionally

  • Ability to thrive in an ambiguous environment

  • Able to work both independently and cooperatively with a positive attitude and work ethic

  • Team player who is willing to help develop the team

Additional Information

  • Class 1 safety shoes required (green triangle patch). 
  • To learn more about us, visit our website: chitchats.com.

Covid-19 update: Chit Chats is an essential service.  We have strict Covid safety protocols in place for both our clients and our staff