About this role
About TechPOS
TechPOS International Corp is a Canadian SaaS company serving more than 1,000 retail stores across North America.
We provide point-of-sale and retail management technology for specialty retailers, with tools across POS, inventory, reporting, e-commerce, digital menus, customer loyalty, and operational management.
We are scaling our sales organization and looking for an Account Executive who can own a personal pipeline, manage accounts with discipline, and help expand TechPOS into new markets and retail groups.
Learn more: techpos.ca
About This Role
This is a remote, full-cycle Account Executive role based in Toronto, Ontario, focused on the Eastern Canadian market.
You will be responsible for building and managing your own pipeline, qualifying opportunities, running discovery calls, delivering product demos, preparing proposals, managing follow-ups, and closing new accounts.
You will work directly with business owners, operators, and decision-makers across Ontario and Eastern Canada. The right person will be comfortable leading conversations, asking strong business questions, understanding operational pain points, and moving deals forward with clear next steps.
This role is best suited for someone who wants ownership. You will not be handed a finished pipeline and asked to maintain it. You will be expected to create opportunities, manage them properly, and close business.
While this is a remote role, the successful candidate must be based in the Greater Toronto Area and comfortable attending in-person meetings, retail visits, trade shows, and industry events when needed.
What You’ll Own
• Building and managing a personal pipeline of qualified opportunities
• Prospecting new accounts through outbound outreach, referrals, inbound leads, and market research
• Growing TechPOS across Ontario and the broader Eastern Canadian market
• Managing accounts from first conversation through signed agreement
• Running discovery calls to understand each prospect’s current systems, operational challenges, and business priorities
• Delivering product demos tailored to each prospect’s needs
• Preparing proposals, follow-ups, and sales documentation
• Managing pricing conversations, timelines, objections, and next steps
• Maintaining accurate HubSpot and CRM records, pipeline updates, and activity tracking
• Collaborating with Customer Success and Onboarding after a deal is closed
• Representing TechPOS professionally in virtual meetings, in-person visits, trade shows, demos, and industry conversations
Who You Are
• You are a sales professional who takes ownership seriously.
• You know how to manage a pipeline without needing constant reminders. You follow up when you say you will. You keep your CRM clean. You understand that sales is not just pitching a product, it is understanding the business case, building trust, and helping a prospect make a confident decision.
• You are comfortable speaking with owners, operators, managers, and multi-location retail teams. You can explain technology clearly without overcomplicating it. You know how to ask direct questions, listen carefully, and connect a prospect’s pain points to practical solutions.
• You are competitive, organized, and accountable.
• You can work remotely without losing structure, urgency, or communication. You are comfortable managing your day, creating opportunities, and staying close to prospects without needing to be in an office.
You Could Be a Great Fit If
• You are based in Toronto or the Greater Toronto Area
• You have a valid driver’s licence, reliable access to a vehicle, and are comfortable driving locally for customer meetings, retail visits, trade shows, and industry events
• You have 2+ years of sales experience in B2B, technology, retail systems, business services, or a related field
• You have experience managing your own pipeline, creating new opportunities through outbound prospecting, and owning accounts from first conversation to close
• You are organized, coachable, and disciplined with CRM updates, follow-ups, discovery calls, demos, and deal management
Nice to Have
• SaaS sales experience
• Experience selling into retail, hospitality, cannabis, franchise, or SMB markets
• Experience with full-cycle sales, from prospecting to close
• Familiarity with POS systems, e-commerce, payments, inventory management, or retail operations
• Existing knowledge of the Ontario retail or cannabis market
You May Not Be a Great Fit If
• Prospecting sounds painful to you
• You want warm leads only
• You treat CRM updates like optional homework
• You like vague “just checking in” follow-ups more than clear next steps
• You do not enjoy learning a product well enough to demo it confidently
• You want a remote role without accountability, structure, or consistent communication
• You are not comfortable attending occasional in-person meetings, store visits, or events in the Toronto area
• You are looking for a maintenance role rather than a growth role
• You are not comfortable being measured by pipeline, activity, and closed revenue
Why TechPOS
TechPOS is already trusted by more than 1,000 retail stores, and we are continuing to scale.
This is an opportunity to join a company with an established customer base, a growing product suite, and a market with clear demand for better retail technology.
You will have direct access to leadership, visibility into the business, and the ability to make a measurable impact on new revenue growth.
How to Apply
Please apply through LinkedIn or the Company Website: techpos.ca/careers