Territory Account Executive-Windsor

Job title: Territory Account Executive, New Brunswick, Canada Square is building a best-in-class, high-impact field sales organization, and we are looking for an exceptional Territory Account Executive — someone who consistently exceeds expectations, takes full ownership of their territory, and brings Square’s mission of economic empowerment directly to the businesses that need it most. This is a field-driven, execution-focused role designed for individuals who thrive in dynamic, demanding environments. You will spend most of your week out in the market — meeting businesses, conducting live demos, and closing deals with confidence. The pace is fast, the expectations are high, and your ability to operate strategically and decisively will determine your success. You will serve as Square’s presence and competitive advantage in one of our highest-opportunity markets — responsible for building pipeline from the ground up, elevating Square’s visibility in your community, establishing high-value partnerships, and helping local businesses grow through our ecosystem of industry-leading software and hardware. If you are motivated by impactful work, driven to outperform, and eager to join a high-performance team with high standards, this role is built for you. You will: Lead your market with disciplined, in-person execution Spend ~80% of your week in the field — walking your territory, engaging local businesses, and driving 50–60 targeted business visits each week. Run a full-cycle, self-sourced sales motion: generate leads, identify needs, deliver compelling demos, and close deals across Square’s full product suite. Establish yourself as the go-to Square expert in your city Build strong, trust-based relationships with local sellers by being present, reliable, and value-driven. Partner cross-functionally to ensure a seamless onboarding experience and fast time-to-value for new sellers. Implement a disciplined referral strategy to turn every new customer into future opportuniti

Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. You will be part of a team that is transforming the way restaurants operate. Using a consultative approach, you will prospect, build relationships, and sign up new restaurateurs in your territory. By understanding their unique needs, you will develop a customized solution that helps their business thrive. We need your passion and sales expertise to help us build Toast across Canada. Must live local to West Toronto or willing to relocate. This is a field sales opportunity with 80% of your time spent in the field and 20% working from home. A day in the life (Responsibilities) Generate a list of prospective restaurants and manage the entire sales cycle from initial call to close (experience with self-sourcing clients is a huge plus). Conduct demos and develop a solution that best meets the prospect’s needs. Partner with teams across the business to ensure that expectations set during the sales process are met in delivery. Leverage Salesforce (our CRM) to manage all sales activities. Understand the competitive landscape and determine how to best position Toast in the market. What you'll need to thrive (Requirements) 1+ years of experience in a sourcing or closing sales role, restaurant operations, or a related field and industry. Since this is a field position, you must have reliable transportation (will reimburse for mileage). Strong communication, organizational and presentation skills with the ability to sell and negotiate at all decision-making levels. Proven track record of success in meeting and exceeding goals. Ability to work in a fast-paced, entrepreneurial and team environment. Self-motivated, creative, and flexible. General technical proficiency with software. Experience with Salesforce CRM is nice to have. AI at Toast At Toast, one of our company values is that we're hun

Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. You will be part of a team that is transforming the way restaurants operate. Using a consultative approach, you will prospect, build relationships, and sign up new restaurateurs in your territory. By understanding their unique needs, you will develop a customized solution that helps their business thrive. We need your passion and sales expertise to help us build Toast across Canada. Must live local to Calgary or willing to relocate. This is a field sales opportunity with 80% of your time spent in the field and 20% working from home. A day in the life (Responsibilities) Generate a list of prospective restaurants and manage the entire sales cycle from initial call to close (experience with self-sourcing clients is a huge plus). Conduct demos and develop a solution that best meets the prospect’s needs. Partner with teams across the business to ensure that expectations set during the sales process are met in delivery. Leverage Salesforce (our CRM) to manage all sales activities. Understand the competitive landscape and determine how to best position Toast in the market. What you'll need to thrive (Requirements) 1+ years of experience in a sourcing or closing sales role, restaurant operations, or a related field and industry. Since this is a field position, you must have reliable transportation (will reimburse for mileage). Strong communication, organizational and presentation skills with the ability to sell and negotiate at all decision-making levels. Proven track record of success in meeting and exceeding goals. Ability to work in a fast-paced, entrepreneurial and team environment. Self-motivated, creative, and flexible. General technical proficiency with software. Experience with Salesforce CRM is nice to have. AI at Toast At Toast, one of our company values is that we're hungry t

Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. You will be part of a team that is transforming the way restaurants operate. Using a consultative approach, you will prospect, build relationships, and sign up new restaurateurs in your territory. By understanding their unique needs, you will develop a customized solution that helps their business thrive. We need your passion and sales expertise to help us build Toast across Canada. Must live local to Brampton/Mississauga or willing to relocate. This is a field sales opportunity with 80% of your time spent in the field and 20% working from home. A day in the life (Responsibilities) Generate a list of prospective restaurants and manage the entire sales cycle from initial call to close (experience with self-sourcing clients is a huge plus). Conduct demos and develop a solution that best meets the prospect’s needs. Partner with teams across the business to ensure that expectations set during the sales process are met in delivery. Leverage Salesforce (our CRM) to manage all sales activities. Understand the competitive landscape and determine how to best position Toast in the market. What you'll need to thrive (Requirements) 1+ years of experience in a sourcing or closing sales role, restaurant operations, or a related field and industry. Since this is a field position, you must have reliable transportation (will reimburse for mileage). Strong communication, organizational and presentation skills with the ability to sell and negotiate at all decision-making levels. Proven track record of success in meeting and exceeding goals. Ability to work in a fast-paced, entrepreneurial and team environment. Self-motivated, creative, and flexible. General technical proficiency with software. Experience with Salesforce CRM is nice to have. AI at Toast At Toast we’re Hungry to Build and Learn. We believe

Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. You will be part of a team that is transforming the way restaurants operate. Using a consultative approach, you will prospect, build relationships, and sign up new restaurateurs in your territory. By understanding their unique needs, you will develop a customized solution that helps their business thrive. We need your passion and sales expertise to help us build Toast across Canada. Must live local to Niagara Falls region or willing to relocate. This is a field sales opportunity with 80% of your time spent in the field and 20% working from home. A day in the life (Responsibilities) Generate a list of prospective restaurants and manage the entire sales cycle from initial call to close (experience with self-sourcing clients is a huge plus). Conduct demos and develop a solution that best meets the prospect’s needs. Partner with teams across the business to ensure that expectations set during the sales process are met in delivery. Leverage Salesforce (our CRM) to manage all sales activities. Understand the competitive landscape and determine how to best position Toast in the market. What you'll need to thrive (Requirements) 1+ years of experience in a sourcing or closing sales role, restaurant operations, or a related field and industry. Since this is a field position, you must have reliable transportation (will reimburse for mileage). Strong communication, organizational and presentation skills with the ability to sell and negotiate at all decision-making levels. Proven track record of success in meeting and exceeding goals. Ability to work in a fast-paced, entrepreneurial and team environment. Self-motivated, creative, and flexible. General technical proficiency with software. Experience with Salesforce CRM is nice to have. AI at Toast At Toast, one of our company values is that w

Job Requisition ID # 26WD101597 Position Overview Are you tenacious and have experience building trusted relationships? Do you love the craft of sales, especially complex enterprise-level sales? Principal, Account Executive, Expansion is responsible for growing sales in 25+ accounts within your assigned portfolio. This job is assigned a sales quota, and performance is measured by meeting quarterly and annual targets by up-selling, add-on sales, and cross-selling. Location: This position is remote and reports to the Manager, Expansion for the Northeast region. The assigned territory is predominantly in Ontario, Canada (Toronto, Ottawa). This role oversees buyer seat expansion, forecasts pipeline performance, and partners with technical and extended sales teams to co-develop customer solutions. Principal, Account Executive, Expansion acts as a trusted advisor to senior customer stakeholders, applying strategic insight, industry knowledge, and adaptive communication to drive long term customer value and business growth. Responsibilities Manage your book of business; sell new products and expand existing renewals to meet quarterly targets Lead account strategy and manage the sales cycle for new sales and renewals Produce new opportunity pipeline each week to meet quarterly and annual quota targets Be a model representative of Autodesk. Lead presentations to clients, build trusted-advisor relationships with customers, and attend marketin