The Mid-Market Sales Executive is responsible for sales and revenue growth in their assigned, targeted accounts. This individual is responsible for building a sales pipeline, managing a sales process for their mid-market brands/group with 40 to 500 units Lead efforts to grow Toast market share in the multi-unit restaurant industry through establishment and cultivation of ongoing relationships at the C-Suite level through research, cold-calling and networking to develop a qualified pipeline of prospects Create demand by educating prospects on the Toast value proposition of products and solutions through demonstrations and presentations communicating a compelling purchase rationale Cultivate relationships with business partner counterparts who sell and support complementary applications and services to point of sale systems serving the restaurant industry Plan, direct and coordinate sales support activities, including management of the sales pipeline through Toast sales tools (Salesforce) Involved in all phases of the sales lifecycle including: identifying and developing leads; meeting with clients; developing value propositions; financial deal structuring; contract negotiation and closing Understand the competitive landscape (strengths, weaknesses, benefits) and determine how to position Toast to win Collaborate with Account Service and Implementation Teams to ensure that expectations set during the sales process are met in delivery Own your own leverage. Continuously identify the repetitive parts of the role — research, prep, notes, follow-up, list building and systematically get them off your plate, so the majority of your week is spent in live conversation with operators Work evidence, not alphabetical order.



Prioritize accounts based on observable change in the operator’s business: expansion, ownership change, hiring patterns, guest feedback trends, visible technology, and disqualify unworkable accounts quickly so your capacity concentrates where it can actually close Treat your book as an asset you maintain. Keep account and contact records accurate, current, and deduplicated, understanding that routing, scoring, and every AI‑assisted workflow is only as good as the data underneath it Untangle who really decides. Resolve complex ownership structures, franchise groups, multiple legal entities, operators running several concepts under different names to identify and reach the actual economic decision maker rather than whoever answers the phone Arrive already informed, and earn trust in a low‑trust market. Focus on the operator’s specific situation rather than a product pitch, and recognize that many operators have been burned by a previous vendor; credibility, not feature comparisons, is often what wins the deal Close the loop on what’s broken. Flag bad data, wrong contacts, and signals that didn’t hold up, so the system your whole team relies on improves rather than quietly eroding Benefits





Peer and company recognition programs Unlimited Vacation Sabbatical opportunity after five years Career development Reimbursement Program Commitment to Employee Wellness through resources such as a quarterly Wellness Stipend Various peer and company recognition programs 401(k) and matching Medical, Dental, & Vision Coverage Subsidized backup childcare Mental Health Benefits Travel 30% or more Demonstrated learning velocity You can point to a capability you taught yourself in the last six months without being asked to, and explain how you now use it You can articulate a problem precisely Comfort framing a messy commercial question clearly and specifically enough that a tool, a teammate or a supporting function can actually act on it Previous success in selling/leading sales efforts in environments with 6 to 12 month sales cycles You manage a territory like a portfolio Comfort making deliberate coverage decisions across a large account base rather than defaulting to whichever deal is loudest this week Genuine curiosity about how restaurants actually operate — margins, labour, throughput, the difference between a 3-location operator and a 30-location one — because that is what earns a second conversation. Comfort working in build mode, where territory definition, process and tooling are actively being shaped and you are expected to have an opinion on them Proven sales skills in complex deal development, financial structuring, negotiations, and closing with both new and existing clients A combination of SaaS, Digital Marketing and Restaurant Industry Technology experience is required Comfortable with process-driven sales, reporting, and tracking 5+ years of relevant successful technology or professional services sales experience Strong written and presentation-based communication skills are required Experience in MEDDPICC Sales Qualification preferred

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📌 Mid Market Account Executive (Winnipeg)
🏢 Toast
📍 Winnipeg