Mid Market Account Executive

A day in the life (Responsibilities)

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.

What you'll need to thrive (Requirements)

A combination of SaaS, Digital Marketing and Restaurant Industry Technology experience is required
5+ years of relevant successful technology or professional services sales experience
Previous success in selling/leading sales efforts in environments with 6 to 12 month sales cycles
Proven sales skills in complex deal development, financial structuring, negotiations, and closing with both new and existing clients
Experience in MEDDPICC Sales Qualification preferred
Travel 30% or more
Comfortable with process-driven sales, reporting, and tracking
Strong written and presentation-based communication skills are required
You've built something to make yourself faster. You can walk us through a repeatable process, template or workflow you personally created to eliminate busywork from your own week, and what it gave you back.
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.
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.

The estimated Total Targeted Cash compensation range for this role is listed below. Total Targeted Cash for this role includes base salary, commission, and bonus (if eligible). This role qualifies for uncapped commissions. The starting salary will be determined based on skills, experience, and geographic location. In addition to cash compensation, our total rewards components include benefits and equity (if eligible).

Total Targeted Cash
$204,000—$326,000 CAD