Regional Hotel Enterprise Account Executive

Toast • Chicago, IL

3d • Hybrid

About The Position

Toast is driven by building an all-in-one Food & Beverage platform that helps hotels adapt, take control, and get back to what they do best: building the businesses they love. We are looking for a Regional Account Executive to grow Toast's presence among hotel management companies and ownership groups operating 5–25 properties with food & beverage outlets. These are portfolios large enough to need a real F&B platform, but nimble enough to move quickly — which makes them one of the most exciting places to sell at Toast. You will own the full sales cycle: building your own pipeline, educating corporate leaders on the Toast value proposition through demonstrations and presentations, and communicating a compelling purchase rationale that turns a first location into a portfolio-wide rollout. Hotels is a high-growth focus area for Toast, and this role sits at the center of it!

Requirements

• 3–6+ years of quota-carrying, full-cycle SaaS or technology sales experience, with a consistent record of meeting or exceeding quota
• Experience across SaaS, payments/credit card processing, or hospitality technology; hotel F&B, restaurant POS, or PMS experience is a significant plus
• Proven success in environments with 3–6 month sales cycles and a high volume of concurrent opportunities
• Comfortable selling to Director- and VP-level operators, owner-operators, and property General Managers, and building consensus across a multi-property group
• Strong outbound prospecting skills and genuine willingness to build your own pipeline
• Solid deal skills — discovery, business case development, pricing and financial structuring, negotiation, and closing with both new and existing clients
• Previous experience with MEDDPICC or a comparable qualification methodology is a plus
• Comfortable with process-driven sales, reporting, and tracking
• Strong written and presentation-based communication skills are required
• Must have the ability to work with minimal supervision
• Comfortable working in an entrepreneurial environment
• Travel approximately 25–35%

Responsibilities

• Own the full sales cycle for hotel management companies and ownership groups with 5–25 properties with F&B — identifying and developing leads, running discovery and demos, building the business case, structuring the deal, negotiating, and closing master service agreements, while handing off individual property deals to the property level hotel account executives.
• Self-source a meaningful share of your pipeline through outbound prospecting, industry associations and events, and referrals, supplemented by inbound and partner-generated leads
• Build multi-threaded relationships across the portfolio — corporate F&B and operations leaders, regional directors, property General Managers, and outlet managers — and navigate the split between management company and ownership decision rights
• Position multi-property rollouts, showing how standardizing F&B technology across a portfolio reduces operating complexity, improves visibility, and scales as the management company adds properties
• Land and expand: win a flagship property or restaurant concept, prove it out, and convert that success into the rest of the management company portfolio
• Cultivate relationships with business partner counterparts and account managers who sell and support complementary applications and services to point of sale systems serving the hotel and restaurant industries — including PMS providers, vendor partners and hospitality technology consultants
• Manage a high volume of concurrent opportunities in Toast sales tools (Salesforce), keeping pipeline, contacts, engagement activity, and forecasts accurate and current
• Understand the competitive landscape (strengths, weaknesses, benefits) and determine how to position Toast to win
• Partner with Sales Engineering, Implementation, and Customer Success to scope rollouts and set accounts up for long-term expansion

Benefits

• Competitive compensation and benefits programs
• Great earnings potential
• Means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs
• Equity (if eligible)

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed