Regional Hotel Enterprise Account Executive

Leadbeam, Inc.; Boston (MA); On-site; USD 217,000 - 347,000; Full time

Job summary

Toast is seeking a Regional Account Executive to grow our hotel F&B footprint. You will own the full sales cycle—from prospecting to closing—building pipelines, running demos, and aligning with hotel management companies and ownership groups with 5–25 properties.

You’ll collaborate with Sales Engineering, Implementation, and Customer Success to scope rollouts, manage multiple opportunities in Salesforce, and position Toast’s platform to drive multi-property rollouts. Travel 25–35%.

Qualifications

• 3–6+ years of quota-carrying, full-cycle SaaS or technology sales experience.
• Experience selling to hotel F&B, PMS, or hospitality technology is a plus.
• Proven success in environments with 3–6 month sales cycles and high volume of opportunities.

Responsibilities

• Own the full sales cycle for hotel management companies and ownership groups with 5–25 properties, including leads, discovery, demos, business case, pricing, negotiation, and closing master service agreements.
• Source pipeline through outbound prospecting, industry events, referrals, and inbound leads.
• Build relationships across the portfolio—corporate F&B/operations, regional directors, GMs, and outlet managers.
• Position multi-property rollouts to show how standardizing F&B tech reduces complexity and scales.
• Land and expand by converting flagship properties into portfolio-wide deals.
• Collaborate with partners and account managers to integrate with POS, PMS, and hospitality tech ecosystems.
• Manage opportunities in Toast sales tools (Salesforce) and maintain accurate pipeline and forecasts.
• Understand competitive landscape and position Toast to win.
• Partner with Sales Engineering, Implementation, and Customer Success to scope rollouts for long-term expansion.

Skills

SaaS sales

Full-cycle sales

Prospecting

Negotiation

Tools

Salesforce

MEDDPICC

Job description

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!

A day in the life (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

What you'll need to thrive (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%

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.

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). You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.

Total Targeted Cash

$217,000 — $347,000 USD

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). You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.

Total Targeted Cash

$188,000 — $301,000 USD

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). You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.

Total Targeted Cash

$169,000 — $271,000 USD

How Toast Uses AI in its Hiring Process

Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. To learn more: https://careers.toasttab.com/ai-in-hiring

Our Approach to Hybrid Working

We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast

Diversity, Equity, and Inclusion is Baked into our Recipe for Success

At Toast, our employees are our secret ingredient—when they thrive, we thrive.The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.

We Thrive Together

We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast.

Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact [e-mail].