Regional Hotel Enterprise Account Executive

United States Digital Space LLC; Miami (FL); On-site; USD 190,000 - 340,000; Full time

Job summary

United States Digital Space LLC is seeking a Regional Account Executive to drive growth among hotel management companies and ownership groups managing 5–25 properties with F&B outlets. You will own the full sales cycle—from discovery and demos to structuring deals and closing multi-property rollouts.

You’ll build your own pipeline through outbound prospecting, industry events and referrals, while aligning with corporate F&B and operations leaders to expand across portfolios.

Qualifications

• 3-6+ years of quota-carrying SaaS or technology sales experience.
• Experience selling to hotel management groups, ownership portfolios or hospitality tech.
• Proven success in multi-threaded sales cycles with 3-6 month timelines.
• Strong outbound prospecting and pipeline development skills.
• Ability to articulate value, build business cases, and negotiate
• Knowledge of MEDDPICC or similar qualification approach is a plus.
• Excellent written and presentation communication; able to work with minimal supervision.
• Willingness to travel 25-35%.

Responsibilities

• Own the full sales cycle for hotel management companies and ownership groups with 5-25 properties.
• Source pipeline via outbound prospecting, industry events, and referrals.
• Build relationships across corporate F&B, operations, and property leaders.
• Position multi-property rollouts to standardize F&B tech across portfolios.
• Land flagship properties and expand into multi-property rollouts.
• Collaborate with partners to align POS, PMS, and hospitality tech consultants.
• Manage opportunities in Salesforce with accurate forecasts.
• Navigate competition and articulate a compelling purchase rationale.

Skills

Outbound prospecting

Pipeline building

Negotiation

Multi-stakeholder alignment

MEDDPICC knowledge

Written & presentation

Independent work

Travel readiness

Tools

Salesforce

Job description

the company 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 the company'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 the company. You will own the full sales cycle: building your own pipeline, educating corporate leaders on the the company 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 the company, 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 the company 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 the company 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 the company

At the company, 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/the company-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.