Territory Account Executive, Retail - Cambridge/Somerville

WinsAbove; Cambridge (MA); On-site; USD 128,000 - 205,000; Full time

Job summary

Toast is expanding its offerings with a new Toast Retail platform and seeks a Retail Account Executive to join a founding team in growing the brand in assigned markets. You will prospect, build relationships, and sign up new convenience stores, grocery stores, and bottle shops, using a consultative approach and delivering tailored solutions.

You will manage the full sales cycle, conduct demos, and partner with cross-functional teams to ensure delivery meets expectations.

Qualifications

• Entrepreneurial and feedback-driven mindset.
• Strong communication, organizational, and presentation skills with the ability to sell and negotiate at all decision-making levels.
• Proven track record of success in meeting and exceeding goals.
• Ability to work in a fast-paced, entrepreneurial and team environment.
• Self-motivated, creative, flexible, and willing to navigate ambiguity.
• Lives in or near assigned market; willingness to travel 25% or more.

Responsibilities

• Use a consultative approach to prospect, build relationships, and sign up new convenience stores, grocery stores and bottle shops.
• Generate lists of prospective stores and manage the entire sales cycle from initial call to close.
• Conduct demos and develop a solution that best meets the prospect’s needs.
• Partner with teams across the business to ensure expectations set during the sales process are met in delivery.
• Leverage Salesforce (our CRM) to manage all sales activities.
• Understand the competitive landscape and determine how to best position Toast in the market.

Skills

Prospecting

Sales

Account management

Demos

Negotiation

CRM

Tools

Salesforce

Job description

After years of building an innovative POS platform for restaurateurs, Toast is expanding its offerings into other food and beverage concepts such as convenience stores, grocery stores, and bottle shops. This role will require a founder’s mindset as we grow Toast’s presence in this new vertical with a new offering: the Toast Retail platform.

As a Retail Account Executive, you will be part of a founding team that is transforming the way convenience stores, grocery stores, and bottle shops operate. Using a consultative approach, you will prospect, build relationships, and sign up new accounts. By understanding their unique needs, you will develop a customized solution that helps their business thrive. We need your passion, sales expertise, and entrepreneurial spirit to help us build the Toast brand in an assigned geographic territory.

Responsibilities

• Use a consultative approach to prospect, build relationships, and sign up new convenience stores, grocery stores and bottle shops
• Generate lists of prospective convenience stores, grocery stores, and bottle shops and manage the entire sales cycle from initial call to close
• Conduct demos and develop a solution that best meets the prospect’s needs
• Partner with teams across the business to ensure that expectations set during the sales process are met in delivery
• Leverage Salesforce (our CRM) to manage all sales activities
• Understand the competitive landscape and determine how to best position Toast in the market

Qualifications

• An entrepreneurial and feedback-driven mindset
• Strong communication, organizational, and presentation skills with the ability to sell and negotiate at all decision‑making levels
• Proven track record of success in meeting and exceeding goals
• Ability to work in a fast‑paced, entrepreneurial and team environment
• Self‑motivated, creative, flexible, and willing to navigate ambiguity
• Lives in or near assigned market; willingness to travel 25% or more

Nice to Haves

• Retail operations experience

Benefits

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.

Compensation

Total Targeted Cash: $128,000 – $205,000 USD. Total Targeted Cash for this role includes base salary, commission, and bonus (if eligible). This role qualifies for uncapped commissions. In addition to cash compensation, our total rewards components include benefits and equity (if eligible).

Legal Statement

For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.