Territory Account Executive, Retail - Cambridge/Somerville

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

Benefits offered by this job

Total rewards package

Equity (if eligible)

Job summary

Toast is expanding its offerings into convenience stores, grocery stores, and bottle shops with the Toast Retail platform. As a Retail Account Executive, you will be part of a founding team shaping this new vertical and helping merchants grow.

You will prospect, build relationships, conduct demos, sign new accounts, and collaborate with cross‑functional teams. This role requires an entrepreneurial mindset, strong communication, a track record of meeting goals, and willingness to travel 25%+ in

Qualifications

• Entrepreneurial mindset with a bias for action.
• Excellent communication and presentation skills at all levels of a buyer organization.
• History of meeting or exceeding sales goals in a B2B environment.
• Comfortable working in a fast-paced, entrepreneurial team.
• Highly motivated, adaptable, and able to navigate ambiguity.
• Willingness to travel 25% or more and operate in assigned markets.

Responsibilities

• Prospect, build relationships, and sign up new convenience stores, grocery stores, and bottle shops.
• Generate prospect lists and manage full sales cycle from initial call to close.
• Conduct product demos and tailor solutions to customer needs.
• Collaborate with cross‑functional teams to ensure delivery aligns with promises.
• Leverage Salesforce to manage all sales activities.
• Understand competitors and position Toast effectively in the market.

Skills

Entrepreneurial mindset

Strong communication

Proven track record

Fast-paced environment

Self-motivated

Willing to travel

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.