Territory Account Executive , Retail - Oshkosh, WI

WinsAbove; Oshkosh (WI); On-site; USD 115,000 - 185,000; Full time

Benefits offered by this job

Uncapped commissions

Equity

Benefits

Job summary

Toast is expanding its offerings with the Toast Retail platform. As a Retail Account Executive, you will join a founding team to prospect, build relationships, and sign up new convenience stores, grocery stores, and bottle shops in your territory, using a consultative approach to understand needs and deliver tailored solutions.

You will demo solutions, collaborate with cross-functional teams, manage the full sales cycle in Salesforce, and travel to meet prospects (approx. 25% or more).

Qualifications

• Proven track record of meeting and exceeding sales targets.
• Ability to prospect, build relationships and close deals.
• Willingness to travel 25% or more.
• Experience in a fast-paced, growth environment.
• Based in or near the assigned market.

Responsibilities

• Prospect, build relationships, and sign up new convenience stores, grocery stores and bottle shops.
• Generate lists of prospective stores and manage the full 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 delivery expectations are met.
• Leverage Salesforce CRM to manage all sales activities.
• Understand the competitive landscape and position Toast effectively.

Skills

Entrepreneurial mindset

Sales experience

Strong communication

Negotiation skills

Presentation skills

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.

A day in the life (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

What you’ll need to thrive (Requirements)

• 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 in proximity to the assigned market and willingness to travel 25% or more

Nice to Have (Additional Qualifications)

• Retail operations experience

Compensation: $115,000 – $185,000 USD total targeted cash compensation includes base salary, commission, and bonus. The role qualifies for uncapped commissions. Additional benefits and equity may be available.

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].

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