Territory Account Executive, Retail - Des Plaines, IL

WinsAbove; Des Plaines (IL); Hybrid; USD 128,000 - 205,000; Full time

Benefits offered by this job

Competitive compensation

Flexible lifestyle options

Career development opportunities

Job summary

WinsAbove is looking for a Retail Account Executive in Des Plaines, IL, to join its pioneering team that aims to revolutionize the operations of convenience stores and grocery shops. This role involves utilizing a consultative approach to build strong relationships with potential clients and ensuring their success through tailored solutions.

The ideal candidate will have exceptional communication and organizational skills, along with a proven ability to thrive in a fast-paced and entrepreneurial environment. A competitive compensation package of $128,000—$205,000 USD is offered, along with opportunities for professional growth.

Qualifications

• An entrepreneurial and feedback-driven mindset.
• Proven track record of success in meeting and exceeding goals.
• Ability to work in a fast-paced and team environment.

Responsibilities

• Use a consultative approach to build relationships and sign up new accounts.
• Manage the entire sales cycle from initial call to close.
• Conduct demos to meet the prospect’s needs.

Skills

Strong communication skills

Organizational skills

Presentation skills

Sales negotiation

Entrepreneurial mindset

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 market and willingness to travel 25% or more

What will help you stand out (Nonessential Skills/Nice to Haves)

• Retail operations experience

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.

Total Targeted Cash Range: $128,000—$205,000 USD. 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.

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

Apply today!

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].

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.