Territory Account Executive , Retail - Hoffman Estates, IL

Toast•Hoffman Estates, IL

2d•Hybrid

About The Position

Toast is expanding its POS platform into convenience stores, grocery stores, and bottle shops with the Toast Retail platform. As part of a founding team building Toast’s presence in this new vertical, the Retail Account Executive will use a consultative sales approach to prospect, build relationships, and sign up new accounts. The role focuses on understanding each prospect’s needs and developing a customized solution to help their business thrive across an assigned geographic territory. The position requires an entrepreneurial, feedback-driven approach, sales expertise, and the ability to work in a fast-paced team environment while navigating ambiguity. It is based in or near the assigned market and requires travel of 25% or more. Toast describes its work model as hybrid, fostering in-person collaboration while valuing individual needs; regional in-office expectations may vary. Compensation is listed as total targeted cash of $128,000–$205,000 USD, including base salary, commission, and bonus if eligible. The role qualifies for uncapped commissions. Benefits and equity may also be included, subject to eligibility.

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.
A proven track record of 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 the market and is willing to travel 25% or more.

Nice To Haves

Retail operations experience.

Responsibilities

Prospect, build relationships with, and sign up new convenience stores, grocery stores, and bottle shops using a consultative approach.
Generate lists of prospective convenience stores, grocery stores, and bottle shops.
Manage the entire sales cycle from initial call through close.
Conduct product demonstrations and develop solutions that best meet prospects’ needs.
Partner with teams across the business to ensure expectations set during the sales process are met in delivery.
Use Salesforce to manage sales activities.
Understand the competitive landscape and determine how best to position Toast in the market.