Territory Account Executive , Retail - Hoffman Estates, IL

Toast•Hoffman Estates, IL

5h•$128,000 - $205,000•Hybrid

About The Position

Toast is expanding its POS platform into convenience stores, grocery stores, and bottle shops with its Toast Retail offering. The Territory Account Executive will join a founding team and help establish Toast’s presence in this new vertical within an assigned geographic territory. The role uses a consultative sales approach to identify prospects, understand their needs, develop customized solutions, and win new accounts. The position involves managing the full sales cycle, conducting product demonstrations, coordinating with internal teams to ensure delivery matches sales expectations, and using Salesforce to manage sales activity. The role requires an entrepreneurial mindset and willingness to travel 25% or more. Toast describes its work model as hybrid, with office expectations varying by region. The estimated total targeted cash compensation is $128,000–$205,000 USD, including base salary, commission, and bonus if eligible. The role offers uncapped commissions; starting salary depends on skills, experience, and geographic location. Benefits and equity may also be included if eligible.

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, team environment.
Self-motivated, creative, flexible, and willing to navigate ambiguity.
Live in or near the market and be willing to travel 25% or more.

Nice To Haves

Retail operations experience.

Responsibilities

Use a consultative approach to prospect, build relationships, and sign up new convenience stores, grocery stores, and bottle shops.
Generate lists of prospective accounts and manage the full sales cycle from initial call through close.
Conduct 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 to position Toast in the market.