Territory Account Executive , Retail - Crystal Lake, IL

Toast • Crystal Lake, IL

2h • $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 platform. The Retail Account Executive will join a founding team responsible for growing Toast’s presence in this new vertical within an assigned geographic territory. Using a consultative sales approach, the role prospects and builds relationships with businesses, understands their needs, and develops tailored solutions to help them succeed. The position requires an entrepreneurial mindset, sales expertise, and a willingness to navigate ambiguity. The role involves travel of 25% or more and follows Toast’s hybrid work approach, with regional in-office expectations described on its career site.

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, if eligible.

Requirements

• Have an entrepreneurial and feedback-driven mindset.
• Demonstrate strong communication, organizational, and presentation skills, including the ability to sell and negotiate at all decision-making levels.
• Have a proven track record of meeting and exceeding goals.
• Be able to work in a fast-paced, entrepreneurial, team environment.
• Be 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

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

Benefits

• Benefits are part of Toast’s total rewards package; specific benefits are available through the linked benefits page.
• Equity, if eligible.
• Uncapped commissions.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed