Remote Territory Account Executive — High-Impact Field Seller

Block; Chicago (IL); On-site; USD 138,300 - 207,500; Full time

Job summary

Block is seeking a Territory Account Executive in Chicago to own a high-velocity sales territory and drive end-to-end deals for Square’s ecosystem. You will spend most weeks in the field, meeting local businesses, conducting live demos, and closing deals across the full product suite.

This role requires building pipeline, developing local partnerships, and staying accountable to quarterly targets. You will work in a fast-paced, high-expectation environment, leveraging Salesforce to track

Qualifications

• 3+ years of sales experience in a full cycle closing role with field sales experience.
• Experience exceeding sales targets, selling a diverse ecosystem of products, and closing complex deals.
• Ability to drive deals independently in a fast-paced, dynamic environment.
• Business development experience (e.g. hunting and cold calling).
• Prior Salesforce experience or equivalent.

Responsibilities

• Spend ~80% of your week in the field, visiting businesses and driving 50–60 targeted visits weekly.
• Run a full-cycle, self-sourced sales motion: generate leads, identify needs, deliver demos, and close deals across Square’s product suite.

Skills

Field sales experience

Full cycle closing

Exceeding targets

Business development

Salesforce experience

Tools

Salesforce

Job description

Block is seeking a Territory Account Executive in Chicago to own a high-velocity sales territory and drive end-to-end deals for Square’s ecosystem. You will spend most weeks in the field, meeting local businesses, conducting live demos, and closing deals across the full product suite.

This role requires building pipeline, developing local partnerships, and staying accountable to quarterly targets. You will work in a fast-paced, high-expectation environment, leveraging Salesforce to track