Remote Territory Account Executive | Field Sales Pro

Square; Annapolis (MD); On-site; USD 155,000 - 233,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Family planning benefits

Job summary

Square is seeking a Territory Account Executive in Annapolis, MD to own a territory and drive growth with local businesses. You will spend most weeks in the field conducting live demos, visiting businesses, and closing deals across Square’s product suite.

The role requires 3+ years in field sales with a proven ability to exceed targets, build strong relationships, and develop a high-velocity pipeline in a fast-paced environment.

Qualifications

• 3+ years of sales experience in a full-cycle, field-sales role.
• Proven track record of exceeding targets and closing complex deals.
• Ability to drive deals independently in a fast-paced environment; business development experience.

Responsibilities

• Spend ~80% of your week in the field—walking your territory and making 50–60 local visits weekly.
• Run a full-cycle, self-sourced sales motion: generate leads, identify needs, demos, and close across Square’s product suite.
• Establish yourself as the go-to Square expert in your city; build trust-based relationships with local sellers.
• Develop a repeatable top-of-funnel engine through door-to-door outreach, community events, and partnerships.
• Sell with precision in verticals like restaurants, retail, and services; maintain pipeline and forecast in Salesforce.

Skills

Full cycle sales

Field sales

Target achievement

Business development

Salesforce

Tools

Salesforce

Job description

Square is seeking a Territory Account Executive in Annapolis, MD to own a territory and drive growth with local businesses. You will spend most weeks in the field conducting live demos, visiting businesses, and closing deals across Square’s product suite.

The role requires 3+ years in field sales with a proven ability to exceed targets, build strong relationships, and develop a high-velocity pipeline in a fast-paced environment.