Territory Account Executive - Calgary, Alberta

Block; Calgary; On-site; CAD 217,788 - 326,750; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Modern family planning

Job summary

Block is looking for an exceptional Territory Account Executive in Calgary, Alberta. In this dynamic role, you will be responsible for leading the market through in-person engagement, generating leads, conducting demos, and closing deals across Square’s product suite. The ideal candidate has over 3 years of sales experience and is proficient in Salesforce. This position offers competitive compensation and benefits including remote work, medical insurance, and retirement savings plans. A strong team-oriented approach is essential.

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.
• Prior Salesforce experience or equivalent.
• Reliable transportation and living in the market you are serving.

Responsibilities

• Lead your market with disciplined, in-person execution and drive 50-60 targeted business visits each week.
• Run a full-cycle, self-sourced sales motion: generate leads, deliver demos, and close deals.
• Establish strong relationships with local sellers and implement a disciplined referral strategy.
• Build a high-velocity pipeline through outreach, community engagement, and targeted partnerships.
• Master key verticals—restaurants, retail, and services—to sell consultatively and competitively.

Skills

Sales experience

Business development

Collaboration

Cold calling

Independent driving deals

Salesforce proficiency

Job description

Territory Account Executive - Calgary, Alberta

Square is building a best-in-class, high-impact field sales organization, and we are looking for an exceptional Territory Account Executive - someone who consistently exceeds expectations, takes full ownership of their territory, and brings Square’s mission of economic empowerment directly to the businesses that need it most.

This field driven, execution focused role is designed for individuals who thrive in dynamic, demanding environments. You will spend most of your week out in the market - meeting businesses, conducting live demos, and closing deals.

Responsibilities

• Lead your market with disciplined, in-person execution: spend ~80% of your week in the field, engaging local businesses, and driving 50-60 targeted business visits each week.
• Run a full-cycle, self-sourced sales motion: generate leads, identify needs, deliver compelling demos, and close deals across Square’s full product suite.
• Establish yourself as the go-to Square expert in your city: build strong, trust-based relationships with local sellers, partner cross-functionally, implement a disciplined referral strategy.
• Build a high-velocity pipeline from the ground up: develop a repeatable top-of-funnel engine through door-to-door outreach, community engagement, events, networking, and targeted partnerships; work with channel partners to generate a consistent, high-quality referral stream that grows over time.
• Master your verticals and sell with precision: build deep expertise in key verticals—restaurants, retail, and services—to diagnose challenges and position the right Square solutions; sell consultatively and competitively.
• Achieve exceptional results in a high-accountability environment: maintain strong operational rigor in Salesforce, measure performance frequently, exceed quota.

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).
• Reliable transportation and living in the market you are serving.
• Collaborative, team-player mentality.
• Prior Salesforce experience or equivalent.
• Preferred: 2+ years of payment processing or related technology (e.g., payroll, loyalty, time management).
• Preferred: 1+ year of experience working in/selling to restaurants, retailers, or services-based businesses.

Compensation

Block takes a market-based approach to pay, and pay may vary depending on your location. The starting pay will be determined based on skills, experience, qualifications, work location, and market conditions. Zone A: $159,900 - $239,900. Zone B: $159,900 - $239,900.

Benefits

Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offerings.