Territory Account Executive, Toronto

Square; Toronto; On-site; CAD 96,000 - 144,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plan

Family planning support

Job summary

Block, Inc. is seeking a Territory Account Executive to own a growing Ontario market. You will spend most of your week out in the field, meeting local businesses, delivering live demos, and closing deals across the full Square product suite.

You will build a high-velocity pipeline from the ground up, develop regional partnerships, and become the go-to Square expert in restaurants, retail, and services. A proven track record in full-cycle sales, self-sourcing leads, and Salesforce discipline will

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).
• Must have reliable transportation and live in the market you are serving.
• Collaborative and team player mentality.
• Prior Salesforce experience or equivalent.
• 2+ years of payment processing OR related technology.
• 1+ years of experience working with restaurants, retailers or service-based businesses.

Responsibilities

• Lead your market with disciplined, in-person execution and ~80% field time.
• Run a full-cycle, self-sourced sales motion: generate leads, identify needs, demo, and close.
• Establish yourself as the go-to Square expert in your city and build trusted local relationships.
• Build a high-velocity pipeline from the ground up via door-to-door outreach, events, networking, and partnerships.
• Master verticals (restaurants, retail, services) and sell Square solutions with consultative, strategic approach.
• Maintain Salesforce discipline: track activity, manage pipeline, forecast accurately.

Skills

Sales experience

Full cycle closing

Field sales

Hunting & cold calling

Salesforce

Exceeding targets

Payment processing knowledge

Restaurant/retail/services experience

Tools

Salesforce

Job description

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 is a field-driven, execution-focused role 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 with confidence. The pace is fast, the expectations are high, and your ability to operate strategically and decisively will determine your success.

You will serve as Square’s presence and competitive advantage in one of our highest-opportunity markets - responsible for building pipeline from the ground up, elevating Square’s visibility in your community, establishing high-value partnerships, and helping local businesses grow through our ecosystem of industry-leading software and hardware.

If you are motivated by impactful work, driven to outperform, and eager to join a high-performance team with high standards, this role is built for you.

You will:

Lead your market with disciplined, in-person execution

• Spend ~80% of your week in the field - walking your territory, 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 by being present, reliable, and value-driven.
• Partner cross-functionally to ensure a seamless onboarding experience and fast time-to-value for new sellers.
• Implement a disciplined referral strategy to turn every new customer into future opportunities.

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 - including restaurants, retail, and services - to diagnose challenges and position the right Square solutions.
• Sell consultatively and competitively, staying proactive and strategic throughout the sales cycle.

Achieve exceptional results in a high-accountability environment

• Maintain strong operational rigor in Salesforce: track activity, manage pipeline, and forecast accurately.
• Measure performance frequently and improve continuously.
• Consistently exceed quota within a culture where high standards are the norm.

You have:

• 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)
• Since this is a field position, you must have reliable transportation and live in the market you are serving
• A collaborative and team player mentality
• Prior Salesforce experience or equivalent
• 2+ years of payment processing OR related technology (i.e. payroll, loyalty, time management)
• 1+ years of relevant audience experience (experience working in/selling to restaurants, retailers or services based businesses)

Block takes a market-based approach to pay, and pay may vary depending on your location. Canada locations are categorized into one of two zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

Zone A:

$95,952 - $143,928 CAD

Zone B:

$95,952 - $143,928 CAD

Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block.

Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.