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About the Role

As a Senior Sales Account Executive on Square's Mid-Market Team, you will re-imagine how mid-market businesses grow by bringing Square’s ecosystem to new sellers. You will build, shape, and close your own pipeline, running sophisticated, multi-product deals from first touch to final close, blending hunter instincts, consultative depth, and strategic execution.

Responsibilities

• Own the full outbound sales cycle — from prospecting to negotiation to close — with mid-market merchants.
• Build and manage a high-quality pipeline through cold outreach, social selling, targeted campaigns, and creative outbound strategies.
• Develop multi-product solutions across Square’s ecosystem and tailor them to each merchant’s unique needs.
• Partner with Business Development on lead flow while independently driving net-new logo acquisition.
• Conduct high-impact discovery, demos, and negotiations with decisiveness across multi-stakeholder deals.
• Act as a consultant and trusted advisor — seamlessly flexing across BDR, AE, and AM responsibilities when needed.
• Collaborate cross-functionally with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.
• Maintain disciplined pipeline management and forecasting accuracy in Salesforce.
• Consistently hit and exceed revenue goals — monthly and quarterly.

Requirements

• 3+ years of full-cycle B2B sales experience with consistent quota achievement.
• Proven success in outbound prospecting and net-new business creation (SaaS or fintech preferred).
• Experience closing complex, multi-threaded deals with longer sales cycles.
• Ability to build pipeline from scratch using targeted, strategic outreach.
• Exceptional communication, presentation, and negotiation skills across phone, video, and written channels.
• Strong consultative selling skills — diagnose business challenges and map tailored solutions.
• A hunter’s mindset — resilient, creative, and driven to win.
• Ability to work independently while contributing to a team-first environment.
• Advanced proficiency with Salesforce and modern sales tools.
• BA/BS degree or equivalent experience.
• Ability to sell in both French and English.

Skills

• Salesforce
• Consultative selling
• Negotiation
• Presentation
• Communication
• Outbound prospecting
• Pipeline management
• Forecasting

Location

• Canada

Work Type

• Remote

Experience Level

• Senior

Education Level

• BA/BS degree or equivalent experience

Salary/Compensations

• $152,300 - $228,500 CAD

Benefits

• Remote work
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning

About the Company

• Square enables anyone to take payments and never miss a sale, expanding into software to build integrated, omnichannel solutions for sellers. They offer tools for online sales, inventory management, buy now, pay later functionality, appointment booking, customer engagement, and staff management. Square also embeds financial services tools at the point of sale, providing access to business loans and cash flow management. Afterpay furthers Square's goal to provide omnichannel tools that unlock value and growth for sellers. Square partners with sellers of all sizes, from large enterprises to small businesses, helping them grow worldwide.
• 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.

Equal Opportunity

• We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws.