Senior Account Executive, Mid-Market

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take ownership of the entire outbound sales cycle, from prospecting to negotiation and closing deals with mid-market merchants.

• Build and oversee a high-quality sales pipeline through cold outreach, social selling, targeted campaigns, and innovative outbound strategies.

• Create multi-product solutions within Square’s ecosystem and customize them to suit each merchant’s requirements.

• Collaborate with the Business Development team on lead generation while independently driving the acquisition of new logos.

• Conduct discovery sessions, product demonstrations, and negotiations involving multiple stakeholders.

• Serve as a consultant and trusted advisor, adapting roles between BDR, AE, and AM responsibilities as necessary.

• Work collaboratively across various functions, including Product, Marketing, Implementation, and Operations.

• Ensure accuracy in pipeline management and forecasting using Salesforce.

• Consistently achieve and surpass monthly and quarterly revenue targets.

⛳️ Requirements

• A minimum of 5 years of full-cycle B2B sales experience with a track record of meeting quotas.

• Demonstrated success in outbound prospecting and generating new business; experience in SaaS or fintech is preferred.

• Experience in closing complex, multi-threaded deals that involve longer sales cycles.

• Proven ability to establish a pipeline from the ground up through targeted and strategic outreach.

• Outstanding communication, presentation, and negotiation skills across phone, video, and written formats.

• Strong consultative selling abilities.

• A hunter's mindset; resilient, creative, and motivated to succeed.

• Capacity to work independently while fostering a team-oriented environment.

• Advanced knowledge of Salesforce and current sales tools.

• BA/BS degree or equivalent professional experience.

🏝️ Benefits

• Opportunity for remote work.

• Medical insurance coverage.

• Flexible time off policy.

• Retirement savings plans available.

• Modern family planning options.

• Reasonable accommodations for disabled applicants throughout the recruitment process.