Mid-Market Account Executive

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

📋 Description

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

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

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

• Collaborate with Business Development to manage lead flow while proactively acquiring new logos independently.

• Execute discovery calls, product demonstrations, and negotiations involving multiple stakeholders.

• Serve as a consultant and trusted advisor, flexibly assuming BDR, AE, and AM roles as necessary.

• Work in partnership with Product, Marketing, Implementation, and Operations teams.

• Ensure accurate pipeline management and forecasting in Salesforce.

• Achieve and surpass monthly and quarterly revenue targets.

⛳️ Requirements

• A minimum of 3 years of full-cycle B2B sales experience with a proven track record of meeting quotas.

• Demonstrated success in outbound prospecting and generating new business, preferably in SaaS or fintech sectors.

• Experience in closing intricate, multi-threaded deals with extended sales cycles.

• Capability to build a pipeline from the ground up through targeted and strategic outreach efforts.

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

• Strong consultative selling abilities.

• Ability to work autonomously while also contributing to a team-oriented atmosphere.

• Advanced proficiency in Salesforce and contemporary sales tools.

• BA/BS degree or equivalent professional experience.

🏝️ Benefits

• Remote work opportunities.

• Medical insurance coverage.

• Flexible time off policy.

• Retirement savings plans.

• Modern family planning benefits.

• Reasonable accommodations provided throughout the recruitment process.