Senior Sales Account Executive

Location: Remote in Toronto, Ontario, Canada

Salary: $116,064–$174,096 CAD annually, depending on location, skills, experience, qualifications, and market conditions.

Company

hirify.global builds technology and financial products through brands including Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto.

What you will do

• Own the full outbound sales cycle for mid-market merchants, from prospecting and discovery through negotiation and close.
• Build and manage a high-quality pipeline through cold outreach, social selling, targeted campaigns, and creative outbound strategies.
• Develop tailored, multi-product solutions across Square’s commerce and financial services ecosystem.
• Close complex, multi-stakeholder deals and act as a trusted consultant across BDR, AE, and AM responsibilities.
• Collaborate with Business Development, Product, Marketing, Implementation, and Operations.
• Maintain disciplined Salesforce pipeline management and accurate forecasting while meeting monthly and quarterly revenue goals.

Requirements

• 5+ years of full-cycle B2B sales experience with consistent quota achievement.
• Proven success in outbound prospecting and net-new business creation.
• Experience closing complex, multi-threaded deals with longer sales cycles.
• Strong communication, presentation, negotiation, consultative selling, and business-discovery skills.
• Advanced proficiency with Salesforce and modern sales tools.
• BA/BS degree or equivalent experience.

Nice to have

• Experience in SaaS or fintech.
• Experience building pipeline from scratch through targeted strategic outreach.

Culture & Benefits

• Remote work with flexible time off.
• Medical insurance and retirement savings plans.
• Modern family-planning benefits.
• Inclusive workplace and interview accommodations for applicants with disabilities.
• Automated AI tools may be used to evaluate applications, subject to local regulations and bias audits.

Hiring process

• Applicants may submit up to 9 active applications within a 60-day period.
• Reapplications to the same role are accepted 90 days after a previous application has been reviewed.