Territory Account Executive

Role

Location:

Winnipeg

As a Sales Account Executive on our Outbound Team, you will bring Square's ecosystem to new sellers across diverse industries by building, shaping, and closing your own pipeline. You will run sophisticated, multi-product deals from the first touch to final close — blending hunter instincts, consultative depth, and strategic execution.

• Own the full outbound sales cycle — from prospecting to negotiation to close — with SMB and 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.
• 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.

• 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.

The successful candidate's starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Pay may vary by zone:
Zone A: $159,900 – $239,900. Zone B: $159,900 – $239,900.