Senior Account Executive, Mid-Market
Toronto · CA - ON - Toronto - Remote · CAD 116,064-174,096 · 5+ years experience · Remote · Posted Sep 23, 2026
At a glance
- Experience
- 5+ years experience
- Workplace
- Remote
- Location
- Toronto · CA - ON - Toronto - Remote
- Salary
- CAD 116,064-174,096
About the role
- As a Senior Sales Account Executive on the Mid-Market Team at Square, 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.
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
- 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.
- 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
Preferred qualifications
- SaaS or fintech experience preferred for outbound prospecting and net-new business creation
Benefits
- Remote work
- Medical insurance
- Flexible time off
- Retirement savings plans
- Modern family planning
Skills
- Salesforce
- B2B Sales
- Outbound Prospecting
- Pipeline Management
- Consultative Selling
- Cold Outreach
- Social Selling
- Forecasting
