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Senior Account Executive, Mid-Market - Canada

CA - ON - Remote💼 Full-time💰 $152,300–$152,300🗓 2026-08-21 → 2026-09-26

Core

Senior B2B sales executive responsible for building, shaping, and closing a full outbound sales pipeline for mid-market merchants across diverse industries.

Role type

Senior Account Executive (Mid-Market)

Builds

Square's integrated omnichannel ecosystem (payments, inventory, BNPL, appointments, staff management) and embedded financial services.

Domain

Fintech / SMB Commerce

Deliverable

Product features (sales solutions)

Required skills

Full-cycle B2B sales, outbound prospecting, multi-product solution selling, complex deal negotiation, consultative selling, pipeline management, Salesforce proficiency

Preferred skills

SaaS or fintech sales experience, net-new business creation, multi-stakeholder deal management

Technologies

Salesforce, modern sales tools

Responsibilities

Own the full outbound sales cycle from prospecting to close; build and manage pipeline via cold outreach and social selling; develop tailored multi-product solutions; conduct discovery, demos, and negotiations; collaborate cross-functionally with Product, Marketing, and Operations; hit and exceed monthly and quarterly revenue goals.

Seniority

Senior, hands-on IC

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