Top Tech Jobs & Startup Jobs in Toronto

Supports global sales and account management enablement through ongoing learning programs, centralized knowledge resources, training content, stakeholder coordination, internal communications, and feedback tracking. The role operationalizes everboarding, maintains learning assets, localizes content for Canada, and measures adoption, knowledge retention, and performance impact while collaborating with Product, Marketing, Sales, and subject matter experts.

Conduct outbound prospecting through cold calls, email, and social selling to identify qualified Square merchants. Manage and prioritize a business pipeline, understand merchant needs, promote Square solutions, meet monthly sales quotas, and pass qualified opportunities to Account Executives. The role offers structured mentorship and career development within sales. Candidates must be bilingual in French and English and reside within 50 miles of the office.

Own the full outbound B2B sales cycle for mid-market merchants, including prospecting, pipeline development, discovery, product demonstrations, negotiations, and closing complex multi-product deals. Build net-new business, tailor Square ecosystem solutions, forecast accurately in Salesforce, collaborate cross-functionally, and consistently achieve revenue targets.

Own the architecture and technical strategy for Square’s go-to-market technology stack. Build and operate production AI agents, automated workflows, and integrations that improve sales productivity. Lead complex technical initiatives across teams, establish reliable and secure AI evaluation practices, make build-versus-buy decisions, and partner with Sales, Product, Data, and Engineering leaders. Mentor engineers, guide design and implementation, and use data and feedback to improve system adoption and business impact.

Own full B2B sales cycle for mid-market merchants: prospect, build and manage pipeline, demo multiproduct Square solutions, negotiate complex contracts, collaborate cross-functionally, maintain Salesforce forecasts, and consistently exceed revenue targets.

Manage the full sales cycle for SMB merchants: convert inbound leads, proactively prospect to build pipeline, close high-volume short-cycle deals, deliver consultative solutions, collaborate cross-functionally, and consistently hit monthly and quarterly revenue targets using Salesforce.

Own the full sales cycle for SMB merchants in Canada: convert inbound leads, prospect outbound, manage pipeline in Salesforce, collaborate with cross-functional teams, and consistently hit monthly and quarterly revenue targets while improving conversion and deal size.

Own the full outbound mid-market sales cycle: prospect, build pipeline, run discovery and demos, negotiate multi-product deals, and close new logo business while collaborating cross-functionally and maintaining accurate Salesforce forecasts to exceed monthly and quarterly revenue targets.

Develop and manage Square’s always-on B2B content engine across social, thought leadership, customer stories, partner content, and industry narratives. Build content calendars, formats, briefs, campaigns, and AI-assisted workflows; coordinate cross-functional teams and external partners; oversee production through launch; and analyze performance to optimize messaging, formats, and distribution.

Manage end-to-end onboarding and implementation for Square merchants, guiding discovery, configuration, training, hardware installation, data migration, and go-live activities. Partner with Sales, Account Management, Customer Success, Engineering, and Product to resolve obstacles, manage timelines, improve onboarding efficiency, and document feature requests. The role requires customer-facing communication, project management, cross-functional coordination, bilingual English and Spanish fluency, and PST or MST time-zone availability, with occasional onsite merchant work.