Top Sales Jobs in Montreal

Own the full enterprise sales cycle for Block’s commerce and payments portfolio, from prospecting and account strategy through negotiation, contracting, launch, and expansion. Build executive relationships with global brands, develop commercial strategies, negotiate complex agreements, coordinate cross-functional teams, and deliver revenue targets. Translate market and customer insights into product and go-to-market feedback while managing strategic pipelines and opportunities.

Leads a team of Product Sales Specialists responsible for product adoption, cross-sell, expansion, pipeline, and revenue outcomes. Coaches consultative selling, manages forecasting and performance, develops scalable sales plays, and partners with Account Executives, Account Managers, Product, Marketing, Operations, Data Science, and Enablement. The role also engages in strategic seller opportunities, improves product expertise across sales teams, and builds repeatable commercial motions for Square’s products.

Drive revenue by acquiring and expanding relationships with mid-size and high-growth brands. Lead commercial negotiations, develop deal strategies, manage sales pipelines and forecasts, close new business, and communicate Block’s payments value proposition to senior decision-makers. Build executive relationships and collaborate with Marketing, Finance, Product, Risk, Legal, Operations, and Customer Service teams to execute commercial and product initiatives.

Own the full outbound sales cycle for mid-market merchants, including prospecting, pipeline development, discovery, demonstrations, negotiation, and closing complex multi-product deals. Build net-new business through strategic outreach, tailor Square solutions to merchant needs, collaborate cross-functionally, maintain accurate Salesforce forecasts, and consistently achieve revenue targets.

Leads Sales Development across North America and the UK, owning top-of-funnel pipeline performance, team integration, reporting, targeting, conversion, and revenue contribution. Builds scalable inbound and outbound motions, expands upmarket coverage, develops managers and representatives, and partners with Marketing, Sales, Finance, Risk, Compliance, Product, and Operations. Uses analytics, automation, and AI to improve prospecting and productivity while establishing rigorous planning, coaching, qualification, and performance standards.

Leads Square’s US BDR organization through managers and frontline teams, owning pipeline generation strategy, forecasting, performance management, coaching, hiring, and talent development. Partners with Sales, Marketing, Revenue Operations, Enablement, Analytics, and Strategy to improve prospecting, lead quality, funnel conversion, tooling, and revenue contribution. Uses metrics, automation, AI, and sales technology to scale outbound motions and build a predictable, high-performing business development organization.

Own Square Hardware’s US retail channel strategy, sales, revenue, and retailer partnerships. Responsibilities include managing existing relationships, sourcing and negotiating new partnerships, developing go-to-market playbooks, forecasting sell-through, coordinating cross-functional launches, and managing retail marketing budgets. The role requires entrepreneurial execution, analytical decision-making, autonomy, and approximately 20% travel.

Own commercialization of Block’s emerging AI portfolio from product and pilot stages through scaled enterprise adoption. Develop market strategy, pricing, packaging, partnerships, and routes to market; secure lighthouse customers and strategic partners; design pilots that convert to production relationships; create repeatable sales and partnership processes; and build the commercial organization as product-market fit develops.

Lead commercialization of emerging AI products by winning enterprise customers and strategic partners, structuring pilots, converting engagements into scaled relationships, and owning partnerships from negotiation through launch and optimization. Collaborate closely with Product and Engineering to shape offerings, validate product-market fit, develop pricing and commercial models, and build a scalable go-to-market strategy.

Own the full-cycle sales process for mid-market commerce merchants across Cash App Pay and Afterpay. Responsibilities include prospecting, pipeline generation, discovery, account planning, business-case development, pricing and contract negotiation, cross-functional deal coordination, forecasting, and closing new business. The role requires building executive relationships, managing complex commercial opportunities, delivering revenue targets, representing the company at events, and contributing to sales enablement and process improvement.