Jobs at Square

Lead approximately 10 senior Account Executives on an outbound mid-market sales team. Responsibilities include hiring and developing talent, coaching through pipeline and performance data, forecasting, improving sales processes, establishing operating rhythms, and partnering with Sales Leadership, Marketing, Enablement, Operations, and Product. The role focuses on building a high-performance organization, strengthening pipeline quality, improving execution, and developing future sales leaders.

Own and grow a Toronto sales territory through extensive in-person business visits, prospecting, networking, partnerships, product demonstrations, and full-cycle deal closing. Build pipeline, sell Square’s software and hardware ecosystem to restaurants, retailers, and service businesses, maintain accurate Salesforce records and forecasts, support onboarding, and consistently exceed sales quotas.

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.

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.

Leads international seller onboarding operations across Europe, the UK, Australia, and APAC. Owns regional execution, staffing, vendor performance, service levels, market readiness, operational scaling, and seller activation outcomes. Develops localized operating models and launch playbooks while maintaining global standards. Uses metrics, dashboards, financial analysis, and AI to improve workflows, cost-to-serve, speed, and quality. Partners with Sales, Product, Finance, Legal, Compliance, and GTM leaders while managing distributed teams and developing regional leadership.

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.

Lead complex card-acquiring projects from design through production, building reliable payment systems, tooling, testing frameworks, and network integrations. Work hands-on with ISO messages, routing, authorization, clearing, settlement, reconciliation, interchange, and tokenization. Set technical direction, mentor engineers, improve reliability, participate in on-call operations, and establish standards adopted across teams. The role requires deep acquiring expertise and experience operating large-scale financial systems.

Own creative and content strategy for a growth portfolio across paid and unpaid channels. Lead audience research, messaging, creative development, experimentation, landing-page optimization, performance analysis, and scaling of successful concepts. Partner cross-functionally with marketing, creative, analytics, SEO, web, CRO, agencies, and technical teams. Develop AI-enabled workflows and testing frameworks while connecting creative decisions to acquisition, conversion, and business outcomes.

Own the post-checkout customer experience for Square’s food ordering and retail ecommerce products. Set product strategy, prioritize investments, align cross-functional teams, define customer journeys, and ship improvements across tracking, delivery, refunds, and support. Use customer research, behavioral data, AI tools, prototyping, GitHub, and automation to improve product quality and outcomes. Lead decisions across engineering, design, sellers, customers, and external partners while measuring resolution time, satisfaction, inquiries, and repeat purchases.

Leads Square’s global external workforce and partner strategy for seller onboarding. Owns vendor, BPO, and third-party operating models; develops build-versus-buy recommendations, partner standards, SLAs, scorecards, governance, and performance mechanisms. Partners with Procurement, Legal, Finance, and regional operations on commercial terms, capacity, quality, cost, and scalability. Manages evolving partner operations teams and drives improved seller outcomes through operational discipline, workflow optimization, and AI-enabled improvements.

Leads the global operating system for seller onboarding by establishing KPI frameworks, reporting cadences, planning processes, capacity models, financial support, and continuous improvement programs. Partners with regional operations, Finance, Product, Analytics, and Enablement teams to standardize workflows, improve efficiency, and scale AI-enabled onboarding processes. Owns performance management routines, workforce modeling, vendor analysis, operational planning, and impact measurement across global delivery models.

Leads US seller onboarding operations across first-party and vendor-supported teams. Owns execution from post-sale handoff through go-live, including staffing, scheduling, routing, quality, service levels, and cost management. Drives operational excellence through KPI analysis, process redesign, tooling improvements, automation, and AI adoption. Partners with Sales, Product, Finance, and regional teams while managing multiple teams and developing operational leaders.

Leads a team of Product Sales Specialists responsible for product adoption, cross-sell, expansion, pipeline, and revenue outcomes. The role coaches sellers, manages forecasting and performance, partners on complex opportunities, develops scalable sales motions, and enables broader sales teams. It also collaborates with Sales, Product, Marketing, Operations, Data Science, and Enablement to improve targeting, commercialization, product expertise, and seller outcomes.

Develop data science solutions for payments across Square and Cash App. Build AI-powered tools, ETL pipelines, dashboards, machine learning models, experiments, and cloud data systems. Partner with Product, Engineering, Finance, and Operations to improve payment success, cost efficiency, risk mitigation, and decision-making. Translate business needs into practical solutions, research questions independently, and operationalize data processes and infrastructure.

Design, build, scale, and operate high-volume payment APIs and distributed systems serving global traffic. Lead complex engineering projects from requirements through production, improve reliability, performance, observability, fault tolerance, and security, and participate in on-call and incident response. Collaborate across product and engineering teams, use AI-assisted development tools responsibly, and mentor engineers through technical reviews and documentation.