Top Tech Jobs & Startup Jobs in Calgary

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.

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.

Leads Square’s US Business Development Representative organization through managers and frontline teams. Owns pipeline generation strategy, operating cadence, performance management, forecasting, capacity planning, outbound execution, and sales technology improvements. Coaches managers, develops BDR talent, hires and retains staff, and partners with Sales, Marketing, Revenue Operations, Enablement, Analytics, and Strategy to improve funnel conversion and revenue contribution. Uses data, automation, AI, and prospecting tools to improve productivity and scale successful programs.

Own Square Hardware sales and revenue across major U.S. retail partners. Build and scale retail partnership strategies, manage existing retailer and distributor relationships, source and negotiate new partnerships, lead cross-functional launches and forecasting, and manage retail marketing budgets through test-and-learn investments.

Coordinate cross-functional product go-to-market programs from planning through launch, adoption, and optimization. Build project plans, operating mechanisms, launch documentation, feedback loops, status updates, and decision logs. Partner with Product, Sales, Marketing, Enablement, Analytics, Finance, and leadership to align stakeholders, manage dependencies, identify blockers, and improve execution. Translate operational data and customer or field feedback into clear priorities and recommendations.

Lead global ecosystem partnerships for Block’s Afterpay, Cash App, and Square products. Develop partner strategies, build executive relationships, design scalable partnership programs, commercialize B2B and B2B2C payment products, negotiate agreements, and expand distribution through third-party platforms. Collaborate with Product, Engineering, Sales, Marketing, Finance, Compliance, and Legal teams to maximize partner performance and commercial growth.

Lead data science initiatives for Risk and Support Operations by analyzing customer and product data, defining metrics, forecasting demand, evaluating experiments and risk policies, and building decision frameworks. Use AI tools and agent workflows to improve analytical efficiency. Partner with product, engineering, and risk teams, communicate insights to senior stakeholders, establish technical standards, mentor data scientists, and support hiring.

Own the architecture and technical strategy for Square’s go-to-market systems. Build and operate production AI agents, automated workflows, and integrations that improve sales productivity. Lead complex initiatives through architecture, implementation, testing, deployment, and operations while establishing AI evaluation, observability, security, reliability, and human-oversight practices. Partner with Sales, Product, Data, and Engineering leaders to translate business needs into scalable solutions, make build-versus-buy decisions, mentor engineers, and improve business impact through data and user feedback.

Own a Santa Clara territory through primarily in-person field sales. Generate pipeline via business visits, networking, events, partnerships, and cold outreach; run full-cycle sales from prospecting through demos and closing; build seller relationships; support onboarding; maintain Salesforce activity and forecasts; master restaurant, retail, and service verticals; and consistently exceed quota.

Own and grow an Oakland territory through primarily in-person field sales. Generate pipeline via business visits, cold outreach, events, networking, and partnerships; conduct demos; sell Square’s software, hardware, and financial solutions; and close full-cycle deals. Build relationships with local businesses, support onboarding, develop referrals, manage pipeline and forecasting in Salesforce, and consistently exceed quota across restaurant, retail, and services verticals.