Top Tech Jobs & Startup Jobs in Calgary

Lead end-to-end delivery of high-priority, cross-functional Revenue initiatives including product and partnership launches. Develop integrated program plans, establish governance and operating cadences, drive cross-functional alignment, manage risks and dependencies, and create repeatable launch frameworks and executive communications to ensure successful market readiness and post-launch stabilization.

Lead and build Square's global commercial operating system, owning Deal Desk, pricing operations, strategic deal support, and commercial governance. Drive pricing execution, approval workflows, AI-enabled automation, reporting, and cross-functional alignment to increase deal velocity, consistency, and profitability while managing a global team.

Lead vision-heavy product design for Square Point of Sale: craft visual and interaction designs, build prototypes, collaborate with product and engineering, integrate AI-driven experiences, and drive projects from concept through shipped product while raising design standards and systems thinking.

The Business Development Rep Associate will drive sales efforts by reaching out to prospective sellers, promoting Square's value, and managing a diverse business pipeline. Success will lead to growth opportunities within the sales organization. Candidates need to possess excellent sales instincts and a desire to grow in a sales career.

Lead GTM strategy and operations for Global Account Management to improve retention, reduce churn, and drive expansion. Build coverage models, book construction, KPIs, dashboards, and operational cadence. Automate workflows and AI-driven experiments across CRM and GTM tools. Partner cross-functionally with Data Science, Product, Engineering, Finance, and AM to translate strategy into scalable programs, technical requirements, and measurable impact.

Own and grow enterprise payment partnerships by sourcing, negotiating, and closing integrations with software platforms. Drive go-to-market execution with Sales and Account teams, develop API expertise, collaborate cross-functionally, and track partner performance and business outcomes tied to GPV, seller acquisition, and enterprise wins.

Lead GTM strategy and operations for Global Sales: design segmentation, territory and coverage models, build data-driven investment cases, analyze funnel performance, own WBR/MBR cadence and dashboards, run cross-functional projects from PRD to launch, and champion AI and automation to increase sales productivity.

Lead Square-wide Trust strategy across Risk and Identity, owning high-stakes Trust bets while coaching senior PMs. Drive product for Identity Verification, Access, Disputes, and Controls; optimize seller experience, risk loss, and ecosystem health. Operate AI-native, engage regulators and partners, and coordinate Product, Engineering, Compliance, Legal, and Operations to deliver Trust and Safety initiatives.

Lead end-to-end enterprise sales for Square9s upmarket business: craft deal strategy, manage complex technical integrations and multi-stakeholder negotiations, partner with Solutions Engineering, align internal teams, represent the company to executives, and close high-value contracts while influencing product and go-to-market strategy.

Lead and coach a remote team of Account Executives to meet individual and team sales quotas. Hire, train, and ramp AEs; manage KPIs, forecasting, and pipeline reviews; participate in client meetings and co-sell. Develop repeatable sales processes, evolve strategy, and use customer feedback to improve products.