AI-Driven Enterprise Account Leader (Canada/US)

STA; Toronto; On-site; CAD 90,000 - 150,000; Full time

Job summary

STA is seeking a Senior Enterprise Account Executive to lead the enterprise motion in Canada and position for U.S. expansion. You will own the end-to-end sales cycle, targeting VP-level and C-suite buyers for complex cloud, modernization, data, and AI services.

The role emphasizes autonomous deal ownership in a lean, founder-accessible team, with a strong emphasis on building pipeline, strategizing account plans, and driving front-line enterprise growth.

Qualifications

• 5+ years of experience selling into enterprise accounts.
• Ability to identify and engage stakeholders in large organizations and close end-to-end sales.
• Up-to-date understanding of how modern software, cloud, and AI influence enterprise decisions.
• Autonomy to lead deals in a lean, high-ownership environment.

Responsibilities

• Own the full sales cycle for Canadian enterprise accounts with U.S. expansion on the horizon.
• Sell complex, six- to seven-figure services engagements to VP-level and C-suite buyers.
• Source and build your own pipeline with support from pre-sales, demand gen, and marketing.
• Help shape the company’s enterprise GTM motion and represent the brand at events.

Skills

Enterprise sales

Consultative selling

Stakeholder management

Account planning

Job description

STA is seeking a Senior Enterprise Account Executive to lead the enterprise motion in Canada and position for U.S. expansion. You will own the end-to-end sales cycle, targeting VP-level and C-suite buyers for complex cloud, modernization, data, and AI services.

The role emphasizes autonomous deal ownership in a lean, founder-accessible team, with a strong emphasis on building pipeline, strategizing account plans, and driving front-line enterprise growth.