Senior Enterprise Account Executive

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

Our client is a fast-growing cloud, DevOps, and generative-AI consultancy based in Toronto, recognized as a top-tier partner within a major cloud provider’s ecosystem for its deep expertise in modernization and applied AI delivery. Built by a small group of cloud architects and engineers, the company has grown from serving startups and SMBs into the mid-market, and has recently opened up its enterprise segment for the first time. As they build out that enterprise motion and prepare for an expansion into the U.S. market, they’re looking for a high-performing Senior Enterprise Account Executive to help continue to build the enterprise motion in Canada.

Why Join?

• A Genuine Cloud Leader — Premier-tier partner status within a major hyperscaler ecosystem, with recognized expertise across generative AI, data, and managed cloud services.
• Real AI Expertise, Not Theory — hands-on delivery experience running AI-augmented modernization projects for enterprise clients today.
• Growth & Compensation — Competitive compensation with commissions, and a clear path for career advancement as the enterprise team scales.
• Keep What You Build — accounts stay with you long-term post-close, and you’re compensated on upsell and expansion revenue, not just the initial sale.
• Room to Build — a lean, founder-accessible team where you help shape the enterprise GTM playbook, with more pricing and deal flexibility than reps at larger, slower-moving competitors.

The Opportunity

• Own the full sales cycle for enterprise accounts across Canada, with U.S. expansion on the horizon — from first meeting to signed statement of work.
• Sell complex, consultative six- and seven-figure services engagements — cloud migration, modernization, data, AI/ML, and managed services — to VP-and-up and C-suite technology buyers.
• Source and build your own pipeline (primarily self-sourced hunting), supported by a technical pre-sales team, demand generation, and marketing.
• Help shape the company’s go-to-market motion as it expands into new verticals and geographies.
• Represent the company at executive events and industry conferences.

Who You Are:

• 5+ years of experience selling into enterprise accounts, ideally in a consulting-services or IT/cloud-services environment — this is a services sale, not a SaaS/product motion.
• Comfortable identifying and engaging the right stakeholders inside large, complex organizations, and running a full sales cycle through to close.
• Up to date on how modern software and AI are changing enterprise technology decisions.
• Doesn’t need to be deeply technical, but needs enough conceptual fluency in cloud and AI to carry a credible conversation.
• Experience in a smaller or leaner organization is a plus — this is an autonomous, high-ownership seat without a large built-out demand-gen machine behind it.
• Based in the Greater Toronto Area or Montreal (French a strong plus); comfortable getting in-person face time with target accounts.

Why Now?

• This is a genuine ground-floor opportunity - the company recently opened its enterprise segment for the first time and is investing seriously in the team and playbook to support it, with U.S. expansion on the horizon. If you’re hungry to build something from scratch, want direct access to founders and leadership, and are excited by real earning upside tied to long-term account ownership, this is the seat for you.