Senior Enterprise Account Executive

About Our Client: 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.

Own the full sales cycle for enterprise accounts in Canada, selling complex six- and seven-figure cloud, AI, and modernization services. Help shape the company's enterprise go-to-market playbook and source a self-driven pipeline of C-suite technology buyers.

Requires 5+ years of experience selling IT or cloud consulting services into enterprise accounts. Candidates must possess conceptual fluency in cloud and AI and be based in the Greater Toronto Area or Montreal.

• Commissions • Career advancement opportunities • Long-term account ownership • Upsell and expansion revenue compensation

Identified from the job description. Confirm important requirements above.

• Enterprise Sales
• Consultative Selling
• Pipeline Generation
• Cloud Services Sales
• Account Management
• Strategic Prospecting
• C-suite Engagement
• Go-to-Market Strategy
• AI/ML Conceptual Fluency
• Deal Negotiation
• Full Sales Cycle Management
• Enterprise Account Planning

• Sales
• Consulting
• Technology
• Software
• Data & Analytics

Minimum experience

5+ years

Apply by

Sep 24, 2026

Posting language

English

Working hours

40 hours per week

Seniority

Mid-Senior level

Application method

Direct apply is available