Remote VP of Sales - Canada (Commission-Only, Equity)

AssistifAI Inc.; Canada; Remote; CAD 180,000 - 430,000; Full time

Job summary

AssistifAI Inc. is expanding across North America, delivering an unified AI workforce with Voice Assistants, Telecalling, Scheduling, and Keeper cross-channel monitoring. The Vice President of Sales - Canada is a remote, commission-only executive role with high-tier splits, lifetime residuals, and equity milestones.

It targets a visionary leader to own the Canadian market and accelerate ARR growth. You will lead the enterprise go-to-market, engage with C-suite stakeholders, own the pipeline, and

Qualifications

• 5+ years of enterprise SaaS or AI software sales in Canada.
• Strong network of CTOs/COOs/VPs in Canadian enterprises.
• Autonomous, self-motivated leader capable of treating the territory as a business.
• Proven track record closing high-value contracts.

Responsibilities

• Develop and execute enterprise go-to-market strategy for Canada.
• Close mid-market and enterprise deals with complex procurement processes.
• Own the complete sales pipeline from networking to ARR contracts.
• Localize messaging to the Canadian regulatory and operational context.

Skills

Enterprise SaaS sales

Canada market knowledge

Executive relationship building

Deal closing

Job description

AssistifAI Inc. is expanding across North America, delivering an unified AI workforce with Voice Assistants, Telecalling, Scheduling, and Keeper cross-channel monitoring. The Vice President of Sales - Canada is a remote, commission-only executive role with high-tier splits, lifetime residuals, and equity milestones.

It targets a visionary leader to own the Canadian market and accelerate ARR growth. You will lead the enterprise go-to-market, engage with C-suite stakeholders, own the pipeline, and