Sales VP – Canada

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

Job Title: Vice President of Sales - Canada (B2B Partnership / Commission-Only)

Location: Remote (Canada)

Compensation: 100% Commission (High Tier Splits) + Lifetime Account Residuals + Equity Milestones

The Opportunity

AssistifAI Inc. is expanding its footprint across North America. We are bypass-engineering traditional, fragmented corporate customer service infrastructure by offering enterprises a unified AI workforce: native Voice Assistants, automated Telecalling, real-time Scheduling, and our proprietary 'Keeper' cross-channel conversation monitoring layer - all running on a single control plane.

Because our platform eliminates the massive development and backend integration costs typically charged by traditional AI vendors, our sales cycle is exceptionally fast, and our product-market fit is highly aggressive.

We are not looking for a salaried manager to build spreadsheets. We are looking for a visionary commercial leader, an elite closer, and an industry veteran to own the Canadian market. This is a high-stakes, maximum-reward executive partnership where your earnings are directly tied to your impact.

Key Responsibilities

• Market Expansion: Own, develop, and execute the enterprise go-to-market strategy for AssistifAI across Canada's key commercial hubs.
• C-Suite Engagement: Navigate complex procurement processes to close mid-market and enterprise deals (dealership networks, commercial operations, multi-channel customer service ecosystems).
• Pipeline Ownership: Drive the complete enterprise sales cycle, from leveraging your personal network to negotiating high-value, multi-license annual recurring revenue (ARR) contracts.
• Localization Strategy: Tailor enterprise messaging to address the distinct operational and regulatory landscape of Canadian businesses.

Who You Are

• The Veteran: 5+ years of enterprise SaaS or AI software sales experience within Canada, preferably with a proven track record of handling high-value contract negotiations.
• The Connected Rolodex: An active, deeply established network of decision-makers (CTOs, COOs, VPs of Customer Experience/Operations) across Canadian mid-to-large enterprises.
• The Self-Governor: A professional who treats their territory like their own business. You do not need a safety net; you thrive on the autonomy of a consultative partnership.
• The Closer: Exceptional skill in navigating legal, procurement, and technical validation hurdles to turn pipeline into closed revenue.

Compensation & Growth Ecosystem

• Top-Tier Commission Splits: Earn a premium percentage of all closed software license revenue and platform usage fees in your region, paid out immediately upon contract signing.
• Lifetime Renewal Residuals: Enjoy continuous financial upside with trailing commissions on account renewals and enterprise expansions for the life of the client contract.
• Strategic Equity: High-performing partners who achieve regional milestones will be fast-tracked for corporate equity and stock options in AssistifAI Inc.
• Total Autonomy: Work on your own schedule, from anywhere in Canada, with full geographic territory flexibility.
• Enterprise Support Matrix: Direct, unhindered access to founding technical teams, comprehensive product marketing materials, pre-sales technical support, and dedicated proof-of-concept environments to maximize your closing rate.

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