Sales Vp - Canada

Job Title: Vice President of Sales - Canada (B2B Partnership / Commission-Only)
Location:
Remote (Canada)Compensation:
100% Commission (High Tier Splits) + Lifetime Account Residuals + Equity MilestonesThe 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.Insights, updates, and smarter automation straight to your inboxAssistifAI automates your workflows and delivers exceptional voice and chat-based customer support helping your business grow faster, save time, impress clients, and stay ahead of the competition.
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