AI Sales Executive (Toronto, ON)

AI Account Executive

Location: Toronto, ON (Preferred) | Open to Remote for Exceptional Candidates

Executive Search Overview

Our client controls an elite portfolio of specialized Managed Service Providers (MSPs) servicing a corporate network of over 600 established, recurring B2B clients. To capitalize on the massive enterprise shift toward automation and applied artificial intelligence, they have launched an internal AI Practice dedicated to designing and delivering commercial-grade managed AI solutions.

This hire represents a core addition to the practice's leadership team. Working directly alongside the VP of AI Services, the successful candidate will inherit a massive, completely warm account ecosystem with zero cold calling required.

Why This Opportunity Stands Out

• 100% Warm Pipeline: Step directly into a captive client base of 600+ enterprise accounts across 17 technology provider subsidiaries. Your entire focus is on account penetration, relationship farming, and solution expansion.
• High-Margin, High-Demand Solutions: Sell high-impact, managed AI architectures that solve real operational bottlenecks, supported by experienced in-house data scientists and technical architects who handle deployment.
• True Collaborative Co-Selling: You own the commercial relationship, pricing strategy, and closing process, working in lockstep with executive technical leadership.
• Fast-Track Trajectory: Direct, daily exposure to practice heads and portfolio executives in a high-growth environment built around practical execution over corporate bureaucracy.

The Role

As an AI Sales Executive, you will guide existing portfolio clients through their enterprise AI transformation journey. You will act as the commercial architect of every engagement—identifying latent operational challenges, framing the business case for AI adoption, presenting compelling financial ROI, and closing multi-stage managed solution agreements.

Primary Mandate:

• Conduct consultative discovery across 600+ warm business accounts to identify high-leverage AI, automation, and workflow modernization projects.
• Direct the commercial process from discovery through contract closure, negotiating commercial terms and scopes of work.
• Partner with the VP of AI Services on enterprise presentations, translating advanced technical architectures into clear executive-level business value.
• Build and manage a transparent, disciplined sales pipeline, delivering predictable revenue forecasting and expanding recurring managed service contracts.
• Position the firm as the indispensable long-term AI advisor to senior client stakeholders.



Candidate Profile

We are seeking an authentic commercial professional who blends consultative sophistication with strong closing instincts:

• Proven B2B AI Solution Sales: Experience selling artificial intelligence, data automation, enterprise SaaS, or managed cloud/IT services to B2B executives. Direct exposure to selling AI as a Managed Service is a distinct asset.
• Strategic Farming Instincts: Exceptional relationship-building skills with a track record of expanding revenue within warm accounts, identifying cross-sell opportunities, and navigating matrixed buying committees.
• Business Acumen & Articulation: Skilled at leading commercial negotiations, simplifying complex technical themes for non-technical buyers, and proving financial return on investment.
• Demonstrated Execution: We prioritize grit, commercial intelligence, and closing consistency over formal credentials or academic pedigrees.
• Location: Candidates located in the Greater Toronto Area (GTA) are strongly preferred for hybrid collaboration with executive leadership; remote candidates with top-tier AI sales backgrounds are encouraged to apply.