AI Account Executive - Canada (Remote)

About Sadie Auto & TAG Software Group

Sadie Automotive AI is a fast-growing startup revolutionizing communication for car dealerships. Our intelligent virtual receptionist answers 100% of inbound calls—24/7—handling service booking and sales inquiries while integrating with major DMS platforms. Backed by TAG Software Group (a division of Valsoft Corporation), we combine the agility of a startup with the massive resources and stability of a multi-billion dollar global portfolio.

Culture

Sadie is more than just a place to work; we’re a team. We mean it when we say people are our greatest assets, so investing in them is our number one priority. We Dream Big, Stay Humble, and Stay Hungry.

Position Description

We are seeking several AI Account Executives to drive a major North American expansion for Sadie Auto. As we scale to triple our business this year, we are establishing a high-performing "Foundational Team" to own and grow key strategic territories. We are looking for high-performing "Hunters" to lead expansion across the US Northeast and Mid-Atlantic (NY, NJ, PA, MA), the Southeast and Texas (FL, GA, TX), the Midwest (IL, MI, OH), the West Coast (CA, WA, OR, AZ), and Canada.

Reporting to the incoming Head of Sales and working in close alignment with the CEO, you will be responsible for new business acquisition and full-cycle sales within your region. This role is built on Territory Ownership: you will manage your region remotely, leveraging your existing industry relationships and digital tools to build a pipeline, while attending key in-person industry events and high-stakes dealership meetings as needed.

Key Responsibilities

• Strategic Territory Management: Own and develop your assigned North American region, using your automotive tech network to accelerate market penetration.
• Outbound Pipeline Generation: Execute modern outbound sequences across phone, email, and LinkedIn, complemented by strategic in-person networking.
• Full-Cycle Sales Execution: Manage the entire sales process from initial prospecting and discovery to demo, proposal, and close.
• High-Impact Demos: Deliver compelling demonstrations of AI-powered communication solutions, articulating clear ROI to General Managers and Dealer Principals.
• Dealership Insights: Conduct discovery calls to understand specific dealership workflows and operational bottlenecks, tailoring the Sadie AI value proposition accordingly.
• Collaborative Growth: Work with the CEO and Head of Sales to provide regional insights into dealership needs and common DMS systems (e.g., CDK, Reynolds, Dealertrack, Tekion, XTime).
• Market Visibility: Represent Sadie Auto at major automotive conferences, trade shows, and dealer-group events within your territory.

CRM Discipline: Maintain accurate pipeline documentation and activity tracking in HubSpot to ensure data-driven territory growth.

Requirements

Requirements

• 5+ years of experience in automotive software sales or dealership-facing vendor roles.
• Proven "Hunter" mentality with a track record of exceeding goals through strategic territory management and relationship leveraging.
• Tech-forward mindset with a strong understanding of AI, SaaS, or dealership operational software.
• Strong communication skills, capable of conducting professional demos for GMs and Dealer Principals.
• Ability to work independently in a remote, territory-based environment.
• Willingness to travel strategically for trade shows, dealer group meetings, or late-stage deal discussions.

Additional or Preferred Qualifications

• Existing relationships with major Dealer Groups or OEM partners.
• Experience with DMS integrations and the broader automotive tech ecosystem.

• Bilingualism (English/French) is a significant asset for the Canada territory.

Why Choose Sadie

• Foundational Impact: Be part of the original 6-territory "blitz" as we triple the business.
• Career Progression: With the simultaneous hiring of a Head of Sales, we are building a structured leadership path. Top-performing AEs will be prioritized for future Team Lead and Sales Management roles.

• Standard Valsoft Benefits package starting from day one.

#SadieAutomotive

Benefits

Ready to join a collaborative and innovative team where you can make an immediate impact?