Head of Sales

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.

We are looking for a visionary Head of Sales to architect, lead, and scale our North American sales organization. This is not just a sales role; it is a leadership mandate to build a world-class team from the ground up.

We are currently in the process of hiring our first six (6) Senior Account Executives across key territories (Northeast, Southeast/Texas, Midwest, West, and Canada). As the Head of Sales, you will be responsible for coaching this foundational team, establishing our North American sales playbook, and preparing the organization to double or triple in size over the next 12–18 months.

Requirements

• Team Leadership & Scaling: Recruit, onboard, and lead a high-performing team of Senior Account Executives across North America. Establish KPIs, coaching frameworks, and performance standards.
• Sales Strategy & Playbook: Design and execute the North American "Go-to-Market" strategy. Refine the outbound sales methodology, from "lot-walking" networking to complex AI-integration demos.
• Full-Cycle Execution: While this is a leadership role, you will lead by example, jumping into high-stakes negotiations with major Dealer Groups and OEMs to help close key accounts.
• Cross-Functional Collaboration: Partner directly with the CEO and Product teams to provide field insights that shape the Sadie AI roadmap and DMS integration strategy.
• Pipeline Management: Maintain ultimate accountability for the North American revenue target. Use CRM data (HubSpot) to optimize outreach strategies and forecast growth with precision.
• Market Evangelism: Represent Sadie Auto as a thought leader at major industry events (NADA, etc.) and build strategic alliances within the automotive ecosystem.

• Proven Leadership: 5+ years of experience in sales leadership, specifically scaling B2B SaaS or Automotive Tech teams. Experience moving a company from "Foundational Team" to "Scaled Organization" is highly preferred.
• Industry Credibility: Deep knowledge of the automotive dealership landscape. You understand the "language of the lot" and the operational bottlenecks of GMs and Dealer Principals.
• Hunter DNA: You still possess the hunger of a top-performing individual contributor. You are comfortable with cold outreach and the grit required to win in a "Greenfield" market.
• AI & Tech Savvy: You have a genuine curiosity for AI technology and can articulate the ROI of automated communication solutions.
• Organizational Architect: You are comfortable with autonomy and can build processes (CRM workflows, comp plans, territory maps) where they don't yet exist.
• Language: Fluent in English is a prerequisite; French or another European language is a significant advantage for our global expansion.

Benefits

• Strategic Impact: A seat at the leadership table where your decisions directly shape the company's trajectory.
• High Earning Potential: Competitive base salary with an aggressive, uncapped OTE structure and performance-based equity/bonus potential.
• The Best of Both Worlds: Startup speed with the institutional backing of Valsoft/TAG.
• Growth Track: As we ramp up from 6 AEs to a significantly larger organization, your role and influence will expand proportionally.

#SadieAutomotive

This recruitment process may use AI tools to assist with candidate screening and assessment. These tools support, but do not replace, human decision‑making, and are used in compliance with applicable Canadian and Quebec privacy laws.

We thank all those who apply for this role, however, only those considered will be contacted.