Account Executive (Hospitality Technology Sales) - Canada

About the Role

Sadie is building technology for hospitality. We're seeking an Account Executive to secure new restaurant customers across major Canadian cities, handling every deal from initial outreach to signed agreements. This is a field-based role where you'll identify potential clients through outbound efforts, networking, and on-site visits, then engage with restaurant owners directly to demonstrate how Sadie’s solutions improve their operations.

You’ll manage your own pipeline, meet monthly and quarterly targets, and ensure the quality of all deliverables under your name. AI will play a key role in your workflow—utilize it for research, demo preparation, proposal drafting, and territory planning. Ownership of your forecast and results is critical.

What We Value

• Sound judgment in evaluating deal potential.
• Self-driven accountability for meeting targets without micromanagement.
• Understanding restaurant revenue models and how Sadie can enhance them.
• Curiosity about lost deals and adaptability in approach.
• Honesty in forecasting—flagging deals at risk before they fail.

The Role

• Winning New Restaurants: Spend time on live deals, conducting in-person demos to showcase how Sadie addresses pain points like missed calls and lost bookings. Qualify leads early to avoid wasting time on unviable opportunities.
• Assess current call-handling processes, propose tailored solutions, and negotiate terms to secure agreements.
• Building Your Pipeline: Generate leads through outreach, networking, and strategic visits to neighborhoods and restaurant groups. Plan visits during optimal hours and follow up relentlessly.
• Meeting Targets: Consistently hit monthly and quarterly sales targets. Maintain accurate records in HubSpot to ensure forecasts are reliable and actionable.
• Representing Sadie: Attend industry events, trade shows, and restaurant meetups to network and convert conversations into meetings. Be the first point of contact for many operators.
• Onboarding Success: Collaborate with onboarding and customer success teams to ensure smooth implementation. Document promises, owner expectations, and potential pitfalls to avoid post-sale issues.

Requirements

• At least 2 years in a closing sales role, preferably selling software or services to businesses.
• Proven track record of meeting targets with clear explanations of your success.
• Experience managing the entire sales cycle—prospecting to signature.
• Comfort with in-person sales, including cold visits and demos in high-pressure environments.
• Strong discovery skills to quickly identify operator needs.
• Clear, concise written communication for proposals and follow-ups.
• Honest forecasting—prioritize accuracy over optimism.
• Daily use of AI for research, preparation, and drafting, with verification of outputs.
• Self-organization and ability to manage a territory independently.

Useful Experience

• Sales in the restaurant or hospitality industry.
• Frontline or management experience in restaurants.
• Selling reservations, POS systems, telephony, or other restaurant tech.
• Existing network among restaurant owners in your area.
• Experience selling AI products to non-technical buyers.
• Early-stage sales roles at startups.

Who Will Thrive Here

You’re detail-oriented and enjoy understanding how businesses operate. When an owner mentions missed calls during peak hours, you dive deeper—how many calls? What was lost? What happened to the guest? Your schedule mirrors the restaurant industry, with visits, demos, and trade shows balancing a dynamic workload.

The challenges are specific: owners are busy and skeptical, and rejection is common. You’ll need resilience to bounce back quickly. Early-stage tools like case studies or playbooks may not exist yet, so you’ll contribute to building them while hitting targets.

Why This Role Matters

Sadie’s mission is to recover lost revenue for restaurants by answering calls. This role is critical—you determine which restaurants engage with Sadie, shape their onboarding experience, and influence guest perceptions when they call to book. Your success directly impacts revenue and operational efficiency.

You’ll own new business across your territory, with full authority to decide how Sadie wins it.