Founding Enterprise Account Executive

Toronto, ON
On-site
Posted May 20, 2026
1 position

$100,000–$150,000 / year

Opens an external site

Employment type: Full-time
Experience level: Mid-level · 2+ years
Posting language: English
Working hours: 40 hours per week

Job summary

The Founding Account Executive will own the full-cycle sales motion for mid-market and early enterprise clients. Responsibilities include prospecting, qualifying, demoing, and closing deals to meet sales quotas.

Job details

About Chatbase Chatbase is the AI agent platform powering millions of customer conversations for 10,000+ of the most recognizable brands and companies across the world. We're bootstrapped, profitable, and growing quickly. There is no better time to join. How we work → High ownership, high output. Everyone on the team owns outcomes end-to-end. We work best with individuals who are precise, fast, and great at unblocking themselves. → Critical feedback is a gift. We give feedback directly and receive it without ego. It's how we get better. → Customer-obsessed. We make an effort to understand our customers and relentlessly deliver value to them. About the role This is a founding AE role on our GTM team, reporting to the Head of GTM. You'll carry a sales quota and own the full sales cycle for enterprise customers: prospecting, qualifying, running demos, and closing your own deals. You'll work with customers to understand their workflows, identify where AI agents can deliver value, and guide them through evaluation and purchase. Product and engineering will support you, but you'll own moving your deals forward. Who we're looking for → 2+ years in tech sales (BDR/SDR, AE), startup operations, or other high-performance environments. → A track record of consistently exceeding goals and taking ownership of results. → A strong communicator who asks thoughtful questions and builds trust with customers. → Deep curiosity about AI, customer workflows, and how our product can solve real business problems. Logistics This role is in-office, five days a week, in downtown Toronto. We offer uncapped commissions and generous equity.

What you’ll do

Requirements

Candidates need 2+ years of experience in tech sales, startup operations, or high-performance environments. A proven track record of exceeding goals and strong communication skills are required.