Enterprise Account Executive (AI)

TL;DR

Enterprise Account Executive (AI): Building enterprise customer relationships and closing complex AI platform deals with an accent on prospecting, consultative selling, and revenue growth. Focus on negotiating six- and seven-figure contracts, managing $1M+ quotas, and using AI-native tools across the full sales cycle.

Location: Remote in Canada

Salary: CA$305,000–CA$370,000 annually, plus equity and commission.

Company

Develops an AI platform that helps consumer brands create more human customer experiences through AI agents for support, commerce, and customer engagement.

What you will do

• Research, prospect, and engage enterprise customers through networking, cold calling, and targeted outreach.
• Build and maintain relationships with key decision-makers at major accounts.
• Lead complex negotiations and close six- and seven-figure annual contract value deals.
• Develop sales strategies, presentations, and proposals to exceed revenue targets.
• Collaborate with go-to-market, marketing, product, technical, operations, legal, and finance stakeholders.
• Use AI tools for account research, personalized outreach, call summaries, forecasting, and deal execution.

Requirements

• 6–8 years of experience in enterprise, customer-facing sales focused on identifying and closing large accounts.
• Experience managing a quota of $1M or more and running complex six- and seven-figure ACV deals.
• Proven success with enterprise prospecting and lead generation through research, networking, and cold calling.
• Exceptional verbal and written communication skills.
• Ability to analyze market trends, identify opportunities, and make data-driven decisions.
• Familiarity with the AI landscape, key players, and emerging trends.

Culture & Benefits

• Values include trust, customer obsession, craftsmanship, intensity, and family.
• Flexible unlimited paid time off.
• Medical, dental, vision, life insurance, and disability benefits for eligible full-time employees.
• Retirement plan, parental leave, and fertility and family-building benefits, varying by country of employment.
• Discretionary benefit stipend, meals, snacks, coffee, and equity plan eligibility.
• Supportive environment focused on balancing high performance with family and personal commitments.