Enterprise Account Executive (AI)

Location: Canada — Remote

Compensation: CA$370,000–CA$415,000 per year, plus equity and commission

Company

Develops a platform for customer-facing AI agents used by major brands, with a focus on healthcare agents that improve patient and policyholder interactions.

What you will do

• Independently manage complex enterprise sales cycles from prospecting through close, including six- and seven-figure deals.
• Manage a broad enterprise account portfolio and proactively identify and mitigate deal risk through rigorous stakeholder mapping.
• Lead VP-level and C-suite conversations, building trusted relationships across customer organizations.
• Partner with management and co-founders on pricing, escalation timing, executive alignment, and deal strategy.
• Act as a visible leader on deal teams and raise execution standards.
• Use AI tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.

Requirements

• 8–10 years of enterprise customer-facing sales experience identifying and closing large accounts.
• Experience managing a $1M+ quota and running end-to-end complex six- and seven-figure ACV deals.
• Proven ability to build trusted relationships and work across customer C-suites.
• Exceptional verbal and written communication skills.
• An analytical mindset, including analyzing market trends, identifying opportunities, and making data-driven decisions.
• Familiarity with the AI landscape, key players, and emerging trends.

Culture & Benefits

• Values include trust, customer obsession, craftsmanship, intensity, and family balance.
• Remote work from Canada with benefits that may vary by employment region.
• Unlimited paid time off, medical, dental, and vision benefits for employees and families.
• Life insurance, disability benefits, retirement plan, parental leave, and fertility and family-building benefits.
• Discretionary benefit stipend, meals, snacks, coffee, and free alphorn lessons.
• Eligible full-time employees may participate in equity plans.