Enterprise Sales Director - Majors
Sierra · Canada - Remote · Toronto
Applied AIremotedirector$264k–$282k
At a glance
Highlights
- Drive complex 6- and 7-figure enterprise deals for customer-facing AI agents.
- Build durable C-suite relationships across the world's biggest brands.
- Partner with co-founders Bret Taylor and Clay Bavor on exec engagement.
What they offer
- Flexible unlimited paid time off
- Medical, dental and vision benefits
- Life insurance and disability benefits
- Retirement plan
- Parental leave
- Fertility and family building benefits through Carrot
- Lunch, snacks and coffee
- Discretionary benefit stipend
- Equity
Ideal candidate
Seasoned enterprise seller who thrives on autonomy, C-suite relationships, and closing complex large deals. Analytical, AI-native, and customer-obsessed with high craftsmanship and intensity.
Requirements
- 8-10 years of enterprise customer-facing sales experience closing large accounts
- Experience managing $1M+ quota and running 6- and 7-figure ACV deals end-to-end
- Proven ability to multi-thread and build trusted C-suite relationships
- Exceptional verbal and written communication skills
- Analytical mindset with data-driven decision making
- Familiarity with AI landscape, key players and emerging trends
Lab profile
About Sierra
Leading platform for customer-facing AI agents for global enterprise brands.
What they build
- Platform for customer-facing AI agents
Known for
- Enterprise customer service transformation
- Trusted by major global brands
- Voice AI and agent analytics
Key facts
- Headquartered in San Francisco
- Offices across North America, Europe, and Asia
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