Enterprise Sales Director
Sierra · Canada - Remote · Toronto
CHECKED 2H AGO
Applied AIremotedirector$228k–$260k
At a glance
Highlights
- Lead complex 6- and 7-figure deals for AI agents used by top global brands.
- Serve as primary contact for largest enterprise customers driving deployments.
- Operate as AI-native seller automating tasks to focus on relationships.
What they offer
- Flexible (unlimited) paid time off
- Medical, dental, and vision benefits for you and family
- Life insurance and disability benefits
- Retirement plan
- Parental leave
- Fertility and family building benefits through Carrot
- Lunch, snacks and coffee
- Discretionary benefit stipend
- Equity participation
Ideal candidate
Enterprise closer who thrives building trusted C-level relationships and winning complex deals. Analytical, driven communicator obsessed with customer outcomes and working smarter with AI.
Requirements
- 6-8 years in enterprise customer-facing sales, identifying and closing large accounts
- Experience managing $1M+ quota and running end-to-end 6- and 7-figure ACV deals
- Exceptional verbal and written communication skills
- Analytical mindset with data-driven decision making
- Proven track record prospecting enterprise clients via research, networking and cold calling
- remote policy
- in-person
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