Enterprise Sales Director - Majors
Sierra · Canada - Remote · Toronto
CHECKED 1H AGO
Applied AIremotedirector$214k–$260k
At a glance
Highlights
- Lead complex enterprise deals for Sierra’s customer-facing AI agent platform.
- Partner with global brands like GAP, SoFi and SoftBank to transform service.
- Operate as an 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
- Commission
Ideal candidate
A seasoned enterprise seller with 8-10 years closing complex deals who thrives on C-suite relationships, operates with autonomy, and is passionate about AI-driven customer transformation.
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 6- and 7-figure ACV deals
- Proven ability to multi-thread and build trusted relationships across customer C-suites
- Exceptional verbal and written communication
- Analytical mindset with data-driven decision making
- 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