About this role
Sierra is seeking an Enterprise Sales Director to lead complex strategic deals and expand customer relationships across Canada on a remote basis. This full-time position suits an experienced sales professional with a strong background in managing multi-million-dollar accounts and leveraging AI-native sales processes.
Role Overview
As an Enterprise Sales Director, the individual will architect Sierra's most complex deals involving multi-business unit and multi-geography opportunities. The role requires designing sophisticated deal structures, managing risk, and operating closely with the customer's internal team. The candidate will regularly engage executive buyers at the C-suite level and partner directly with company co-founders during strategic customer pitches.
Key Responsibilities
Requirements
Nice to Have
Salary and Benefits
About the Company
Sierra creates customer-facing artificial intelligence agents utilized by major global brands like The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. Co-founded by industry veterans Bret Taylor and Clay Bavor, the organization operates under core values that include Trust, Customer Obsession, Craftsmanship, Intensity, and Family.
How to Apply
Interested candidates should visit the official Sierra careers page to submit an application for this remote opportunity.
Questions candidates ask
What is the salary range for the Enterprise Sales Director position?
The annual salary for this role is between $375,000 and $430,000 CAD.
Is this position remote?
Yes, this role is listed as Canada - Remote.
How many years of experience are required for this role?
Candidates must have 10 to 12+ years of enterprise and strategic sales experience handling large, complex accounts.
What benefits are offered with this full-time job?
Full-time employees receive flexible paid time off, medical, dental, vision, life insurance, disability benefits, retirement plans, parental leave, fertility benefits through Carrot, a discretionary stipend, and equity plan eligibility.
Who co-founded Sierra?
Sierra was co-founded by Bret Taylor and Clay Bavor.