About this role
Sierra is currently hiring an Enterprise Sales Director for a remote position based in Canada. This full-time role involves driving revenue growth, managing major enterprise accounts, and closing complex deals for a leading customer-facing AI agent platform. It is an ideal fit for an experienced sales professional with a strong background in navigating multi-figure enterprise quotas.
Role Overview
As an Enterprise Sales Director, the primary objective is to build new relationships with large enterprise customers and prospects to drive pipeline, revenue, and deployment capacity. The position requires operating as an AI-native seller by leveraging artificial intelligence tools across every stage of the sales cycle, from account research and personalized outreach to call summarization and pipeline forecasting. The individual will work collaboratively across the organization to deliver industry-leading products to major global brands.
Key Responsibilities
Requirements
Nice to Have
Skills and Tools
Salary and Benefits
About the Company
Sierra is a prominent platform for customer-facing artificial intelligence agents, partnering with globally recognized brands such as The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. Co-founded by industry veterans Bret Taylor and Clay Bavor, the organization is guided by core cultural values emphasizing trust, customer obsession, craftsmanship, intensity, and family balance.
How to Apply
Interested candidates should visit the official Sierra careers page to submit an application and learn more about open opportunities.
Questions candidates ask
What is the salary range for the Enterprise Sales Director position?
The annual salary for this full-time role ranges from $325,000 to $370,000 CAD.
Where is the job located?
This role is a remote position based in Canada.
What level of experience is required for this sales role?
Candidates must have 6 to 8 years of experience in an enterprise customer-facing sales role, including managing a $1M+ quota and complex 6- and 7-figure ACV deals.
What does it mean to be an AI-native seller at Sierra?
An AI-native seller leverages artificial intelligence tools across the entire sales cycle—including account research, personalized outreach, call summarization, and pipeline forecasting—to automate low-value tasks and prioritize high-value customer relationships.
What benefits are offered to full-time employees?
Full-time employees receive flexible paid time off, medical, dental, vision, life, and disability benefits, retirement plans, parental leave, Carrot fertility benefits, a discretionary benefit stipend, and free alphorn lessons, alongside potential equity plan participation.