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Enterprise Sales Director - Majors

SierraCanada - RemoteSales
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Salary
$305K - $370K CAD
Job type
Full-time
Work mode
Remote
Posted
22 Jul 2026
Status
Open · checked 7d ago

About this role

Role Overview

The Enterprise Sales Director position at Sierra is a remote, full-time sales role based in Canada that focuses on driving complex enterprise deals for customer-facing AI agents. This opportunity suits an experienced, results-driven sales professional who excels at managing high-value accounts and building relationships with executive leadership.

Key Responsibilities

Independently drive complex enterprise deals end-to-end, managing a broad enterprise book with strong autonomy for 6- and 7-figure deal cycles from prospecting to close.
Multi-thread to the C-suite by leading VP-level conversations, building durable relationships across customer organizations, and earning quick credibility with new stakeholders.
Manage risk proactively by identifying deal risks early and building rigorous stakeholder maps for assigned accounts.
Make hard calls regarding pricing, escalation timing, executive alignment, and deal strategy in partnership with management.
Leverage leadership and co-founders effectively for executive engagement when needed to advance deals.
Raise the bar by acting as a visible, steady leader on deal teams and proactively elevating team standards.
Operate as an AI-native seller by leveraging AI tools across the sales cycle for research, outreach, forecasting, and deal execution.

Requirements

Possess 8 to 10 years of enterprise customer-facing sales experience identifying and closing large accounts.
Bring direct experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Demonstrate a proven ability to multi-thread and build trusted relationships across customer C-suites.
Exhibit exceptional verbal and written communication skills alongside an analytical mindset to make data-driven decisions.

Nice to Have

Familiarity with the AI landscape, key players, and emerging trends.

Skills and Tools

Enterprise sales management
C-suite relationship building
Deal risk assessment and strategy
AI sales productivity tools
Market and data analysis

Salary and Benefits

Annual salary ranging from $305,000 to $370,000 CAD
Flexible, unlimited paid time off
Comprehensive medical, dental, and vision benefits for employees and their families
Life insurance and disability benefits
Country-dependent retirement plan
Parental leave along with fertility and family building benefits through Carrot
Discretionary benefit stipend
Eligibility to participate in company equity plans

About the Company

Sierra is the leading platform for customer-facing AI agents, collaborating with major global brands like The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. Co-founded by Bret Taylor and Clay Bavor, the company is guided by core 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 for this remote role.

Questions candidates ask

Is this position fully remote?

Yes, this role is listed as Canada - Remote.

What is the salary range for the Enterprise Sales Director role?

The annual salary ranges from $305,000 to $370,000 CAD.

How many years of experience are required?

Candidates need 8 to 10 years of enterprise customer-facing sales experience.

What kind of quota management experience is expected?

Applicants must have experience managing a $1M+ quota and running complex 6- and 7-figure ACV deals.

Who founded Sierra?

Sierra was co-founded by Bret Taylor and Clay Bavor.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site