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Enterprise Sales Director - Strategic, Retail

SierraCanada - RemoteSales
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Salary
$375K - $430K CAD
Job type
Full-time
Work mode
Remote
Posted
5 Aug 2026
Status
Open · checked 7d ago

About this role

Role Overview

Sierra is seeking an Enterprise Sales Director for Strategic Retail to lead complex multi-BU and multi-geo sales opportunities across Canada on a remote basis. This remote full-time role is well-suited for a seasoned sales professional with extensive experience managing high-value enterprise accounts and driving top-line revenue growth through customer-facing AI technology.

Key Responsibilities

Architect and lead Sierra's most complex, multi-million dollar deals involving multiple business units and geographic regions.
Build and maintain trusted relationships directly with customer C-suites and working teams.
Partner directly with company co-founders in front of strategic clients, pitching with high-level expertise and conviction.
Apply exacting standards of precision in messaging, timing, and strategic account positioning.
Influence go-to-market strategies for key retail accounts and establish best practices for the broader sales organization.
Function as an AI-native seller by utilizing modern AI tools for account research, pipeline forecasting, outreach, and deal execution.

Requirements

Bring 10-12+ years of enterprise and strategic sales experience handling the most demanding accounts.
Proven track record of successfully closing multi-million-dollar deals involving diverse stakeholders and geographies.
Demonstrated history of managing quotas of $1 million or more while executing complex 6- and 7-figure ACV deals.
Possess deep C-suite connections and the executive presence required to engage peer-to-peer with senior buyers.
Advanced expertise in complex pricing, risk navigation, and deal structuring.
Exceptional executive communication skills built on a foundation of trust and precision.

Nice to Have

Strong familiarity with the broader artificial intelligence landscape, with the ability to converse credibly with technical and business leaders alike.
Direct exposure to working alongside executives and founders during customer pitches.

Skills and Tools

Enterprise sales strategy
Complex deal structuring and pricing
Executive communication and relationship building
AI-native sales and productivity tools
Pipeline forecasting and account research

Salary and Benefits

Annual base salary ranging between $375,000 and $430,000 CAD
Flexible, unlimited paid time off policy
Comprehensive medical, dental, and vision insurance coverage for employees and dependents
Life insurance and disability benefits
Country-dependent retirement plan options
Parental leave alongside fertility and family building support through Carrot
Discretionary benefit stipend
Participation in company equity plans for eligible full-time staff

About the Company

Sierra develops leading customer-facing AI agents that help global brands transform customer engagement, support, and revenue generation. Co-founded by industry veterans Bret Taylor and Clay Bavor, the company fosters an internal culture driven by trust, customer obsession, craftsmanship, intensity, and family values.

How to Apply

Interested candidates should submit their application directly on the official Sierra careers page to be considered for this remote opportunity.

Questions candidates ask

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

The annual salary for this position ranges from $375,000 to $430,000 CAD.

Is this position remote?

Yes, this role is listed as Canada - Remote.

How many years of experience are required?

Candidates must have 10-12+ years of enterprise or strategic sales experience handling large, complex accounts.

What benefits are provided for full-time employees?

Benefits include flexible unlimited paid time off, medical, dental, vision, life and disability insurance, retirement plans, parental leave, Carrot family-building benefits, a discretionary stipend, and equity plan participation.

How do I apply for this job?

You should apply directly on the official Sierra careers page.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site