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Enterprise Sales Director - Majors, Retail

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

About this role

Role Overview

The Enterprise Sales Director - Majors, Retail position at Sierra is a remote, full-time opportunity based in Canada that suits an experienced sales professional ready to drive complex enterprise deals. This role focuses on transforming customer engagement for major retail brands using advanced AI agent technology.

Key Responsibilities

Independently manage a broad enterprise book with strong autonomy, leading six- and seven-figure deal cycles from prospecting to close.
Engage in multi-threading with the C-suite, leading VP-level conversations and establishing durable relationships across customer organizations.
Proactively identify and manage deal risk while building rigorous stakeholder maps for accounts.
Partner with managers on pricing, escalation timing, executive alignment, and overall deal strategy.
Collaborate with company leadership and co-founders for strategic executive engagement during deals.
Act as a visible and steady leader on deal teams to consistently elevate the team standard.
Operate as an AI-native seller by leveraging artificial intelligence tools across the entire sales cycle for account research, personalized outreach, and pipeline forecasting.

Requirements

Possess 8 to 10 years of enterprise customer-facing sales experience focused on identifying and closing large accounts.
Demonstrate proven experience managing a quota of $1M+ and executing end-to-end complex 6- and 7-figure ACV deals.
Exhibit a proven ability to multi-thread and build trusted relationships with customer C-suites.
Display exceptional verbal and written communication skills.
Maintain an analytical mindset to review market trends, spot opportunities, and make data-driven decisions.

Nice to Have

Familiarity with the artificial intelligence landscape, key players, and emerging trends.

Skills and Tools

Enterprise sales methodologies and multi-threading
Complex 6- and 7-figure deal management
Executive C-suite relationship building
AI tools for account research, outreach, call summarization, and forecasting
Data-driven market analysis and strategic planning

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-specific retirement plans and parental leave.
Fertility and family-building benefits through Carrot.
Discretionary benefit stipends and free alphorn lessons.
Eligibility for company equity plans.

About the Company

Sierra is a leading platform for customer-facing AI agents, partnering with globally recognized brands such as The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The company was co-founded by Bret Taylor, former co-CEO of Salesforce and CTO of Facebook, and Clay Bavor, who spent 18 years leading Google Labs and major products like Google Lens and Project Starline. Sierra operates on core cultural values of trust, customer obsession, craftsmanship, intensity, and family.

How to Apply

Interested candidates should visit the official Sierra careers page to submit their application for this remote role.

Questions candidates ask

What is the salary for the Enterprise Sales Director position?

The salary ranges between $305,000 and $370,000 CAD per year.

Is this job remote?

Yes, this position is remote and based in Canada.

How much experience is required for this role?

Candidates need 8 to 10 years of enterprise customer-facing sales experience in identifying and closing large accounts.

What benefits does Sierra offer to full-time employees?

Sierra offers flexible unlimited paid time off, medical, dental, vision, life and disability insurance, parental leave, retirement plans, fertility benefits, discretionary stipends, and equity plan participation.

Who co-founded Sierra?

Sierra was co-founded by Bret Taylor, former co-CEO of Salesforce and CTO of Facebook, and Clay Bavor, former head of Google Labs.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site