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Enterprise Sales Director - Majors, Retail

SierraUS - RemoteSales
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Salary
$260K - $325K USD
Job type
Full-time
Work mode
Remote
Posted
10 Jul 2026
Status
Open · checked 9d ago

About this role

Role Overview

The Enterprise Sales Director - Majors, Retail role at Sierra is an opportunity for an experienced sales professional to drive complex enterprise deals remotely within the United States. This position suits an autonomous sales leader ready to manage major retail accounts and help transform customer-facing AI agent adoption.

Key Responsibilities

Independently manage a broad enterprise book with strong autonomy, driving six- and seven-figure deal cycles from prospecting to close.
Engage with senior leadership by leading VP-level conversations and building durable C-suite relationships across customer organizations.
Identify and manage deal risk early while building rigorous stakeholder maps for accounts.
Partner with managers on pricing, escalation timing, executive alignment, and deal strategy, bringing a distinct point of view to the table.
Engage company co-founders strategically when executive involvement helps move a deal forward.
Act as a visible, steady leader on deal teams to proactively elevate standards.
Operate as an AI-native seller by utilizing AI tools across the entire sales cycle for tasks like account research, personalized outreach, call summarization, and pipeline forecasting.

Requirements

Possess eight to ten years of enterprise customer-facing sales experience focused on identifying and closing large accounts.
Bring proven experience managing a quota of one million dollars or more while running complex, end-to-end six- and seven-figure annual contract value deals.
Demonstrate a proven ability to multi-thread and establish trusted relationships across customer executive suites.
Exhibit exceptional verbal and written communication skills.
Maintain an analytical mindset capable of analyzing market trends, spotting opportunities, and making data-driven decisions.

Nice to Have

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

Skills and Tools

Enterprise sales management and end-to-end deal execution
Executive C-suite engagement and multi-threading
Deal risk management and strategic stakeholder mapping
Data-driven market analysis and pipeline forecasting
AI-native sales enablement tools for outreach and research

Salary and Benefits

Annual base salary ranging from $260,000 to $325,000 in USD.
Flexible, unlimited paid time off.
Comprehensive medical, dental, and vision insurance for employees and their families.
Life insurance and disability benefits.
Retirement plans based on the country of employment.
Parental leave alongside fertility and family-building benefits through Carrot.
Office perks including lunch, snacks, and coffee for local visits, plus a discretionary benefit stipend.
Eligibility to participate in company equity plans and even free alphorn lessons.

About the Company

Sierra is a leading platform specializing in customer-facing artificial intelligence 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 organization is guided by core cultural values emphasizing trust, customer obsession, craftsmanship, intensity, and family balance. While maintaining an in-person hub in San Francisco, Sierra continues to grow its presence across North America, Europe, and Asia, building technology designed to make shopping effortless, personal, and delightful.

How to Apply

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

Questions candidates ask

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

The annual base salary ranges from $260,000 to $325,000 USD.

Is this job remote?

Yes, this position is listed as US - Remote.

How many years of experience are required?

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

What specific sales quota experience is expected?

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

What benefits are offered for full-time employees?

Benefits include flexible unlimited paid time off, medical, dental, and vision insurance, life and disability insurance, retirement plans, parental leave, Carrot fertility benefits, a discretionary benefit stipend, equity plan eligibility, and free alphorn lessons.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site