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Enterprise Sales Leader, Retail

SierraUS - RemoteSales
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Salary
$450K - $470K USD
Job type
Full-time
Work mode
Remote
Posted
10 Jul 2026
Status
Open · checked 7d ago

About this role

Role Overview

Sierra is seeking an Enterprise Sales Leader, Retail to join their team in a remote capacity within the United States. This position is ideal for an experienced sales professional with a strong background in managing enterprise accounts and leading high-performing teams within the retail technology space.

Key Responsibilities

Hire, onboard, and develop Account Executives across the region while coaching team members on deal strategy and pipeline execution.
Maintain accountability, foster collaboration, and identify future leaders within the sales organization.
Own regional performance metrics, deliver accurate forecasts, and inspect pipeline quality to unblock stalled opportunities.
Collaborate closely with RevOps to maintain clean data and generate actionable business insights.
Participate actively in key customer meetings to help sales representatives navigate complex buying committees and late-stage deals.
Support pricing strategy, negotiations, and closing procedures for major accounts.

Requirements

Possess 10 to 15+ years of extensive experience in enterprise, customer-facing sales roles focusing on identifying and closing large accounts.
Bring a minimum of 5 years of people leadership experience managing, mentoring, and developing enterprise sales teams.
Demonstrate a proven track record of running and managing end-to-end complex deals valued at $1 million or more.
Exhibit exceptional verbal and written communication abilities.
Apply an analytical mindset to evaluate market trends, spot growth opportunities, and execute data-driven decisions.

Nice to Have

Familiarity with the artificial intelligence landscape, emerging trends, and fluency in AI tooling and workflows.
Direct experience in building go-to-market strategies, sales teams, and sales motions from the ground up or during early-stage growth.

Skills and Tools

Enterprise account management and closing strategies
Complex deal negotiation ($1M+)
Sales pipeline management and forecasting
Team leadership and mentorship
Data-driven market analysis

Salary and Benefits

Annual salary ranging from $450,000 to $470,000 USD
Flexible, unlimited paid time off policy
Comprehensive medical, dental, and vision coverage for employees and their families
Life insurance and disability benefits
Retirement plan options based on the country of employment
Parental leave alongside fertility and family building benefits through Carrot
Discretionary benefit stipend and free alphorn lessons
Eligibility to participate in company equity plans

About the Company

Sierra builds the leading platform for customer-facing artificial intelligence agents, partnering with major global brands to transform customer service and business growth. Co-founded by industry veterans Bret Taylor and Clay Bavor, the company is anchored by core values of trust, customer obsession, craftsmanship, intensity, and a commitment to family balance.

How to Apply

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

Questions candidates ask

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

The annual salary for this position ranges from $450,000 to $470,000 USD.

Is this job remote?

Yes, this is a remote position based in the United States.

How many years of experience are required for this job?

Candidates must have 10 to 15+ years of enterprise customer-facing sales experience, including at least 5 years of people leadership experience managing enterprise sales teams.

What benefits are provided to full-time employees?

Full-time employees receive flexible paid time off, medical, dental, vision, life and disability insurance, retirement plans, parental leave, fertility benefits through Carrot, a discretionary stipend, equity eligibility, and more.

How do I apply for this position?

You can apply by visiting the official company careers page on the Sierra website.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site