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Enterprise Sales Director

SierraUS - RemoteSales
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Salary
$280K - $300K USD
Job type
Full-time
Work mode
Remote
Posted
5 Aug 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 focused on driving revenue and building relationships with top enterprise clients. This opportunity suits an experienced sales professional with a strong background in managing complex, high-value deals within the technology sector.

Key Responsibilities

Identify and target potential enterprise customers through cold calling, networking, and research to build a robust pipeline.
Cultivate strong relationships with key decision-makers and serve as the primary point of contact for major clients.
Lead contract negotiations, address objections, and close complex deals efficiently in partnership with legal and finance teams.
Formulate and execute comprehensive sales strategies, create tailored proposals, and collaborate with marketing on campaigns.
Partner cross-functionally with go-to-market, product, technical, and operations teams to deliver customer solutions.
Function as an AI-native seller by utilizing artificial intelligence tools for account research, personalized outreach, call summarization, and pipeline forecasting.

Requirements

Possess 6 to 8 years of professional experience in an enterprise, customer-facing sales role focused on identifying and closing large accounts.
Bring proven enterprise experience managing quotas of $1 million or more while executing complex 6- and 7-figure ACV deals.
Demonstrate exceptional written and verbal communication skills.
Apply an analytical mindset to evaluate market trends, spot opportunities, and make data-driven decisions.
Maintain a proven track record in prospecting and lead generation targeting enterprise clients.

Nice to Have

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

Skills and Tools

Enterprise sales strategies and execution
Lead generation, prospecting, and cold calling
Contract negotiation and closing complex agreements
Cross-functional collaboration with GTM, product, and technical teams
Data-driven analysis of market trends
AI-powered sales tools for outreach, forecasting, and research

Salary and Benefits

Annual base salary ranging from $280,000 to $300,000 USD.
Flexible, unlimited paid time off.
Comprehensive medical, dental, and vision insurance for employees and their families.
Life insurance and disability benefits.
Country-dependent retirement plans and eligible equity plan participation.
Parental leave alongside fertility and family building benefits via Carrot.
On-site lunch, snacks, and coffee (applicable to office locations), plus a discretionary benefit stipend and free alphorn lessons.

About the Company

Sierra is the leading platform for customer-facing AI agents, collaborating with global brands like The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. Co-founded by industry veterans Bret Taylor and Clay Bavor, the company is driven by a culture built on 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 position.

Questions candidates ask

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

The annual base salary for this position is between $280,000 and $300,000 USD.

Is this position remote?

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

How many years of experience are required?

Applicants must have 6 to 8 years of experience in an enterprise customer-facing sales role closing large accounts.

What benefits does Sierra offer full-time employees?

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

What does it mean to be an AI-native seller at Sierra?

An AI-native seller leverages artificial intelligence tools across the entire sales cycle—such as for account research, personalized outreach, call summarization, and pipeline forecasting—to automate low-value tasks and focus on high-value relationships.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site