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Enterprise Sales Director - Majors

SierraUS - RemoteSales
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Salary
$300K - $345K USD
Job type
Full-time
Work mode
Remote
Posted
22 Jul 2026
Status
Open · checked 9d ago

About this role

Role Overview

The Enterprise Sales Director - Majors position at Sierra is a remote, full-time sales role focused on driving complex enterprise software deals within the United States. This opportunity suits an experienced sales professional with a background in managing large accounts and navigating executive-level relationships.

Key Responsibilities

Independently manage a broad enterprise book of business, taking ownership of high-value deal cycles from initial prospecting through to the final close.
Engage with Vice Presidents and build durable relationships across customer C-suites to earn quick credibility with new stakeholders.
Identify and address deal risks early while constructing rigorous stakeholder maps for assigned accounts.
Partner with leadership on pricing, escalation timing, executive alignment, and overall deal strategy by bringing an informed perspective to the table.
Involve company co-founders strategically for executive engagement when necessary to advance a deal.
Act as a visible and steady leader on deal teams to proactively elevate standards.
Operate as an AI-native seller by utilizing artificial intelligence tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.

Requirements

Possess 8 to 10 years of enterprise customer-facing sales experience focused on identifying and closing large accounts.
Demonstrate past success in managing a quota of $1 million or more while running complex, end-to-end 6- and 7-figure ACV deals.
Show proven ability to multi-thread and cultivate trusted relationships across customer C-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 and account management
C-suite relationship building and multi-threading
Deal strategy, risk management, and pricing negotiation
AI-native sales tools for account research, outreach, call summarization, and pipeline forecasting
Market analysis and data-driven decision making

Salary and Benefits

Annual salary ranging from $300,000 to $345,000 USD.
Flexible, unlimited paid time off.
Comprehensive medical, dental, and vision coverage for employees and their families.
Life insurance and disability benefits.
Retirement plan options dependent on the country of employment.
Parental leave along with fertility and family building benefits through Carrot.
Office perks including lunch, snacks, and coffee.
Discretionary benefit stipend and free alphorn lessons.
Eligibility to participate in company equity plans.

About the Company

Sierra is a leading platform for customer-facing AI agents that collaborates with major global brands such as The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank to transform customer service and business growth. Co-founded by Bret Taylor and Clay Bavor, the organization is guided by core values emphasizing 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 - Majors role?

The annual salary for this position is between $300,000 and $345,000 USD.

Is this a remote position?

Yes, this role is listed as US - Remote.

What level of experience is required for this sales position?

Candidates must have 8 to 10 years of enterprise customer-facing sales experience, including managing a $1 million plus quota and closing large 6- and 7-figure ACV deals.

What benefits are offered to full-time employees?

Benefits include flexible unlimited PTO, medical, dental, vision, life insurance, disability benefits, retirement plans, parental leave, Carrot fertility benefits, a discretionary stipend, and equity plan eligibility.

How should I apply for this job?

You should apply directly on the official company careers page.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site