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Enterprise Sales Director - Strategic, Retail

SierraUS - RemoteSales
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Salary
$315K - $370K USD
Job type
Full-time
Work mode
Remote
Posted
5 Aug 2026
Status
Open · checked 7d ago

About this role

Role Overview

Sierra is seeking an Enterprise Sales Director - Strategic, Retail to join their remote team in the US. This full-time position suits an experienced sales professional ready to drive revenue and transformation for top global retail brands using advanced customer-facing AI agents.

Key Responsibilities

Architect and lead the most complex, multi-business unit, and multi-geographical deals with sophisticated structures and precise risk management.
Establish trusted partnerships across customer C-suites and working teams while operating as an integral part of the client's team.
Collaborate directly with company co-founders during customer presentations, applying expert conviction and messaging.
Apply exacting craft to positioning, timing, and communication across all interactions to influence overarching sales strategies.
Utilize AI tools throughout the sales cycle for account research, personalized outreach, call summarization, and pipeline forecasting to maximize efficiency.

Requirements

Ten to twelve plus years of enterprise and strategic sales experience managing the largest and most complex accounts.
Proven track record of closing multi-million-dollar, multi-stakeholder deals across various business units and regions.
Demonstrated history of managing a quota exceeding $1 million and handling end-to-end six- and seven-figure annual contract value transactions.
Established C-suite relationships with the executive presence to engage peer-to-peer with buyers.
Strong expertise in complex deal structuring, pricing, and navigating risk with precision and trust.

Nice to Have

Comprehensive familiarity with the artificial intelligence landscape and the capability to communicate credibly with both technical and business audiences.
Prior background working closely alongside company founders and executives in front of strategic clients.

Skills and Tools

Enterprise sales strategy
Complex deal structuring and risk management
C-suite relationship building
AI-native sales tools for forecasting and research
Executive communication and positioning

Salary and Benefits

Annual salary range between $315,000 and $370,000 in USD.
Flexible and unlimited paid time off.
Comprehensive medical, dental, and vision coverage for employees and families.
Life insurance, disability benefits, and retirement plan options.
Parental leave alongside fertility and family building benefits through Carrot.
Discretionary benefit stipend, free alphorn lessons, and daily lunch, snacks, and coffee.
Participation in company equity plans for eligible full-time employees.

About the Company

Sierra is a leading platform providing customer-facing AI agents that help global brands transform consumer engagement and business growth. Co-founded by Bret Taylor and Clay Bavor, the company values trust, customer obsession, craftsmanship, intensity, and family balance. Sierra operates primarily out of San Francisco alongside growing hubs across North America, Europe, and Asia.

How to Apply

Interested candidates should visit the official Sierra careers page to submit an application.

Questions candidates ask

What is the salary for the Enterprise Sales Director role?

The annual salary ranges from $315,000 to $370,000 USD.

Is this position remote?

Yes, this role is designated as US - Remote.

How many years of experience are required?

Candidates need 10-12+ years of enterprise and strategic sales experience managing complex accounts.

What benefits are offered to full-time employees?

Benefits include flexible paid time off, medical, dental, and vision coverage, life and disability insurance, parental leave, fertility benefits through Carrot, a discretionary benefit stipend, equity plan participation, and daily meals and snacks.

Who founded Sierra?

Sierra was co-founded by Bret Taylor and Clay Bavor.

Ready to apply?

The application is on the official Sierra careers page.

Apply on company site