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Enterprise Sales Director - Strategic

SierraUS - RemoteSales
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Salary
$300K - $345K 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 - Strategic position at Sierra is a remote, full-time opportunity based in the US that involves leading major multi-BU and multi-geo sales opportunities for customer-facing AI agents. This role is well-suited for a seasoned sales professional with extensive experience managing high-value, complex deals and building trusted executive relationships.

Key Responsibilities

Architect and lead Sierra's most complex, multi-business unit, and multi-geographic opportunities with precision and risk management.
Act as an extension of the customer's team by establishing trusted advisory relationships across C-suites and working groups.
Collaborate closely with company co-founders during customer pitches, leveraging founder-level expertise and messaging.
Shape overarching sales strategy for top-tier accounts and establish performance standards for the broader sales organization.
Utilize AI-native tools across the entire sales cycle—from account research and outreach to forecasting and deal execution—to automate low-value tasks and prioritize customer relationships.

Requirements

Bring 10-12+ years of strategic and enterprise sales experience managing the largest and most complex accounts.
Proven track record of successfully closing multi-million-dollar deals across multiple stakeholders and geographies.
Demonstrated history of managing a quota of $1M+ and running end-to-end 6- and 7-figure annual contract value (ACV) deals.
Possess established C-suite relationships and the executive presence required to engage directly with high-level buyers.
Expert knowledge in complex deal structuring, pricing models, and risk navigation.

Nice to Have

Comprehensive familiarity with the artificial intelligence landscape, including the ability to communicate credibly with both technical and business audiences.
Prior background working alongside executive leadership and founders during customer-facing strategic engagements.

Skills and Tools

Enterprise sales strategy and execution
Complex deal structuring, pricing, and risk management
Executive communication and C-suite relationship building
AI-native sales tooling for pipeline forecasting, research, and deal execution

Salary and Benefits

Annual salary range between $300,000 and $345,000 USD.
Flexible, unlimited paid time off.
Comprehensive medical, dental, and vision coverage for employees and their families.
Life insurance, disability benefits, and applicable retirement plans.
Parental leave alongside fertility and family-building support via Carrot.
Daily lunch, snacks, coffee, and a discretionary benefit stipend.
Access to company equity plans and even free alphorn lessons.

About the Company

Sierra is a prominent platform specializing in customer-facing AI agents, collaborating with major global brands like The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. Co-founded by industry veterans Bret Taylor and Clay Bavor, the organization is anchored by core values including trust, customer obsession, craftsmanship, intensity, and family support. While maintaining physical offices across North America, Europe, and Asia, the company champions a culture dedicated to balancing professional intensity with personal well-being.

How to Apply

Interested candidates should submit their application directly through the official Sierra careers page.

Questions candidates ask

What is the salary for the Enterprise Sales Director - Strategic role?

The annual salary for this position ranges from $300,000 to $345,000 USD.

Is this a remote position?

Yes, this role is designated as US - Remote.

How many years of experience are required for this job?

Applicants must bring 10-12+ years of enterprise and strategic sales experience managing complex accounts.

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, 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