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Enterprise Sales Leader, Consumer Business Services

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

About this role

Role Overview

Sierra is seeking an Enterprise Sales Leader for the Consumer Business Services team to direct regional sales performance and guide high-performing account executives. This remote opportunity is well-suited for a seasoned sales professional with a strong background in managing complex enterprise deals and developing talent within the technology sector.

Key Responsibilities

Build, onboard, and mentor a high-performing team of account executives within the assigned region.
Direct regional performance by maintaining forecast accuracy, inspecting pipeline quality, and partnering with RevOps.
Participate actively in key customer and prospect meetings to help navigate complex buying committees.
Support deal execution through strategic pricing, negotiation oversight, and close strategies.

Requirements

Ten to fifteen plus years of extensive experience in enterprise customer-facing sales roles.
Five or more years of leadership experience managing and developing enterprise sales teams.
Proven track record of running end-to-end complex deals valued at one million dollars or more.
Exceptional verbal and written communication abilities.
Strong analytical mindset for evaluating market trends and making data-driven decisions.

Nice to Have

Familiarity with the artificial intelligence landscape, key players, emerging trends, and AI tooling.
Background in building go-to-market strategies and sales motions from scratch or early-stage growth.

Skills and Tools

Enterprise sales strategy and pipeline management
Revenue operations collaboration and data analysis
Deal navigation, pricing, and negotiation
Team leadership and coaching

Salary and Benefits

Annual salary ranging from $450,000 to $470,000 in USD.
Flexible, unlimited paid time off.
Comprehensive medical, dental, and vision coverage for employees and families.
Life insurance, disability benefits, and retirement plans.
Parental leave alongside fertility and family-building benefits through Carrot.
Discretionary benefit stipend and participation in equity plans.

About the Company

Sierra is a leading platform providing customer-facing artificial intelligence agents for major global brands. Co-founded by industry veterans Bret Taylor and Clay Bavor, the enterprise operates on core values centered around 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 this role?

The annual salary for this position is between $450,000 and $470,000 USD.

Is this a remote position?

Yes, this position is designated as US - Remote.

What level of leadership experience is required?

Candidates must have 5+ years of experience managing, mentoring, and developing high-performing enterprise sales teams, alongside 10-15+ years of overall enterprise sales experience.

What benefits does Sierra offer full-time employees?

Sierra provides flexible paid time off, medical, dental, vision, life insurance, disability benefits, retirement plans, parental leave, fertility benefits through Carrot, equity plan participation, and a discretionary benefit stipend.

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