Remote opportunity at
SierraEnterprise Sales Leader, Retail
Sierra is seeking an Enterprise Sales Leader, Retail to head up its retail sales initiatives. Sierra operates a leading customer-facing artificial intelligence agent platform utilized by…
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About This Role
Sierra is seeking an Enterprise Sales Leader, Retail to head up its retail sales initiatives. Sierra operates a leading customer-facing artificial intelligence agent platform utilized by major brands like The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank to improve consumer interactions and business growth. Co-founded by Bret Taylor and Clay Bavor, the organization is anchored by core principles such as trust, customer obsession, craftsmanship, intensity, and family. This position…
Job Description
Sierra is seeking an Enterprise Sales Leader, Retail to head up its retail sales initiatives. Sierra operates a leading customer-facing artificial intelligence agent platform utilized by major brands like The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank to improve consumer interactions and business growth. Co-founded by Bret Taylor and Clay Bavor, the organization is anchored by core principles such as trust, customer obsession, craftsmanship, intensity, and family.
This position involves driving regional performance, guiding deal executions, and managing a team of account executives within the retail sector. The retail vertical covers apparel, beauty, grocery, big-box, home and auto, consumer services, marketplaces, and consumer technology. Artificial intelligence agents assist millions of shoppers with tasks ranging from order tracking and product discovery to bookings and issue resolution, while also generating revenue through personalized recommendations, cart recovery, and win-back campaigns.
Responsibilities
- Hire, onboard, mentor, and foster the professional growth of account executives across the region
- Coach sales representatives regarding pipeline management, sales execution, and deal strategy
- Manage regional performance to hit assigned revenue targets and maintain accurate forecasts
- Inspect pipeline health, help advance stalled opportunities, and ensure consistent sales process execution
- Collaborate with Revenue Operations to maintain reliable data insights
- Participate directly in key prospect and customer meetings, guiding teams through complex buying committees and late-stage transactions
- Assist with pricing structures, negotiations, and closing strategies
Requirements
- Possess 10 to 15+ years of background in enterprise-facing sales roles focusing on identifying and closing major accounts
- Bring at least 5 years of experience managing, mentoring, and scaling high-performing enterprise sales teams
- Demonstrate hands-on experience handling end-to-end complex deals valued at $1M or greater
- Display exceptional verbal and written communication abilities
- Exhibit strong analytical skills to interpret market movements, spot opportunities, and execute data-driven choices
Qualifications
- Familiarity with the artificial intelligence ecosystem, key market participants, emerging patterns, and fluent use of AI workflows and tooling
- Background in formulating go-to-market strategies, building sales teams, and launching sales motions from the ground up or during early-stage expansion
Core Skills
Benefits
- Flexible and unlimited paid time off
- Medical, dental, and vision insurance coverage for employees and dependents
- Life insurance and disability protection
- Retirement savings plan tied to the country of employment
- Paid parental leave
- Family building and fertility support through Carrot
- Provided lunch, snacks, and coffee
- Discretionary benefit allowance for personal spending
- Complimentary alphorn lessons
- Equity plan participation for eligible full-time staff
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the salary for the Enterprise Sales Leader, Retail role?
The salary for this position is between USD 450,000 and 470,000 per year.
What is the employment type?
This position is full-time.
What is the location or remote policy for this job?
The job posting lists the location as remote.
Sample Interview Questions
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