Opportunity at
SierraEnterprise Sales Director, Retail
Sierra is seeking an Enterprise Sales Director to focus on the retail sector and help major consumer brands transform their customer engagement through AI agents. The…
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About This Role
Sierra is seeking an Enterprise Sales Director to focus on the retail sector and help major consumer brands transform their customer engagement through AI agents. The company builds platforms for customer-facing artificial intelligence used by global brands like The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. Co-founded by Bret Taylor and Clay Bavor, Sierra operates primarily as an in-person company based in San Francisco with additional offices in North…
Job Description
Sierra is seeking an Enterprise Sales Director to focus on the retail sector and help major consumer brands transform their customer engagement through AI agents. The company builds platforms for customer-facing artificial intelligence used by global brands like The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. Co-founded by Bret Taylor and Clay Bavor, Sierra operates primarily as an in-person company based in San Francisco with additional offices in North America, Europe, and Asia.
In this role, the selected candidate will drive revenue growth and pipeline expansion by partnering with retailers across apparel and beauty, grocery, big-box, home and auto, consumer services, marketplaces, and consumer technology. The position involves prospecting, managing complex multi-million dollar sales cycles, and operating as an AI-native seller to automate routine tasks and prioritize high-value customer relationships.
Responsibilities
- Identify and target potential enterprise clients through research, networking, and cold calling
- Establish and nurture relationships with key decision-makers and stakeholders among major accounts
- Lead complex negotiation processes and finalize agreements by coordinating with internal finance and legal departments
- Design and execute sales strategies to achieve or surpass revenue objectives
- Create customized sales proposals and presentations for enterprise prospects
- Partner with the marketing department to run effective presentations and sales campaigns
- Coordinate cross-functionally with product, technical, operations, and go-to-market teams
- Utilize AI tools across all stages of the sales cycle for account research, outreach, pipeline forecasting, and deal execution
Requirements
- Possess six to eight years of professional background in enterprise customer-facing sales closing large accounts
- Demonstrate experience managing a quota of one million dollars or higher
- Manage end-to-end complex deals with six- and seven-figure annual contract values
- Exhibit strong verbal and written communication abilities
- Apply an analytical mindset to review market data and drive data-backed decisions
- Show a proven background in prospecting and lead generation through cold calling and networking
Qualifications
- Familiarity with the artificial intelligence industry landscape, key market players, and emerging trends
Core Skills
Benefits
- Flexible and unlimited paid time off
- Medical, dental, and vision insurance coverage for employees and families
- Life and disability insurance plans
- Retirement plan options dependent on the country of employment
- Parental leave along with fertility and family building benefits via Carrot
- Daily lunch, snacks, and coffee provided on-site
- Discretionary benefit stipend
- Complimentary alphorn lessons
- Participation in equity plans 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 location and work policy for this role?
Sierra is primarily an in-person company based in San Francisco with growing offices across North America, Europe, and Asia. The posting indicates an on-site remote status.
What is the salary range for the Enterprise Sales Director position?
The salary range for this full-time role is USD 325,000 to 365,000 per year.
What level of experience is required for applicants?
Candidates must have 6 to 8 years of experience in an enterprise customer-facing sales role, including managing a $1M+ quota and handling end-to-end complex 6- and 7-figure ACV deals.
Are benefits offered with this position?
Yes, full-time employees receive flexible paid time off, medical, dental, and vision benefits, life and disability insurance, a retirement plan, parental leave, fertility benefits, meals and snacks on-site, a discretionary benefit stipend, alphorn lessons, and equity plan participation.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.
