Enterprise Sales Director - Strategic, Retail
SierraVisit Sierra website
Enterprise conversational-AI platform that helps businesses build and operate customer-experience agents across channels.
San Francisco, United States
About Sierra
Sierra provides an AI platform for businesses to build, deploy, analyze, and optimize customer-facing agents across chat, SMS, WhatsApp, email, voice, and ChatGPT.
Skills
Candidate Availability
Required and preferred rules are kept separate and reflect the wording in the original posting.
About the Role
You will lead complex, multi-business-unit and multi-geography enterprise opportunities in retail. You will build trusted C-suite relationships, structure and negotiate deals, manage risk, refine account strategy, and use AI tools throughout the sales cycle to improve research, outreach, forecasting, and execution.
Requirements
- 10-12+ years of enterprise or strategic sales experience
- Experience closing multi-million-dollar, multi-stakeholder deals across business units and geographies
- Experience managing a $1M+ quota and complex 6- and 7-figure ACV deals
- Deep C-suite relationships
- Expertise in complex deal structuring, risk navigation, and pricing
- Exceptional executive communication
Responsibilities
- Lead complex multi-business-unit and multi-geography enterprise deals
- Build trusted relationships with customer executives and working teams
- Engage company founders in customer-facing sales conversations
- Develop precise messaging, positioning, and deal timing
- Influence strategy for key accounts
- Use AI tools for account research, outreach, call summaries, forecasting, and deal execution
Benefits
- Equity
- Flexible unlimited paid time off
- Medical, dental, and vision benefits for employees and their families
- Life insurance and disability benefits
- Retirement plan dependent on country of employment
- Parental leave
- Fertility and family-building benefits through Carrot
- Lunch, snacks, and coffee
- Discretionary benefit stipend
- Free alphorn lessons