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Enterprise Sales Director, Retail
SierraEnterprise Sales Director selling Sierra’s AI customer-experience platform to major retail brands. Building enterprise relationships, negotiating complex deals, and driving revenue through AI-native sales execution.
Posted 8/5/2026full-timeRemote • California, New York • 🇺🇸 United StatesLead💰 $260,000 - $280,000 per yearWebsite
Core Competencies
Role fitCore Competencies
Use this summary to align your resume positioning with the role.
Demonstrates expertise in enterprise sales, including identifying and closing large accounts, managing significant quotas, and developing tailored sales strategies. Proficient in leveraging AI tools for sales productivity and maintaining strong relationships with key decision-makers.
Highest-signal resume keywords
Enterprise Sales ExperienceLarge Account ManagementComplex Deal NegotiationSales Strategy DevelopmentAI Tools Utilization
ATS Keywords
Tailor your resumeApplicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills
Sales StrategyAccount ManagementCold CallingNegotiationMarket AnalysisData-Driven Decision MakingSales PresentationsPipeline ManagementQuota ManagementContract Navigation
Soft Skills
Verbal CommunicationWritten CommunicationRelationship BuildingProblem SolvingCollaboration
Tools & Technologies
AI ToolsSales Automation SoftwareCRM SystemsMarket Research ToolsPresentation Software
Industry Keywords
Enterprise SalesCustomer-Facing RoleGTM CollaborationStakeholder EngagementSales Campaigns
About the role
Key responsibilities & impact- Identify and target potential customers through research, networking, and cold calling
- Build new relationships with enterprise customers and prospects to drive revenue, pipeline, and deployment capacity
- Build and maintain relationships with key decision-makers and stakeholders at largest customers
- Serve as primary point of contact and exceed customer expectations
- Lead negotiations, address objections, and close complex deals
- Navigate contracts and agreements with legal and finance stakeholders
- Develop and execute sales strategies to meet or exceed targets
- Create tailored sales presentations and proposals
- Collaborate with marketing on sales campaigns and presentations
- Work with GTM, product, technical, and operations organizations
- Leverage AI tools across account research, outreach, call summarization, forecasting, and deal execution
- Continuously adopt and experiment with new tools to improve sales productivity
Requirements
What you’ll need- 6–8 years of experience in an enterprise customer-facing sales role
- Experience identifying and closing large accounts
- Experience managing a $1M+ quota
- Experience running end-to-end complex 6- and 7-figure ACV deals
- Exceptional verbal and written communication abilities
- Ability to analyze market trends, identify opportunities, and make data-driven decisions
- Proven track record of enterprise prospecting through research, networking, and cold calling
- Familiarity with the AI landscape, key players, and emerging trends is an advantage
Benefits
Comp & perks- Flexible (unlimited) paid time off
- Medical, dental, and vision benefits for you and your family
- Life insurance and disability benefits
- Retirement plan dependent on country of employment
- Parental leave
- Fertility and family building benefits through Carrot
- Lunch, as well as delicious snacks and coffee
- Snacks and coffee
- Discretionary benefit stipend
- Free alphorn lessons
- Eligible full-time employees can participate in Sierra's equity plans
- Offers commission