Enterprise Sales Director – Strategic, Retail

Sierra

Enterprise Sales Director leading complex, multi-million-dollar retail deals for Sierra’s AI customer-experience platform. Building C-suite relationships, shaping account strategy, and partnering with founders on strategic customer opportunities.

Posted 8/5/2026full-timeRemote • 🇺🇸 United StatesLead💰 $315,000 - $370,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in enterprise sales, particularly in managing complex, multi-million-dollar deals and building deep C-suite relationships. Proficient in utilizing AI tools for account management and sales execution while maintaining exceptional communication and trust with executive stakeholders.

Highest-signal resume keywords

Enterprise Sales ExperienceComplex Deal StructuringC-Suite Relationship ManagementAI Tools UtilizationExecutive Communication

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Deal StructuringRisk NavigationPricing StrategyAccount ManagementSales ForecastingQuota ManagementMulti-Stakeholder Deal ClosingACV Deal ManagementSales Strategy DevelopmentPipeline Management

Soft Skills

Trust BuildingInfluencing StrategyPrecision in MessagingGravitasExceptional Communication

Tools & Technologies

AI ToolsSales ToolsAccount Research ToolsPersonalized Outreach ToolsCall Summarization Tools

Industry Keywords

Enterprise SalesStrategic AccountsMulti-Business-Unit DealsGeographic Sales StrategyC-Suite Engagement

About the role

Key responsibilities & impact

Lead the largest and most complex multi-business-unit, multi-geography opportunities
Design sophisticated deal structures and manage deal risk
Build trusted relationships across customer C-suites and working teams
Regularly engage Sierra’s co-founders in front of customers
Deliver precise messaging, positioning, and timing across interactions
Influence strategy for Sierra’s most important accounts
Set standards for the broader sales organization
Use AI tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution
Continuously adopt and experiment with new sales tools

Requirements

What you’ll need

10–12+ years of enterprise/strategic sales experience owning the largest and most complex accounts
Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies
Experience managing a $1M+ quota
Experience running end-to-end complex six- and seven-figure ACV deals
Deep, sustained C-suite relationships
Gravitas to be treated as a peer by executive buyers
Mastery of complex deal structuring, risk navigation, and pricing
Exceptional executive communication
Reputation for precision and trust
Deep familiarity with the AI landscape is advantageous
Ability to speak credibly to technical and business stakeholders
Experience operating alongside founders/executives in front of strategic customers is advantageous

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
Discretionary benefit stipend
Free alphorn lessons
Equity plans for eligible full-time employees
Commission
Offers equity