Enterprise Sales Director – Strategic

Sierra

Enterprise Sales Director closing complex, multi-million-dollar deals for Sierra’s AI customer-experience platform. Building C-suite relationships and shaping strategic sales execution.

Posted 8/5/2026full-timeRemote • California, New York • 🇺🇸 United StatesLead💰 $300,000 - $345,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in managing complex strategic deals and building C-suite relationships, with a strong focus on precision in communication and deal structuring. Proven ability to leverage AI tools to enhance sales efficiency and execute high-value contracts across multiple business units.

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

Strategic SalesDeal ExecutionRisk ManagementAccount ManagementQuota ManagementPricing StrategyMulti-Stakeholder NegotiationACV Deal ManagementSales Efficiency ImprovementCustomer Engagement

Soft Skills

Trust BuildingInfluencing StrategyPrecision in MessagingGravitasExceptional Communication

Tools & Technologies

AI ToolsPipeline ForecastingCall SummarizationPersonalized OutreachAccount Research

Industry Keywords

Enterprise SalesStrategic AccountsMulti-Business-Unit DealsC-Suite EngagementSales Organization Standards

About the role

Key responsibilities & impact

Lead Sierra’s largest multi-business-unit, multi-geography opportunities and design sophisticated deal structures
Manage risk and execute complex strategic deals
Build trusted relationships with customer C-suite executives and working teams
Regularly engage Sierra’s co-founders in front of customers
Bring precision to messaging, positioning, timing, and customer interactions
Influence strategy for Sierra’s most important accounts
Set standards for the broader sales organization
Leverage AI tools across account research, personalized outreach, call summarization, pipeline forecasting, and deal execution
Continuously experiment with new tools to improve sales efficiency and customer relationships

Requirements

What you’ll need

10–12+ years of enterprise or strategic sales experience
Experience owning the largest and most complex accounts
Demonstrated success closing multi-million-dollar, multi-stakeholder deals across 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 an advantage
Ability to speak credibly to technical and business stakeholders
Experience operating alongside founders or executives in front of strategic customers is an advantage
Legal authorization to work in the United States is requested in the application

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
Remote work option