Enterprise Sales Director – Strategic, Retail

Sierra

Enterprise Sales Director closing complex, multi-million-dollar deals for Sierra’s AI customer-experience platform with strategic Canadian retailers. Managing C-suite relationships, founder-level engagements, and AI-enabled sales execution.

Posted 8/5/2026full-timeRemote • 🇨🇦 CanadaLead💰 CA$375,000 - CA$430,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates extensive experience in enterprise sales, particularly in managing complex, multi-million-dollar deals and building C-suite relationships. Proficient in utilizing AI tools to enhance customer engagement and sales processes.

Highest-signal resume keywords

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

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Deal StructuringRisk NavigationPricing StrategyAccount ManagementSales ForecastingPipeline ManagementQuota ManagementClosing StrategiesMulti-Stakeholder EngagementCustomer Engagement

Soft Skills

Trust BuildingPrecision CommunicationInfluencing StrategyRelationship ManagementCollaboration

Tools & Technologies

AI Customer-Experience PlatformSales Automation ToolsAccount Research ToolsCall Summarization ToolsPersonalized Outreach Tools

Industry Keywords

Enterprise SalesStrategic AccountsC-Suite EngagementMulti-BU OpportunitiesConsumer BrandsSales Cycle ManagementExecutive Buyer CredibilityCanada Work Authorization

About the role

Key responsibilities & impact

Lead Sierra's largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk
Build trusted relationships across customer C-suites and working teams
Regularly engage and manage Sierra's co-founders in front of customers
Apply precise messaging, positioning, and timing across interactions
Influence Sierra's strategy for important accounts and set standards for the broader sales organization
Use AI tools throughout the sales cycle, including account research, personalized outreach, call summarization, pipeline forecasting, and deal execution
Transform customer engagement for major consumer brands through Sierra's AI customer-experience platform

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 across business units and geographies
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals
Deep, sustained C-suite relationships and executive-buyer credibility
Mastery of complex deal structuring, risk navigation, and pricing
Exceptional executive communication and a reputation for precision and trust
Deep familiarity with the AI landscape is an advantage
Experience operating alongside founders/executives in front of strategic customers is an advantage
Legally authorized to work in Canada
Able to work from Canada

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