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Enterprise Sales Director – Strategic
SierraEnterprise Sales Director closing complex strategic deals for Sierra’s AI customer-experience platform in Canada. Building executive relationships, structuring high-value opportunities, and shaping enterprise sales strategy.
Core Competencies
Role fitCore 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 accounts and structuring sophisticated deals. Proven ability to build and maintain deep C-suite relationships while leveraging AI tools to enhance sales processes and strategies.
Highest-signal resume keywords
Enterprise Sales ExperienceComplex Deal StructuringC-Suite Relationship ManagementAI Tools UtilizationGTM Strategy Development
ATS Keywords
Tailor your resumeApplicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills
Deal StructuringRisk NavigationPricing StrategySales Quota ManagementAccount ManagementPipeline ForecastingSales ExecutionMulti-Stakeholder Deal ClosingACV Deal ManagementSales Motion Development
Soft Skills
Executive CommunicationTrust BuildingInfluencing StrategyPrecision in MessagingGravitas
Tools & Technologies
AI ToolsSales Automation ToolsAccount Research ToolsPersonalized Outreach ToolsCall Summarization Tools
Industry Keywords
Enterprise SalesStrategic AccountsC-Suite EngagementGTM StrategiesSales Teams Development
About the role
Key responsibilities & impact- Lead Sierra's largest multi-business-unit, multi-geography opportunities and design sophisticated deal structures
- Manage deal risk, pricing, and execution for complex strategic accounts
- Build trusted relationships across customer C-suites and working teams
- Engage Sierra's co-founders in front of customers and manage founder-level customer interactions
- Develop precise messaging, positioning, and timing across sales interactions
- Influence Sierra's strategy for important accounts and set standards for the broader sales organization
- Leverage AI tools across account research, personalized outreach, call summarization, pipeline forecasting, and deal execution
- Automate low-value sales tasks and reinvest time in high-value customer relationships
- Continuously adopt and experiment with new AI 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 6- and 7-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 and ability to speak credibly to technical and business stakeholders alike
- Experience operating alongside founders/executives in front of strategic customers
- Experience building GTM strategies, sales teams, and sales motions from scratch or during early-stage growth
- Must be legally authorized to work in Canada
- Must be 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
- Eligible full-time employees can participate in Sierra's equity plans
- Commission
- Equity