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About the role
- Enterprise 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.
Responsibilities
- 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
- 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
- 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
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Degree requirement
No Education Requirement
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