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About the role
- Enterprise Sales Director selling Sierra’s AI customer-experience platform to Canadian businesses. Managing enterprise relationships, complex six- and seven-figure deals, negotiations, and revenue growth.
Responsibilities
- Identify and target potential customers through research, networking, and cold calling
- Build new relationships with enterprise customers and prospects to drive revenue, pipeline, and deployment capacity
- Build and maintain relationships with key decision-makers and stakeholders at the largest customers
- Serve as the primary point of contact for key customers and exceed their expectations
- Lead negotiations with existing and prospective customers, address objections, and close complex deals
- Navigate contracts and agreements with legal and finance stakeholders
- Develop and execute sales strategies to meet or exceed sales targets
- Craft tailored sales presentations and proposals for enterprise customers
- Collaborate with marketing on sales campaigns and presentations
- Work with the broader GTM team and product, technical, and operations organizations
- Leverage AI tools across account research, personalized outreach, call summarization, pipeline forecasting, and deal execution
- Continuously adopt and experiment with new tools to automate low-value tasks and focus on customer relationships
Requirements
- 6–8 years of experience in an enterprise customer-facing sales role identifying and closing large accounts
- Experience managing a $1M+ quota
- Experience running end-to-end complex 6- and 7-figure ACV deals
- Exceptional verbal and written communication abilities
- Ability to analyze market trends, identify opportunities, and make data-driven decisions
- Proven track record of identifying and targeting enterprise clients through research, networking, and cold calling
- Familiarity with the AI landscape, key players, and emerging trends is an advantage
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 to keep you energized
- Discretionary benefit stipend giving people the ability to spend where it matters most
- Free alphorn lessons
- Eligible full-time employees can participate in Sierra's equity plans
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