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About the role
- Enterprise Sales Director growing Sierra’s AI healthcare platform among Canadian health plans, providers, and healthcare technology customers. Leading complex enterprise deals, customer relationships, negotiations, and AI-enabled sales strategy.
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 deals
- Navigate contracts and agreements with legal and finance stakeholders
- Develop and execute sales strategies to meet or exceed sales targets
- Create tailored sales presentations and proposals for enterprise customers
- Collaborate with marketing on sales campaigns and presentations
- Work with the broader GTM, product, technical, and operations organizations
- Leverage AI tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution
- Continuously adopt and experiment with new tools to improve sales productivity
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 identifying and targeting potential enterprise clients through research, networking, and cold calling
- Familiarity with the AI landscape, key players, and emerging trends is an advantage
- Legally authorized to work in Canada
- 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 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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Degree requirement
No Education Requirement
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Enterprise Sales Director leading complex healthcare deals for Sierra, which builds AI - powered customer - experience platforms. Managing C - suite relationships, founder - level engagements, strategic accounts, and AI - enabled sales execution across Canada.