Associate Medical Director ensuring oncology trial medical and safety integrity. Supporting biopharmaceutical clients through medical monitoring, regulatory review, and clinical study oversight.
About the role
- 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.
Responsibilities
- Lead the largest multi-business-unit, multi-geography opportunities and design sophisticated deal structures while 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 customer interactions
- Influence Sierra's strategy for important accounts and set standards for the broader sales organization
- Leverage AI tools throughout the sales cycle for 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 tools to work faster and smarter
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 and running end-to-end complex six- and seven-figure ACV deals
- Deep, sustained C-suite relationships and gravitas to be treated as a peer by executive buyers
- 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
- Ability to speak credibly to technical and business stakeholders alike
- Experience operating alongside founders/executives in front of strategic customers is an advantage
- 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 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 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.