Strategic Enterprise Sales Director - AI-Native & C-Suite Ready

Sierra; Canada; Hybrid; CAD 180,000 - 240,000; Full time

Benefits offered by this job

Flexible (unlimited) paid time off

Medical, dental, and vision benefits

Life insurance and disability benefits

Retirement plan and equity eligibility

Parental leave

Fertility and family building benefits

Lunch and snacks

Job summary

Sierra is seeking a senior enterprise sales leader to own the most strategic, multi-geo accounts and close multi-million-dollar deals across diverse industries. You will partner with C-level executives, architect complex agreements, and drive the full sales cycle with an AI-forward mindset.

This role demands a track record of large quota attainment, executive communication, and the ability to collaborate with founders and cross-functional teams to accelerate growth.

Qualifications

• 10-12+ years of enterprise/strategic sales experience.
• 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 6- and 7-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.

Responsibilities

• Architect Sierra's most complex deals: Lead large multi-BU, multi-geo opportunities with sophisticated deal structures and risk management.
• Operate as part of the customer's team: Maintain trusted relationships across the customer C-suite and teams.
• Engage at the founder level: Regularly engage and present to Sierra's co-founders with conviction and expertise.
• Bring precision to everything: Ensure messaging, positioning, and timing are exact across interactions.
• Shape strategy: Influence Sierra's approach to key accounts and set the standard for sales excellence.
• Operate as an AI-native seller: Leverage AI tools across the sales cycle to automate low-value tasks and deepen relationships.

Skills

Enterprise sales

C-suite relationships

Complex deal structuring

Quota management

Executive communication

AI industry familiarity

Job description

Sierra is seeking a senior enterprise sales leader to own the most strategic, multi-geo accounts and close multi-million-dollar deals across diverse industries. You will partner with C-level executives, architect complex agreements, and drive the full sales cycle with an AI-forward mindset.

This role demands a track record of large quota attainment, executive communication, and the ability to collaborate with founders and cross-functional teams to accelerate growth.