AI-Powered Enterprise Sales Director — Global Retail

Sierra; Canada; Hybrid; CAD 180,000 - 300,000; Full time

Benefits offered by this job

Flexible paid time off

Medical, dental, and vision benefits

Life insurance and disability benefits

Retirement plan

Parental leave

Fertility and family building benefits

Lunch and snacks

Discretionary benefit stipend

Free alphorn lessons

Job summary

Sierra, the leading AI-native sales platform, seeks an accomplished enterprise/strategic sales executive to own the largest multi-geo accounts in North America. You will close multi-million-dollar deals, shape complex terms, and manage risk with executive stakeholders across brands.

Work with founders and senior leaders, ensuring precise messaging, pricing, and timing. Build trusted C-suite relationships and drive revenue through high-impact strategic partnerships.

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.

Responsibilities

• Architect Sierra's most complex deals: Lead multi-BU, multi-geo opportunities and design sophisticated deal structures.
• Operate as part of the customer's team with trusted relationships across the C-suite and working teams.
• Engage at the founder level and regularly engage Sierra's co-founders in front of customers.

Skills

Enterprise sales

Strategic deals

C-suite relationships

Executive communication

Deal structuring

Pricing

Job description

Sierra, the leading AI-native sales platform, seeks an accomplished enterprise/strategic sales executive to own the largest multi-geo accounts in North America. You will close multi-million-dollar deals, shape complex terms, and manage risk with executive stakeholders across brands.

Work with founders and senior leaders, ensuring precise messaging, pricing, and timing. Build trusted C-suite relationships and drive revenue through high-impact strategic partnerships.