AI-Native Enterprise Sales Director - Retail

Sierra; Canada; Hybrid; CAD 120,000 - 180,000; Full time

Benefits offered by this job

Unlimited PTO

Medical benefits

Dental benefits

Vision benefits

Parental leave

Discretionary benefit stipend

Free alphorn lessons

Job summary

Sierra is seeking an experienced Enterprise Sales professional to drive revenue with large enterprise accounts across North America. You will lead prospecting, build relationships with decision-makers, negotiate complex deals, and shape sales strategy in collaboration with product, marketing and operations teams.

The role emphasizes leveraging AI tools to enhance outreach and efficiency. The ideal candidate has a track record closing multi-million ACV deals, strong communication skills, and an

Qualifications

• 6–8 years in enterprise customer-facing sales
• Experience managing large quotas and end-to-end 6- to 7-figure ACV deals
• Strong communication skills (verbal and written)
• Analytical mindset with ability to identify opportunities and trends
• Proven track record in prospecting and lead generation for enterprise clients

Responsibilities

• Prospecting & lead generation: identify and target potential customers; build relationships with enterprise customers
• Manage relationships: serve as primary contact for key decision-makers and stakeholders
• Negotiating & closing complex deal cycles: lead negotiations and finalize contracts with cross-functional teams
• Sales strategy & planning: develop and execute strategies to meet targets and craft tailored proposals
• Collaborate cross-functionally: work with GTM, product, technical and operations teams
• Operate as an AI-native seller: leverage AI tools across the sales cycle to improve efficiency and outcomes

Skills

Enterprise sales

Relationship building

Negotiation

Communication

Data-driven decisions

Job description

Sierra is seeking an experienced Enterprise Sales professional to drive revenue with large enterprise accounts across North America. You will lead prospecting, build relationships with decision-makers, negotiate complex deals, and shape sales strategy in collaboration with product, marketing and operations teams.

The role emphasizes leveraging AI tools to enhance outreach and efficiency. The ideal candidate has a track record closing multi-million ACV deals, strong communication skills, and an