AI-Driven Enterprise Sales Director

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

Benefits offered by this job

Unlimited PTO

Medical, dental, vision

Retirement plan

Equity plans

Parental leave

Job summary

Sierra in Canada is seeking an experienced Enterprise Sales professional to drive new business and manage strategic accounts. You will identify opportunities, build relationships with C-level buyers, and close complex deals.

You will lead strategy, collaborate with product, marketing, and operations, and leverage AI-powered tools to improve efficiency. A proven track record of $1M+ ACV and 6–8 years in enterprise sales is expected.

Qualifications

• 6–8 years of enterprise, customer-facing sales experience.
• Experience managing a $1M+ quota and closing 6- to 7-figure ACV deals.
• Strong communication skills, both written and verbal.
• Analytical mindset with data-driven decision making.
• Proven track record in prospecting and lead generation.

Responsibilities

• Prospecting & lead generation: identify and target enterprise customers; build relationships to drive revenue and pipeline.
• Manage relationships: maintain relationships with key decision-makers; be primary contact.
• Negotiating & closing complex deal cycles: lead negotiations; manage contracts with legal/finance teams.
• Sales strategy & planning: develop strategies to meet targets; craft tailored presentations; collaborate with marketing.
• Collaborate cross-functionally: work with GTM, product, technical, and operations teams.
• Operate as an AI-native seller: leverage AI tools across research, outreach, and forecasting to boost efficiency.

Skills

Enterprise sales

Quota management

Negotiation

CRM proficiency

Communication

Lead generation

Salesforce

HubSpot

Tools

Salesforce

HubSpot

Job description

Sierra in Canada is seeking an experienced Enterprise Sales professional to drive new business and manage strategic accounts. You will identify opportunities, build relationships with C-level buyers, and close complex deals.

You will lead strategy, collaborate with product, marketing, and operations, and leverage AI-powered tools to improve efficiency. A proven track record of $1M+ ACV and 6–8 years in enterprise sales is expected.