AI-Driven Enterprise Sales Director | High-Impact, $1M+ Quota

Sierra; Canada; On-site; CAD 120,000 - 180,000; Full time

Benefits offered by this job

Flexible PTO

Medical, dental, and vision benefits

Life insurance

Parental leave

Equity plans

Lunch and snacks

Job summary

Sierra is hiring an enterprise sales professional in Canada to drive revenue with major accounts. You will prospect, lead generate, and manage relationships with key decision-makers, closing complex deals while collaborating with product, marketing, and operations.

You’ll leverage AI tools to streamline workflows and strengthen customer partnerships. The role demands 6–8 years in enterprise sales, a $1M+ quota background, and a data-driven approach to exceed targets in a fast-growing

Qualifications

• 6–8 years in enterprise customer-facing sales
• Experience managing a $1M+ quota and 6-7 figure ACV deals
• Strong communication and analytical mindset
• Proven track record of identifying and targeting enterprise clients through research, networking, and cold calling

Responsibilities

• Prospecting & lead generation to drive revenue and pipeline
• Manage relationships with key decision-makers and stakeholders with large customers
• Negotiate and close complex deals, navigating contracts with legal and finance teams
• Develop and execute sales strategies to meet or exceed targets
• Collaborate cross-functionally with GTM, product, and operations teams
• Leverage AI tools across the sales cycle to automate low-value tasks and enhance relationships

Skills

Enterprise sales

Account management

Negotiation

Communication

Cold calling

Job description

Sierra is hiring an enterprise sales professional in Canada to drive revenue with major accounts. You will prospect, lead generate, and manage relationships with key decision-makers, closing complex deals while collaborating with product, marketing, and operations.

You’ll leverage AI tools to streamline workflows and strengthen customer partnerships. The role demands 6–8 years in enterprise sales, a $1M+ quota background, and a data-driven approach to exceed targets in a fast-growing