Senior Enterprise AI Sales Director

Sierra; Toronto; On-site; CAD 120,000 - 200,000; Full time

Benefits offered by this job

Unlimited PTO

Medical, dental, vision benefits

Life insurance

Retirement plan

Parental leave

Fertility and family-building benefits

Lunch and snacks

Discretionary benefit stipend

Free alphorn lessons

Job summary

Sierra is seeking an enterprise sales professional to drive revenue in Toronto, focusing on targeting and closing large accounts. You will own complex deal cycles, manage executive relationships, and exceed ambitious sales targets.

You will leverage AI tools across the sales cycle, craft tailored proposals, and collaborate with product, marketing, and operations to deliver exceptional customer outcomes.

Qualifications

• 6–8 years of experience in an enterprise customer-facing sales role.
• Experience managing a $1M+ quota and closing 6- and 7-figure ACV deals.
• Strong written and verbal communication skills.
• Analytical mindset to identify trends and opportunities.
• Proven track record of identifying and targeting enterprise clients.

Responsibilities

• Prospect and lead generate to build new enterprise relationships and pipeline.
• Manage relationships with key decision‑makers and stakeholders at top accounts.
• Lead negotiations and close complex deal cycles with cross‑functional teams.
• Develop and execute sales strategies to meet or exceed targets.
• Collaborate with GTM, product, technical, and operations teams to deliver the product.
• Operate as an AI-native seller using AI tools to increase efficiency.

Skills

Prospecting

Lead generation

Enterprise sales

Relationship management

Negotiation

Closing deals

Sales strategy

Cross-functional collaboration

AI-enabled selling

Job description

Sierra is seeking an enterprise sales professional to drive revenue in Toronto, focusing on targeting and closing large accounts. You will own complex deal cycles, manage executive relationships, and exceed ambitious sales targets.

You will leverage AI tools across the sales cycle, craft tailored proposals, and collaborate with product, marketing, and operations to deliver exceptional customer outcomes.