Enterprise Sales Director

Sierra

Enterprise Sales Director selling Sierra’s AI customer-experience platform to Canadian businesses. Managing enterprise relationships, complex six- and seven-figure deals, negotiations, and revenue growth.

Posted 8/5/2026full-timeRemote • 🇨🇦 CanadaLead💰 CA$305,000 - CA$330,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in enterprise sales, focusing on building relationships with key decision-makers and exceeding sales targets. Proficient in leveraging AI tools for account research and sales strategy execution.

Highest-signal resume keywords

Enterprise Sales ExperienceComplex Deal NegotiationQuota Management Over $1MMarket Trend AnalysisAI Tools Familiarity

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales Strategy DevelopmentCold CallingRelationship BuildingSales PresentationsPipeline ForecastingContract NavigationData-Driven Decision MakingAccount Research

Soft Skills

Exceptional CommunicationNegotiation Skills

Tools & Technologies

AI Tools

Industry Keywords

Enterprise CustomersGTM Team CollaborationStakeholder EngagementSales Campaigns

About the role

Key responsibilities & impact

Identify and target potential customers through research, networking, and cold calling
Build new relationships with enterprise customers and prospects to drive revenue, pipeline, and deployment capacity
Build and maintain relationships with key decision-makers and stakeholders at the largest customers
Serve as the primary point of contact for key customers and exceed their expectations
Lead negotiations with existing and prospective customers, address objections, and close complex deals
Navigate contracts and agreements with legal and finance stakeholders
Develop and execute sales strategies to meet or exceed sales targets
Craft tailored sales presentations and proposals for enterprise customers
Collaborate with marketing on sales campaigns and presentations
Work with the broader GTM team and product, technical, and operations organizations
Leverage AI tools across account research, personalized outreach, call summarization, pipeline forecasting, and deal execution
Continuously adopt and experiment with new tools to automate low-value tasks and focus on customer relationships

Requirements

What you’ll need

6–8 years of experience in an enterprise customer-facing sales role identifying and closing large accounts
Experience managing a $1M+ quota
Experience running end-to-end complex 6- and 7-figure ACV deals
Exceptional verbal and written communication abilities
Ability to analyze market trends, identify opportunities, and make data-driven decisions
Proven track record of identifying and targeting enterprise clients through research, networking, and cold calling
Familiarity with the AI landscape, key players, and emerging trends is an advantage

Benefits

Comp & perks

Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
Eligible full-time employees can participate in Sierra's equity plans