Enterprise Sales Director, Retail

Sierra

Enterprise Sales Director growing Sierra’s AI customer-experience platform among Canadian retail brands. Managing complex enterprise deals, strategic relationships, negotiations, and AI-native sales execution.

Posted 8/5/2026full-timeRemote • 🇨🇦 CanadaLead💰 CA$305,000 - CA$370,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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

Demonstrates expertise in enterprise sales, including identifying and closing large accounts, managing significant quotas, and developing tailored sales strategies. Proficient in leveraging AI tools for account research and sales effectiveness while maintaining strong communication and relationship-building skills.

Highest-signal resume keywords

Enterprise Sales ExperienceQuota Management ($1M+)Complex Deal Negotiation (6- and 7-Figure ACV)Market Trend AnalysisAI Tools Familiarity

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales Strategy DevelopmentCold CallingRelationship BuildingNegotiationData-Driven Decision Making

Soft Skills

Exceptional CommunicationStakeholder Management

Tools & Technologies

AI ToolsSales PresentationsSales Campaigns

Industry Keywords

Enterprise CustomersPipeline ForecastingAccount ResearchCustomer ExpectationsGTM Collaboration

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 and exceed customer expectations.
Lead negotiations with existing and prospective customers, address objections, and close deals.
Navigate contracts and agreements with legal and finance stakeholders.
Develop and execute sales strategies to meet or exceed sales targets.
Create tailored sales presentations and proposals for enterprise customers.
Collaborate with marketing on sales campaigns and presentations.
Collaborate with the broader GTM, product, technical, and operations teams.
Use AI tools across account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.
Continuously adopt and experiment with new tools to improve sales effectiveness.

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 potential enterprise clients through research, networking, and cold calling
Familiarity with the AI landscape, key players, and emerging trends is an advantage
Legally authorized to work in Canada
Able to work from Canada

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
Discretionary benefit stipend
Free alphorn lessons
Equity plans for eligible full-time employees
Commission
Toronto office option for those interested in working in an office