Enterprise Sales Director, Retail

Job not on LinkedIn

🕒 August 5

🇨🇦 Canada – Remote

💵 CA$305k - CA$370k / year

⏰ Full Time

🔴 Lead

🤑 Sales

👻 Ghost score 28%

What it means: the chance that no one is really hiring for this job.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Sierra

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Artificial Intelligence • B2B • SaaS

Sierra is a company that specializes in transforming customer experiences through the power of conversational AI. Their platform enables businesses to deploy AI agents that are empathetic, always available, and aligned with the brand's tone and voice. Sierra offers capabilities for real-time support, seamless integration into existing technology stacks, and the capacity to solve complex issues while continuously improving the customer experience. Trusted by leading brands, Sierra's AI platform is designed with a strong commitment to security and privacy, ensuring safe and secure interactions. The platform allows for personalization, enabling companies to imbue their AI agents with their own identity and processes, ensuring consistency and reliability across all customer interactions.

📋 Description

• 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

• 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

• 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

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