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Enterprise Sales Director

Sierra· Sales
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RemoteCA$325k - CA$365kFull-timePosted 8mo ago

About the role

Enterprise Sales Director responsible for prospecting, managing enterprise relationships, negotiating and closing complex deals, and defining sales strategy in a remote Canada-based role.

Responsibilities

  • Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
  • Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
  • Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
  • Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
  • Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
  • Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.

Qualifications

  • 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
  • Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
  • Strong communication skills: Exceptional verbal and written communication abilities.
  • Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
  • Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.

Skills

Required:Enterprise salesCommunication

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 to keep you energized
  • Discretionary benefit stipend giving people the ability to spend where it matters most
  • Free alphorn lessons
Last updated Sep 30, 2026. Interested? Apply on the company site.
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About Sierra

Better customer experiences. Built on Sierra.

Sierra helps businesses build better, more human customer experiences with AI.

AICustomer ExperienceCustomer SupportVoiceai-agents-and-applicationsorchestrationvoice-ai-stackwing-list-2026
Company profileWebsite

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