Sales Director

Sierra
Toronto
Workplace: RemoteFull timeCAD 290,000 - 335,000 annuallyFunction: SalesExperience: 8-12 yearsSkills: ["Communication","Analytical thinking","Problem-solving","Negotiation","Leadership"]

Senior enterprise-facing sales leader responsible for prospecting, nurturing and closing multi‑million deals. Drives revenue through strategic account planning, manages relationships with key decision‑makers, negotiates complex contracts, and shapes GTM strategy while collaborating with product, marketing and operations to scale Sierra’s enterprise motion.

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Sierra
Sierra
6 months ago

Sales Director

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Last checked: 55 minutes agoStatus: Live

Job Summary

Senior enterprise-facing sales leader responsible for prospecting, nurturing and closing multi‑million deals. Drives revenue through strategic account planning, manages relationships with key decision‑makers, negotiates complex contracts, and shapes GTM strategy while collaborating with product, marketing and operations to scale Sierra’s enterprise motion.
Location: Toronto
Workplace: Remote
Employment Type: Full time
Job Function: Sales
Seniority: Director level

Key Responsibilities

  • •Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling; build new relationships with our enterprise customers to drive revenue and pipeline.
  • •Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers; serve as their primary contact and exceed expectations.
  • •Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, address objections and close deals; navigate contracts with legal and finance stakeholders.
  • •Sales strategy & planning: Develop and execute sales strategies to meet or exceed targets; craft tailored presentations and collaborate with marketing to run campaigns.
  • •Collaborate cross-functionally: Work with GTM, product, technical and operations teams to deliver the product and drive sales success.

Pay and Benefits

Salary: CAD 290,000 - 335,000 annually
Equity and Bonus:Equity
Perks:Paid LeaveHealth InsuranceDentalVisionLife Insurance401kPar Parental

Key Requirements

  • •8-12+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Experience:8-12 yearsAIEnterprise softwareSaaS
Skills:CommunicationAnalytical thinkingProblem-solvingNegotiationLeadership
Languages:English

Company Brief

Sierra
Develops advanced AI agents and tools focused on building autonomous, generalist machine learning systems to assist developers and enterprises in automating complex workflows, decision-making, and application-level tasks.
Industry: AI & Machine Learning
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