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Sierra helps businesses build better, more human customer experiences with AI.
Currency and observation date were not supplied; this is not a current valuation or a funding round.
Sierra has 25 open jobs in Canada as of November 6, 2026. Top locations: Toronto.
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Sierra
4+ YOECandidates need 4-6+ years in sales engineering or customer-facing technical sales, including leading large enterprise deals of $500K to $1M. They must be skilled at building demos, presenting to executives and technical leaders, and explaining solutions to both technical and non-technical audiences.
AI tools
Sierra
7+ YOECandidates need 7+ years in sales engineering or technical sales, a record of closing $1M+ strategic deals, and strong relationships with C-suite and technical leaders. A bachelor's degree or equivalent experience is required, and familiarity with AI tools is expected.
AI tools
Sierra
3+ YOECandidates need 3-4+ years in sales engineering or technical sales with enterprise deals, strong demo and presentation skills, and a bachelor's degree or equivalent experience. They must use AI tools responsibly and be accountable for the accuracy of everything they present to customers.
AI tools
Sierra
7+ YOECandidates need 7+ years in sales engineering or technical sales, experience leading $1M+ strategic deals, and strong relationships with C-suite and technical leaders. Experience with demos, architecture and security discussions, and a bachelor's degree or equivalent are also expected.
Sales, Leadership, Relationship building, Computer science
Sierra
4+ YOECandidates need 4 to 6 or more years in sales engineering or technical sales with large enterprise customers, plus demo-building and executive relationship skills. A bachelor's degree or equivalent experience is required, and comfort using AI tools in the sales process is expected.
AI tools
Sierra
3+ YOECandidates need 3 to 4 or more years in sales engineering or technical sales with enterprise customers, including demo building and relationship-building with executives and technical leaders. A bachelor's degree or equivalent experience is required, and computer science is a bonus.
AI tools
Sierra
7+ YOECandidates need 7+ years in sales engineering or technical sales, a record of leading $1M+ strategic deals, and strong relationships with executives and technical leaders. A bachelor's degree or equivalent experience is required.
Sales, Leadership, Relationship building, Computer science
Sierra
7+ YOECandidates need 7+ years in sales engineering or technical sales, a record of leading $1M+ strategic deals, and strong relationships with executives and technical leaders. A bachelor's degree or equivalent experience is required.
AI tools
Sierra
4+ YOESierra needs candidates with 4 to 6+ years in sales engineering or technical sales, including large enterprise deals. They must present demos, build relationships with executives, and explain AI solutions to technical and non-technical audiences.
AI tools, Demo and prototype tools
Sierra
3+ YOECandidates need 3-4+ years in sales engineering or technical sales, experience leading enterprise deals, and strong demo-building and presentation skills. A bachelor's degree or equivalent experience is expected, and AI tools are used regularly in the sales process.
AI tools
Sierra
4+ YOECandidates need 4 to 6+ years in sales engineering or technical sales with large enterprise deals, demo-building and presenting skills, and the ability to explain solutions to technical and non-technical audiences. A bachelor's degree or equivalent experience is required.
Sales, Procurement, Relationship building, Computer science
Sierra
7+ YOECandidates need 7+ years in sales engineering or technical sales, a record of leading $1M+ strategic deals, and strong demo and executive relationship skills. A bachelor's degree or equivalent experience is required, and using AI tools for sales work is expected.
Sales, Go, Leadership, Relationship building, Computer science
Sierra
7+ YOECandidates need 7+ years in sales engineering or technical sales, a record of leading $1M+ strategic deals, and strong relationships with executives and technical leaders. They also need a bachelor's degree or equivalent experience and the ability to use AI tools while owning the accuracy of their work.
AI tools
Sierra
Candidates need professional fluency in both Spanish and English, experience building and scaling end-to-end production systems, and strong problem-solving skills in fast-changing environments. Customer-facing communication and a hands-on builder mindset are also required.
Research, Troubleshooting, Problem solving, Communication skills, React, TypeScript
Sierra
Candidates need experience building and scaling end-to-end production systems and strong problem-solving skills in ambiguous settings. Customer-facing communication and interest in retail are also expected.
React, TypeScript, Go
Sierra
6+ YOECandidates need 6-8 years of enterprise, customer-facing sales experience closing large accounts, including a $1M+ quota and 6- and 7-figure deals. Strong communication, analytical and prospecting skills, and familiarity with the AI landscape, are also needed.
Sales forecasting tools, AI sales tools
Sierra
6+ YOECandidates need 6-8 years in enterprise customer-facing sales, experience managing a $1M+ quota and closing large deals, and strong written and verbal communication. Familiarity with the AI landscape is an asset.
Salesforce
Sierra
10+ YOESierra needs 10-12+ years of enterprise or strategic sales experience, including closing multi-million-dollar, multi-stakeholder deals and managing a $1M+ quota. Candidates should have strong C-suite relationships, mastery of deal structuring and pricing, and excellent executive communication.
Salesforce, AI sales tools
Sierra
10+ YOECandidates need 10 to 12+ years of enterprise or strategic sales experience, with a record of closing multi-million-dollar deals and managing a $1M+ quota. Sierra also needs strong executive communication, C-suite relationships, and deal structuring skill.
Sales, Communication skills
Sierra
6+ YOECandidates need 6-8 years of enterprise sales experience, including managing a $1M+ quota and closing large six- and seven-figure deals. Strong communication, prospecting and data-driven analysis skills are essential, and knowledge of the AI landscape is an asset.
AI sales tools
Sierra
8+ YOESierra needs candidates with 8-10 years of enterprise sales experience, a track record closing large accounts and managing a $1M+ quota, and strong communication skills. An analytical mindset and familiarity with the AI landscape are assets.
AI sales tools
Sierra
8+ YOESierra needs candidates with 8-10 years of enterprise sales experience, a track record of closing large accounts, and experience managing a $1M+ quota. Strong written and verbal communication and an analytical mindset are required, with familiarity with the AI landscape as an asset.
Sales, Health care system, Cold calling, Leadership, Communication skills
Sierra
Candidates need experience building and scaling end-to-end production systems, strong problem-solving skills and clear communication with technical and non-technical people. Experience with AI or LLM systems in production, React, TypeScript or Go, and working with customers is a plus.
React, TypeScript, Go
Sierra
8+ YOESierra needs 8 to 10 years of enterprise customer-facing sales experience, including managing a $1M+ quota and closing 6- and 7-figure ACV deals. Candidates must have a proven record of building trusted relationships across customer C-suites and strong written and verbal communication.
Salesforce
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