Enterprise Account Executive growing Overstory’s AI and satellite - imagery vegetation - risk business with Canadian electric utilities. Managing complex sales cycles, executive relationships, demonstrations, and seven - figure agreements.
About the role
- Enterprise sales expert creating realistic scenarios to train and evaluate advanced AI systems. Supporting Gramian Consultancy’s IT services and engineering talent solutions.
Responsibilities
- Create expert-level B2B sales tasks and reference solutions based on realistic enterprise scenarios
- Develop scenarios covering prospecting, discovery, qualification, solution positioning, and deal strategy
- Evaluate account plans, opportunity strategies, negotiation approaches, and commercial recommendations
- Review scenarios involving complex multi-stakeholder buying groups, including executives, technical teams, procurement, legal, and finance
- Assess pipeline quality, forecasting assumptions, deal risks, and next-step strategies
- Apply formal sales methodologies and established evaluation rubrics to project work
- Review feedback from senior evaluators and refine outputs accordingly
- Maintain consistent quality, realism, and commercial accuracy across assigned tasks
- Contribute to calibration and quality-review cycles
Requirements
- 8–15 years of quota-carrying B2B or enterprise sales experience
- Proven track record of meeting or exceeding revenue targets and closing high-value, complex deals
- Experience managing strategic accounts and long, multi-stakeholder sales cycles
- Strong command of MEDDIC/MEDDPICC, Challenger, SPIN, or a comparable formal sales methodology
- Strong expertise in account planning, opportunity qualification, competitive positioning, and deal strategy
- Advanced experience with commercial negotiation, pipeline management, and forecasting
- At least 4 hours per day and up to 40 hours per week, including 4 hours of PST overlap
- Successful completion of a 60-minute online test (MCQ and short tasks)
Job title
Job type
Experience level
Salary
Not specified
Degree requirement
No Education Requirement
Location requirements
Report this job
Found something wrong with the page? Please let us know by submitting a report below.
Account Executive selling ShareGate’s Microsoft 365 migration and governance platform. Owning consultative, multi - stakeholder new - business sales cycles from discovery through close.
Enterprise Account Executive selling Redis Enterprise, a real - time data platform and database, to Quebec businesses. Building pipeline, closing net - new logos, and exceeding territory quotas through consultative enterprise software sales.
Senior Account Executive selling Cohere’s enterprise AI platform to Global 2000 and large enterprises across Western Canada. Owning strategic partnerships, deployments, and the full SaaS sales cycle.
Senior Account Director driving enterprise growth for INSTANDA’s no - code insurance platform. Expanding strategic accounts, influencing C - suite stakeholders, and closing complex multi - million - dollar agreements.
Account Executive selling SINGU’s CAFM platform to Canadian real estate operators. Building pipeline, winning complex enterprise deals, and driving multi - country expansion.
Account Executive selling LexisNexis CounselLink enterprise legal management software to Canadian corporate legal departments. Managing consultative sales cycles, territory growth, proposals, and revenue targets.
Founding Account Executive selling Featherless.ai’s open - model AI inference cloud. Owning enterprise sales, technical demos, negotiations, and pipeline development across US and Canada.
Account Executive selling hybrid IT, cloud, cybersecurity, and digital - transformation solutions to Ontario public - sector and enterprise clients. Managing strategic accounts, complex sales cycles, and cross - functional delivery for Long View, a Canadian IT provider.
Outbound Capital Account Executive promoting Lightspeed Capital to SMB merchants. Managing customer relationships, financial - services opportunities, contracts, and territory sales targets.