Founding Head of Enterprise Sales

New

Creative MarketDigital Assets Marketplace

We’re building a fully remote team across Canada and the United States.Full-TimeSenior

Salary$200,000 - $300,000, including base salary and variable compensation (OTE)

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Job Details

4–7+ years of B2B sales experience in SaaS, marketplaces, enterprise software, or data licensing.
Proven experience selling to large organizations or Fortune 1000 companies via procurement-led sales.
Strong ability to manage full-cycle sales from prospecting to closing and forecasting.
Experience selling to stakeholders such as design managers, creative operations, marketing teams, and legal.
Demonstrated ability to create structure and repeatable sales playbooks in ambiguous, early-stage environments.
Strong commercial judgment for prioritizing high-value opportunities.
Technical proficiency in CRM management for pipeline hygiene and forecasting.
Ability to translate customer needs into actionable internal product and engineering feedback.
Self-directed, resilient, and organized work style.

Own qualified enterprise opportunities from initial conversation through close, targeting Fortune 1000 brands, agencies, and AI companies.
Partner with SDR contractors to field inbound requests and qualify lead interest.
Build outbound prospecting strategies, stakeholder maps, and messaging tailored to enterprise use cases.
Run full-cycle sales processes including discovery, demo, negotiation, and closing.
Navigate complex objections related to licensing, AI training, procurement, and legal review.
Build and refine commercial processes, pricing frameworks, and contract handoff workflows for AI training deals.
Provide structured market feedback to product, engineering, and leadership teams to improve enterprise sales motions.

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