Founding Head of Enterprise Sales

About the role:

We're looking for a Founding Head of Enterprise Sales to own sales execution across strategic accounts, with a particular focus on Fortune 1000 brands, large enterprise design teams, procurement‑led buying processes, and AI training data opportunities.

This is a high‑ownership role for someone who can operate as a solo sales representative while also helping build the sales process, playbooks, reporting, and feedback loops needed to scale. You will manage inbound demand, develop targeted outbound opportunities, run discovery and negotiation, close new business, forecast pipeline, and build a repeatable process for expanding client relationships and bookings over time.

You will be supported by SDR contractors who help field and qualify inbound requests, but you will own the full sales cycle for qualified enterprise opportunities.

Women, people of colour, members of the LGBTQ+ community, and individuals of all backgrounds, religions, gender identities, and veterans are strongly encouraged to apply. We provide an accessible candidate experience and accommodations throughout the interview process.

We're building a fully remote team across Canada and the United States. Creative collaboration can happen anywhere, and remote work does not sacrifice cohesion or community.

You are a builder, seller, and operator. You are comfortable owning revenue conversations directly, but you are also excited by the opportunity to build the process behind the motion.

You know how to sell to large companies where buying decisions often involve procurement, legal, design leaders, and multiple internal stakeholders. You can manage a deal from first inquiry to signed agreement, but you can also step back and ask: what should the process be, how should we qualify these opportunities, how should we price them, and how do we turn one successful deal into a repeatable sales motion?

You are especially energized by emerging opportunities in AI training, enterprise licensing, and strategic brand relationships. You can bring structure to ambiguous customer requests, identify what matters commercially, and help internal teams understand what the market is asking for.

You are not looking for a fully‑built sales machine. You are looking for a role where you can help build one.

• Own qualified enterprise opportunities from initial conversation through close, with a focus on Fortune 1000 brands, large design organizations, agencies, marketplaces, technology companies, and AI companies.
• Partner with SDR contractors who help field inbound requests, qualify initial interest, and route opportunities appropriately.
• Identify, prioritize, and develop high‑value accounts across procurement, design, creative operations, brand, legal, technical, and AI‑related stakeholders.
• Build outbound account lists, stakeholder maps, messaging, and prospecting strategies tailored to enterprise use cases, including creative asset licensing, brand design workflows, team access, procurement needs, and AI training applications.
• Run full‑cycle sales processes, including discovery, demos, proposals, pricing discussions, stakeholder follow‑up, negotiation, and closing.
• Navigate objections related to usage rights, licensing, AI training, compliance, procurement, budget, implementation, legal review, and vendor approval.
• Build a repeatable process for expanding client relationships and bookings over time through additional licenses, expanded usage rights, new business units, larger creative teams, recurring marketplace spend, AI‑related opportunities, and broader enterprise agreements.
• Own pipeline management, CRM hygiene, forecasting, deal reporting, and key sales metrics, including qualified opportunities, pipeline value, conversion rates, average deal size, sales cycle length, win rate, expansion bookings, and closed revenue.

• Build and refine the commercial process for AI training‑related deals, including qualification criteria, discovery questions,…