This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Founding Head of Enterprise Sales based in Canada. You will take ownership of enterprise revenue generation for a fast-scaling global creative marketplace serving millions of digital assets used by designers, brands, and creators worldwide. This is a high-impact founding sales role where you will drive strategic enterprise deals while also helping define how enterprise sales is built from the ground up. You will work directly with Fortune 1000 companies, large design organizations, and emerging AI-focused buyers to unlock new commercial opportunities. Beyond closing deals, you will shape pricing models, sales processes, and scalable playbooks for long-term growth. The role blends hands-on full-cycle selling with strategic input across product, legal, and operations. It is an opportunity to build a foundational revenue engine in a globally distributed, fully remote environment. \n

Accountabilities: Own the full enterprise sales cycle from prospecting and discovery to negotiation and closing, focusing on Fortune 1000 companies, large creative organizations, agencies, and AI-driven buyers. Manage and convert qualified inbound opportunities in collaboration with SDR contractors who support lead qualification and routing. Build and execute outbound strategies, including account targeting, stakeholder mapping, and tailored messaging for enterprise use cases. Navigate complex sales processes involving procurement, legal, security, and multi-stakeholder decision-making environments. Develop and expand strategic account relationships through upselling, cross-selling, and long-term licensing or enterprise agreements. Maintain accurate pipeline forecasting, CRM discipline, and reporting across key sales metrics such as conversion rates, deal size, and revenue performance. Identify patterns and insights from customer interactions to refine sales strategy and improve conversion efficiency. Requirements: 4–7+ years of experience in B2B enterprise sales, ideally in SaaS, marketplaces, digital platforms, data licensing, or creative technology environments. Proven experience managing full-cycle enterprise deals, including negotiation with procurement, legal, and senior stakeholders. Strong track record of selling into large organizations such as Fortune 1000 companies or similarly complex enterprise environments. Ability to build sales structure, playbooks, and repeatable processes in early-stage or evolving sales organizations. Strong commercial acumen with the ability to prioritize high-value opportunities and manage long, complex sales cycles. Excellent communication, presentation, and stakeholder management skills. High discipline in CRM usage, forecasting accuracy, and pipeline management. Ability to translate customer feedback into actionable insights for product, legal, and leadership teams. Benefits: Competitive total compensation package including base salary and variable pay (OTE aligned with senior enterprise sales benchmarks). Fully remote work model across Canada and the United States. Comprehensive health and dental coverage for employees and dependents. Generous paid vacation, sick leave, and extended holiday breaks. Paid volunteer days to support community engagement and nonprofit work. Retirement savings plan with employer contribution matching. Home office, fitness, and learning & development stipends. Monthly wellbeing and remote work support allowances (e.g., coffee budget, equipment support). Access to high-quality tools, equipment, and continuous professional development resources. Inclusive, distributed team culture focused on flexibility, autonomy, and collaboration.

\n How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best! Why Apply Through Jobgether? Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time. #LI-CL1