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About the Role

We are seeking a Founding Head of Enterprise Sales to lead sales execution for strategic accounts, focusing on Fortune 1000 brands, large enterprise design teams, procurement-led buying, and AI training data opportunities. This is a high-ownership role where you will build the sales process, playbooks, reporting, and feedback loops needed for scaling, while managing inbound demand, developing outbound opportunities, running discovery and negotiation, closing new business, and forecasting pipeline.

Responsibilities

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, pricing frameworks, proposal templates, approval workflows, and contract handoff processes.
Partner with leadership, legal, product, and engineering to define how Creative Market evaluates, packages, prices, negotiates, and fulfills AI training opportunities.
Assess AI training opportunities based on use case, data needs, licensing requirements, budget, technical requirements, legal considerations, operational feasibility, strategic fit, and long-term expansion potential.
Capture market feedback around buyer demand, objections, required rights, dataset needs, compliance expectations, competitive alternatives, licensing complexity, product gaps, and enterprise workflow needs.
Provide structured feedback to product and engineering based on customer conversations, especially around AI training requirements, content discovery, marketplace data, asset rights, fulfillment constraints, and technical questions.
Identify patterns across buyer segments, use cases, deal types, objections, and conversion points.
Recommend improvements to sales process, qualification, pricing, packaging, lead routing, product capabilities, and internal workflows.
Partner cross-functionally with product, engineering, legal, finance, and leadership to improve the enterprise sales motion and unlock larger strategic opportunities.

Requirements

4–7+ years of B2B sales experience, ideally in SaaS, marketplaces, enterprise software, data licensing, creative technology, design tools, media, or digital assets.
Experience selling to large organizations, with Fortune 1000, enterprise, or procurement-led sales experience strongly preferred.
Proven ability to manage full-cycle sales, including prospecting, discovery, stakeholder management, proposal development, negotiation, closing, and forecasting.
Experience selling to or working with procurement, design managers, creative operations teams, marketing teams, legal stakeholders, or enterprise brand teams.
Strong comfort with ambiguous or emerging deal types, especially where sales process, packaging, pricing, and internal workflows are still being built.
Ability to create structure, process, and repeatable playbooks without needing a large sales organization around you.
Excellent written and verbal communication skills.
Strong commercial judgment and ability to prioritize the highest-value opportunities.
CRM discipline and ability to maintain clean pipeline data and reliable forecasts.
Ability to translate customer conversations into actionable feedback for product, engineering, legal, and leadership.
An approach that is self-directed, resilient, organized, and comfortable operating as the primary sales owner.
Experience with AI training data, data licensing, content licensing, rights management, or enterprise licensing deals.
Experience selling into design, creative, brand, marketing, or procurement teams.
Experience working with marketplaces, creator platforms, design platforms, stock content, fonts, templates, or creative asset businesses.
Familiarity with complex commercial conversations involving usage rights, licensing terms, legal review, compliance, or technical evaluation.
Experience building sales processes, outbound campaigns, enterprise account plans, or expansion playbooks from scratch.
Experience working with SDRs, contractors, or outsourced lead qualification support.

Skills

Sales Execution
Strategic Account Management
Fortune 1000 Sales
Enterprise Sales
Procurement-Led Sales
AI Training Data Sales
Sales Process Development
Sales Playbook Creation
Reporting
Feedback Loops
Inbound Demand Management
Outbound Prospecting
Discovery
Negotiation
Closing New Business
Pipeline Forecasting
Client Relationship Management
SDR Collaboration
Full Sales Cycle Management
Commercial Process Development
Market Feedback Analysis
Cross-Functional Partnership
Written Communication
Verbal Communication
Commercial Judgment
Prioritization
CRM Management
Forecasting Accuracy
Product Feedback
Engineering Feedback
Leadership Collaboration
Self-Directed Work
Resilience
Organization
Data Licensing
Content Licensing
Rights Management
Enterprise Licensing
Design Team Sales
Creative Operations Sales
Marketing Team Sales
Legal Stakeholder Engagement
Brand Team Sales
Marketplace Sales
Creator Platform Sales
Design Platform Sales
Stock Content Sales
Font Sales
Template Sales
Creative Asset Sales
Usage Rights Negotiation
Licensing Term Negotiation
Legal Review Navigation
Compliance Navigation
Technical Evaluation
Sales Process Building
Outbound Campaign Development
Enterprise Account Planning
Expansion Playbook Creation
SDR Management
Contractor Management
Lead Qualification Support

Location

Remote (Canada)
Remote (United States)

Work Type

Fully Remote

Experience Level

Founding Head
4-7+ years B2B sales experience

Salary/Compensations

$200,000 - $300,000 (OTE)

Benefits

100% remote work environment
Generous medical and dental insurance for employees and dependents
Ample paid vacation time
Paid sick time
Paid volunteer days
Observation of US and Canadian holidays
Week-long holiday break in December
Paid family leave
401k/RRSP with employer match
Fitness fund
Home office equipment fund
Monthly coffee budget
Paid learning and development opportunities (courses, books, conferences)
Culture events, Friday socials, and virtual/in-person team gatherings
Pro tools including MacBook Pro (or Air)

About the Company

Creative Market is the world’s preferred one-stop shop for the creator community, a platform where creators buy and sell digital high-quality design assets.
We are passionate about building tools and experiences that make design beautiful, effective, and accessible to everyone.
We offer the opportunity to have a huge impact on the organization and the world by working on a digital asset marketplace with over 30 million resources created by artists in 148 countries.
We are building a fully remote team across Canada and the United States, believing that creative collaboration can happen anywhere.
We foster thoughtful collaboration, frequent communication, and freedom for employees to be their authentic selves.

Equal Opportunity

We are dedicated to fostering an inclusive and diverse environment for employees from all walks of life.
Women; people of colour; members of the LGBTQ+ community; and people of all backgrounds, religions, gender identities, individuals with disabilities, and veterans are strongly encouraged to apply.
We provide an accessible candidate experience, and if you need any accommodations or adjustments throughout the interview process and beyond, please let us know.