Founding Head of Enterprise Sales

Creative Market•Chicago, IL

2d•$200,000 - $300,000•Remote

About The Position

Creative Market is the world’s preferred one-stop shop for the creator community - a platform where creators from across the globe buy and sell digital high-quality design assets. We’re passionate about building tools and experiences that make design beautiful, effective, and accessible to everyone. With many jobs, you have to pick between having a huge impact on the organization (small team) or having a huge impact on the world (big product), but at Creative Market - you get to do both! You get to work on a digital asset marketplace, as part of a fully remote team, that has more than 30 million quality resources created by artists in 148 countries around the world. At Creative Market, we serve a global community and we need a diverse team to do that successfully. 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. We’re dedicated to fostering an inclusive and diverse environment for employees from all walks of life. We’re building a fully remote team across Canada and the United States. We believe that creative collaboration can happen anywhere, and that working remotely shouldn’t have to mean sacrificing a sense of cohesion, community, and connection. We’ve seen that by combining thoughtful collaboration, frequent communication, and the freedom for people to be their authentic selves, you can do your best work and inspire others to do the same. 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.

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.

Nice To Haves

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.

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.

Benefits

100% remote: so you can work where you feel most comfortable and inspired.
generous medical and dental for both you and your dependents.
plenty of paid vacation, and paid sick time for when you need it.
Paid volunteer days: for you to spend giving back to non profits/organizations that are important to you.
we observe both US and Canadian holidays - and a whole week of rest in December.
paid time off for when your family grows.
put pre-tax savings into a 401k/RRSP - we’ll match a portion of your contributions.
Fitness fund: to help you feel your very best.
Equipment fund: so you can deck out your home office.
Monthly coffee budget: grab that latte - it’s on us.
Learning and development: keep growing with paid courses, books, and conferences.
spend time together with your team virtually or in-person through culture events, Friday socials, and more.
MacBook Pro (or Air) and all the tools you need to do a great job.