The World's Marketplace for Design
Founding Head of Enterprise Sales
Location
California + 2 moreAll locations: California | Illinois | New York
Posted
3 days ago
Salary
$200K - $300K / year
Seniority
Lead
Job Description
Founding Head of Enterprise Sales
Creative Market
• 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.
Job 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.
Benefits
- 100% remote: so you can work where you feel most comfortable and inspired.
- Stay healthy: generous medical and dental for both you and your dependents.
- Relax and unwind: with 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.
- Celebrate: we observe both US and Canadian holidays - and a whole week of rest in December.
- Family leave: paid time off for when your family grows.
- Save up: 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.
- Hang out: spend time together with your team virtually or in-person through culture events, Friday socials, and more.
- Pro tools: MacBook Pro (or Air) and all the tools you need to do a great job.
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