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. Diversity & Inclusion 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. About the team 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. About our ideal candidate: 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. Key Responsibilities Enterprise Sales, Pipeline Development & Deal Execution 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. AI Training Commercial Process, Market Feedback & Cross‑Functional Partnership 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. What success looks like First 30 Days Understand Creative Market's marketplace, customer base, content supply, licensing model, enterprise opportunity areas, and current inbound demand. Review existing enterprise, procurement, licensing, and AI training‑related requests. Begin managing qualified inbound opportunities with support from SDR contractors. Build an initial view of target buyer personas, including procurement, design management, creative operations, legal, and AI stakeholders. Identify immediate gaps in qualification, CRM hygiene, lead routing, proposals, and sales process. First 60 Days Run enterprise discovery and sales conversations independently. Establish qualification criteria for inbound enterprise and AI training opportunities. Build initial sales materials, discovery questions, pipeline stages, proposal templates, and forecasting practices. Begin targeted outreach into Fortune 1000 and other high‑potential enterprise accounts. Provide leadership with clear visibility into pipeline, deal risk, expected bookings, and priority opportunities. First 90 Days Close or materially advance qualified enterprise opportunities. Deliver a defined process for managing AI training‑related deals from inquiry through qualification, pricing, proposal, legal review, and close. Build an initial account expansion framework for growing customer relationships and bookings over time. Improve CRM reporting, pipeline discipline, and sales forecasting. Provide structured product and engineering feedback based on recurring enterprise and AI buyer needs. Key Qualifications 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. Bonus Qualifications 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. Compensation At the time of this posting, and in good faith, we expect to pay this role an annual total compensation of $200,000 - $300,000 , including base salary and variable compensation (OTE). In order to make sure we're on the same page, we will always ask for your expectations upfront. An offer will balance your expectations with a variety of relevant business and candidate factors including, for example, education, qualifications, certifications, experience, skills, and business or organizational needs. 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. #J-18808-Ljbffr