Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together. So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale. Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same. The Role Square is looking for a Senior Creative Strategist to independently lead creative and content strategy for a defined growth portfolio within Demand Generation. You’ll own initiatives from audience insight and strategic planning through development, launch, experimentation, and optimization across paid and unpaid experiences. This senior individual contributor role combines marketing, creative strategy, content development, and experimentation. You’ll translate business priorities, audience insights, product messaging, and performance data into programs that drive consideration, acquisition, and conversion. Your scope will connect mid- and lower-funnel creative with corresponding landing pages and content experiences. Our creative model is increasingly self-serve and AI-enabled. You’ll identify what we should build and test, develop messaging and creative hypotheses, and choose the right approach to delivery—creating directly with self-serve tools or leading creative and technical partners. Your work may include ads, SEO-informed website content, educational resources, and interactive tools such as calculators that help sellers evaluate Square and take action. You’ll co-develop the broader DG creative and content tactical plan with the Creative & Optimization Strategy Lead and cross-functional partners, then take independent ownership of agreed portfolios and initiatives. You’ll become a subject matter expert on your audiences and acquisition journey, working across channels and influencing partners without relying on formal reporting authority. You Will • Own creative and content strategy for an assigned growth portfolio, connecting business objectives, audience needs, product value propositions, and channel behavior across mid- and lower-funnel experiences. Lead initiatives from strategy through delivery and optimization. • Build audience-specific and audience-agnostic messaging frameworks and hierarchies that establish what we need to communicate and how it should flex across paid and unpaid channels, funnel stages, formats, and corresponding landing pages. • Identify unmet audience needs and opportunities for creative, content, and experience experimentation. Use performance data, customer research, channel trends, and business priorities to develop hypotheses and make a clear recommendation on what to build or test next. • Co-develop quarterly tactical plans with the Creative & Optimization Strategy Lead and channel partners. Own the testing roadmap for your portfolio, defining hypotheses, isolated variables, success measures, resource needs, and tradeoffs. • Lead net-new creative and content development from insight and concept through launch. Write strategic briefs, develop messaging and content, provide actionable feedback, and coordinate creative, agency, and technical partners. Use self-serve tools to produce and iterate directly when appropriate. • Own performance reviews for your initiatives with channel and analytics partners. Use quantitative and qualitative evidence to understand what performed and why, distinguish creative signals from media delivery and audience effects, and recommend the next action. • Synthesize learnings across experiments and channels, identifying patterns beyond individual test results and using them to inform future messaging, creative, audience, and channel strategies. • Scale winning messages and concepts across paid social, display, native, online video, streaming/CTV, mobile, digital out-of-home, direct mail, and emerging channels. Extend relevant learnings into unpaid content, website experiences, and other seller touchpoints. • Identify, prioritize, and execute landing page experiments to improve conversion, translating audience insights and creative learnings into tests of messaging, content, and page experiences. Make updates directly through self-serve tools or work with cross-functional partners to launch tests, evaluate results, and iterate. • Develop and improve self-serve, AI-enabled frameworks, templates, tools, and workflows that increase creative and content quality, testing speed, and scale. Apply AI across research, ideation, briefing, development, experimentation, and analysis, evaluating output for accuracy, brand alignment, and usefulness. • Connect creative and content decisions to business outcomes. Prioritize opportunities and resources based on likely impact, effort, and evidence, and communicate recommendations, progress, and results clearly to stakeholders and leadership. • Bring structure to ambiguous, complex initiatives: define the problem, develop a point of view, align stakeholders, resolve dependencies, and drive delivery independently. Build trusted partnerships across channel marketing, creative, agencies, analytics, CRO, Web, SEO, and other teams. You Have • 6+ years of relevant experience across creative strategy, performance marketing, growth marketing, integrated marketing, content strategy, advertising, or a related discipline, with demonstrated ownership of complex programs and measurable business outcomes. • A marketer’s mindset with strong creative judgment and business acumen. You can develop strategy across distinct audiences and acquisition journeys, connect mid- and lower-funnel experiences, and turn business needs into effective creative and content. • Advanced fluency with AI-powered tools and workflows, with a demonstrated ability to use AI as an integral part of creative strategy. You regularly apply AI across research, ideation, briefing, creative development, analysis, and optimization; build repeatable workflows that improve speed, quality, and scale; and bring a critical, experimental mindset to emerging tools and capabilities. • Strong analytical and experimentation skills, with experience forming hypotheses, designing or evaluating creative tests, interpreting performance data, and translating results into clear recommendations for what to test next. • Experience developing messaging strategies, value propositions, creative territories, or messaging hierarchies and translating them across audiences, funnel stages, channels, and formats. • Experience independently leading complex creative or content initiatives from audience insight and strategic planning through launch and iteration, including writing clear briefs, developing messaging, and guiding creative and production partners. • A strong understanding of performance marketing and the relationship between creative, media, content, and the post-click experience. You can identify how messaging and experience changes may improve conversion and partner with specialists to test them. • The ability to synthes…