Creative Strategist, Demand Generation

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.

We're looking for a Creative Strategist who sits at the intersection of art, science, and performance — someone who can craft breakthrough ideas that don't just capture attention, but drive measurable action.

As part of Square's Demand Generation team, you'll develop and optimize creative that converts — from first touch to sign-up and identity verification. You'll combine storytelling instincts with analytical rigor, using data and experimentation to inform creative direction and optimization.

You'll collaborate closely with channel, CRO, and analytics partners — as well as production teams — to scale creative systems that are both inspiring and performance-driven. Bonus points if you've led creative strategy for large-scale productions (e.g., streaming video, studio shoots, modular content libraries) and are curious about leveraging AI tools to enhance creative workflows and insights.

• Develop creative strategies that drive measurable conversion outcomes across key DG channels (paid social, programmatic, You Tube, streaming, web and new channels)
• Translate performance data, audience insights, and testing results into actionable creative direction and optimization hypotheses
• Collaborate with creative, CRO and channel teams to test, learn, and iterate — continuously improving creative impact and efficiency
• Lead and shape creative direction for high-production initiatives such as streaming spots, full-funnel shoots, and modular library builds that scale globally
• Partner with production teams to ensure storytelling consistency and a clear through line from ad creative to landing experience
• Experiment with AI tools for ideation, creative versioning, and performance analysis to accelerate learnings and enhance creative development
• Build and refine creative frameworks and best practices that can scale across markets and verticals while maintaining brand integrity and performance rigor
• Collaborate with cross-functional partners to align creative with broader business goals and customer insights

• 5–7 years of experience in creative strategy, performance marketing, or conversion-focused content development (brand or agency side)
• A proven record of driving measurable outcomes through data-backed creative insights and experimentation
• Experience in creative optimization, including A/B testing, message hierarchy development, and funnel-stage performance analysis
• Ability to synthesize performance data into clear, creative insights — and communicate recommendations to cross-functional partners
• Hands-on familiarity with AI-driven creative tools (e.g., for concepting, scriptwriting, asset versioning, or audience analysis)
• Strong collaboration skills and comfort working cross-functionally with media, analytics, CRO, and production teams
• A passion for blending storytelling with performance — and a bias toward testing, learning, and continuous…