Each of our brands unlocks different aspects of the economy for more people. Squaremakes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we're helping build a financial system that is open to everyone. The Role Block is seeking a Staff Ecosystem Analyst to join the Customer Insights team. In this high-impact role, you will drive strategic analytics shaping the direction of the company by leveraging advanced analytics and a profound understanding of user behavior across the entire Block ecosystem, including Square and Cash App. The ideal candidate is a "Generalist-Strategist"-a proactive and agile data practitioner who thrives on ambiguity. You are not just a technical expert who "pulls data"; you are a storyteller who investigates the why behind the what . You will translate complex behavioral and attitudinal signals into a cohesive narrative that influences high-stakes business decisions and shapes long-term strategy. You Will Lead Strategic Data Initiatives: Spearhead strategic analyses connecting data across Block's entities to form authoritative points of view on complex business challenges. Synthesize Holistic Insights: Partner with UX researchers, market researchers, and data scientists to integrate behavioral, survey, financial, and spatial data into a single, comprehensive source of truth. Serve as a Strategic Thought Partner: Act as an advisor to leadership, product managers, marketers and designers. You will provide the rigorous, timely analysis necessary to inform product roadmaps and drive innovation. Innovate with AI: Proactively leverage AI and automation tools (including LLMs and agents) to accelerate workflows and synthesize structured and unstructured data with high velocity. Collaborate by Default: Navigate the complexities of a multi-business organization with a "one-team" mentality, ensuring analytical insights align with both technical and business priorities. Drive End-to-End Excellence: Own the full project lifecycle-from first-principles problem definition to final executive presentation-with total autonomy and an uncompromising standard for quality. Master Complex Datasets: Utilize SQL and scripting languages to navigate massive, intricate datasets, surfacing actionable opportunities that others might miss. Execute as a Practitioner-Leader: Design and build sophisticated behavioral analyses leveraging log and usage data. Develop statistical models (e.g., driver analysis, clustering) to uncover deep user relationships. Conduct network and spatial analyses, utilizing mapping tools like Tableau, ArcGIS, or Carto to visualize geographic trends. You Have Exceptional Communication: The ability to translate complex technical concepts into compelling narratives for both technical and non-technical executive audiences. Leadership & Influence: A proven track record of leading cross-functional projects and influencing strategy without direct authority in a fast-paced environment. Strategic Problem Solving: Experience resolving ambiguous, high-impact business issues by translating high-level needs into robust analytical frameworks. Technical Mastery: SQL: Advanced proficiency in writing complex, eloquent, and efficient queries (Snowflake experience preferred). Programming: Advanced proficiency in Python or R for data science and automation. Visualization: Mastery of data exploration tools such as Tableau, Mode, or Looker. Adaptability: A growth mindset with the ability to ramp up quickly on new business domains and pivot strategies as conditions evolve. Experience: 10+ years of related experience (Data Science, Statistics, Management Consulting or related field) with a Bachelor's degree; or 8 years with a Master's; or 6 years with a PhD. Experience in Fintech or Payment Analytics is a plus. We're working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and "fair chance" ordinances. We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we're doing to build a workplace that is fair and square? Check out our I+D page . While there is no specific deadline to apply for this role, U.S. roles are typically open for an average of 55 days before being filled by a successful candidate. Please refer to the date listed at the top of this job page for when this role was first posted. Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate's starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

• Build marketing into a measurable revenue engine and establish our brand as the definitive authority in AI-era intelligence • Architect modern systems while personally driving execution during transformation • Modernize our brand positioning, design scalable demand generation, and enable sales through AI-powered, data-driven marketing infrastructure • Build demand generation engines that consistently deliver qualified pipeline to tech vendor clients across enterprise and digital motions • Track record repositioning B2B tech/data brands against entrenched competitors with measurable market share gains • Design and execute co-marketing programs with technology partners that drive mutual revenue growth • Translate complex intelligence/data offerings into compelling value propositions for tech vendors and IT Buyers

• Develop and own the product positioning, messaging framework, and value propositions for both B2B (payers, employers) and B2C (members) audiences. • Create compelling narratives that translate the new concept of AI care into clear, differentiated, and emotionally resonant stories. • Build sales enablement materials, pitch decks, case studies, and competitive positioning that help close enterprise deals. • Partner with product, clinical, and commercial teams to ensure messaging aligns with product capabilities and market needs. • Lead a new product and feature launches, coordinate cross-functional go-to-market activities, and measure launch effectiveness. • Serve as the voice of the market, translating customer insights and competitive intelligence into actionable marketing and product strategies. • Design and execute multi-channel acquisition strategies across digital, email, direct mail, partnerships, and other channels. • Apply performance marketing rigor to all campaigns, setting clear targets, measuring incrementality, and optimizing based on CAC, LTV, and payback periods. • Build and manage email and direct mail programs that drive initial sign-ups and early engagement. • Partner with commercial teams to support enterprise client acquisition and expansion. • Develop creative testing roadmaps to continuously improve conversion rates across the funnel. • Balance brand building with performance-driven tactics to achieve both short-term and long-term growth goals. • Own the end-to-end member journey from onboarding through long-term engagement and retention. • Build sophisticated lifecycle marketing programs including welcome sequences, nurture campaigns, re-engagement flows, and winback strategies. • Segment members based on behavior, risk, and engagement levels to deliver personalized, timely communications. • Partner with product team to align marketing touchpoints with in-product experiences and clinical milestones. • Design and execute campaigns that drive sustained behavior change and clinical outcomes over 4-12 month timeframes. • Measure and optimize key retention metrics including activation rates, engagement frequency, and member LTV. • Lead creative strategy and execution across all marketing touchpoints including web, email, direct mail, social, video, and sales collateral. • Write compelling copy that resonates with diverse audiences, from healthcare executives to members seeking support. • Work with designers and agencies to produce high-quality creative assets, while maintaining hands-on involvement in the work. • Develop and maintain brand guidelines, voice and tone standards, and visual identity for the new initiative. • Stay current on healthcare marketing trends, consumer insights, and creative best practices. • Build and mentor a small, high-performing marketing team as the initiative scales, enabled to work at scale with AI tools. • Partner closely with product, commercial, clinical strategy, operations, and executive leadership. • Translate business goals into growth strategies and communicate progress to stakeholders. • Manage external vendors, agencies, and contractors to extend team capabilities.

The Problem We’re Solving 🎯 Most DTC brands are leaving revenue on the table. They spend millions acquiring customers through paid channels, then lose 60%+ of high-intent shoppers to cart abandonment, anonymous browsing, and missed retargeting opportunities. The issue isn't traffic—it's conversion architecture. Brands lack the infrastructure to capture intent signals, recognize returning visitors, and re-engage shoppers at the moments that matter most. That's where Checkmate comes in. Our AI-powered platform captures shopping intent from 100M+ shoppers across the web—wishlists, carts, browsing sessions—and turns it into high-converting campaigns that consistently deliver revenue uplift in 30 days. But here's the thing: selling this solution requires more than a good pitch deck. It requires someone who can walk into a growth team's meeting, diagnose where they're leaving money on the table, and prescribe a strategic path forward. About Checkmate 🛍 📲 Checkmate is an AI marketing platform that helps DTC brands capture anonymous shoppers, launch targeted campaigns, and drive measurable revenue. Our platform uses AI to de-anonymize site traffic, uncover missed conversion opportunities, and launch high-performance campaigns that engage the 100M+ high-intent shoppers in our network. We offer three core products for brands: - Enrichment: Reveal and resolve anonymous visitors to fuel smarter lifecycle flows. - Targeting: Deliver single-use offers through high-converting surfaces like our app, extension, email, and SMS. - Audiences: Capture pre-checkout emails via gated discounts and gain competitive insights. We work with leading DTC brands like Stanley, Quay, ColourPop, Laneige, and Dockers. Backed by Google Ventures, Fuel Capital, and others. ------------------------------------------------------------- About the Role Checkmate is building the next generation savings brand, and we need a strategic, execution-focused Head of Marketing to lead the charge. You'll drive both B2C brand perception and B2B sales growth, with a core focus on building cultural relevance through strategic brand associations, amplifiable moments, and community-driven experiences. This is a high-impact role where you'll architect and drive growth across both B2C (app downloads, influencer marketing, consumer brand) and B2B (cold lead generation, community building, sales enablement) channels. The key insight: winning consumer perception unlocks B2B success. Brands want to associate with what's trendy, exclusive, and culturally relevant. You'll turn our activations, partnerships, and community moments into high-engagement content that drives lead generation and brand equity. This role is uniquely positioned: Our company is transforming from just a consumer app, to a growth engine for brands. Brands can use our channels to directly speak to our users, or use our data to supplement their marketing efforts. You’ll be responsible for the strategy of growing both - no easy feat. The ideal candidate should have either a growth marketing or product marketing background. Location: Remote (NYC or LA strongly preferred) ------------------------------------------------------------- What You'll Own Strategic Marketing 🎯 Our current strategy is often a bit scattered. A large portion of this job will be to build out a thesis and really go ham on a bi-lateral B2B/B2C strategy and work in partnership with the team to execute on that strategy.  - Develop unified marketing strategy across B2C and B2B channels. - Create clear, simple product marketing that makes complex offerings digestible - Stay on the pulse of cultural trends to position Checkmate as the "cool" choice in savings and marketing tech B2B Marketing & Lead Generation 💼 - Generate cold leads beyond our current agency-dependent sourcing. North star is diversifying our sales funnel and bolstering direct sales vs. referrals at a low CAC. - Create viral-worthy content from conferences, partnerships, and B2B events (LinkedIn, podcasts, etc.) - Build B2B community through experiences, dinners, and thought leadership - Develop product marketing materials (decks, videos, guides) that clearly communicate value - Help with the overhaul of our website to better align with the B2B/B2C strategy you set - Support sales, partnerships, and customer success with quality lead gen B2C Brand Building ⚡ - Execute social media strategy focused on amplifiable moments - own the conversation. North star is growing MAU MoM - Develop TikTok strategy around savings hacks and relatable content - Turn UGC, influencer partnerships, and power users into compelling ads and organic reach - Design community moments (events, giveaways, surprise and delight) that create content opportunities - Build relationships with trending brands and influencers Product Marketing 💡 - Simplify and unify how we explain our products - make complex offerings clear and accessible - Bridge the gap between our consumer savings narrative and B2B marketing platform positioning - Develop product marketing materials (decks, videos, guides, website content) that clearly communicate value across all customer segments and are consistent across all touchpoints  - Own the product narrative so brands and consumers quickly understand what Checkmate does and why it matters Community Building 🌟 We've built momentum with events that generate LinkedIn buzz and drive real business outcomes. Now we're scaling to the next level: building a comprehensive ecosystem for ecommerce brands where community becomes our competitive moat. You won't build every event yourself, but you'll ensure every activation drives maximum impact: - Cold lead gen events with influencers that draw brands into our ecosystem - Curated experiences and dinners to close warm leads and upsell customers - Turn in-person moments into viral online engagement - Scale from individual activations to a must-attend community ecosystem - KPIs: deals sourced, deals closed, upsells, social engagement Success Metrics 📈 - Cold B2B lead generation through marketing initiatives - Deals closed and upsold from marketing touchpoints - Brand perception as culturally relevant and performance-driven - Social media reach, engagement, and viral moments - Simplified, unified product narrative, with an easy to understand website and supplemental sales assets that can scale a growth team -------------------------------------------------------------