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Provide frontline customer support through live chat and email, troubleshooting account, billing, domain, and transactional issues. Meet quality, productivity, and customer satisfaction targets; maintain product knowledge; identify and escalate significant customer issues. The role requires weekend and holiday availability, reliable home internet, and a dedicated workspace.

Staff Software Engineer responsible for architecting and evolving billing, payment, and order systems supporting Squarespace’s monetization platform. The role provides technical leadership across high-visibility initiatives, translates system vision into project plans, leads cross-functional engineering efforts, mentors engineers, drives engineering best practices, and contributes code to critical backend services. Candidates need extensive experience with complex distributed systems, Java and related technologies, architecture decisions, and large-scale billing, ordering, or payment platforms.

Lead enterprise procurement strategy and supplier relationships, drive strategic sourcing and cost savings across technology and marketing spend, manage supplier risk and contracts, implement procurement transformation and tools, and build a high-performing procurement team aligned with business goals.

Run global paid social campaigns across Meta, TikTok, Reddit, and Pinterest to drive subscription conversions. Build, launch, and optimize full-funnel campaigns, design structured tests, use AI to automate reporting and workflows, validate platform-reported results with incrementality measurement, and partner cross-functionally with creative, analytics, finance, and platform partners.

Lead operational planning and reporting for Applied Data & Insights; codify operating model, prioritize and resource cross-functional projects, partner with Finance, People, TPMs, and product teams, govern vendor/tooling decisions, and standardize practices across analytics, data science, and platform teams.

Lead and mentor an engineering team building and scaling payments infrastructure. Drive delivery against company goals, ensure regulatory compliance, set technical direction, partner with Product/Design/Operations, and improve processes and culture to support merchant payments and revenue growth.

Lead and grow a business development team to drive strategic partnerships, optimize reseller and payment channels, and deliver subscription revenue. Own partner portfolio performance, collaborate cross-functionally (Product, Legal, Finance), serve as executive-level advisor to top-tier partners, and influence product and commercial strategy to expand Squarespace's platform and customer segments.

Serve as enterprise design authority for financial systems transformation: define initiative structure and sequencing, align cross-functional leaders, resolve dependencies, translate business needs into technology solutions, and drive scalable continuous improvement.

Lead Squarespace's partnership strategy for AI discoverability and the Acuity Scheduling ecosystem. Build and manage strategic partner relationships, influence product roadmaps, drive ecosystem integrations with AI platforms, define KPIs and commercial terms, and coordinate cross-functional teams to scale partner initiatives and measure business impact.