Content Operations Lead

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

We are seeking a Content Operations Lead to lead a cross-functional team responsible for creating and managing technical documentation, educational content, and resources that empower Square’s Sellers and Customer Success teams globally. This role will oversee the performance and growth of a team that provides product documentation, policies, and support resources to improve the Seller experience. You will partner closely with cross-functional teams including Customer Success (CS), Marketing, Product, Globalization, Legal, and Engineering to ensure the content strategy drives improvements in Seller self-service, launch workflows, and overall customer experience.

You Will

• Lead and manage a growing international team of technical writers.
• Develop and drive the strategy and vision for the team, ensuring content aligns with organizational goals such as increased self-service adoption, improved support experiences, and higher seller satisfaction.
• Coach and mentor team members, fostering a culture of continuous learning, growth, and high performance.
• Actively analyze team performance and content impact, using data to drive improvements and visibility on team projects and outcomes.
• Own the full content lifecycle—planning, creation, localization, editing, publishing, and maintenance—across technical resources, policies, and internal procedures, ensuring timely delivery within team SLAs.
  Collaborate with global stakeholders (Product, Marketing, CS, etc.) to design content that supports product launches, from small feature updates to large-scale releases, across hardware, POS, SaaS, and other product lines.
• Partner with Product, Engineering, Localization, and other internal teams to ensure timely and high-quality content delivery.
• Participate in and lead cross-functional project planning, ensuring all content-related deliverables are clearly defined, prioritized, and tracked.
• Manage project scope, timelines, and quality, ensuring successful completion of nebulous or high-priority projects through structured project management.
• Analyze content performance through metrics such as self-service adoption, customer satisfaction, and team KPIs.
• Identify trends in customer support interactions and content usage to drive improvements and inform content strategy.
• Stay updated on industry trends, emerging technologies, and content best practices to continuously improve documentation standards and workflows.

You Have

• 5+ years of experience managing technical/product writing teams with a Bachelor’s degree; or 3+ years with a Master’s degree.
• Proven experience leading cross-functional projects, influencing decisions without direct authority, and collaborating across diverse teams.
• Expertise in creating and managing technical content and documentation for both internal and external audiences, with a focus on clarity and usability.
• Strong project management and organizational skills, with the ability to manage multiple competing priorities and deadlines.
• Ability to analyze complex issues, propose creative solutions, and translate technical concepts into clear, user-friendly documentation.
• Strong knowledge of content management systems, knowledge management tools, and user research techniques.
• Exceptional communication skills, with the ability to engage and explain complex concepts to diverse audiences, both in writing and verbally.
• Knowledge of SaaS, e-commerce, customer support, and/or financial services is a plus.

Technologies We Use and Teach

• Jira
• Bloomfire
• Contentful Notion
• GSuite
• Slack
• Snagit
• Figma