Learning Delivery Senior Lead, Customer Operations

Block is one company built from many blocks, all united by the same purpose of economic empowerment. The blocks that form our foundational teams — People, Finance, Counsel, Hardware, Information Security, Platform Infrastructure Engineering, and more — provide support and guidance at the corporate level. They work across business groups and around the globe, spanning time zones and disciplines to develop inclusive People policies, forecast finances, give legal counsel, safeguard systems, nurture new initiatives, and more. Every challenge creates possibilities, and we need different perspectives to see them all. Bring yours to Block.

About Block Customer Operations

Block is a global technology company with a mission to help more people participate and thrive in the economy. Across our brands, we provide tools that empower businesses, customers, creators, and communities worldwide.

Customer Operations at Block supports every brand in the ecosystem, making sure customers, sellers, shoppers, and artists receive the support they need to succeed. Our global teams deliver trusted service, training, and knowledge that keep our products running smoothly and our customers confident in using them.

We support:

• Square — integrated commerce and financial services for millions of sellers.


• Cash App — financial tools to send, spend, save, invest, and borrow.


• Afterpay & Clearpay — "buy now, pay later" solutions for 24M+ customers and 250K+ retailers worldwide.


• TIDAL — an artist-first music platform that helps creators connect with fans.


• Spiral — open-source projects advancing bitcoin as a tool for economic empowerment.


• Proto — building self-custody wallets and decentralized bitcoin mining solutions.

Our Role in Block

Customer Operations connects all of these brands to the people who use them. Whether supporting a business scaling with Square, a Cash App customer exploring new financial tools, a shopper checking out with Afterpay, or an artist streaming on TIDAL, we help make these experiences work. By supporting every corner of Block, we make sure our brands can continue to grow, adapt, and deliver on their missions.

The Role

The Learning Delivery & Performance Support team ensures frontline teams across Square, Afterpay, and Cash App have the right training and support to perform at their best in real time. Sitting within Customer Operations, this team is responsible for evolving delivery from traditional training toward a performance support model that enables speed, adaptability, and measurable impact. As a Senior Lead, you’ll set the direction for delivery strategy, lead a team of Learning Delivery Leads, and partner across BPOs and internal operations to close performance gaps and improve outcomes at scale.

You Will

• Lead the shift from traditional training delivery to a performance support model focused on real-time application and on-the-job enablement.


• Oversee delivery of learning programs across global sites, BPOs, and internal teams, ensuring consistency in quality and learner experience.


• Partner with operational leaders and frontline managers to identify performance gaps and deliver targeted interventions.


• Leverage insights from QA, performance data, and learner feedback to adapt delivery methods and improve impact.


• Ensure delivery teams are equipped to use emerging technology and data to support rapid changes in business needs.


• Manage Learning Delivery Leads, driving high performance, innovation, and operational alignment.

You Have

• 6+ years of experience in Learning Delivery, Knowledge & Content Experience, or Learning & Development (L&D), with a strong track record of driving measurable business outcomes.


• 3+ years of people management experience, including directly managing and developing other managers or team leads.


• Proven record of leading learning delivery teams at scale across multiple brands, geographies, or business units.


• Deep expertise in performance support strategies, facilitation, and adult learning principles, with the ability to apply these in fast-paced, dynamic environments.


• Experience overseeing the end-to-end delivery of learning programs (from design through execution and measurement), including within BPO or vendor environments.


• Strong data-driven decision-making skills and the ability to translate operational performance insights into effective learning interventions.


• Comfort with emerging technology and digital tools to enable rapid adaptation in learning delivery.


• Ability to influence and collaborate with senior leaders, operational managers, and cross-functional partners

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.