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 through Afterpay, 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 helping sellers worldwide do the same. Square is part of Block, Inc. (NYSE: SQ), a global technology company with a focus on financial services.
Remote · Toronto, Ontario, Canada
Lead the technical strategy for the Cash App Banking server engineering team and drive cross-cutting architectural decisions to improve system scalability. Partner with product and business leads while mentoring engineers to expand their technical influence.
Remote · Toronto, Ontario, Canada
You will own the technical strategy and architecture for go-to-market systems while building AI-powered automated workflows to enhance sales productivity. You will lead cross-functional initiatives and mentor engineers to deliver scalable, reliable solutions that solve complex business problems.
Remote · United States
You will independently own end-to-end reconciliation and reporting workstreams, ensuring financial accuracy across card networks, banking partners, and internal ledger data. Additionally, you will define key metrics, drive process automation, and collaborate with cross-functional teams to resolve discrepancies and improve financial controls.
Remote · United States, Canada
Own end-to-end research problems to build Customer World Models and proactive intelligence systems. Develop methods for representation learning and agentic decision systems to anticipate customer needs and improve from real-world feedback.
Remote · Toronto, Ontario, Canada
Own the full outbound sales cycle for mid-market merchants, from prospecting and lead generation to negotiation and closing. Develop tailored multi-product solutions across the Square ecosystem to help businesses grow.
Remote · Toronto, Ontario, Canada
Manage the full sales cycle by converting inbound leads and proactively sourcing new SMB opportunities through outbound prospecting. Collaborate with internal teams to deliver consultative solutions and consistently exceed revenue goals using Salesforce for tracking.
Remote · Canada
The Regulatory Program Lead will oversee compliance frameworks for Canadian entities, including AML/ATF, RPAA, and consumer protection. They will act as a designee for the Chief Compliance Officer in governance forums and lead cross-functional regulatory programs.
Remote · Toronto, Ontario, Canada
Lead the architecture and scaling of the financial technology stack across Accounting, Tax, Treasury, Procurement, and FP&A. Drive AI-first development to automate financial workflows and build seamless integrations between accounting systems and data lakes.
Remote · Toronto, Ontario, Canada
Lead the architecture and scaling of the financial technology stack across Accounting, Tax, Treasury, Procurement, and FP&A. Drive AI-first development to automate financial workflows and build seamless integrations between accounting systems and data lakes.
On-site
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 perspectiv…
On-site
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 bus…
On-site
It all started with an idea at Block in 2013. Initially built to take the pain out of peer-to-peer payments, Cash App has gone from a simple product with a single purpose to a dynamic ecosystem, developing unique financial products, including Afterpay/Clearpay, to provide a better way to send, spend, invest, borrow and save to our 50+ million monthly active customers. We want to redefine the world's relationship with money to make it more relatable, instantly available, and universally accessible. Today, Cash App has thousands of employees working globally across office and remote locations,…
On-site
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 bus…
On-site
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 bus…
