Guide Jobs in Santa Rosa, CA (NOW HIRING)

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.

Launched in October 2025, Neighborhoods is a new network between Cash App and Square that gives local businesses the ability to offer online ordering with the power of a mobile app. Sellers get their own branded storefront, accessible on both web and inside Cash App. Customers can seamlessly order ahead, reorder, earn rewards and stay connected to support the businesses they love. With 4 million sellers using Square and 57 million monthly active accounts on Cash App, we have a unique opportunity to connect local sellers and local customers in their area. Learn more about Neighborhoods in the 2025 Fall Square Release announcement.

As a staff iOS engineer on the Neighborhoods team, you will help bring the vision of the neighborhood network to life. You will guide the technical direction for Neighborhoods mobile experiences across Cash App and Square Point of Sale, connecting product strategy to durable mobile architecture while staying hands-on with the systems and features that help customers discover and support local businesses. You will lead complex cross-organizational technical decisions with teams across Square and Cash App, build alignment with senior engineering and product partners, and help engineers across partner teams deliver reliable, high-quality product experiences.  

We are a small, collaborative and remote-friendly team. We believe in people over process, value authenticity and openness, and have a bias for action. Come join us! 

Guide Neighborhoods mobile technical direction across Cash App and Square

• Lead strategic, cross-organizational mobile workstreams within a company-level initiative to redefine local commerce and connect the Square and Cash App ecosystems
• Drive cross-organizational architecture and execution with teams across Square and Cash App to deliver seamless integration of Neighborhoods loyalty, marketing, and ordering features in Cash App running on Square's platform
• Guide the architecture of mobile systems that connect customer discovery in Cash App with seller ordering and fulfillment workflows in Square Point of Sale
• Stay hands-on in iOS development using SwiftUI, Workflow, and related technologies across the Square Point of Sale and Cash App codebases, making architectural tradeoffs that keep mobile experiences reliable, scalable, and polished
• Partner with backend, web, and Android engineers to ship features with a focus on quality and craft, while mentoring engineers and raising technical standards across the team and partner teams
• Work cross-functionally with product managers, designers, and engineering leaders to define product scope, sequence ambiguous cross-team work, and make clear technical and product tradeoffs

Lead as an AI-native product engineer

• Use AI tools as a native part of feature development: exploring unfamiliar codebases, prototyping product ideas, accelerating implementation, generating tests, improving observability, and tightening documentation
• Identify, teach, and scale practical AI-assisted workflows for product engineering, especially in cross-codebase feature work, migration, debugging, QA, experimentation, and rapid iteration
• Apply strong judgment around AI-generated work: verify behavior, protect customer trust, preserve maintainability, and use AI to raise the team's technical bar
• Model how a staff engineer uses AI to multiply impact without losing product taste, architectural ownership, or accountability for the systems we ship

• 12+ years of relevant experience with iOS engineering design and implementation, including deep Swift and Objective-C experience
• Experience guiding iOS architecture with organizational impact, including unidirectional data flow, declarative UI frameworks, and scalable mobile patterns
• Experience leading strategic, complex mobile product or platform initiatives with organizational impact, from ambiguous problem framing through delivery, including applying AI tools thoughtfully to improve engineering speed, quality, and learning
• Proven ability to drive collaboration across team, organizational, and discipline boundaries to deliver remarkable solutions to customers
• Track record shaping organizational technical direction, rallying teams around long-term architecture and product strategy, and mentoring engineers to expand their scope and impact

• SwiftUI, UIKit, Swift Concurrency, Combine
• Protocol Buffers
• Bazel for our build environment
• AI tools including Cursor, Claude Code, Goose