Role Description Ollie is seeking a Principal Software Engineer, within our Core Platform team, who thrives in a small team and is excited to learn from teammates in a collaborative environment. This position is great for you if you are a curious, collaborative, and open-minded engineer. You have built and used many APIs before, and know the pitfalls and challenges involved with supporting and scaling them in the real world. You are someone who loves programming and is passionate about making a better product. You use AI tools to boost your productivity and knowledge while maintaining strict quality control over its outputs. You enjoy delivering reliable, performant, well-tested code that powers all your clients! This is a remote role based in the Northeast U.S., with monthly in-person co-working sessions. The position collaborates across the organization and reports to the Senior Technical Lead, Platform. What You'll Do: - Design, build, and maintain APIs, interfaces, and technical infrastructure that power Ollie’s subscription platform. - Contribute to all stages of the software development lifecycle - from planning to implementation, deployment, and maintenance. - Collaborate closely with engineers and product managers in an agile environment to deliver high-quality, impactful features. - Develop and integrate 3rd-party services to enhance functionality and improve the customer experience. - Write reliable, performant, and well-tested code that scales with our growing business. - Continuously improve existing systems through refactoring, performance optimization, and automation. - Participate in code reviews, knowledge sharing, and technical discussions to uphold best practices and foster team learning. - Troubleshoot production issues and help maintain a stable and resilient platform. - Stay curious - explore new tools, technologies, and techniques to improve developer experience and product quality. Who You Are: - You have 7+ years of professional experience building applications in a Python framework (Django, Flask, etc.). - You have 10+ years of experience building API systems, including technologies such as REST, OAuth2 and integrations with 3rd party services using REST APIs and JSON. - You have an understanding and professional experience working in a Javascript frontend framework (React, Angular, Etc.). - You have an understanding of and professional experience using a relational database (PostgreSQL, MySQL, etc.) including SQL language. - You have strong technical knowledge and deep understanding of time/maintainability/quality trade-offs. - You have experience writing unit tests. - You have experience with using version control (git, svn, etc.). - You have excellent communication & collaboration skills. - You have experience using AI models and tooling (Claude code, Cursor, etc.). - You’re a self-starter, positive and excited to work with a small dedicated team. - You are passionate about using technology to streamline business processes. Bonus Points if: - You’re a dog owner or lover. - You have experience with Django. - You have experience with React. - You have experience with NodeJS. - You have experience with Shopify. - You have experience documenting with JSON Schema and OpenAPI. - You have experience with Docker/Containerization. - You are a master prompt writer. - You are an open source community contributor. What You'll Get: - Competitive salary. - Sponsored 401k program with employer match up to 4%. - Comprehensive health coverage including medical, dental and vision. - Unlimited vacation policy that you're encouraged to use. - Paid parental leave. - 1-week paw-ternity leave for new dog parents. - Free Ollie subscription. - Inspiring pack members! What We Value: - Keeping Dogs At The Heart: Our profound love for dogs unites us and drives and inspires every aspect of our business. - Being Courageous And Kind: We create a safe, inclusive space for everyone to show up as their authentic selves. - Setting New Standards: We believe in continually raising the bar, never settling for less than our best as a team and individuals. - Making Ollie The Best Chapter: We are building an impactful business while making memorable experiences with one another.

• Provide technical leadership for support, corrective maintenance, and evolution of the SASGC • Guide and support the team in the analysis, diagnosis, and resolution of incidents in Linux environments • Perform code reviews in C/C++, ensuring quality, stability, security, and adherence to software engineering best practices • Investigate crashes, hangs, performance degradations, memory leaks, concurrency failures, and unexpected application behavior • Conduct root-cause analyses using logs, core dumps, traces, and advanced diagnostic tools • Respond to critical incidents classified as P0 and P1, coordinating technical actions for rapid service restoration • Define workarounds and contingency plans to minimize impact in production environments • Support the creation and improvement of Shell scripts for automation of operational routines, monitoring, data processing, and log analysis • Ensure correct usage of processes, threads, memory, sockets, files, CPU resources, and inter-process communication mechanisms • Manage and evolve build processes, library versioning, and dependency management • Analyze integrations between C/C++ applications, databases, APIs, messaging systems, and file-exchange mechanisms • Support the analysis and optimization of queries in Oracle and PostgreSQL databases • Identify technical risks, structural debt, and opportunities for improvement in the solution's architecture and support model • Guide the team in adopting observability practices, proactive monitoring, and reducing incident recurrence • Prepare technical documentation, operational procedures, recovery plans, and root-cause records • Work closely with Product Owners, managers, infrastructure, database, security teams, and other technology squads • Assist in prioritization among structural fixes, production incidents, and operational requests • Provide technical mentoring and promote the team's knowledge growth in C/C++, Linux, and troubleshooting

Role Description As a Senior Software Engineer on the POS team, you'll work directly across the core POS codebase: the React Native and Expo application, the Python and FastAPI backend service, the Terraform infrastructure, and the Argo CD and Helm deployment configuration. You'll design, build, deploy, and operate the next generation of Cloudbeds' point-of-sale experience for hospitality properties, covering: - Staff and device access - Floor and table management - Menus, orders, kitchen operations - Split bills, tips, payments - Room charges, receipts - Offline operation and synchronization This is a hands-on product engineering role with end-to-end ownership across application code, services, infrastructure, delivery, and production reliability. Your goal is to help us deliver a POS that is intuitive for hospitality teams, dependable under real-world conditions, and scalable across properties and markets. Qualifications - 5+ years of software engineering experience building, shipping, and operating production applications - Strong proficiency in Python and/or TypeScript - Hands-on experience with modern mobile or frontend development - Strong software engineering fundamentals - Solid understanding of relational data modeling, PostgreSQL, caching, API design, distributed systems, and asynchronous or event-driven workflows - Experience owning cloud-native delivery and operations - Experience building point-of-sale or adjacent real-time transactional systems - Experience building offline-first applications, synchronization engines, or conflict-resolution workflows - Experience with native mobile capabilities and hardware integrations - Experience with payment processing, e-invoicing, and fiscalization - Strong product sense and customer empathy - Business-level English fluency Requirements - Design, build, and operate customer-facing POS experiences across React Native, Expo, TypeScript, and Python services - Develop offline-first capabilities using SQLite, write-ahead logging, synchronization, retry, and conflict-handling patterns - Build and operate Python/FastAPI backend services - Design reliable APIs, data models, caching, synchronization, and recovery paths - Own observability, automated testing, release quality, performance, security, and production support - Own changes across the POS application, backend services, infrastructure, and deployment configuration - Contribute as a senior individual contributor through architecture decisions, code reviews, pair programming, documentation, mentoring, and continuous improvement Benefits - Remote First, Remote Always - PTO in accordance with local labor requirements - Monthly Wellness Fridays - enjoy an extra long weekend every month - Full Paid Parental Leave - Home office stipend based on country of residency - Professional development courses in Cloudbeds University - Access to professional development, including manager training, upskilling and knowledge transfer

Role Description We are seeking a talented and innovative Full Stack Developer with a passion for building modern web applications and leveraging the latest advancements in Artificial Intelligence. You will be responsible for designing, developing, and maintaining end-to-end software solutions while identifying opportunities to integrate AI technologies that improve products, automate processes, and enhance user experiences. The ideal candidate is a strong problem solver who enjoys working across both front-end and back-end development, stays current with emerging AI trends, and is excited about building intelligent, scalable applications. - Design, develop, test, and maintain scalable web applications. - Build responsive, intuitive, and high-performing user interfaces. - Develop secure back-end services, APIs, and database solutions. - Integrate third-party APIs and cloud-based services. - Optimize applications for performance, scalability, and security. - Write clean, maintainable, and well-documented code. - Participate in code reviews and software testing. - Troubleshoot, debug, and resolve application issues. - Research and evaluate the latest AI technologies and industry trends. - Recommend innovative AI solutions to improve business processes and customer experiences. - Stay up to date with emerging AI frameworks, tools, and best practices. Company Description