Senior level full-stack/mobile software engineer with a specialty in native iOS development (Objective-C & Swift), object-oriented Python backends, SQL and NoSQL databases, Bootstrap/Tailwind and React/vanilla JavaScript web frontends, and AWS infrastructure. More specifically, someone who has significant experience in modernizing and maintaining legacy stacks. This person will spend a lot of time upgrading/migrating/optimizing our stack to meet today's standards. They will need to swiftly gain fluency in our business, our customers, our industry, our internal operations, our product offerings, and our technology stack, and within a few months, will be expected to be able to lead the development of our software, hand-in-hand with our other senior engineer. They will be tasked with preparing and presenting compelling component-by-component technical recommendations for the stack modernization, creating full specifications, architectural diagrams, project timelines and requirements documentation to support their proposal. They will then be responsible for all resulting implementation efforts (across every layer of the stack.) Additionally, the person will be tasked with triaging, diagnosing and resolving time-sensitive bugs as reported by clients, as well as rectifying issues, crashes, deprecations, performance bottlenecks and errors detected by our various monitoring and telemetry tools. Once the stack migration is completed, the person will have the opportunity to help us grow our products in many areas, including: further integrating AI and ML technologies into our solutions expanding our platform into other subject areas beyond wine developing inventory modules architecting API connectors/middleware to interact with POS systems enhancing our GIS/interactive mapping implementations extending into other clients/interfaces beyond iPad CURRENT AND FUTURE TECH STACK Currently we have two primary products that each have mobile and web application components. Both products are built on a LEMP + iOS (Obj-C) stack and predominantly utilize AWS services. iOS We are intent on migrating our iOS applications from Objective-C with UIKit & Core Data to Swift 5+ with SwiftUI & SwiftData Backend/Web Services While our current backend is PHP-based (and familiarity with that language would be valuable), we intend to migrate our server-side stack to Python, utilizing the Django framework. Additionally, we will be exchanging our current MySQL databases for a combination of PostgreSQL and MongoDB. Web Frontend Our web frontend, presently built with Bootstrap 2.X and jQuery, will be upgraded to LTS Bootstrap/Tailwind CSS and all jQuery will be migrated to React and vanilla JavaScript. PROFICIENCIES Soft Skills You are able to confidently present solutions to all stakeholders and swiftly execute them. You do not need a project manager to keep you on track, to review your work or to proactively communicate to the team. You have a track record of setting realistic/accurate milestones & timelines and hitting them. You are opinionated, yet flexible. When asked a question of preference, you answer assertively, but are willing to hear out others' responses and discuss. You are honest, transparent and communicative. No 'radio silence.' Everyone is on the same page. You are resourceful; you use appropriate tools to optimize your efforts, always thoroughly read the documentation, know how and where to search for things, and have an active peer group where you can direct questions in areas or circumstances in which you are less familiar. You are capable of admitting when you need help or don't know how to do something. You are always seeking ways to enhance the product portfolio, proactively researching, developing functional prototypes and making recommendations to the Chief Product Officer in order to ensure the Company remains competitive and at the forefront of the industry. You are eager to dive deep into the areas of both wine and restaurant operations, and are willing to put the effort into becoming fluent in each. Technical Fit You have demonstrated expertise in o iOS development (Objective-C, UIKit, Core Data, Swift, SwiftUI, SwiftData) o full-stack Python development using the Django web framework o relational and NoSQL databases (MySQL, PostgreSQL, MongoDB) [key-value, in-memory & document db experience would be valuable] o RESTful APIs o Linux and Mac OSes o Nginx Web Servers o JavaScript (vanilla JavaScript, TypeScript and React), HTML and CSS (Bootstrap and Tailwind CSS frameworks) o Python, Bash and Node.js Scripting When faced with challenges, you can pinpoint a solution while taking into account the big picture: o all technological touchpoints - codebases, data flows, user interfaces, web services, third-party tools, DevOps resources, etc. o all customers/use-cases - solutions utilized, unique deployment environments, different network conditions, varying deployment locations & time zones, particular technical requirements, etc. You have extensive experience with DevOps (especially with AWS) - provisioning, configuring and securing technological resources; building CI/CD pipelines; implementing full-lifecycle backup and recovery plans; constructing centralized observability watchtowers; maintaining and updating all resources; carrying out routine security, performance and cost audits & optimizations. You are Apple-centric. You primarily use Mac, iPhone, iPad and other Apple products in your professional and personal life. You watch all Apple announcements and annually participate in WWDC. You routinely install beta OSes and test out SDKs prior to their GA release. You have a solid grasp on Apple's Human Interface Guidelines and App Store Review Guidelines, as well as all APIs, frameworks, resources and developer tools available to you via the Apple Developer Program. In your professional career, you have undertaken the task of transitioning a complete technology stack from out-of-date or deprecated versions to the latest LTS or stable release. Additionally, you have previously migrated a complete codebase from a particular programming language or framework to a different one. Debugging is second nature to you. Regardless of the platform, you know what questions to ask and which variables to look for in order to swiftly diagnose, isolate, reproduce and resolve. You have a keen eye for detail in interface design and an acute understanding of UX best practices. If delivered a UI design, you can replicate it in code without explicit documentation. If delivered a brief without a UI design, you are able to create a logical, complete and user-friendly interface. You take into account your past experiences, learnings and industry best-practices when making decisions, as to reduce the likelihood of bugs, errors, breaches, spikes or regressions. You understand that you will be inheriting codebases that have been discretely contributed to by over a dozen different developers over a period of a decade, and what that means for you. Your code is always written in grammatically correct English, is clean & organized, follows SOLID principles, adheres to language conventions, features comprehensive inline documentation, contains proper error & exception handling, and is self-reviewed and tested prior to committing to the source repo or pushing live. You enjoy contributing to the open source community, and are always exploring & evaluating new languages, frameworks, libraries, databases, software and hardware. Culture-Fit You are seeking an opportunity that will last in terms of years, not months. While on paper you might be a full-time contractor, you are treated as full members of our team, and we want you to grow with us. You are comfortable in a flexible, dynamic working environment. If a time-sensitive 'fire' arises [i.e. an outage or a customer-impacting P1 incident], you are expected to help put it out ASAP, even if it's in the middle of the night or on a holiday. We approach this reciprocally; if you experience a circumstance requiring unexpected time off in your personal life, we are understanding and compassionate of the situation. You have the willingness to go above and beyond what is asked of you, be it working over the weekend in order to hit deadlines or taking on duties not explicitly listed in this job description. You are comfortable and willing to be on Slack throughout your working day, and have the ability to receive and respond to after-hours notifications in cases of urgency. As a bootstrapped startup, we are always hustling and consider flexibility and follow-through to be paramount. '9-to-5' is simply not us. Nor are methodologies like 'Agile/Scrum.' You, too, embrace flexibility and hustle over all else.