[Remote] Staff Software Engineer, AI & Automation

Note: The job is a remote job and is open to candidates in USA. Gladly is a customer experience AI company focused on delivering cost savings and customer devotion. They are seeking a Staff Software Engineer to lead the AI Knowledge team, owning the integration architecture and enhancing the AI's capabilities through effective customer interactions and technical solutions.ResponsibilitiesOwn the integration architecture. Set the technical direction for how external systems connect to Gladly's AI. Evolve what exists, design what doesn't, and know when to do whichBuild the connective tissue for AI. The LLM needs context to be useful and pathways to take action. You will build both, expanding what the AI can see and what it can do across the customer's full tech stackSolve product-level problems, not just technical ones. Partner with product and design on how integrations should feel for customers, not just how they work under the hood. Your work does not stop at the API boundaryShip at a high bar, fast. Features go from idea to production with direct input from customers like Crate & Barrel and REI. You will build, iterate, and ship, not design in a vacuumMentor and raise the bar. Demo your work, share what you learn, and help Senior engineers grow into Staff. You will be the senior technical IC the rest of the team looks toCollaborate across the company. Work closely with product managers, designers, and customer-facing teams to solve problems that matter to the businessSkills8+ years of full-stack engineering experience with a track record of shipping large-scale product. Comfortable across the stackProven Staff or Principal-level ownership. You have owned domains end to end, made architectural decisions independently, and driven projects to completion with minimal oversightDaily, hands-on use of AI coding tools (Copilot, Cursor, Claude, or similar) as part of how you build. You have opinions on where they help, where they get in the way, and when to override themA strong track record of turning ambiguous ideas into shipped product, especially in 0-to-1 settingsDeep experience with, or real willingness to learn, TypeScript, React, Go, and PostgreSQLThe ability to go deep on root cause rather than stopping at the first plausible answer. You are the person others bring the hardest bugs toStrong communication skills. You can zoom out and explain a system at a high level of abstraction, and zoom in and debug a specific behavior in the codeA customer-centric mindset. You care about what you are building and who you are building it forExperience building integration platforms, API ecosystems, or developer-facing toolsFamiliarity with protocols like MCP (Model Context Protocol) or similar LLM integration patternsHands-on experience with LLMs (OpenAI, Claude, etc.), embeddings, or vector search in productionFamiliarity with operational tools like DataDog, SumoLogic, and LangSmithOpen source work, public talks, or thought leadership in AI or engineeringBenefitsEquityBenefitsCompetitive salaries, stock options, and comprehensive benefitsGenerous paid time off, parental leave, and home office stipendsA fully remote work environment with opportunities for in-person team gatheringsA strong commitment to professional growth and an inclusive workplace where diverse perspectives thriveCompany OverviewCustomer Experience AI Platform It was founded in 2015, and is headquartered in San Francisco, California, USA, with a workforce of 201-500 employees. Its website is https://www.gladly.ai/get-started/?utm_source=crunchbase&utm_medium=referral.Company H1B SponsorshipGladly has a track record of offering H1B sponsorships, with 1 in 2026, 3 in 2025, 1 in 2023, 2 in 2022, 2 in 2021, 2 in 2020. Please note that this does not guarantee sponsorship for this specific role.