Staff Software Engineer, AI & Automation

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.

Responsibilities:

• Own 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 which
• Build 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 stack
• Solve 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 boundary
• Ship 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 vacuum
• Mentor 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 to
• Collaborate across the company. Work closely with product managers, designers, and customer-facing teams to solve problems that matter to the business

Requirements:

• 8+ years of full-stack engineering experience with a track record of shipping large-scale product. Comfortable across the stack
• Proven Staff or Principal-level ownership. You have owned domains end to end, made architectural decisions independently, and driven projects to completion with minimal oversight
• Daily, 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 them
• A strong track record of turning ambiguous ideas into shipped product, especially in 0-to-1 settings
• Deep experience with, or real willingness to learn, TypeScript, React, Go, and PostgreSQL
• The ability to go deep on root cause rather than stopping at the first plausible answer. You are the person others bring the hardest bugs to
• Strong 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 code
• A customer-centric mindset. You care about what you are building and who you are building it for
• Experience building integration platforms, API ecosystems, or developer-facing tools
• Familiarity with protocols like MCP (Model Context Protocol) or similar LLM integration patterns
• Hands-on experience with LLMs (OpenAI, Claude, etc.), embeddings, or vector search in production
• Familiarity with operational tools like DataDog, SumoLogic, and LangSmith
• Open source work, public talks, or thought leadership in AI or engineering