Staff Software Engineer, AI & Automation

About Gladly For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world's most customer-centric brands including Crate Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient. At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 300M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT scores, this is a team where your work has real impact at scale. Learn more at www.gladly.ai . The Team The AI Knowledge team owns the surface that makes Gladly's AI actually useful. Our AI is only as good as what it can see and what it can do, and we control both. We build the integrations that give the AI real-world context (customer data, product catalogs, external systems) and the integrations that let it take action on a customer's behalf. If the AI can look up an order, check inventory, or trigger a return, our team built the path. We provide all the Knowledge and Connectors that our AI needs to be effective. We are a small, senior team that ships fast, debates openly, and goes deep on root causes. We over-communicate, we care about the craft, and we expect a lot of each other. If you want a front-row seat to how AI gets applied in a real product at real scale, this is the team. The Opportunity We are looking for a Staff Software Engineer, ideally bordering on Principal, to be the most senior individual contributor on the AI Knowledge team. This is a deeply technical, high-autonomy seat, not a management role. You will own the full connector and knowledge surface that feeds Gladly's AI, and you will set the direction for how that surface evolves over time. Your first six months will likely center on two things: making the actions our AI can take easier for customers to configure and extend, and building tooling that lets customers stand up new integrations without writing custom code. You will work shoulder to shoulder with product, design, and customer-facing teams, and you will have real customers on the other end of your decisions. You are the kind of engineer who owns problems end to end, keeps digging when everyone else has accepted an answer, and raises the bar of the team around you without being asked. You are comfortable moving between domains, you enjoy mentoring, and you use AI coding tools every day because they make you faster, not because it is trendy. What You'll Do 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 produc ... (truncated, view full listing at source)