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 Opportunity We’re at the forefront of using AI to improve how customer service works in the real world. From helping agents respond faster to automating common questions, we’re building AI features that actually get used—and make a difference. What makes Gladly special for AI work is the combination of real customers, rich data, and strong product teams . We work closely with some of the most innovative brands out there, giving us a direct line to real problems and the opportunity to build thoughtful solutions that impact millions of people. We’re a remote-first company that values flexibility, curiosity, and collaboration. If you’re excited about using AI to solve real problems for real people, Gladly is a great place to do it. Why This Role Is Special This is not just another AI job. As a Software Engineer focused on AI and Automation , you’ll help define the future of customer service by applying generative AI in meaningful, real-world ways. You'll work on products that touch millions of people—and you’ll collaborate directly with iconic brands that are eager to innovate with us. We’re not chasing hype. We’re building production-grade AI systems that help real agents work faster, smarter, and more humanely. This is your chance to have a huge technical and product impact at a company where AI is central—not bolted on. What You’ll Do Lead Major AI & Automation Initiatives Architect and drive high-impact projects involving LLMs, embeddings, RAG, agentic workflows, and more. Ship Real Products Build features that move from idea to production quickly—often with direct input from leading customers like Crate & Barrel and REI. Design Foundational Systems Create scalable infrastructure and reusable components that power teams across Gladly. Collaborate Closely Work shoulder-to-shoulder with product managers, designers, and customer-facing teams to solve meaningful problems. Drive Innovation Stay on the cutting edge of AI, evaluate new tools and models, and continually introduce new best practices at Gladly. What You Bring 5-10+ years of full-stack engineering experience, including large-scale product development and team leadership A proven ability to turn ambiguous ideas into shipped product , especially in early-stage, 0-to-1 settings A passion for AI and automation —you stay current on the latest trends and are eager to apply them creatively Deep experience, or willingness to learn, TypeScript, React, Go, and PostgreSQL Strong communication and collaboration skills—you’re as comfortable mentoring as you are coding A customer-centric mindset—you care about what you’re building and who you’re building it for A data-driven approach—you use metrics and insights to guide decisions and measure impact Bonus Points For Hands-on experience with LLMs (OpenAI, Claude, etc.), embeddings, vector search, RAG pipelines Familiarity with operational monitoring tools like DataDog, SumoLogic, and LangSmith Open-source work, public talks, or thought leadership in AI or engineering Compensation $183,000 to $215,000 annual salary + equity + benefits For cash compensation, we set standard ranges for all U.S.-based roles based on function, level, and geographic location, benchmarked against similar-stage growth companies. In order to be compliant with local legislation, as well as to provide greater transparency to candidates, we share salary ranges on all job postings regardless of desired hiring location. Final offer amounts are determined by multiple factors, including geographic location as well as candidate experience and expertise, and may vary from the amounts listed above. Why Join Gladly? Gladly is redefining customer experience AI — designed for devotion, not deflection. We put people at the center of everything we build, from our platform to our culture. When you join us, you'll enjoy: Competitive salaries, stock options, and comprehensive benefits Generous paid time off, parental leave, and home office stipends A fully remote work environment with opportunities for in-person team gatherings A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive A company where AI is not a buzzword. We build AI products and we expect our team to use AI tools daily We're a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together. Top talent, good vibes, no politics. If this role excites you but you don't meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box.