Staff Software Engineer, AI & Automation

Summary

Join Gladly, a customer-centered AI customer support platform company, as a Staff Software Engineer focused on AI and Automation. You will help define the future of customer service by applying generative AI in meaningful ways, working on products that impact millions of conversations and collaborating with iconic brands. This role involves leading major AI & automation initiatives, architecting high-impact projects, building features from idea to production, mentoring other engineers, designing foundational systems, collaborating with various teams, and driving innovation. You will need 10+ years of full-stack engineering experience, a proven ability to turn ideas into shipped products, a passion for AI and automation, and deep experience in TypeScript, React, Go, and PostgreSQL. Gladly offers competitive salaries, stock options, comprehensive benefits, generous paid time off, parental leave, home office stipends, a fully remote work environment, and a commitment to professional growth.

Requirements

• 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

Responsibilities

• Lead Major AI & Automation Initiatives
• Architect and drive high-impact projects involving LLMs, embeddings, RAG, agent 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 Allbirds
• Mentor & Multiply
• Spend ~50% of your time leading and leveling up other engineers—especially senior engineers—and raising the bar for technical excellence
• 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 new introduce best practices at Gladly

Preferred Qualifications

• 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

Benefits

• 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