Staff Software Engineer, AI & Automation
About Gladly:
Uniquely powered by Customer AI, Gladly is the only CX platform that puts the customer —not tickets —at the center of every conversation. Trusted by the world’s most customer-centric brands, including Crate & Barrel, Ulta Beauty, and Tumi, Gladly delivers radically efficient and radically personal experiences.Gladly was built for B2C leaders who refuse to compromise on operational efficiency or experience. With Gladly, every conversation feels uniquely tailored and instantly responsive, emotionally intelligent and operationally precise, deeply personal and effortlessly scalable. At the heart of our simply powerful platform is Gladly Customer AI —uniquely designed to maintain a single, continuous conversation across all channels while striking the perfect balance of technology and human connection. Learn more at www.gladly.ai.
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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
Why Join Gladly?
At Gladly, we’re not just building software—we’re transforming an industry. We take a people-first approach, both in our product and 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
At Gladly, we believe in challenging the status quo, celebrating grit, and striving for excellence. We thrive as a team by embracing transparency, collaboration, and a customer-first mindset. If this role excites you but you don’t meet every qualification, we still encourage you to apply. Diverse perspectives and experiences are the cornerstone of our success.
Perks and Benefits
Health and Wellness
Parental Benefits
Work Flexibility
Office Life and Perks
Vacation and Time Off
Financial and Retirement
Professional Development
Diversity and Inclusion