Staff Software Engineer, AI & Automation

About Gladly:

Gladly, the customer-centered AI customer support platform is built around people, not tickets. Unlike traditional ticket-based customer support solutions, our software helps brands deliver radically personal service at scale by integrating every channel—voice, email, SMS, chat, social messaging, and self-service—into a single, lifelong conversation stream. Companies like Allbirds, Bombas, Crate & Barrel, and Warby Parker use Gladly to create exceptional customer experiences, transforming everyday customer interactions into lasting connections.

Gladly is a fully distributed company that embraces remote work and believes in flexibility, innovation, and inclusivity. We foster a collaborative, inclusive culture that prioritizes growth, DEIB, and meaningful connections. At Gladly, people are at the heart of everything we do.

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 Staff 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 conversations—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, 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.

What You Bring

• 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

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

For U.S. based hires: $156,000 to $215,000 per annum base 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?

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.