Staff Software Engineer, AI & Automation

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.