[Hiring] Staff Software Engineer, AI & Automation @Gladly

Role Description

We are looking for a Staff Software Engineer, ideally bordering on Principal, to be the most senior individual contributor on the AI Knowledge team. This is a deeply technical, high-autonomy seat, not a management role. You will own the full connector and knowledge surface that feeds Gladly's AI, and you will set the direction for how that surface evolves over time.

Your first six months will likely center on two things:

• Making the actions our AI can take easier for customers to configure and extend.
• Building tooling that lets customers stand up new integrations without writing custom code.

You will work shoulder to shoulder with product, design, and customer-facing teams, and you will have real customers on the other end of your decisions.

You are the kind of engineer who:

• Owns problems end to end.
• Keeps digging when everyone else has accepted an answer.
• Raises the bar of the team around you without being asked.
• Is comfortable moving between domains.
• Enjoys mentoring.
• Uses AI coding tools every day because they make you faster.

What You'll Do

• Own the integration architecture.
• Set the technical direction for how external systems connect to Gladly's AI.
• Build the connective tissue for AI.
• Solve product-level problems, not just technical ones.
• Ship at a high bar, fast.
• Mentor and raise the bar.
• Collaborate across the company.

Qualifications

• 8+ years of full-stack engineering experience with a track record of shipping large-scale product.
• Proven Staff or Principal-level ownership.
• Daily, hands-on use of AI coding tools (Copilot, Cursor, Claude, or similar).
• A strong track record of turning ambiguous ideas into shipped product, especially in 0-to-1 settings.
• Deep experience with, or real willingness to learn, TypeScript, React, Go, and PostgreSQL.
• The ability to go deep on root cause rather than stopping at the first plausible answer.
• Strong communication skills.
• A customer-centric mindset.

Bonus Points For

• Experience building integration platforms, API ecosystems, or developer-facing tools.
• Familiarity with protocols like MCP (Model Context Protocol) or similar LLM integration patterns.
• Hands-on experience with LLMs (OpenAI, Claude, etc.), embeddings, or vector search in production.
• Familiarity with operational tools like DataDog, SumoLogic, and LangSmith.
• Open source work, public talks, or thought leadership in AI or engineering.

Compensation

$183,000 to $246,000 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. Final offer amounts are determined by multiple factors, including geographic location as well as candidate experience and expertise.

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.
• A company where AI is not a buzzword.
• We're a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together.