Staff Software Engineer, AI & Automation
About Gladly
For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world's most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.
At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 300M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT scores, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.
The AI Knowledge team owns the surface that makes Gladly's AI actually useful. Our AI is only as good as what it can see and what it can do, and we control both. We build the integrations that give the AI real-world context (customer data, product catalogs, external systems) and the integrations that let it take action on a customer's behalf. If the AI can look up an order, check inventory, or trigger a return, our team built the path.
We provide all the Knowledge and Connectors that our AI needs to be effective. We are a small, senior team that ships fast, debates openly, and goes deep on root causes. We over-communicate, we care about the craft, and we expect a lot of each other. If you want a front-row seat to how AI gets applied in a real product at real scale, this is the team.
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, and 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, and raises the bar of the team around you without being asked. You are comfortable moving between domains, you enjoy mentoring, and you use AI coding tools every day because they make you faster, not because it is trendy.
$183,000 to $246,000 annual salary + equity + benefits
Important: 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.
Gladly is redefining customer experience AI — designed for devotion, not deflection. We put people at the center of everything we build, from our platform to our culture. When you join us, you'll enjoy:
We're a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together. Top talent, good vibes, no politics. If this role excites you but you don't meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box.
USD 183,000 - 246,000
Annually
Health Insurance
Dental Insurance
Vision Insurance
Employee Assistance Program
Life Insurance
Fitness Stipend
Pet Insurance
Disability Insurance
Health Savings Account (HSA)
Mental Health Benefits
401(k) / Retirement Plan
Stock Options
Performance Bonus
Flexible Spending Account
Parental Leave
Fertility Benefits
Adoption Assistance
Unlimited PTO
Learning & Development
Flexible Schedule
Volunteer Time Off
Home Office Stipend
Company Offsites / Retreats
Employee Referral Bonus