Senior Engineering Manager - AI Insight & Control
Thankful
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.
About the Agent Insight & Control Team
Our mission is to make Gladly’s agentic AI platform understandable, steerable, and improvable by humans — through the right tooling, reporting, and feedback loops.
This team builds the control surface for agents on the platform: reports that help users understand how their agents are performing, and the configuration tools that let them adjust and improve behavior. We’re designing the interfaces — technical and human — that make a complex AI system transparent, trustworthy, and tunable.
Why This Role Is Special
This is not just another AI job..
As the Engineering Manager for Agent Insight & Control, you’ll lead the team that empowers users to understand and steer their agentic AI systems. You’ll design the reports, dashboards, and configuration UX that let real people take meaningful control over their agents’ behavior.
We’re not chasing hype—we’re building a production-grade AI platform for agents that are explainable, configurable, and trustworthy. This is your chance to have a huge technical and product impact, shaping the way humans interact with autonomous AI at scale.
What You’ll Do
- Lead a cross-functional product team (backend engineers, frontend engineers, and data scientists) building the control plane for our agentic platform: dashboards, reporting pipelines, configuration UXs.
- Own the feedback loop between performance insights and agent configuration — enabling users to see what’s happening and confidently act on it.
- Develop the infrastructure that powers these loops: telemetry pipelines, evaluation metrics, and APIs that expose agent performance in understandable ways.
- Collaborate closely with Product, Design, and Data science to define what “steerability” means in practice — from reports and dashboards to in-product tuning experiences.
- Deliver production-ready tools that help users analyze agent behavior and adjust their configuration, improving outcomes in real time.
- Drive innovation, staying on the cutting edge of AI and introducing new best practices for interpretable, configurable, and human-controllable AI systems
- Mentor engineers and foster a culture of clarity, data-driven iteration, and thoughtful system design.
What You Bring
- Engineering leadership experience: 5+ years leading teams including delivering large-scale, complex systems.
- Bias for action: Proven ability to take ambiguous, early-stage ideas to production—especially in 0-to-1 contexts.
- Customer- and user-centric mindset: Deep empathy for how people interact with intelligent systems; you balance simplicity with control.
- Product intuition: Experience creating intuitive, actionable product experiences that help non-technical users manage complex systems.
- Technical depth: Strong foundation in backend systems, data pipelines, and observability tooling, with a willingness to learn about LLMs and agentic AI workflows.
- Collaborative leadership: Excellent communication skills—you mentor engineers and bridge between research, infrastructure, and product disciplines.
- Data-driven approach: You define success through metrics and measurable impact, not just code delivery.
Bonus Points For
- Hands-on experience with LLMs, embeddings, RAG pipelines, or agentic workflows.
- Familiarity with observability and monitoring tools such as DataDog and LangSmith.
- Background in AI tooling, evaluation, or configuration systems for real-world applications.
- Open-source contributions, 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.
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.