Senior Engineering Manager - AI Steering

Gladly is the platform for building enterprise agentic systems, trusted by the world’s most customer-centric brands, including Crate&Barrel, Ulta Beauty, and Tumi. We’re at the forefront of using AI to improve how customer service works in the real world. 

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 offers a unique environment where advances in AI connect directly to products driving customer impact.

About the AI Steering 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.

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.

• 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.

• 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.

• 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.