Gladly
Senior Engineering Manager - AI Steering
Gladly, San Francisco, California, United States, 94199
Join to apply for the
Senior Engineering Manager – AI Steering
role at
Gladly .
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, instantly responsive, emotionally intelligent, and operationally precise.
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 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.
Why This Role Is Special This is not just another AI job. As the Engineering Manager for AI Steering, 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, and configuration UX.
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. 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?
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
Seniority level Mid‑Senior level
Employment type Full‑time
Job function Engineering and Information Technology
#J-18808-Ljbffr
Senior Engineering Manager – AI Steering
role at
Gladly .
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, instantly responsive, emotionally intelligent, and operationally precise.
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 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.
Why This Role Is Special This is not just another AI job. As the Engineering Manager for AI Steering, 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, and configuration UX.
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. 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?
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
Seniority level Mid‑Senior level
Employment type Full‑time
Job function Engineering and Information Technology
#J-18808-Ljbffr