Senior Engineering Manager – AI Insight, Control

November 14

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Gladly

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SaaS • B2B • Artificial Intelligence

Gladly is a customer service platform that centers on AI to enhance customer interactions. The platform offers an all-in-one solution with features like People Match®, real-time CSAT feedback, and personalized self-service options, integrating seamlessly with popular tools such as Shopify and Klaviyo. With a focus on enhancing efficiency and decreasing costs, Gladly supports communication across voice, email, SMS, and social media channels. Its AI-driven approach helps businesses drive revenue and promote customer satisfaction by prioritizing personal, lifelong conversations over traditional ticketing systems.

51 - 200 employees

☁️ SaaS

🤝 B2B

🤖 Artificial Intelligence

📋 Description

• 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.

🎯 Requirements

• 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.

🏖️ 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