Senior Product Manager, AI CSM

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. At the center of this vision is Toast IQ: a single, unified assistant that orchestrates specialized agents across the Toast ecosystem. The AI CSM team is on a mission to use Toast IQ to make sure that all Toast customers have the support they need to get the most out of Toast and grow. About the Role As the Senior Product Manager, AI CSM, you will define and scale the AI-powered Customer Success Manager for every Toast customer. Your mission is to build an intelligent, proactive AI system that helps restaurants onboard successfully, adopt more of Toast’s products, improve performance, and grow over time. This role sits at the intersection of AI, growth, customer success, and product. You will own the strategy and roadmap for transforming Customer Success from a human-only function into a hybrid AI-powered model, delivering personalized guidance, insights, and action at scale. This is a high-impact, cross-functional role that will shape how Toast builds durable customer relationships in the AI era. A Day in the life (Responsibilities): Define the vision and roadmap for the AI CSM: a proactive, data-driven agent that supports customers across onboarding, adoption, performance optimization, and expansion Identify the highest-leverage customer moments where AI can drive measurable improvements in activation, product adoption, retention, and growth Partner with GTM, Care, and CSM teams to design a hybrid success model that balances automation with high-touch engagement Develop experimentation frameworks to evaluate impact on adoption, retention, expansion, and customer health Define quality standards for AI-driven guidance, ensuring accuracy, trust, and brand alignment Work closely with AI/ML, Engineering, Design, and Analytics to ship experiences that operate reliably at scale Establish feedback loops from customers and internal teams to continuously improve agent performance Ensure responsible AI practices, including transparency, guardrails, and clear escalation paths to human teams What you'll need to thrive (Requirements) 4+ years of product management experience, ideally with ownership of growth, customer success, or AI-powered systems Experience launching 0→1 products and scaling them through iteration and measurable impact Experience building products that leverage behavioral data, personalization, or recommendation engines Strong understanding of SaaS customer lifecycle metrics (activation, engagement, retention, expansion, churn) Technical fluency: comfortable working closely with ML engineers, understanding data models, experimentation frameworks, APIs, LLMs, and production AI systems Strong systems thinking, able to connect product usage signals, business outcomes, and customer workflows Proven ability to operate cross-functionally across Product, Engineering, Design, Data, Sales, and Customer Success A deep customer mindset: excited about building AI that genuinely improves how restaurants run their businesses AI at Toast At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture. Our Total Rewards Philosophy We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyl ... (truncated, view full listing at source)