Principal Product Manager, AI People Products

We are seeking a strategic and visionary Principal AI Product Manager to lead the development of AI-driven solutions that revolutionize how we attract, retain, and empower our workforce. Our People and Places team's goal is that our People Experience is a key differentiator and reason for candidates to choose Toast and employees to stay at Toast, as much as our Products are today. Our People Products team works to help the People's Team. We create AI products that are simple to use. These products give employees custom experiences and helpful information while they work. They use cloud technology, can grow with demand, and are legally compliant. This boosts work efficiency and commitment among Toasters. We might also provide these products to Toast customers.

In this role, you will collaborate with various teams. You will work with People and Talent Operations, HR leaders, analytics experts, data scientists, business stakeholders and teams focusing on Privacy, Security, and Compliance. You will also work with AI councils. Your aim is to develop and launch new AI-powered tools for conversations. These solutions will enhance employee self-service, optimize People Operations and Centers of Excellence, and drive organizational excellence.

You will own and drive complex initiatives from ideation through delivery and change management, connecting AI-driven experiences to measurable business value. We are seeking a candidate with a proven track record in product management, deep technical understanding, customer empathy, and the ability to deliver impactful results through well-developed business partnerships.

Key Responsibilities:

Product Strategy & Vision

• Define and own the AI product vision and roadmap for the People Department, ensuring alignment with business objectives and employee needs.
• Explore how AI can help with HR tasks, support employees, and enhance their experience. Use AI to better hiring processes, increase employee satisfaction, teach new skills, and manage staff effectively.
• Stay informed on HR Tech industry trends to guide innovation, and apply emerging technologies, and best practices in AI (e.g. Large Language Models (LLMs),, agentic frameworks, natural user interactions (i.e., voice) in designing and building multimodal, conversational experiences that enable personalized employee experiences.
• Conduct data-driven build-vs-buy analyses and present actionable recommendations to senior management.

Product  Development

• Lead end-to-end product lifecycle management, from ideation to deployment and iterative improvements.
• Conduct user-focused research and sentiment analysis to understand employee journeys, behaviors, and pain points.
• Define and prioritize AI use cases that align with organizational goals, delivering measurable business value.
• Balance technical requirements, user needs, compliance, and security to design scalable AI solutions  based on impact, feasibility, and alignment with organizational priorities.
• Develop and maintain comprehensive product roadmaps, release notes, and marketing materials to ensure alignment and transparency.
• Provide clear direction to execution teams, advancing AI and automation initiatives from vision and scoping through delivery and change management in collaboration with data and technology partners.
• Employ rigorous A/B testing and data-driven insights to refine solutions and ensure continuous experience improvements.
• Apply design thinking and user research methodologies specific to generative and conversational AI, delivering intuitive, high-impact solutions employees love.
• Add features that understand text, voice, and images to make our product user-friendly and effortless.
• Develop advanced strategies for AI memory and context management to enable personalized, continuous conversations across the employee lifecycle.

Stakeholder Engagement

• Collaborate with HR executive team and business units to translate challenges into AI-driven requirements.
• Communicate the value and functionality of AI products to non-technical stakeholders through presentations, documentation, and training.
• Work with various stakeholders to base your decisions on data. Consider all choices, views, and information to develop a recommendation that gains consensus.

Cross-Functional Leadership

• Foster collaboration, synthesize multiple points of view to make decisions and drive alignment between design, data, technology teams, and HR leads to explore and deliver AI-driven innovations.
• Partner with data scientists, development, and third-party vendors to develop and deploy impactful AI models.
• Present complex AI concepts and solutions to executive stakeholders in a clear, compelling manner.
• Be skilled at explaining complex ideas simply, identifying risks and dependencies, and operating within technological constraints.

Ethical AI and Compliance

• Ensure AI solutions adhere to ethical guidelines, organizational values, and regulatory requirements (e.g., data privacy, bias mitigation).
• Champion transparency, accountability, and ethical standards in all AI initiatives.

Performance Measurement & Optimization

• Establish success metrics and KPIs to evaluate the impact of AI products on HR outcomes.
• Continuously gather feedback and analyze performance to refine and enhance AI tools.

Qualifications:

Required:

• Bachelor’s degree in Computer Science, Data Science, Business Administration, or a related field; advanced degree preferred.
• 8+ years in a D2C/B2C product management role leading and testing products at scale (millions of customers or 10K+ employee base), with at least 3+ years focused on conversational AI or related fields (e.g. CoPilot development, AI assistants, etc) (preferred in HR or employee exp domains)
• Experience working in a large People and Places AI-focused department, product companies specializing in AI-driven employee or customer experience solutions, or consulting roles focused on People and Places AI products.
• Deep product sense, with abilities in strategy formation, navigating ambiguity in complex spaces, and deep experience with rigorous AB testing.
• Proven success managing complex, cross-functional projects in areas such as big data, analytics, artificial intelligence, and machine learning.
• Robust communication and leadership skills with the ability to influence and inspire teams and stakeholders without relying on direct authority.
• A love for technology, and an insatiable curiosity for AI to solve real problems with deep understanding of AI technologies, including natural language processing, predictive analytics, and machine learning models.
• A clear understanding and point of view on how artificial intelligence will change user experiences
• Proven experience in defining big visions and inspiring teams to deliver new innovations and impactful products.
• Solid business acumen, stakeholder management skills, and experience collaborating across diverse teams.
• Able to create highly collaborative team spirit and able to take in multiple points of view, synthesize decisions, and communicate outcomes across the organization
• Artistry and excellence in simplifying complex ideas, identifying risks and dependencies, and delivering for customers within the constraints of technology
• Experience working in a large People and Places AI focused department or product companies that build AI customer / employee experience conversational products, or consulting background focus on People and Places AI Products

Preferred:

• Knowledge of ethical AI practices and regulatory frameworks such as GDPR, CCPA, or EEOC guidelines.
• Hands-on experience with AI tools, frameworks, or platforms.
• Proven hands-on design experience with the ability to create low-to-high-fidelity wireframes and develop product marketing enablement materials.

Equal Employment Opportunity (EEO) Statement

Our company does not discriminate in employment on the basis of race, color, religion, sex (including pregnancy and gender identity), national origin, political affiliation, sexual orientation, marital status, disability, genetic information, age, membership in an employee organization, retaliation, parental status, military service, or other non-merit factor.

Our Spread* of Total Rewards
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 lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.