Define and maintain a clear AI product strategy and multi-year roadmap that cuts across all R365 product pillars (Accounting, Inventory & Sales, Workforce & Payroll, Platform, etc.)
Lead end-to-end execution of strategic AI initiatives that span multiple product lines, acting as the initiative owner responsible for outcomes, not just outputs
Ground AI strategy in a deep understanding of restaurant operators’ pain points, jobs-to-be-done, and desired outcomes, not just AI technology for its own sake
Lead structured discovery for AI initiatives to validate problems, solutions, and value before large-scale investment
Define and run the operating rhythm for AI initiatives across Product, Engineering, R&D Operations, and Go-To-Market teams

Requirements

8–12+ years of experience in Product Management or closely related roles in B2B SaaS, including significant work on data, analytics, or AI/ML-powered products.
Proven track record leading cross-functional, cross-product strategic initiatives from concept through launch and iteration—ideally in a high-growth SaaS environment - influencing without direct authority/
Strong understanding of modern AI/ML capabilities and patterns (e.g., predictive models, recommendations, generative AI, copilots/assistants, workflow automation) and how they can be applied to real-world business workflows.
Experience partnering closely with Engineering, Data/AI, and Design teams to ship AI-powered experiences that are usable, trustworthy, and deliver measurable value.
Comfort working at both strategic and tactical levels: able to set multi-quarter direction while also writing detailed requirements, reviewing designs, and guiding day-to-day trade-offs.
Excellent communication and storytelling skills, with the ability to explain complex AI concepts and trade-offs in clear, non-technical language to executives, cross-functional partners, and customers.
Strong analytical and data-driven mindset; comfortable defining metrics, analyzing results, and using insights to drive decisions and prioritization.
Experience in restaurant technology, hospitality, financial operations, workforce management, or other complex operational domains is a strong plus.
Familiarity with agile development practices and modern product discovery methods.

Benefits

Comprehensive medical benefits, 100% paid for employee
401k + matching
Equity Option Grant
Unlimited PTO + Company holidays
Wellness initiatives

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills

Product ManagementAIMachine LearningData AnalyticsPredictive ModelsGenerative AIWorkflow AutomationRequirements WritingAgile DevelopmentProduct Discovery

Soft skills

CommunicationStorytellingAnalytical MindsetCross-Functional LeadershipInfluencing Without AuthorityStrategic ThinkingTactical ExecutionProblem SolvingCollaborationDecision Making