Director Strategic Initiatives, AI

How you'll add value:

• AI Strategy & Portfolio Leadership: 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.), aligned with the overall product vision and company objectives; identify and prioritize high-impact AI opportunities (e.g., predictive insights, automation, copilots/ assistants, intelligent workflows) that create differentiated value for restaurant operators and internal users; build and manage a portfolio of AI initiatives—from discovery through launch—that leverages shared platform capabilities and avoids one-off, siloed solutions; partner with the CPTO and product line leaders to ensure AI investments are tightly integrated into product line roadmaps, with clear success metrics and trade-offs.
• Cross-Product Initiative Ownership: 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; drive cross-functional alignment on problem definition, scope, sequencing, and success criteria for each initiative, balancing customer impact, technical feasibility, and operational readiness; coordinate with Product Directors, Product Managers, and Design leaders to embed AI experiences into existing workflows and UI surfaces in a coherent, user-centered way; ensure AI initiatives are designed as reusable capabilities (models, services, patterns) that can be extended and adopted across product lines.
• Customer, Data, and Market Insight: 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; partner with Customer Experience, Sales, and Marketing to identify recurring themes where AI can meaningfully reduce friction, improve decision-making, or automate routine work; collaborate with Data, Analytics, and AI/ML teams to understand available data assets, model capabilities, and constraints, shaping initiatives that are both ambitious and feasible; monitor competitive landscape and broader AI trends in vertical SaaS and restaurant/hospitality tech, translating insights into pragmatic, differentiated bets for R365.
• Product Discovery, Experimentation & Delivery: Lead structured discovery for AI initiatives (e.g., customer interviews, workflow mapping, prototyping, experimentation) to validate problems, solutions, and value before large-scale investment; define clear hypotheses, success metrics, and experiment plans (A/B tests, pilots, beta programs) to de-risk AI features and experiences; translate strategic intent into clear, actionable product requirements and stories that Product and Engineering teams can execute against; partner with Engineering, Data, and Architecture leaders to ensure technical approaches are scalable, secure, governable, and aligned with R365’s platform strategy.
• Operating Rhythm & Cross-Functional Collaboration: Define and run the operating rhythm for AI initiatives across Product, Engineering, R&D Operations, and Go-To-Market teams (e.g., initiative reviews, roadmap checkpoints, risk/issue management); ensure AI initiatives are visible, well-planned, and accurately represented in portfolio planning, capacity planning, and executive reporting; act as a visible connector and communicator across R&D and our GTM partners, ensuring everyone understands where AI is going, how initiatives fit together, and what is expected from each team; work with Product Marketing and Enablement teams to shape messaging, positioning, and go-to-market plans that clearly articulate the value of AI initiatives.

What you'll need to be successful in this role:

• 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.

R365 Team Member Benefits & Perks

• This position has a salary range of $166,800 - $250,200. The above range represents the expected salary range for this position. The actual salary may vary based upon several factors, including, but not limited to, relevant skills/experience, time in the role, business line, and geographic location. Restaurant365 focuses on equitable pay for our team and aims for transparency with our pay practices.
• Comprehensive medical benefits, 100% paid for employee
• 401k + matching
• Equity Option Grant
• Unlimited PTO + Company holidays
• Wellness initiatives