Director Strategic Initiatives, AI

Restaurant
365 is a SaaS company disrupting the restaurant industry! Our cloud-based platform provides a unique, centralized solution for accounting and back-office operations for restaurants. Restaurant
365’s culture is focused on empowering team members to produce top‑off results while elevating their skills. We’re constantly evolving and improving to make sure we are and always will be “Best in Class” ... and we want that for you too!

The Director of Strategic Initiatives, AI is a cross‑cutting product leadership role responsible for defining, driving, and operationalizing Restaurant
365’s most important AI‑focused product strategies across all product pillars. Reporting to the CPO, this leader partners closely with Product Line leaders, Product Management, Design, Engineering, Customer Experience, and R&D Operations to deliver AI‑powered capabilities that unlock measurable value for restaurant customers and improve the way R365 builds products.

This role overlays the existing product line structure: the Director of Strategic AI Initiatives leads cross‑product, multi‑quarter AI initiatives that span the entire portfolio.

• 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…