Director Strategic Initiatives, AI

Restaurant365 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. Restaurant365’s culture is focused on empowering team members to produce top-notch 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 Strategic Initiatives, AI is a cross-cutting product leadership role responsible for defining, driving, and operationalizing Restaurant365’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.  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