Restaurant365 · 2 days ago
Director Strategic Initiatives, AI
United States
Full-time
Remote
Director/Executive
$167K/yr - $250K/yr
8+ years expRestaurant365 is a SaaS company disrupting the restaurant industry! The Director Strategic Initiatives, AI is responsible for defining and driving AI-focused product strategies across all product pillars, ensuring that AI investments are integrated into product line roadmaps and deliver measurable value for restaurant customers.
AccountingProductivity ToolsRestaurantsSaaSSoftware
Responsibilities
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
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
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
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
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
Qualification
Required
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
Preferred
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
Company
Restaurant365
Restaurant365 is an enterprise management software for restaurants that provides accounting, inventory, scheduling, and payroll solutions.
501-1000 employees
H1B Sponsorship
Restaurant365 has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (2)
2024 (2)
2023 (1)
2022 (1)
2021 (1)
Funding
Current Stage
Late StageTotal Funding
$437.5MKey Investors
ICONIQ GrowthBessemer Venture Partners
2024-05-15Private Equity· $175M
2023-05-19Private Equity· $135M
2019-06-27Series C· $88M
Leadership Team
Morgan Harris
Co-Founder
Kate Kemp
Chief People Officer
Recent News
2025-09-17
Company data provided by crunchbase