Director, Strategic Initiatives – AI

Artificial IntelligenceArtificial IntelligenceFull TimeRemoteLeadTeam 501-1,000H1B SponsorCompany SiteLinkedIn

Location

United States

Posted

68 days ago

Salary

$166.8K - $250.2K / year

Seniority

Lead

Bachelor Degree8 yrs expEnglishGo

Job Description

• 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

Job 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

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