Director Strategic Initiatives, Restaurant365
Artificial Intelligence
$166.8-250.2k
+ Equity Option Grant
Restaurant management software
Open for applications
Restaurant management software
1001+ employees
Open for applications
$166.8-250.2k
+ Equity Option Grant
1001+ employees
Company mission
To help restaurants increase sales control food costs, and optimize labor.
Role
Who you are
- 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
What the job involves
- 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
- 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
Our take
Restaurant management can be rather outdated, often relying on spreadsheets and physical receipts. Restaurant365 develops all-in-one management software solutions for the restaurant industry, encompassing accounting, analytics, staff, and inventory management within its toolkit.
Restaurant365’s customer base isn’t just restaurants though, it’s software attracts accounting firms that work with restaurants as well as small eateries and large franchises. It’s expansive customer base is reflected in the amount of funding that it has received since its founding in 2011, now making it a verified Unicorn.
Restaurant365’s most recent round of funding came in 2024, and its $175 million will be invested into further enhancing its product. The company's success is unprecedented, as most would bet that restaurant industries post-pandemic would struggle to get back on their feet. Restaurant365 defied expectations though, and actually turned out to be the company that COVID-hit restaurants relied on to keep their heads above water. This goes some way to explain the success of Restaurant365, which is a proven aid for the ailing dining industry.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
118% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
May 2024
$175m
GROWTH EQUITY VC
May 2023
$135m
LATE VC
Total funding: $437.5m
Company benefits
- Fully Covered Health Insurance: R365 provides comprehensive medical, dental, and vision coverage—100% paid for full-time employees.
- Flexible Time Off: Recharge when you need, so you can stay energized and focused.
- 401k with employer math.
- Stock options to purchase equity.
- Health Savings and Flexible Spending Accounts.
- Employee discount programs to lifestyle vendors and servcies.
- Annual learning and development reimbursement.
- Access to LinkedIn Learning.
- Employee recognition and TIP program.
- Fertility guidance and support.
- Online legal solutions.
- Paid parental leave.
- Disability insurance.
- Pet and life insurance.
- Wellness programs.
- Health concierge and support.
- Meditation and mindfulness courses.
- Gym discounts and virtual fitness classes.
Company HQ
East Irvine, Irvine, CA
Leadership
Tony Smith
(Co-Founder & CEO)Previously on the Board of Directors at Dynamic Methods. Before that, they were a Director of Services there.
Morgan Harris
(Co-Founder & Chief Customer Advocate)Previously Partner and Co-Founder at Dynamic Methods, Account Executive/Senior Consultant at Foreshock and Auditor at PriceWaterhouseCoopers.
John Moody
(Co-Founder, Chief Strategist & Board Member)Previously CRM Managing Partner and Board Member at Dynamic Methods.
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