Senior AI Enablement Manager, Restaurant365
$116-174k
+ Equity
Restaurant management software
Open for applications
Restaurant management software
1001+ employees
Open for applications
$116-174k
+ Equity
1001+ employees
Company mission
To help restaurants increase sales control food costs, and optimize labor.
Role
Who you are
- 8+ years of experience in change management, organizational effectiveness, learning and development, communications, transformation, strategy, or program management
- Experience designing and launching enterprise-wide programs that change behaviors or how work gets done
- Strong program management discipline and the ability to manage multiple initiatives simultaneously
- Excellent communication and storytelling skills, with the ability to translate technical concepts for non-technical audiences
- Sufficient technical literacy to understand AI capabilities, limitations, and responsible-use considerations without being a technologist or developer
- Experience using data and dashboards to measure adoption, fluency, engagement, or business impact
- Credibility and influence across functions and senior leadership without direct authority
- Demonstrated curiosity and hands-on use of AI tools
- Builder mindset; comfortable creating programs from scratch, operating in ambiguity, and improving the playbook as the organization learns
- Strong judgment, operational rigor, and commitment to responsible and practical AI adoption
What the job involves
- R365 is committed to becoming an AI-first organization. Enterprise Technology owns AI architecture, security, tooling, and technical delivery. The Senior Manager, AI Adoption & Enablement owns the People-side strategy that ensures those investments translate into employee adoption, AI fluency, behavior change, and measurable business value
- This role bridges the gap between what gets built and what the organization actually uses. The role designs and runs enterprise AI adoption programs, activates the AI fluency framework, leads internal communications and storytelling, and ensures every significant AI capability launch has a coordinated enablement and adoption plan
- This is a People Team role. It does not own AI architecture, tooling, security, enterprise AI portfolio prioritization, or workforce strategy decisions
- Partners closely with: Enterprise Technology, Performance & Capability, People Analytics, Total Rewards, Communications, PBPs, and functional leaders
- Design and execute company-wide AI adoption programs, including office hours, lunch and learns, use-case spotlights, adoption challenges, champions, and self-serve resources
- Build and maintain an internal AI community where employees can share successes, ask questions, and learn from one another
- Partner with People Analytics to establish adoption metrics and report progress across functions
- Define launch-readiness requirements so new AI tools and capabilities have a parallel adoption plan, communications plan, and support model
- Own the AI Champions Program, including defining the champion role, recruiting cross-functional representatives, providing onboarding and ongoing enablement, facilitating regular community sessions, and creating feedback loops that surface use cases, adoption barriers, and business needs to People and Enterprise Technology
- Leads AI-enabled improvements and coaches others on best practices, driving AI adoption, fluency, and measurable business impact across R365
- Partner with Performance & Capability to activate R365’s AI fluency framework through role-based development content, learning pathways, manager toolkits, and practical use cases
- Partner with Talent Solutions and Enterprise Technology to curate, define, and build role-based AI training paths that develop deeper technical capabilities across R365, including appropriate progression for employees, champions, and technical practitioners
- Help employees and leaders understand how to apply AI responsibly and effectively in their work
- Design and run the annual cross-functional AI Hackathon, tied to real business problems and measurable outcomes
- Build and maintain AI awards and recognition programs that reinforce fluency, experimentation, and innovation
- Coordinate administration of the $100K AI accelerator bonus program in partnership with Total Rewards
- Define program requirements and qualifying criteria in partnership with the appropriate owners
- Lead program communications, eligibility tracking, and employee support
- Partner with People Analytics to make fluency scores and bonus eligibility transparent through appropriate reporting and dashboards
- Ensure the program reinforces desired AI adoption and behavior without owning compensation or bonus structure design
- Own the internal AI communications cadence, including what is being built, what is available, what is working, and what employees should do next
- Develop AI win stories, use-case spotlights, adoption updates, release communications, and leadership narratives
- Partner with Enterprise Technology on communications timing so employee messaging aligns with tool launches and capability rollouts
- Translate technical capabilities into clear, relevant guidance for non-technical audiences
- Serve as the primary People-side liaison to Enterprise Technology for AI adoption and enablement
- Participate in roadmap and planning conversations to understand upcoming capabilities and translate them into adoption plans
- Provide employee and business feedback to Enterprise Technology to inform rollout priorities and support needs
- Ensure major AI launches include coordinated training, communications, support, and adoption measurement
- Define People Team requirements and partner on internal AI use cases that improve how the People Team operates; this role does not own technical architecture or infrastructure delivery
- Manage a portfolio of AI adoption, fluency, communications, and recognition initiatives from design through execution
- Maintain integrated plans, milestones, risks, dependencies, and stakeholder communications
- Establish repeatable program standards, playbooks, and governance rhythms
- Influence leaders and employees across Sales, CS, R&D, Finance, People, and other functions without relying on direct authority
- Identify adoption barriers and design practical interventions that help teams move from awareness to sustained use
- Year-One Success Measures
- AI fluency scores are transparent, tracked, and improving quarter over quarter
- Adoption of key AI tools is measurably higher than at program launch
- The AI accelerator bonus program is live, well communicated, and credibly connected to fluency and performance data
- The annual AI Hackathon launches with cross-functional participation and produces at least one documented use case shipped into production
- A consistent internal AI communications cadence is operating, with employees clear on available tools, use cases, and support resources
- Major AI tool and capability launches include a coordinated adoption and enablement plan
- People Team AI use cases are identified, piloted, and adopted where they can improve efficiency or workforce experience
- A curated, role-based AI training path is available across R365, with measurable participation and progression into more technical AI capabilities
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. Its 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 in further enhancing its product. The company's success is unprecedented, as most would bet that the post-pandemic restaurant industry would struggle to get back on its feet. Restaurant365 defied expectations 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 the company, 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)Previously CRM Managing Partner and Board Member at Dynamic Methods.
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