Senior AI Enablement Manager

Job Description

Job Description

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!

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 

 

How you'll add value:

AI Adoption Programs 

• 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. 

AI Fluency Development 

• 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. 

AI Accelerator Bonus Program 

• 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. 

Internal Communications and Storytelling 

• 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. 

Enterprise Technology Partnership 

• 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. 

Program Management and Change Leadership 

• 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. 

What you'll need to be successful in this role:

• 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. 

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. 

R365 Team Member Benefits & Perks

• Competitive compensation package
• Ability to work remote or hybrid
• Comprehensive medical benefits
• 401k + matching
• Equity Option Grant
• Unlimited PTO + Company holidays
• Wellness initiatives

Why join our amazing team?

• We're a community that prides itself in creating innovative solutions and producing quality work
• Our product is the secret ingredient that makes a real difference to restaurants nationwide
• The open concept work environment that we've created is causal, collaborative, and cultivates communication

 

This role is hybrid, balancing flexibility with the value of in-person collaboration. To support connection, partnership, and team effectiveness, employees are expected to work onsite each Tuesday and Wednesday.

Internal Employees - R365 is committed to growing talent from within. If you see a role that excites you and you meet the qualifications, we encourage you to apply -regardless of your current location or work arrangement. Reach out to your People Business Partner if you have questions.

 

DYN365, Inc d/b/a Restaurant365 is an equal opportunity employer.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.