Head of Artificial Intelligence, Way

• The ideal candidate brings a combination of technical proficiency, product and operational experience, and a strong bias toward action.In addition to internal automation and tooling
• This is not a research or theoretical role. We are looking for someone who has previously deployed AI tools, automation, and customer-facing features in real business environments and can do the same here—designing, building, and shipping AI-enabled functionality into a production SaaS product as well as internal systems
• 3-5+ years of experience in a technical or operational leadership role with a strong focus on automation and applied AI
• Demonstrated experience building or shipping AI-powered features in a SaaS or platform product
• Hands-on experience implementing AI tools or LLM-based systems in a real business environment
• Strong working knowledge of current AI platforms and frameworks (e.g. OpenAI, Anthropic, LangChain, Pinecone, etc)
• Familiarity with prompt engineering, vector databases, RAG pipelines, and related AI infrastructure
• Ability to manage projects from strategy through to delivery without requiring a large team
• Strong analytical skills and sound business judgment
• Excellent written and verbal communication skills
• Experience working in high-growth startups or fast-moving technology companies
• Experience in B2B SaaS and/or hospitality/consumer markets

Desirable

• We are hiring a Head of AI to lead the development and implementation of AI-driven systems and workflows across the company
• This role will be responsible for both setting the strategic vision for AI and executing it directly
• This role will also lead the integration of AI capabilities into the core
• Way platform—developing and delivering features that create real value for our customers and enhance the end-user experience
• This is an opportunity for some to blend a passion for end consumer markets, experiences, hospitality, and more, with their skills and track record in AI
• This role reports directly to the company’s Co-Founder & CEO
• Define and execute the company-wide AI strategy for internal operations
• Identify and prioritize high-impact opportunities to apply AI and automation across departments (e.g. customer success, product development, sales, finance, operations)
• Lead the evaluation, implementation, and management of AI tools and platforms
• Build internal tooling and workflows as needed, using APIs, LLMs, and off-the-shelf models
• Collaborate with team leads to redesign existing operational processes and standardize using AI-based solutions
• Partner with Design and Engineering to design, prototype, and implement new, AI-driven products and features within the Way platform
• Own the end-to-end implementation of internal AI projects, including requirements gathering, prototyping, deployment, training of team members, and adoption
• Monitor performance and maintain quality standards for AI-enabled processes