Head of AI

Head of AILocation: On-Site in Austin, TX, or Paris, FR
Position Summary 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. 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 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 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.
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.
Key ResponsibilitiesDefine 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.
Qualifications3-5+ 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.
Additional PreferencesBackground in AI engineering, systems design, or data science.Experience in B2B SaaS and/or hospitality/consumer marketsPrior experience leading cross-functional transformation or automation initiatives.