Principal AI Search & Conversation Architect; AskOle

Principal AI Search & Conversation Architect (Ask Ole)

The Principal AI Search & Conversation Architect will be responsible for designing and leading the architecture of a next-generation conversational AI platform that replaces traditional search with intelligent dialogue. This role owns the systems that understand user intent, determine what information is needed to satisfy a request, retrieve data from multiple real-time providers, reason across competing options, and generate conversational responses that lead users from discovery to transaction.

The successful candidate will architect the AI orchestration layer that coordinates multiple large language models, specialized agents, retrieval systems, recommendation engines, and external APIs into a single seamless conversational experience. Rather than returning lists of search results, the platform will assemble and rank information from ticketing providers, hotels, airlines, restaurants, transportation services, mapping platforms, weather services, and other third-party data sources, presenting recommendations through natural conversation.

This role requires deep experience designing AI-native systems capable of planning multi-step tasks, maintaining conversational context, coordinating tool execution, ranking competing results, and continuously adapting recommendations based on user feedback throughout a conversation.

The Principal Architect will define the technical vision, establish architectural standards, evaluate emerging AI technologies, mentor senior engineers, and make long-term decisions regarding LLM strategy, retrieval architecture, agent design, memory management, semantic search, vector databases, knowledge graphs, and AI evaluation frameworks.

The position requires extensive experience building large-scale distributed systems, production AI platforms, retrieval-augmented generation (RAG), multi-agent orchestration, function calling, Model Context Protocol (MCP), recommendation systems, API orchestration, prompt architecture, conversation state management, personalization, and low-latency cloud infrastructure. Experience with OpenAI, Anthropic, Gemini, open-source language models, Lang Graph, Llama Index, DSPy, vector databases, graph databases, and modern AI infrastructure is highly desirable.

The Principal AI Search & Conversation Architect will work closely with the company's other Principal Architects responsible for backend infrastructure, payments, blockchain, messaging, mini-programs, and platform services to ensure the conversational platform integrates seamlessly across the entire ecosystem while maintaining exceptional scalability, reliability, performance, and user experience.

Qualifications

• Proven experience architecting and delivering production-scale AI platforms used by large numbers of users.
• Demonstrated leadership as a Principal Engineer, Chief Architect, Distinguished Engineer, or equivalent senior technical role.
• Deep expertise in Large Language Models (LLMs), AI agents, multi-agent systems, Retrieval-Augmented Generation (RAG), semantic search, and modern AI orchestration frameworks.
• Strong understanding of recommendation engines, ranking algorithms, personalization, and conversational AI.
• Extensive experience designing distributed, cloud-native systems capable of operating at global scale with high availability and low latency.
• Hands-on experience integrating complex third-party APIs and building systems that combine multiple real-time data sources into a unified experience.
• Exceptional architectural judgment with the ability to simplify complex technical problems into scalable, maintainable solutions.
• Proven ability to lead senior engineering teams, mentor architects and principal engineers, establish engineering standards, and make long-term technical decisions.
• Strong communication skills with the ability to collaborate across engineering, product, and executive leadership.
• Entrepreneurial mindset with a passion for building category-defining products and solving problems that have not been solved before.
• A track record of shipping ambitious, innovative products rather than simply maintaining existing platforms.

Solutions not problems.

• Creative problem solver who can courageously propose and support new ideas to our organization. Not interested in best practices, let's build something better!
• Ability to adapt. An ideal candidate will welcome the opportunity to solve a broad range of problems using a wide array of technologies.
• Comfortable with ambiguity, shifting priorities and general growing pains of an early-stage technology company
• An exceptional entrepreneurial judgment that fosters independence over micro-management
• Understanding of football and international sports a huge plus

Ole Ole is located in beautiful Austin Texas, however, this role requires some travel we are privately held and rapidly growing!