Principal AI Search & Conversation Architect (AskOle)

Company Description

Build the AI that replaces search with conversation.

AskOle is building something fundamentally different from today’s ticket exchanges, online travel agencies, and search engines.

Today, users do all the work. They search, filter, compare, open dozens of tabs, read reviews, check maps, compare hotels, look for restaurants, and try to figure out the best option.

We’re eliminating that entire experience.

A fan should simply say:

“I need two tickets for Manchester United vs Arsenal on Saturday.”

AskOle responds naturally:

“I found four excellent ticket options based on value and location. Since you’re traveling from London, would you like me to recommend hotels within walking distance of Old Trafford? I also found several restaurants that match your preferences and the best pub for pre-match atmosphere. I can book everything together in one transaction.”

That conversation replaces hundreds of clicks.

We’re looking for the Principal Architect who will build the intelligence behind that experience.

What You’ll Build

You’ll architect the AI orchestration layer that powers every AskOle conversation.

This is not another chatbot.

You’ll build a conversational commerce platform capable of understanding intent, gathering information from dozens of independent systems, reasoning over the results, ranking recommendations, asking intelligent follow-up questions, and delivering answers that feel like speaking to an expert concierge.

The platform will combine live inventory from ticket providers, hotels, airlines, restaurants, transportation, hospitality providers, maps, weather, events, reviews, and future partners into a single conversational experience.

The user never searches.

The AI does.

No pathetic AI inflated resumes or using someone else's resume

OleOle is building a global football super app combining social networking, messaging, live scores, short-form video, gambling, commerce, payments, translation, and mini programs into a single ecosystem focused entirely on football.

The vision is to create the first true “WeChat for football” — a platform where fans, clubs, brands, leagues, sportsbooks, creators, and merchants can communicate, transact, and engage directly inside one global environment.

Unlike traditional social media platforms, OleOle is built specifically for sports fans and designed around communication, real-time engagement, commerce, and community.

The platform combines elements of:

• Twitter/X style social conversation
• TikTok-style short-form video
• WhatsApp-style messaging
• live score platforms
• programmable commerce
• mini program ecosystems similar to WeChat

All integrated into a single football-first platform.

Core Platform Vision

OleOle is designed around several key ideas:

Communication First

Fans can communicate directly with:

• clubs
• brands
• sportsbooks
• creators
• media companies
• other fans

through follows, messaging, sharing, comments, and real-time translated conversations.

Mini Program Ecosystem

OleOle is building a mini program platform that allows brands and partners to launch experiences directly inside the platform without requiring fans to download separate applications.

Initial mini program categories include:

• Games
• News
• Merchandise
• Ticket Sales
• VIP Hospitality
• Gambling

Fans can:

• follow or unfollow mini programs
• communicate directly with brands
• share mini programs with friends
• receive translated content automatically

Brands can communicate directly with followers within platform communication limits designed to prevent spam and preserve user experience.

Real-Time Translation

A core component of the platform is AI-driven real-time translation across conversations, content, video, messaging, and mini programs.

The goal is to remove language barriers between global football fans and allow mini programs to operate across dozens of languages automatically.

This creates a global communication layer connecting fans, clubs, brands, and creators worldwide.

Wallet + Payments Infrastructure

OleOle includes an integrated Wallet ID and payment infrastructure powering:

• commerce
• rewards
• gambling
• digital collectibles
• mini program transactions
• creator payouts

The platform is designed around programmable commerce and frictionless fan engagement.

Technology Stack

OleOle is being built as a native Rust platform focused on:

• scalability
• performance
• real-time communication
• low-latency systems
• global infrastructure
• payments
• social engagement
• video delivery

The company is also building:

• AI translation systems
• football history AI infrastructure
• developer platforms
• mini program tooling
• programmable payment rails

The Long-Term Vision

OleOle’s long-term vision is to become the global operating system for football fans:

• social networking
• communication
• commerce
• gaming
• gambling
• content
• ticketing
• rewards
• programmable fan experiences

all inside one interconnected ecosystem.

OleOle – Where Fans Kick Off

Job Description

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, LangGraph, LlamaIndex, 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

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.

Additional Information

Solutions not problems .

• Creative problem solver who can courageously propose and support new ideas to our organization. Not interested in best practices, lets 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!