About Us

The rules of discovery have changed. The search bar is becoming a conversation, and brands need a new playbook to win. That's where Yolando comes in. We are the command center for the AI era, helping marketers move from simple visibility to true velocity. Backed by $12M in funding (including Drive Capital and MaRS Discovery District), our tight-knit team of 15 is building the engine that defines how brands get found, cited, and recommended by AI. We aren't just building a roadmap; we're building the standard for Generative Engine Optimization.

Role Overview

We are looking for a Senior Software Engineer to drive the technical direction of Yolando, our flagship AI Search Optimization platform. You will own AI/LLM systems end-to-end, designing production agents using Pydantic AI for content generation and competitive intelligence. As a technical leader, you will architect scalable backend services using FastAPI and PostgreSQL, build real-time collaborative systems with WebSockets, and mentor engineers to establish patterns that scale.

Key Responsibilities

• Own AI/LLM Systems End-to-End: Design and build production AI agents using Pydantic AI for content generation, brand analysis, and competitive intelligence. Implement tool-based architectures that enable agents to explore signals and generate recommendations at scale.

• Architect Scalable Backend Services: Build and evolve FastAPI microservices that power real-time content workflows, handling complex state machines for onboarding, content generation, and recommendation pipelines. Optimize PostgreSQL with pgvector for embedding-based semantic search and deduplication.

• Build Real-Time Collaborative Systems: Implement WebSocket-based real-time collaboration features, including document synchronization, streaming AI responses, and live status updates using technologies like Yjs CRDTs.

• Drive Infrastructure Excellence: Own service deployment on GCP/Kubernetes with KEDA event-driven autoscaling. Design ScaledJobs for background processing, implement zero-downtime migrations, and establish observability patterns with Logfire.

• Lead Technical Direction: Mentor engineers, drive architectural decisions, and establish patterns that scale. Own complex features from design through production rollout, coordinating across frontend and data engineering teams.

What We're Looking For

• 5+ years backend engineering with Python and production experience with FastAPI or similar async frameworks.

• Proven track record building AI/LLM-powered applications in production (prompt engineering, agent architectures, tool use patterns).

• Deep experience with PostgreSQL, including query optimization, indexing strategies, and migrations at scale.

• Strong understanding of distributed systems: event-driven architectures, background job processing, caching patterns.

• Experience with GCP, Kubernetes, and Terraform for production infrastructure.

• Track record of technical leadership: mentoring, architectural decision-making, cross-team coordination.

• Ownership mindset: you drive features end-to-end, from design through production support.

Bonus if you have:

• Experience with vector databases (pgvector, Pinecone) and embedding-based search/RAG systems.

• Background in real-time systems: WebSockets, CRDTs, collaborative editing.

• Familiarity with Pydantic AI or similar structured LLM frameworks.

• Experience with KEDA or other event-driven autoscaling patterns.

• Background in SEO, content marketing, or marketing technology.

Our Stack

• Backend: Python 3.11, FastAPI, SQLModel, PostgreSQL/pgvector, Pydantic AI, Redis

• Frontend: Next.js 14+ (App Router), React 19, TypeScript, Plate.js, Radix UI

• Infrastructure: GCP (Cloud Run, Pub/Sub, AlloyDB), Kubernetes, KEDA, Terraform, GitHub Actions

• Observability: Logfire, PostHog

• Data: Databricks, Protocol Buffers, Alembic migrations

Why Join Us?

• Join an innovative, fast-growing startup building cutting-edge AI marketing solutions.

• Make a meaningful impact by shaping the platform's user experience, design identity, and overall success.

• Dynamic environment with opportunities for real ownership, learning, and growth.

• Competitive salary and support for professional development.

How to Apply

• Please send your resume and a brief note about why you're interested in joining us.

• We'd love to see your work and hear your story!

• This is a hybrid role, with 4 days per week in our downtown Toronto office.