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Pioneer Square Labs

Senior Engineer, AI & Backend Systems - Picco

Pioneer Square Labs, Seattle

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About Picco
At Picco , we're building AI-powered teammates - not bots. Our intelligent systems automate GTM business workflows across Sales, Marketing, Contracts & Legal, Support , taking on repetitive, manual tasks so teams can focus on what truly matters.
Our platform orchestrates tasks across tools like Salesforce, Slack, Notion, Gong Transcripts, Notetakers, HubSpot , and other tools like Service Desk. serving as the connective tissue across the enterprise stack. Backed by top-tier investors and led by founders and engineers from leading tech companies, Picco is tackling one of the most important challenges in enterprise software: end-to-end, context-aware automation powered by AI .
As one of our first engineering hires , you'll work across product, infrastructure, AI systems, and integrations - helping set the foundation for our engineering culture, tools, and long-term technical strategy.
What You'll Do
  • Design and build scalable, reliable backend services and APIs for AI-powered enterprise workflows
  • Develop AI-driven applications using LLMs , embeddings, and traditional ML models
  • Build data pipelines for real-time inference, evaluation, and model lifecycle management
  • Collaborate cross-functionally with AI/ML engineers, frontend developers, and product managers
  • Mentor peers and help foster a culture of engineering excellence
  • Lead improvements in CI/CD , observability , security , and testing
  • Diagnose and resolve issues across the AI + backend stack
  • Stay on top of trends in AI infrastructure , SaaS architecture , and scalable systems
  • Influence and contribute to the technical roadmap and strategic direction of the platform
Must-Haves
  • 7+ years of experience in backend development using Python , TypeScript , or Go
  • Proven experience fine-tuning foundational LLMs and deploying models (e.g., LLMs , embeddings , NLP , CV ) into production
  • Experience with tools like LangChain , LangGraph , vector databases (e.g., Pinecone, Weaviate), and model gateways
  • Experience with RAG pipelines , semantic search , or advanced LLM orchestration
  • Strong understanding of microservices , RESTful APIs , and event-driven systems
  • Proficiency with AI/ML frameworks such as PyTorch , TensorFlow , Hugging Face , or scikit-learn
  • Experience with SQL and NoSQL databases and building scalable data architectures
  • Solid experience with AWS services (e.g., S3 , Lambda , ECS , Step Functions , EventBridge , CloudWatch , and other cloud services)
  • Excellent communication , collaboration , and problem-solving skills
Nice-to-Haves
  • Experience building SaaS platforms , especially multi-tenant systems and third-party integrations
  • Familiarity with MLOps practices , including model monitoring, versioning, and deployment pipelines
  • Hands-on experience with Docker and Kubernetes
  • Contributions to open-source projects in AI/ML or backend infrastructure
You Might Be a Great Fit If:
  • You've built or shipped early-stage products , ideally in a startup or founder-like role
  • You're excited by greenfield challenges , rapid iteration, and owning projects end-to-end
  • You enjoy wearing multiple hats - from system design to debugging user issues
  • You care about building something meaningful with a small, mission-driven team
  • You want to help shape not just the codebase, but the company itself
Why Join Picco?
  • Help define a new category of enterprise software - AI-powered teammates
  • Join a fast-moving, high-caliber team backed by top-tier investors and operators
  • Build at the frontier of agentic AI , LLM orchestration , and enterprise workflow automation
  • Collaborate with leaders and engineers from Amazon, Microsoft, OpenAI , and more
  • Competitive salary + generous early-stage equity grant - real ownership from day one