Pioneer Square LabsPL

Senior Engineer, AI & Backend Systems - Picco

Pioneer Square Labs is a Seattle-based startup studio and early-stage venture capital fund that helps exceptional founders build and launch category-defining technology companies.

Pioneer Square Labs

Employee count: 11-50

United States only

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

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

About the job

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Job type

Full Time

Experience level

Senior

Location requirements

Hiring timezones

United States +/- 0 hours

About Pioneer Square Labs

Learn more about Pioneer Square Labs and their company culture.

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Born from a desire to ignite and build the next wave of world-changing companies, Pioneer Square Labs (PSL) embarked on its journey in Seattle as a unique hybrid: a startup studio and an early-stage venture capital fund. The founders, a collective of seasoned entrepreneurs, investors, and builders, recognized the immense challenges that even the most brilliant founders face. They envisioned a new model for company creation, one that went beyond just writing a check. Their background was forged in the trenches of the startup world, with direct experience in launching ventures from the ground up and scaling them from a million in revenue to billion-dollar enterprises. This deep operational expertise became the bedrock of PSL's mission: to bring together world-class talent, transformative ideas, and the necessary capital to build venture-scale companies from scratch.

The journey for a founder partnering with PSL is designed to be an intense, rewarding rollercoaster. From the very first day, entrepreneurs are not alone; they are integrated into the PSL ecosystem and paid for their work, removing the financial barriers that often stifle early-stage innovation. They work shoulder-to-shoulder with PSL's dedicated in-house team of digital marketers, designers, software engineers, data scientists, and business analysts. This collaborative force acts as a powerful co-founder, equipped with many arms and legs to rapidly validate concepts, build prototypes, and find the elusive product-market fit. The path involves relentless refinement, customer-centric iteration, and sometimes, the tough decision to pivot or abandon an idea. PSL's role is to provide the speed, A+ execution, and network connectivity needed to navigate this process, helping founders build an exceptional team, hone their vision, and ultimately secure the right investment partners to join them on their ambitious journey.

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Pioneer Square Labs hiring Senior Engineer, AI & Backend Systems - Picco • Remote (Work from Home) | Himalayas