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Pablo JacobiPJ
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Pablo Jacobi

@pablojacobi1

Senior software engineer and AI engineering lead building production-grade APIs, web apps, and RAG-powered analytics end to end.

Chile
Message

What I'm looking for

I’m looking to lead end-to-end engineering for AI/RAG-powered products and production APIs—shipping reliable multi-tenant systems with strong testing, observability, and cross-functional collaboration.

I’m a senior software engineer and hands-on engineering leader with 12 years of Ruby on Rails and 3 years of Django experience, delivering APIs, web applications, AI products, and production systems end-to-end. I build and lead multidisciplinary teams—owning delivery, mentoring, driving the technical roadmap, and coordinating cross-functionally to ship product outcomes.

I’ve built multiple AI-enabled products, including RAG assistants, document-understanding pipelines, ecommerce analytics, and conversational recommendation systems, using LLMs, vector search, and evaluation workflows to solve real business problems. Recently, I’ve developed an ecommerce AI analytics platform with Shopify and Google Workspace integrations, and I’ve led AI real estate assistant work using RAG (PostgreSQL + pgvector) plus event-driven ingestion on Azure.

Experience

Work history, roles, and key accomplishments

PL
Current

Freelance AI Product Engineer

Plenix

Mar 2026 - Present (4 months)

Developing an AI analytics platform for ecommerce merchants that supports natural-language questions across sales, customers, inventory, marketing, fulfillment, and store performance. Built production-grade Shopify and Google Workspace integrations and AI-assisted query flows with answer evaluation via golden test suites.

DP
Current

Fullstack Developer

Dualboot Partners

May 2024 - Present (2 years 2 months)

Develop and maintain production Ruby on Rails fintech applications, including services for CreditNinja. Design microservices and REST APIs and implement async processing with queues while collaborating with distributed teams across Ukraine, the US, and Spain.

CC

Freelance AI Engineer

Colliers International Chile

Jan 2025 - Jan 2026 (1 year)

Built an internal AI real estate assistant for property search, document understanding, and data extraction. Implemented a RAG pipeline using PostgreSQL + pgvector with hybrid retrieval, and deployed an event-driven ingestion system on Azure with Azure OpenAI for embeddings.

BU

Senior Developer

Buk

Jan 2023 - Dec 2023 (11 months)

Built a Ruby on Rails platform for health-insurance sales using Delayed Job, Jenkins, and Docker, serving 2,000+ insured users. Partnered with cross-functional teams across multiple countries to deliver features end-to-end.

HE

Chief Technology Officer

HelloWine

Mar 2020 - Dec 2022 (2 years 9 months)

CTO and hands-on engineer building a React app backed by Rails and Django, processing 13,000 monthly transactions. Migrated AWS ECS to Railway, cutting infrastructure costs by 90%, and built and led a 6-person multidisciplinary tech team.

BE

Startup Founder

Beerly

Built a monthly subscription web system delivering a curated box of beers.

CA

Fullstack Developer

Capitalizarme.com

Worked on a real estate marketplace built on Ruby on Rails, deployed on AWS EC2 and ECS.

Education

Degrees, certifications, and relevant coursework

University of Pennsylvania logoUP

University of Pennsylvania

Santander Language Course, English Language

Grade: C1 (EF SET)

Activities and societies: Cambly 1:1 lessons

Completed the Santander Language Course at the University of Pennsylvania in 2021 and achieved C1 level on EF SET.

Santa María Technical University logoSU

Santa María Technical University

Civil Computer Engineering, Computer Engineering

Completed Civil Computer Engineering at Santa María Technical University in 2012.

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