Cristian Calabro's Work | ContraWork by Cristian Calabro
Cristian Calabro

Cristian Calabro

Engineering & AI Advisor for early-stage startups

Cover image for Company metrics database with an
Company metrics database with an AI query layer Led the build of a central metrics database for a B2B data company, with an LLM query layer on top so people can ask questions in plain English and get answers from one trusted source instead of scattered spreadsheets and dashboards.
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Cover image for Spec-driven development workflow
A CLI that
Spec-driven development workflow A CLI that turns a Jira epic into a reviewed spec, user stories and tasks, with review gates at each step. AI drafts the work and engineers approve it before any code is written, so the team ships with clearer scope and fewer surprises.
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Cover image for Technical Due Diligence: sample report
A
Technical Due Diligence: sample report A sample of the technical due diligence I run for investors and acquirers, based on a fictional 12-person SaaS company. It covers the whole company: architecture and cloud, delivery, code quality, security, data, team and AI use. Each area gets a rating, red flags come with an estimated cost to address them, and actions are split into pre-close and first 100 days. It ends with a clear verdict: proceed, proceed with conditions, or don't proceed. Offered as a 5-day red-flag review ($1,500) or a 7-day full review ($2,500).
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Cover image for Foundations Review: sample report
A sample
Foundations Review: sample report A sample of my Foundations Review for early-stage founders, based on a fictional 12-person field-service SaaS company. Over about two weeks I review the technology, how the dev team works and how the team uses AI, through interviews and read-only access to code, cloud and tools. The report gives a clear verdict, the top issues to tackle first, an effort estimate, what's already in good shape, and a 30/60/90-day plan. It's handed over in a session with the team, followed by two weeks of async questions.
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