Engineering Manager, Financial Compliance

Alejandro
Gonzalez

14+ years leading engineering teams where software meets money: payroll at Wave, multi-currency at Shopify, financial compliance at Clio. Now building AI-native engineering teams that ship production software with humans in the loop.

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Role
Engineering Manager
Focus
Fintech, AI-native
Experience
14+ years

About

For 14+ years I've worked where software meets money. I led payroll and tax services at Wave, drove multi-currency and local payment expansion at Shopify, and today I manage the Financial Compliance team inside Billing Services at Clio, where we own tax, government regulations, and the audit and controls work that comes with preparing a company for public-market scrutiny.

It's a domain with no tolerance for hand-waving. A rounding error is a regulatory finding, and "we'll fix it next sprint" is not an answer when a tax authority is asking. That constraint shapes how I build systems and how I build teams.

I'm building toward AI-native engineering. Not a chatbot bolted onto a workflow, but an AI factory: agents, harnesses, evaluation loops, and guardrails wired into the delivery pipeline so a team can ship real production code at a pace that used to be impossible. What I mean by that: an engineering system where agents handle the repeatable implementation work, harnesses give them the context and tooling to do it, and evals measure what comes out. The humans stay in the loop at the points where judgment actually matters, which in regulated financial systems is not optional.

I care as much about the people as the systems. Engineers do their best work when they understand why it matters, so I lead with context, not tickets. I want a team where problems get raised early, questions are welcome, and people are trusted to make the call. The measure I care about most is simple: are the people around me growing?

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Toolkit
Agentic AI AI-Native Delivery Agent Harnesses Evals Human-in-the-Loop Claude Code Financial Compliance Payments Tax Engines Multi-currency Audit Readiness Ruby on Rails Python Django GraphQL PostgreSQL MySQL Docker AWS Datadog Sentry

Where I've worked

2023 - Present

Engineering Manager, Financial Compliance

  • Lead the Financial Compliance team within Clio's Billing Services group, owning tax, government regulations, and the reporting obligations that come with collecting money across jurisdictions.
  • Drive audit and controls readiness, hardening financial reporting and evidence trails so they hold up to the scrutiny that comes with preparing for an IPO.
  • Building an AI-native delivery model for the team: agent harnesses, evaluation loops, and human review at the decision points, so we ship production code faster without loosening a single compliance guarantee.
Jul 2021 - May 2023

Development Manager

  • Spearheaded a successful multi-currency growth campaign for the Markets team, resulting in a remarkable 38% surge in GMV and driving revenue expansion.
  • Drove international growth for merchants and Shopify by expanding local payment method offerings in 5 countries, increasing accessibility and merchant success.
  • Recognized and promoted exceptional talent, elevating multiple engineers to the senior engineer level, fostering professional growth and strengthening the team's expertise.
Nov 2017 - Jul 2021

Engineering Lead

  • Led a high-performing team of seven engineers, fostering a culture of excellence and achieving outstanding results.
  • Expanded tax services to fourteen states, broadening geographic reach and providing comprehensive tax solutions.
  • Implemented COVID-19 relief policies for US and Canadian payroll, providing crucial financial support to employees and ensuring regulatory compliance.
Jun 2012 - Nov 2017

Development Manager

  • Executed end-to-end implementation of Ruby on Rails projects, providing architectural guidance and collaborating with contractors for project success.
  • Managed and led a team of two developers and four contractors, optimizing their performance to achieve project objectives.
  • Evaluated tools, technologies, and frameworks to drive efficiency and enhance project outcomes.

What I've built

All repositories on GitHub

Find me elsewhere

Get in touch

Have a question or want to work together? Send a message and I'll get back to you, or email me directly.

contact@alejandrok5.com