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Case Studies & Learnings

Longer-form thinking on product management, growth, and building things. Case studies from work, frameworks I've developed, and lessons from failures.

01

Case Study 2026-01-13

Migrating 50M ARR Without the Big Bang: Lessons from a NextGen Product Migration

After migrating $50M in ARR from our legacy product to NextGen over 22 months, we learned that the difference between success and disaster comes down to one core insight: you can have fixed scope or fixed timeline, but never both. Here's everything we learned the hard way.

02

Case Study 2026-01-13

AI Features that Earn Trust in Enterprise Workflows

When the stakes involve legal compliance, workplace safety, and regulatory penalties, enterprise clients need more than impressive AI demos. They need proof that your specialized solution won't become a liability.

03

Framework 2025-09-20

Integration Complexity: A Mental Model

A framework for evaluating and prioritizing integration work based on customer value, technical effort, and strategic alignment.

04

Reflection 2025-08-05

What I Learned From a Failed Product Launch

Sometimes the best lessons come from things that don't work. Here's what went wrong and what I'd do differently.

Let's build
something together.

Whether you need help clarifying a product problem, shutting down a legacy system, or untangling integration complexity - I'd love to hear from you.

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Location

Toronto, Canada

Current Role

Director of Product Management

Focus Areas

AI Products • Integrations • Growth

© 2026 Andrew Giffen. Built with curiosity.

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