About - Andrew Giffen

I run the largest business unit at a global compliance SaaS company. I built the product organization from one person to roughly two dozen PMs, POs, and program managers. The team ships steadily; the customer base sticks; the NPS keeps climbing. That's the scale I've been operating at.

The work isn't only strategic. When the company restructured in 2018, I stepped in as interim CTO for eight months - stabilized delivery, shipped a new authoring platform, and created the competitive-intelligence application that became the company's flagship product and primary growth vehicle. When the eight months were up I went back to product, with a much sharper understanding of what engineering organizations actually need from their product leader.

More recently I've been building the AI systems that make the compliance platform smarter. I built the EHS Applicability Engine - a production AI system that runs 500+ facility-level screening questions in batch and returns structured decisions auditors act on. I built PM Insights - a system that queries 74,000+ recorded calls and 2.5 million transcript sentences and changed how the product team prioritizes. These aren't prototypes. They're in production, and they've changed how the work gets done.

I'm based in Toronto. I'm actively exploring CTPO and CPO roles at vertical AI companies in the EU and UK - particularly in RegTech, LegalTech, and compliance-adjacent SaaS. If you're building something in that space and need someone who can own the product and technology organization, I'd like to talk: andrew@giffen.me.

How I work

Lead with the real problem

I don't start with solutions. Before anything gets on a roadmap, I want to understand what's actually broken - for the customer, for the business, for the people doing the work. Most product failures I've seen weren't execution failures. They were diagnosis failures. We built the wrong thing well.

Write to align, not to document

My best thinking happens on paper before it happens in a room. I write strategy docs, decision memos, and one-pagers because the act of writing forces clarity. When a team can read a document and execute without me in the room, that's leverage.

Ship to learn - and to de-risk

Speed matters, but so does direction. I bias toward shipping small working things over perfect large ones. Not because I don't care about quality - because I've seen too many long-horizon plans collapse the moment they hit real users. A working prototype tells you more in a day than a roadmap tells you in a month.

Make complexity legible

Regulated industries are full of complexity that experts have stopped noticing. My job - in product, in strategy, in AI - is to find the underlying structure in that complexity and make it something a team can act on. Find the structure, surface it, act on it.