Exclusive: Shopify's VP of Finance shares AI secrets
A new template for every CFO and finance team that wants to stay relevant.
READ TIME: 7 MINUTES
The last 3 to 4 months is the fastest I've ever seen technology change in my career. Just when you learn something new, another breakthrough advancement comes along.
That’s not me talking.
That’s Jason Kilpela, VP of Finance at Shopify, speaking from the front lines of AI transformation in finance.
I recently sat down with Jason (great guy). He loves reading this newsletter and shared that the themes resonated with the shift he’s leading.
Shopify, as you might have seen from CEO Tobi Lütke’s memo, is not treating AI as an option. It’s a must!
But while most companies are stuck in the "what if" stage, Shopify, the leading global commerce company powering millions of independent brands, is deep in the "how to" phase. They are actively building the future of finance, and Jason gave us an unprecedented look under the hood.
What You’ll Get in This Edition
What follows is a blueprint that shows how a finance team can move from a backward-looking cost center into a forward-looking, AI-powered growth engine with humans at the center.
Here’s what’s inside:
Phase 1: The Foundation. Why upskilling and data infrastructure, not “AI hacks”, are the real first steps.
Phase 2: The Agent Revolution. How a single AI agent replaced days of manual analysis, transforming the weekly reporting grind into instant insight.
ROI Reframed: Why the value isn’t in headcount cuts but in radical leverage and more engaged teams.
The New Skills Paradox: The urgent warning for every leader, why pure coders or classic finance pros will both struggle, and who actually thrives.
From Buyer to Maker: The endgame, where finance teams don’t just use tools but build them on the fly, becoming architects of intelligent systems.
But what you’re about to read isn’t just about Shopify.
It’s the new template for every CFO and finance team that wants to stay relevant and actually lead through the AI shift.
Read on.
Phase 1: The Foundation is Everything (Don't Skip This Step)
You can't just sprinkle some AI on a broken process and expect magic. Shopify's journey didn't start 4 months ago. It started years ago with a deliberate, foundational shift.
As Jason put it, they transformed the FP&A team from what used to be kind of like accountants looking backwards into something entirely new.
We turned data wranglers into financial technologists.
This wasn't an overnight change.
It was a strategic decision to upskill the entire team, making SQL, GitHub, and Python the new languages of finance.
In partnership with data science, they built a rock-solid data infrastructure with BigQuery as the source of truth, moving away from legacy tools that demo well but fail to scale.
The legacy approach was a patchwork of disparate systems and manual processes that created bottlenecks. By contrast, their new foundation treats data as a product, with clear lineage, documentation, and automated quality checks.
Only with that foundation in place could they layer on tools like Cursor and begin the next phase of their evolution: building an agent-assisted FP&A team. The groundwork made everything else possible.
Phase 2: The Agent in Action (The Shopify Capital Case Study)
This is where theory becomes reality. One of the team’s key responsibilities is analyzing the weekly performance of their merchant funding product, Shopify Capital.
The Old Way: For several days, multiple analysts painstakingly navigated Looker dashboards, delving into segmentations, cohorts, and other splits to construct the weekly funnel's narrative. This was a slow process, as extracting genuine insight proved time-consuming.
The New Way: They built an AI agent.
This isn’t a simple chatbot. It’s a sophisticated system designed to replicate and accelerate the entire analytical process.
Here’s how it works:
The Agent's Brain (Context): The agent was given access to three critical sources of information.
The Data: Direct query access to the core BigQuery tables.
The Product Context: Access to all internal product documentation. The agent knows when features were launched and what changed in the product.
The Human Process: The team documented their exact analytical workflow, every step an analyst would take, and fed it to the agent.
The Result:
The impact is profound. When the FP&A team gets into a meeting with product and engineering leads, the discovery phase is already done. The conversation starts at a higher level:
"So, what should we do?"
The Real ROI: It's Not About Headcount, It's About Leverage
When I asked Jason about ROI and if this meant cutting team members, his answer was clear.
AI lets us scale our expertise and tackle bigger challenges without missing a beat. We have the ability to do more with the same team. We’re empowering our team to be more strategic, creative, and valuable than ever.
This is the true financial unlock.
Shopify can continue its massive growth without proportionally increasing its finance headcount. AI extends the reach and impact of everyone on the existing team.
But the human ROI is massive.
The team is more engaged and motivated than ever.
They’ve been elevated from data watchers to strategic partners.
As Jason said,
No one starts a job hoping to spend their entire day moving data around. They’re now crafters of Shopify’s future, and that’s a powerful talent magnet.
A Warning: The New Skills Paradox
Interestingly, the journey hasn't been a straight line.
Jason shared a crucial, non-obvious insight:
At times, we’ve probably leaned too far technically. The real unlock isn’t just technical skill or business acumen, it’s mastering both. The people who are thriving at Shopify are those who can bridge data and business, using automation to make sharper, faster decisions.
This is a warning for every leader.
The future isn't just about hiring coders.
It’s about cultivating a rare hybrid:
A finance professional who understands both the technical stack and the strategic business landscape. The goal is not just to build models but to understand the market and use those models to make better, faster decisions.
The Vision: From Buyer to Maker
Where is this all heading?
Jason envisions a future where building a complex financial model is as simple as having a conversation.
You should be able to hit the Mac whisperer button and say, ‘hey, I want to build a model. These are the key drivers. This flows into that.’ And at the end of it… it just goes and builds the first pass of the model.
This is the end game.
It's a world where finance leaders are no longer just managers of people and processes but architects of intelligent systems.
Instead of buying software, you build it, perfectly customized to your needs, almost instantly.
Shopify's transformation offers a glimpse into this future.
Where decisions happen in near real-time, not days, and human talent focuses on the strategic work that matters.
The future of finance doesn’t belong to tool buyers.
It belongs to toolmakers.
Start today. Try building your own forecasting app.
So you want to use AI to build your own forecasting tool in 5 minutes?
While most CFOs wait to adopt AI, I built a forecasting tool in 5 minutes without hiring a single engineer. Here's how CFOs can use AI to build tools.
And that’s all for today.
See you on Thursday!
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I’m Wouter Born. A CFOTech investor, advisor, and founder of finstory.ai
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