Table of Contents
Key takeaways
- Square, Cash App, and Afterpay operate as one company under Block. But Gurneet Kaur has watched two teams define the same metric two different ways, which is exactly the kind of drift that can undermine a shared language.
- Gurneet's response is a judgment call she repeats everywhere: build enough shared structure first, then trust people to run with it. That means aligning on measurement before any tool gets picked.
- Block's sales reps used to ask the comp operations team where their numbers stood. With Pigment, they check their own attainment instead.
- Gurneet lets AI handle repetitive, well-defined work while keeping humans on top of anything ambiguous or high-stakes.
- Looking ahead, Gurneet turns that same judgment on herself. She trusts her own ability to figure AI out as she goes, rather than waiting until she has all the answers first.
Block operates as one company built from several distinct businesses. Square serves local sellers, Cash App serves consumers, and Afterpay sits at the intersection of commerce and financial services. Gurneet Kaur, Go-To-Market Finance and Strategy Leader at Block, sits inside the foundation team responsible for making sure all of them can scale together without losing their shared purpose of economic empowerment.
Her approach rests on three principles: connect the businesses, give teams back the time that manual work consumes, and build enough agility to respond when plans change shape. Each one comes down to the same underlying judgment: knowing when a team needs more structure and when they're better off being trusted to move on their own.
Running several businesses under one roof creates a specific kind of tension. Each business needs room to move fast in its own context, and none should be pulled into a playbook built for someone else. But left alone, they lose the leverage of working as one organization.
Connecting the blocks without collapsing the differences
Block has increasingly embraced what Gurneet calls a functionalized operating model. She sits on the foundation team, but stays connected with marketing, Square, Cash App, and Afterpay, building common forums where the businesses can work through shared planning frameworks and a pipeline every team can draw from. The goal is autonomy without disconnection.
Getting there is a layered challenge, and Gurneet sequences it deliberately, starting with people rather than tools. Two teams have to agree on what they're measuring and why before she'll touch data or process. Technology comes last, as the layer that reinforces a shared language once a trusted data foundation already exists.
Freed-up time only matters once it earns confidence
The compensation and quota model Block launched via Pigment this quarter shows what giving time back actually looks like.
Before Pigment, reps learned where their commissions stood only when pay was due, at the end of the month or the end of the quarter. In between, they'd come to the comp operations team asking where their numbers stood and what was driving them. Answering those questions one rep at a time ate up a large share of the team's time. Now, reps can log in, see their live attainment, and run what-if calculators to estimate their own commissions. That frees the ops team to spend that time with business partners on questions about performance and incentive design instead.
Freed-up time only matters if it goes somewhere, and Gurneet doesn't think the shift from operational to strategic work happens on its own. It takes deliberate coaching. Rather than letting her team hand over a finished number, she pushes them to explain what it means and what to do about it, whether it's a forecast or a variance report.
That same instinct, building people's judgment rather than just their output, extends to how she thinks about change more broadly. She describes agility as adaptability rather than speed: noticing when reality has diverged from a plan, understanding why, and responding with confidence, even without the full picture.
Letting AI take the predictable work and keeping people on the rest
Gurneet has firm views on what must be true before AI can actually help planning and decision-making, and none of them start with the sophistication of the model. The foundation is trusted data: if people don't trust what's going in, they won't trust the insight coming out. Next comes process clarity, since AI sitting on top of an ambiguous process only amplifies the ambiguity. Underlying both is culture, like whether an organization is structured to receive AI's insight, debate it, and act on it.
Where AI actually gets to lead a decision comes down to the nature of the task. The more repetitive, data-intensive, and rules-based the work, the more comfortable Gurneet is letting AI handle it. The higher the stakes and the more ambiguity involved, the more she wants a person making the call.
Gurneet applies the same rule to her own day-to-day. She connects Pigment with Claude to pull insights, and when she's in 10 meetings and needs to switch context fast, she feeds project documentation into Block's internal tool, Goose, for a summary before she walks into the next conversation. She also spends time in Pigment's Modeler Agent making changes to the models her team maintains.
Staying a beginner on purpose
For all the frameworks, Gurneet describes her own relationship with AI as still taking shape. She's comfortable not having it all figured out yet, and she’s willing to ask basic questions and try things without waiting until she's sure.
Looking further out, Gurneet is most occupied with Block's operating model and team structure. AI has lowered the barrier to information that once required a specialist to access, and she's watching how the lower barrier reshapes what roles and skills the business needs next, both on her own team and across the entire organization she works with.
What she keeps circling back to is less the technology itself and more whether the people and structures around it will keep pace. Staying curious, as Gurneet tells it, is a habit to keep practicing for as long as the tools keep changing.
