Diya Jolly
Chief Product and Technology Officer, Xero. On 1 show, 1 appearance. The Shows tab opens the full record on each.
executiveoperatorLinkedIn ↗xero.com ↗
Diya Jolly oversees product management, engineering, design, and data across Xero’s global cloud accounting and small business platform. Before joining Xero, she served as Chief Product Officer at Okta and spent several years at Google leading product management for YouTube monetization and Google Assistant.
1shows
1appearances
25statements
0resolved
0supported
0contradicted
Everything Diya Jolly said on any show that made the record, most notable first. Each card names its show and opens the statement there.
A 100% success rate on major decisions indicates insufficient executive risk-taking
“If every one of the big decisions you take turns out correct, you're doing something very wrong. Like, you're not taking enough risk. Something's very wrong. So the batting average, again, like, I say this, like, on big decisions is, like, if your batting aver…”
CPOs under founder CEOs must surrender product autonomy to succeed
“The difference is you have to be willing to give up some level of autonomy when thinking about the product. In a founder-like company. And you have to be willing to, you have to know how to influence really well, and you have to be able to understand what infl…”
An inability to monetize proves a product failed to deliver customer value
“I am a firm believer that if you add value to the customer, you will find a way to capture the value eventually. And yes, I almost think of it as if you cannot capture value, then you are fooling yourself that you added value to the customer, right? Or enough …”
Product teams building solely for current customer requests will fall behind
“If all you're doing is what customers are asking for right now, I think you'll get left behind.”
AI transformations require senior product executives to operate at lower altitudes
“Here's why you're flying at a lower altitude, because you're trying to change the way people work. You're trying to change people, because you as one of, as you as the senior product and engineering leader are the catalyst for change right now, right? Because …”
Xero built and shuttered an experimental AI chat-based accounting app
“So for example, we took a bet where we said, and I did this, I'm like, I don't want to wake up in two years and find out that the entire App is agents in a chat. So we're going to go off and build our own app on the side. That is where you're going to do accou…”
Product leaders must spend half their time thinking to remain competitive
“Right now, if you are not spending 50% of your time thinking about what
Your product will look like, what a value it will deliver.
It's just gonna be hard to compete.”
Xero's AI financial chatbot hits 95% accuracy on scenario and advice queries
“One is like, we're ahead in the market. Nobody else does it. Second, and we're at like, 95% accuracy or something, like in the answers written on.”
Compliance demands ensure traditional accounting SaaS workflows will not disappear
“Will SaaS apps completely disappear? I, will the workflows disappear? SaaS is an overload of terms. Probably not, at least in our category, just because it's compliance. You need, like, you need the workflows to prove that you're doing the right thing to submi…”
A single underperformer drags down total team performance by up to 30%
“Even one person can push, pull a performance of a team down by 20, 20, 30%, right? Because other people are carrying the weight.”
Jolly secretly called in sick as a director to protect thinking time
“When I was a director, I literally would call in sick to get my thinking time once in a while, because I'm like, I just like, there's like, and I would tell my manager, I'm doing this because you'll respect the fact that I'm, I need to get stuff done, and I ne…”
CPOs must set strategic vision instead of micromanaging product features
“The key job of a great chief product officer is essentially setting the direction, not worrying about every single feature, not worrying about even big, even reasonably, reasonable sized products down to every feature level. But setting the vision and the dire…”
Org design and resource allocation must be revisited quarterly
“People think resource allocation or organization is a one-time thing, but it's not. The world around us these days changes every quarter. So these are decisions you have to revisit almost every quarter.”
Product vision is synthesized from collaborative customer insights, not invented solo
“The other thing everybody thinks is like PMs or CPOs are supposed to come up with The vision, like, honestly, like, a vision is a collection of people coming together and understanding customers deeply enough and stitch, and then, yes, usually a CPO will stitc…”
Users distrust AI automation without a transparent, verifiable audit trail
“And then the thing we learned and we iterated our way into was people are uncomfortable till they can see what you did. The second you can show them exactly what you did, People are happy.”
Jolly: Small teams can now validate product directions quickly
“Resource allocation used to be a problem. Today, you can get a lot of certainty whether you're in the right direction or not with a very small team reasonably fast.”
Internal business model pivots fail without structurally isolated tiger teams
“SaaS versus a license-based model versus if you wanted to build a transaction-based model. Super hard to do it in the current system. Existing customers will revolt. Billing systems won't work. Sales incentives won't work, but if you put someone on the side, t…”
Modern product design shifted from delivering capabilities to collapsing workflows
“It is more now, the way you need to think is, how do I make their workflows easier, right? It's shifted from, here's the capability, do they do utilization? To how do I take what exists in front of me and collapse the workflows and make it easier so that in a …”
Executive intervention in cross-team disputes incentivizes internal political lobbying
“When a leader jumps in and solves problems across their teams, there is a lot of reason for the teams to lobby for their self-interest, right? Which then creates a me versus them.”
Jolly: High demands without psychological safety cause roadmap sandbagging and stagnation
“If you demand without giving people the support to succeed, And letting them know that taking risk is okay and failure is okay. You're going to have a culture where nobody takes risks. Nobody tries to grow. And everybody is, it's a fear-based culture. There's …”
Jolly: Senior product leadership requires spending more time thinking than doing
“And I think the more senior you get in any role, especially in the product role, it is about making a few decisions that are big and irreversible. And you need more time to think than to do.”
Jolly: Highly ambiguous strategic decisions cannot be delegated by executives
“I put decisions in three buckets. One is, like, impact on the business, but, like, not make or break for the business. Those are delegated down until somebody escalates. Decisions that have big impact on the business, but what you have to do is fairly certain,…”
Leaders must maintain multiple probabilistic hypotheses about future market trends
“I think today, if you have one hypothesis on how the world will work, very dangerous. If you have, I'd say, somewhere around two to four hypotheses of where the world will be, and then your probability is on that, and then you line up your bets accordingly.”
Jolly: Carving Out Thinking Time Is Hardest for Middle Managers
“You have the most flexibility to carve out thinking, thinking time, I think at the two ends. Either you're very senior or you're very junior. In the middle, it's very hard to carve out your own thinking time because you're at the behest of too many people and …”
One line per show, most statements first. The link opens Diya's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
 IN DEPTHLEDGER | Chief Product and Technology Officer, Xero | 1 | 25 | — | full record on In Depth → |