Most advice about a leader’s first 90 days is written in hindsight, after the dust has settled and the mistakes have been solved. This episode is different — when we recorded this, Maya Keekattil was ending her third week as CPO at Cin7. She was working through her first 30 days in real time.
Maya started as a software engineer and DBA before she moved into project management, taking on product leadership at Smarsh, where she spent nearly five years as VP of Product Management. Now she’s learning a new vertical at a PE-backed company, where the board, leadership, and her team all have high expectations.
In this episode, Maya shares:
Why every product leader’s first 30 days should be reserved for listening and learning, and the three questions she asks in every one of her cross-functional one-on-one meetings
How to find fast operational wins without accidentally ripping out something load-bearing
How she’s restructuring product teams around outcomes, not products, in the AI era
1. The first 30 days are for listening and learning
Maya understands that new leaders feel pressure to bring change quickly and to prove results and ROI — this is especially true in the PE world. But Maya emphasizes the importance of learning how things work before you shake anything up. In three weeks, she scheduled 51 one-on-ones across her org, and she’s aiming for 75. Those meetings go beyond her own team, into sales, marketing, finance, engineering, and operations. She told us she started booking conversations a few weeks before her official start date.
Every conversation comes back to three questions: What’s working? What’s not working? And what do you expect product to do for you?
“The company has been here for a decade and more. So there has been stuff that is successful. Coming in and thinking that I’m going to change it all is probably a big mistake a lot of leaders make.”
Product takeaway: Product means something different at every company, and you can’t meet expectations you don’t understand. Before you change anything, learn what each cross-functional partner expects from product. That should be your first scorecard.
2. Patch the holes in the boat first
How do you get quick results without pulling out a beam that’s holding up the building? Maya’s answer is to start with operational efficiency: the small process gaps that slow everyone down.
Often, she says, other people noticed these gaps long ago. They didn’t fix them because they lacked the operational expertise or they simply didn’t have the authority to do so. A new leader with fresh eyes and the mandate to act can rally people quickly around the right fixes.
“Most of the time, others would have observed it. They probably either lacked the expertise to do something about it, were hesitant to do it, or their role did not allow them to do it. Where I stand today, my role allows it, I have the authority to do it, and I come with this fresh perspective.”
Product takeaway: Your fastest credible wins usually aren’t new features. They’re process fixes that your peers have quietly wanted for a long time. Ask where things get stuck, fix what you can in the first 30 to 60 days, and you’ll build the trust you need for bigger bets down the line.
3. Strategy can’t wait for onboarding to end: Don’t wait until day 61 to think strategically
Many 30-60-90 plans treat strategy as a phase you reach once onboarding is finished. Maya warns that this creates a gap between your arrival and your first real impact. Strategic changes need alignment, investment, and often board involvement, so they take longer to show results.
“I don’t think it’s a switch. You start rolling on this innovation and strategy perspective even through the 30/60, but it is not apparent to the cross-functional teams.”
Product takeaway: Run operational and strategic work at the same time. Fix things in the open, and start the slower alignment conversations with your executive peers in the background.
4. Every mandate should go back to the customer
Every new leader arrives with a mandate. Maya argues that the mandate itself is too short-sighted to plan around. Her starting point is two things: why customers buy, and why they leave.
“We are not looking at just numbers. We are looking at why is the customer buying us today and why is the customer leaving us today. Just those two things will get you to the gist of where you are succeeding versus where you are not.”
She says even customers who have already left are worth talking to:
“Even a customer who has left is very happy to talk to you, and they spend the time because they are invested. They’ve used your product.”
Product takeaway: When the board hands you a target, don’t work backward from the number. Work forward from churn. In Maya’s experience, building around the customer’s view beats the mandate. Building to the mandate rarely does.
5. Structure the team around outcomes, not products
Maya saw Y2K and the move to the cloud, and she says now is the fastest she has ever seen technology move — thanks to AI pushing companies to organize around outcomes, which shows up in everything from team structure to outcome-based pricing models.
Instead of splitting PMs by product line, Maya thinks in layers. Platform-focused technical PMs build the foundation. AI product managers operationalize AI across the organization. Growth PMs are tied to customer outcomes.
Before assigning anyone to a role, she starts with an honest look at each person’s strengths. And on whether to hire for new skills or develop the team she has, Maya puts a high value on domain expertise:
“Even if you hire for a talent gap, you need to bring someone up to speed on the domain. So I would rather trust the teams that you have on the domain expertise and build that up. You are influencing and not just using your authority. That goes a long way.”
Product takeaway: Before you reorganize for AI, separate true talent gaps from skills your current team can learn. Hire for the first, then invest in the second. Domain knowledge is the hardest thing to buy and the slowest to rebuild.
Chapters
00:00 Introduction
02:07 Maya’s path from software engineer to chief product officer
03:38 Why your first 30 days should be for listening and learning
06:10 Three questions to ask in every cross-functional one-on-one
07:59 Finding quick operational wins without breaking what works
11:09 When to shift from operational fixes to long-term strategy
16:09 Defining success by why customers buy and why they leave
22:17 How AI is reshaping product team structure around outcomes
27:17 Developing the team you inherited vs. hiring for talent gaps
29:29 Conclusion
Links
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