When Product Meets Engineering at the Top: Lessons from the ex-CPTO at Kickstarter.
The rise of AI-assisted development is collapsing traditional role boundaries. Engineers are thinking like product managers. Product managers are shipping code. And at the executive level, some leaders are doing both - deliberately. We sat down with Mahesh Guruswamy, COO at Kajabi, previously Chief Product and Technology Officer at Kickstarter, for a candid conversation on what it actually takes to hold that dual mandate, how to lead across functions without losing your footing, and what good leadership really looks like at the top.
Here are six takeaways from that conversation:
1. Great executives are capital allocators, not functional experts
The best executives aren't defined by their domain mastery. According to Mahesh, what separates elite leaders isn't being a great people manager, a compelling visionary, or even a skilled board communicator, though they do all of those things. What sets them apart is an exceptional ability to allocate capital.
That means assessing the resources available to them like headcount, budget, and tooling, and deploying them where they'll generate the greatest return. It's a general management mindset, not a functional one. If your instinct is to go deeper into your craft, the C-suite may not be the right destination. But if you're constantly asking where do these resources create the most value?, you're already thinking like an executive.
2. The CPTO path starts with a single ask
There's no formal pipeline to the CPTO title. For Mahesh, it started simply: when recruiters approached him about CTO roles, he asked whether there was an opportunity to own product as well. At Kickstarter, he came in as CTO, took on product responsibilities informally, and eventually earned the "P" after demonstrating he could carry both.
The CPTO role suits leaders who naturally move between problem spaces, people who don't feel constrained by a single function and are energized by the breadth of the work. If that describes you, the path is more accessible than it might appear. You may just need to ask.
3. Know your blind spots and hire into them
Broader scope means less depth everywhere. That's not a flaw; it's a structural reality of the role. What matters is how honestly you assess where you're strong and where you're not.
Mahesh puts it plainly: he considers himself a capable product manager, but not a strong researcher. So he makes sure to invest in research capabilities within his organization. That kind of self-awareness isn't just a nice-to-have, it's what allows you to build a team that compensates for your gaps rather than mirrors them. Leveling up your org often starts with leveling up your honesty about yourself.
4. Build an advisory network, inside and out
No matter how experienced you are, there are areas where you'll need trusted guidance. Mahesh maintains a network of advisors both inside and outside his companies, particularly in domains where he has less firsthand experience.
For a product leader taking on engineering accountability, that might mean cultivating relationships with senior engineers who can serve as informal thought partners. For a technology leader expanding into product, it might mean finding advisors who can pressure-test roadmap decisions. The goal is confident decision-making in unfamiliar territory and diverse perspectives that keep you from operating in an echo chamber.
5. Consider the single-threaded leader model
Mahesh first encountered this approach at Amazon, and it's shaped how he thinks about team structure. The single-threaded model places full decision-making authority and accountability with one person, rather than creating deliberate tension between product and engineering leadership.
This runs counter to the "healthy tension" philosophy that some organizations favor. But Mahesh finds it particularly effective in revenue-generating teams, where clarity of ownership drives faster, sharper decisions. (It may be less suited to environments that require extensive cross-functional negotiation.) For leaders on the path to a CPTO role, operating as a general manager in this way is also excellent preparation, as it builds the instincts you need to hold both functions at once.
6. Learn to apologize well
This one is personal, and arguably the most transferable.
Earlier in his career, Mahesh focused on being right: out-reading, out-thinking, out-maneuvering. Over time, he came to understand that the goal isn't being right, it's creating an environment where your team can surface problems and help solve them. When leaders express frustration in ways that put their teams on the defensive, they don't get better outcomes. They get fear.
Mahesh credits his son with teaching him what a real apology looks like. The lesson applies directly to leadership: when you acknowledge mistakes genuinely and invite your team into the gaps, you build the kind of trust that makes organizations resilient. Recognizing your blind spots and welcoming others to help fill them isn't weakness, it's the job.
The bottom line
The CPTO role is still relatively rare, but it reflects something real about where leadership is heading: toward generalism, capital thinking, and comfort with breadth over depth. Whether or not you're pursuing that title, the principles Mahesh shared apply broadly. Know where you create value. Know where you don't. Build the networks and teams that fill the gap. And learn to apologize like you mean it.
Regardless of title, these are incredibly insightful takeaways that can be applied across many executive level roles.
