From Big Company to AI Startup, a product, and revenue in 12 Months: How Fast Execution Beats Perfect Planning with Uday Chakravarthi
In this episode of Executives Unplugged, Keith Cowing sits down with Uday Chakravarthi, former head of product at Atlassian and current CEO of Clinch AGI, an agentic AI company revolutionizing how companies sell and grow. Uday shares his journey from idea to his first $100K in revenue in just 12 months, revealing the strategies that fueled his success: ruthless prioritization, weekly sprints, and a customer-first mindset. From managing a costly API glitch in the middle of the night to leveraging advisors for go-to-market mastery, Uday’s story is packed with actionable insights for CEOs, founders, or anyone looking to accelerate team performance and growth.
Listen on: Youtube, Spotify, Apple Podcasts, or wherever you get your podcasts.
Key topics:
The zero-to-one journey: How Uday refined his idea, assembled a core team, and got first customers quickly.
Time-zone challenges: Strategies for async communication, “bat phone” emergencies, and using Loom/WhatsApp for round-the-clock collaboration.
Surrounding yourself with expertise: Building advisory boards, the difference between “cheerleader” advisors and hands-on experts, and how to get real-time coaching on your sales calls.
Fast execution: Why shipping weekly sprints and labeling “deal-breaker” features help close deals and energize the team.
Real-world examples: How a coding error led to thousands of dollars in AI API charges—and why having rapid response processes in place was critical.
Show Notes:
[0:00] Intro: Uday’s runaway API call costing thousands overnight.
[1:25] Uday’s Journey: From Atlassian to founding Clinch AGI in the agentic AI space.
[3:39] Speed Secrets: Building a core team, async communication, and customer collaboration.
[8:14] Advisory Boards: How Uday strategically filled skill gaps with experts.
[17:48] Actionable Advice: Validate problems early, invest in relationships, and prioritize ruthlessly.
[19:31] Execution Hacks: Weekly sprints, AI-driven prioritization, and “deal breaker” focus.
Where to Find Uday:
Connect with Uday Chakravarthi on LinkedIn: https://www.linkedin.com/in/abhyuday/
Learn more about Clinch AGI: clinchit.io
References from the Show:
Executive Product Leadership Program: Unlock AI’s potential for your team with this two-day in-person workshop at Cornell Tech in September. Details at kc.coach/cornell
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Full Transcript
Uday Chakravarthi [0:00]:
Our developer put something in the code, and it repeatedly kept calling OpenAI's API. So I was getting charged $500 for every 15 minutes. My notifications kept going off, and it was nighttime in India. So I suddenly saw thousands of dollars on my credit card—it was just getting charged. So I had to call somebody and then get on a call. And we basically changed the code. Yeah, if I was sleeping, they were sleeping, we probably would have had a huge bill.
Keith Cowing [0:24]:
Welcome to Executives Unplugged, where leaders get real about what it takes to lead a winning team. I'm Keith Cowing, executive coach to CEOs and product leaders. And with me today is Uday Chakravarthi. Uday is a former head of product at Atlassian, and he is now CEO of Clinch AGI, a company at the center of agentic AI, changing the future for sales teams. And in today's conversation, we talk about how Uday went from zero to an idea, to a product, to first customers and a hundred thousand dollars in annual revenue in just 12 months—about how ruthless prioritization and weekly sprints and extreme focus can help with collaboration and velocity, even across time zones. And we'll talk about how fast execution beats perfect planning every time and how to build an advisory board and surround yourself with the right people to augment your skills. If you're a CEO, a founder, a startup exec, or anybody who wants to do more with less, this one's for you. Let's dive in. Uday, welcome. Great to see you.
Uday Chakravarthi [1:25]:
Great to see you, Keith. Excited to be on your podcast.
Keith Cowing [1:28]:
I've been observing your extra-fast entrepreneurial velocity from the sidelines. You've been running Clinch AGI, you've been moving really quickly. And one of the topics that we wanted to talk about today was how do you surround yourself with the right expertise, with the right people, putting together your team, your advisory board, et cetera. And so maybe we could just start off—explain a little bit about your background and how Clinch AGI came to be.
Uday Chakravarthi [1:55]:
You know, I started my journey as a software engineer building tech products, and I then got into product because I really enjoyed talking to customers. I spent some time in different companies, all the way from PayPal to Microsoft and more recently at Atlassian. And I really enjoyed the journey of, you know, that zero-to-one journey—really taking an idea and building a valuable product or a business out of it and seeing customers use it. While I enjoyed the whole space, I always felt that I really wanted to be that operator who can really start something from scratch and get it to something that's huge. So that was what was, I would say, the main driver in me moving from working at a big company to starting my own company.
Keith Cowing [2:33]:
And in making that career decision, you knew you liked to build, you knew you maybe wanted to start something of your own. What was that timeline?
Uday Chakravarthi [2:40]:
Four to six months is what it took me to really get clarity on what I really wanted to build. And while I was at Atlassian, I saw an opportunity with AI to really accelerate sales and growth. I was on the product side of things and working closely with a lot of go-to-market teams. AI is very good at research, AI is very good at summarizing things, it can do tasks, execute tasks, and if we can bring in all that into a product itself, it can really help accelerate growth. And, you know, I could launch my products faster.
Keith Cowing [3:12]:
So you came up with this general idea, you narrowed it down, you launched Clinch AGI. There are articles out there that say you went from zero to revenue in six months, you went zero to a hundred K in ARR in 12 months. I've noticed you have extremely fast product velocity, and you have a product background, so it’s probably very comfortable to you being a CEO. What were some of the things that were new to you and were outside of your comfort zone now that you have to manage every function, not just product?
Uday Chakravarthi [3:39]:
Yeah, a few things that really helped us accelerate to begin with was one of them is the team itself. You know, you need to have the right people to build something fast. And, you know, I was fortunate enough to build that core team with some of the experts in the area of AI engineering, and that helped us build a strong core foundation, and that really helped us bring in the right folks further along. The second one was effectively working with folks in different time zones. We have folks who are in Australia, India, East Coast, West Coast. And oftentimes, it’s really hard to work fast when you are in different time zones. So we made sure that we had the right set of processes in place, communication-wise, the right tools we were using to really help the team work closer. And then the last piece I would say is the customer-focused mindset. We were not building products in isolation, we were building products with them. Even the first iteration of our product, which was just a prototype, we were working with customers and validating as we went along. So I would say some of those philosophies helped us going from idea to revenue. And also, you know, we didn’t really have any venture funding. We had to be extremely lean and revenue-focused right from day one because, if you want to survive with limited funding, you need to be able to also generate revenue and cash flow, right? Those were some of the things that really helped us move quickly.
Keith Cowing [5:05]:
Can you give me some examples of things that didn’t work and how you learned from that, and then processes that you put in place that did work in order to still move fast even with such a time zone challenge?
Uday Chakravarthi [5:16]:
We were doing daily syncs with folks and two times a day—morning and once in the night. And the idea was we can work closely with the teams and move really quickly and also address any blockers. The challenge that we saw was because of the time zones, not everyone would be able to make it to a meeting, whether it’s engineering or design. And if we didn’t have that one person in the meeting, then the other person would slow down because they’re dependent on this one person. So that model didn’t work very well for us. And then that’s when we decided to use more async communications with respect to audio and video tools. So we used tools like Loom where we would record questions. We would also use it for testing things out. We would also use it for customer feedback. It’s a quick 30, 40-second video or audio, and you’re done. And that really became the mode of communication. And then we didn’t need to be in a meeting to resolve issues. And I think that really helped us initially to speed up some of the communication and collaboration. We also use WhatsApp a lot, and oftentimes it will be just like a quick message recording, et cetera—especially if you have teams in different time zones who may not have access to their laptops all the time.
Keith Cowing [6:25]:
You’re a speed guy, you’re pushing hard. Does that work well for the team? Or is that sort of overly intense for some people?
Uday Chakravarthi [6:33]:
Yeah. So, you know, advisors, it works well because they also—a lot of our advisors are pretty senior people. They understand the urgency a startup has. Now, sometimes, there are one or two engineers who may not respond right away. But I also try not to message them as much as needed. It’s more like I communicate this to say, “Hey, look, we’re going to be using Slack and some of these other channels to communicate, yes, but if it is urgent, I would need your WhatsApp number.” Urgent means something like our site is down, you know, we were losing revenue. Yesterday, actually, this happened. Our developer put something in the code, and it repeatedly kept calling OpenAI's API. So I was getting charged $500 for every 15 minutes. My notifications kept going off, and it was nighttime in India. So I suddenly saw thousands of dollars on my credit card—it was just getting charged. So I had to call somebody and then get on a call. And we basically changed the code. Yeah, if I was sleeping, they were sleeping, we probably would have had a huge bill. Now I have to fight with them, but that’s a different story. I think they should be okay given the situation, but yeah, that’s an example where I had to call. I didn’t look at time back then because, yeah, it would have brought us down.
Keith Cowing [7:45]:
And you’re using your judgment to say, “Hey, we need the bat phone because occasionally it’s going to be, it doesn’t matter what time of day it is, I have to call you, we got to fix this now, but I’m only going to use the bat phone when it’s truly urgent. When it’s not, we can use these other channels.”
Uday Chakravarthi [7:59]:
That’s right. Yeah. And it’s the level of urgency as well. Like, a phone call is the most urgent. You can also send a message on WhatsApp, which is, and you can explain it clearly so that they know the urgency. So it’s really like different levels of urgency depending on what the situation is.
Keith Cowing [8:14]:
And then you also mentioned team as a really important part of enabling you to move fast. And you’ve got a particular set of experiences you’re selling to go-to-market teams. Now talk a little bit about how you designed your executive team, how you designed your advisory board, brought in investors. How did you think about augmenting yourself so you could be as successful as possible?
Uday Chakravarthi [8:37]:
For example, engineering was really important. So we brought in David, who has a lot of experience in building engineering systems from scratch, from zero to one. AI is a big part of it. So we brought in somebody who has a PhD and has done patents in the technology that we are building. Similarly, we also brought in other folks who are really good at B2B, SaaS, enterprise, because that’s where we are really selling our products to. So that really helped us build a strong core team, and then the gaps that we had is where we brought in some advisors or, you know, we were strategic about getting the right angel investors.
Keith Cowing [9:17]:
How did you find—and maybe you can walk us through a couple examples—people that had expertise in areas that weren’t your background and bring them into the fold?
Uday Chakravarthi [9:26]:
In my case, marketing was a very key part of our go-to-market strategy, especially, you know, when you’re selling in the AI space, and there is a lot of noise here. So getting the messaging right, the story right, differentiates your product, et cetera, was very important. I used to work closely with one of our advisors back at Atlassian, and we brought him as one of the advisors very early in the process, and that really helped us—not just, I would say, giving us strategic inputs on advice on positioning, but also making the right corrections and also, like, checking sometimes that, “Hey, just validating some of the hypotheses we had.” Because of the startup, you’re making decisions so quickly on a daily basis. And we needed, you know, somebody who has seen that and can just make sure that we’re heading in the right direction. And similarly, another area where we needed some expertise on was sales. And we brought in a couple of advisors who were not very industry-specific—I would say we didn’t want to go too narrow, like we didn’t want to go only health tech or e-commerce, for example. We looked at, “What is our ICP like? What are the customers we’re looking to target? Are they enterprises? Are they mid-market?” And we brought in a couple of folks who have experience in selling to those specific businesses, whether it’s enterprises or mid-market. And that really helped us because we were able to get connected to the right people, but also build those playbooks—those repeatable sales processes around that—that can help us move fast.
Keith Cowing [10:50]:
And for people who don’t know, ICP means ideal customer profile. This is the exact type of person that you’re selling to. And so you’re very thoughtful about bringing these folks in. Let’s get tactical for entrepreneurs when you’re putting together the advisory board. Did you set aside a certain amount of equity for this? Talk to me about how you recruited people, how you budgeted for it, and how you engage them, how you keep them motivated and involved.
Uday Chakravarthi [11:15]:
We did set aside part of the equity for advisors. And we also looked at what stage the advisors are coming in. For a startup, if it’s an early stage—it’s an idea stage—you probably need more help than, let’s say, you’ve already built a product and, you know, you’re now growing. There are a couple of different types of advisors, I would say, in general. One of the categories is more like cheerleaders—they will tell you what the problem is and give you some advice, may not help you really come up with the right solution or go beyond that. And there are some advisors that are more strategic—they are available, I can text them anytime. They’re also invested in you. So they’re also checking with you: “Hey, how are things going? How did this meeting go? Can I help you?” I found that second category pretty effective because one, they’re invested in your success—they’re not just there to essentially add a label that, “Hey, I work for this company as an advisor.” So that was important, and we also keep them updated on a regular basis, whether it is through weekly syncs that we have or it could be, you know, monthly updates that we send to investors and advisors so they know what’s going on. Some advisory roles might be more helpful in making the right introductions. Some might be more helpful in brainstorming: “Hey, what is the right pricing strategy? Like, how do you sell in this, let’s say, this new country that we have no experience with?” So depending on the role and what you’re looking for, it also depends on how much they work with you on a regular basis.
Keith Cowing [12:35]:
Are there some examples of people that have been the most helpful for you? And what kind of advice have they given you that really changed some of the decisions you’re making?
Uday Chakravarthi [12:42]:
I’ll give you maybe a couple of specific examples that really helped us. One of the examples is somebody who has a lot of experience in selling to enterprises, and the sales cycles are longer, you have multiple decision-makers involved. Somebody who had a lot of experience in that helped us create our deck—not only, like, you know, making the right introductions, but also giving us some insights into what are the things that they care about mostly, you know, whether it’s from a security perspective or it’s privacy, like, how do you work through the ranks to really get to the right people and then sell it. That really helped us in making sure that we had a strong story right from the first meeting. So that was one example where we worked with this person to really nail down our pitch, our story, and then move the deal forward. We’ve had advisors that have looked at our recordings—we’ve done pitch calls, et cetera, or sales calls—and then given very specific feedback right after the call on a text message or on a call saying, “Hey, these are the next—you missed out on these next steps. For example, you should have booked that meeting right away in five minutes before you closed that first discovery call—you didn’t do that.” I would be texting my co-founder when we were having a call, like, “Hey, let’s make sure we get this thing,” because sometimes you can forget in a conversation.
Keith Cowing [13:53]:
Did you invite those folks onto the calls? Were they on a Zoom call with a customer, or were they just listening afterward because you recorded it? What did that look like? So other folks can implement this. There’s a lot of founders that are running companies that were not salespeople by background that need to learn sales. And there’s no better way to coach them than to watch you sell and give you feedback.
Uday Chakravarthi [14:12]:
Yeah, we did both, actually. You know, we had calls where we’d have our advisor on a call and essentially see how we are navigating a call. Some calls are easier, some calls, you know, where it’s not too complex, but sometimes when you—especially when you have larger companies you’re working with—unexpected things can come up, and somebody who’s actually been there, closed those deals, could help you. And similarly, it would be—sometimes it’ll be after a call recording, like, “Hey, let’s have a quick chat, let’s come up with the right follow-up here,” because this is a deal that could close, or maybe this is, like, on the fence, but it would happen right after. So I think that some of those things helped us too.
Keith Cowing [14:46]:
I think that can be really helpful advice for other entrepreneurs—of bringing people in the fold, they can give you advice in real time as things happen, and particularly for go-to-market advice, having people shadow your calls in one way or another and give you coaching. When you look at big sales teams that are effective, they’re constantly coaching their salespeople, but there are a lot of CEOs that just go out there and hack it and don’t get any coaching and don’t get any feedback in those meetings. And so, man, that’s a huge missed opportunity if you’re not taking advantage of that.
Uday Chakravarthi [15:12]:
So every deal is important. And if you can close a few deals faster, it also motivates the whole team. Everybody is even more excited. And we could see that, you know, whenever we have that momentum—that growth story going on—our engineering team is more excited, they are shipping things faster. The advisors are even more excited to make more introductions or get more involved. So it’s—it has a viral effect on everybody that everyone is more excited.
Keith Cowing [15:37]:
You clearly have a learning mindset—not just from a company perspective, but from a leadership perspective—where CEOs face this dichotomy of, you have to have your armor on when you go out in the world and you have to look confident, you have to promote the success that you’re having, but you also have to take the armor off at times and say, “Okay, what did I do wrong? What can I do better?” And you’re showing that vulnerability here by bringing people in the fold and saying, “Hey, I don’t know everything, tell me where I could improve.” Where does that mindset come from? Is that just something you naturally have? Is that easy for you? Is it uncomfortable, but you know it’s important? How can you coach other CEOs to have that mindset of bringing people into the fold on what are pretty important, intimate conversations at times, but you need feedback and coaching on?
Uday Chakravarthi [16:16]:
It was not natural to me. I learned through the process, and giving feedback and getting feedback is generally not very comfortable, especially, you know, if you are giving it to somebody who’s at a similar level or above you. I look at it more as constructive feedback that could be helpful versus something that is more negative. So it’s really about how you frame it. One of the core values for the way we operate is we are very honest and direct about feedback, and we give feedback or take it—we typically do it whenever we see something. We feel that, you know, you should not be waiting for one week to have a discussion with me about one-on-one. So it’s instant, pretty much.
Keith Cowing [16:52]:
That’s fast. Instant is very fast. One other thing I heard in there is your advisors were coaching you, but then you are leveraging that to also coach your team members and your co-founder. When you think about what you’ve learned from bringing advisors on board, bringing other executives on board that have a different skillset than you, what have you learned about yourself as a leader from that feedback, from the introspection that comes with it?
Uday Chakravarthi [17:15]:
When you are building a company, initially there can be a lot of things that you may want to do. And so that initial advice was really helpful—always checking it: Who is your customer? Who is going to be the buyer? Who is going to be the user? Who is going to be the influencer? That clarity really helped us because we could refine our messaging all the way from the first time a customer interacts with our product to continuing to use our product.
Keith Cowing [17:38]:
What advice do you have for entrepreneurs that want to move fast and go from zero to revenue in six months and zero to a hundred K in ARR in less than a year?
Uday Chakravarthi [17:48]:
Yeah, I would say before you get started, spend some time—a couple of months or longer if you need—to really have confidence in that, you know, you’re trying to solve a real-world problem. It’s okay to not have a solution, not know what you’re going to do, but as long as you can really identify and validate that. Because, as an entrepreneur, you’re spending a significant amount of your life in building something—it could be a few years or longer—and before you jump into that, making sure that, you know, you’re making the right decision, you’re going after the right problem. I think that’s very important—spending that initial time. And then the second thing is don’t look at hiring as something that you would do when the right time comes, like, “Hey, when we’re going to start closing a fundraise, let’s start looking at hiring.” You have to build relationships with folks you bring in. For example, our CTO—he started off as an advisor for us. And after seeing, you know, our progress, our growth, for six to nine months, he said, “Hey, you know what? I want to be your CTO. Let’s make it happen.” So invest in relationships, just like you’re investing in customers—invest in building your team. And that will really help you. It may take time to find the right people, but once you find them, man, it can really accelerate your growth.
Keith Cowing [18:57]:
And what advice do you have on the speed side when it comes to taking action? I see you, and we talk about an idea, and then the next week the idea is already implemented—it’s in place, and you’ve got three more ideas, and two of those are already in action. I talk to some folks, and they have ideas, and they have the same idea months later, and nothing has happened. And it’s just such a difference. And I know I can get in my head sometimes as a perfectionist—I want to sit down, I want to think through it, I want to plan it all out. And I have to fight my own perfectionism to go and just take action. You’re excellent at this. What advice do you have for people to get out of their own way and just take more action and move with speed?
Uday Chakravarthi [19:31]:
Prioritization is one of the most important things, and you have limited resources and time. Anything that you’re building that you don’t need is hurting your startup, if you think about it. I use AI to actually know what my customers want. I mean, we also use our own product to extract ideas, and it automatically prioritizes based on the deal value. I have an automatic integration with my Jira—so the moment the top three or four features get automatically added to a board. And then we review that during our sprint planning. We also do weekly sprints instead of two weeks, which is more standard, because it helps us—one, move faster, and plan things at a faster pace. The third thing I would say is we also use different labels to identify the initiatives or projects we are building. We have a label called “deal breaker,” and we use that for things that we know will close the deals for us—there are features that customers want that they will sign the deal for, right? That are basically, “Get a subscription.” And sometimes you have existing customers—you need to keep them from churning, and there are features that they want as well. So we have different labels for these different kinds of priorities because then I can see within my board, like on a Sunday, “Okay, this is what is going to be shipped for next week, and are these all things that will help us give value to our customers or grow?” And if we don’t see enough labels, then it’s really questioning, “Are we actually prioritizing the right things?” And even, like, engineers—they really like it. If somebody is getting a “deal breaker” project, that means that their impact is going to be significant when they ship it. So they’re extra careful in terms of building it or testing it out, asking the right questions. So, yeah, I’m a data guy as well. So I use data wherever I can to make the team move in the right direction.
Keith Cowing [21:07]:
So you’re dogfooding your own product. You’re using AI to prioritize what your customers really want. And you’re doing one-week sprints instead of two or three. So you just up the intensity on that iteration loop. And you’re labeling and organizing things in a pretty rigorous way to make sure that it’s very clear what the deal breakers and most important things are—and everybody knows that and rallies around it.
Uday Chakravarthi [21:27]:
That’s right. And one more thing to add is also, I’m also talking to our customers during the process. We recently built an Intercom integration to essentially bring some support insights. During part of the project, I was constantly chatting with a potential customer who’s going to be using it to also validate some of the things. The traditional way would have been, “Okay, you want this? Let’s build it.” And then you get the feedback, and then you would say, “Oh, you know what? We need to change it.” But in this case, we’re building something with customers, which means, you know, we’re more likely to build something that they want, and they’re willing to use it right away.
Keith Cowing [22:01]:
This is incredible advice for entrepreneurs and leaders of all kinds. Thank you so much for joining me on Executives Unplugged.
Uday Chakravarthi [22:07]:
Absolutely. It was a pleasure, Keith, sharing some of these stories. Hopefully, it’s useful, especially for entrepreneurs and startup founders who are trying to navigate this challenging journey—but fruitful.
Keith Cowing [22:17]:
It’s already been useful for me. I’m sure it will be useful for others. Thank you. If you enjoyed this conversation with Uday, please share it with a friend or provide a five-star review on your favorite platform—it helps other people find the content and benefit from it. This episode was brought to you by the Executive Product Leadership Program at Cornell Tech in New York City. In September, it is a two-day program where you can hear more from people like Uday and network directly in person for two straight days of amazing relationships and networking and workshops on how to unlock the power of AI for your team, for your company, and for yourself as a leader. So if you’d like to learn more, you can check out kc.coach/cornell. I hope to see you there, and until next time, enjoy the ride.
