$11B CEO: The Great Career Reset in the Age of AI | Yamini Rangan, HubSpot CEO

Today with AI, there is no map. So you have to get comfortable with being an explorer.

You know, you land in Silicon Valley, which is mostly male, right? I still feel it. I go into some rooms and I'm like, can I do this?

First day of my job, they laid off half the class.

And he called me from the hospital and he was like, "Look, I need time to recover, so just run the company." I was like, "Really? What do I do?" And he's like, "Don't screw it up."

A lot of people think functionally. I started in sales. Now I'm going to become a senior manager and then I'll become a director. That is great if you want to be just in a function. But sometimes things that got us here are not enough for us to get to our path forward.

Yeah, I grew up in India in a family of, you know, two girls. I know you have two girls. We grew up in a super small town, so we should not have, you know, been dreaming big, but my mom was just, you know, amazing. And she really helped us think beyond our little town, our little school. The school didn't go all the way till, you know, 12th. So she moved to a different city to make sure that we got an education. And look, I think, Marina, if someone takes you seriously, you begin to take yourself very seriously. And so that was a huge thing. So the rest of the story is I did come here after my undergrad in electronics engineering. I came here, I did a master's in computer engineering, worked as an engineer for a handful of years, and then I was still searching for something. I was like, ah, this is not the thing, and I want to do something more. And so, you know, as everybody who doesn't quite know exactly what they want to do, I went to business school.

Oh yeah. And I went to business school here in Berkeley and I graduated literally at the worst time because it was right after the bust. My first job after business school was Siebel Systems. The first day of my job they laid off half the class and then they somehow looked at me and said you should be in sales and I was like, sales, okay, I have no idea what I will be doing but that's how I got started in sales. And then the next decade was at companies like Workday and Dropbox, which was an incredible experience of being very cross-functional in nature. So I went from sales to sales strategy and operations and then marketing and customer success and then I landed at HubSpot in 2020 and it was crazy times. But I will tell you that that's in a nutshell my career: started as an engineer, went into sales, and then went into multiple customer-facing roles and have just enjoyed every bit of it.

Well, mindset is a really important, you know, kind of like word because you have to have a growth-oriented mindset to figure things out. I mean, here I was, newly minted MBA, and I was in the sales organization. I had like a quota and, you know, Marina, I looked around the room and there were not that many Asian women in the sales organization at that time. And initially I kind of like looked at that and I said, who's the successful person here and how do I kind of become them? Turns out they were all men playing golf and they were incredible at their job but they were also exceptionally extroverted and they had like a method about that. And I was like, you know, I'm an engineer, introverted Asian woman and I'm like, I'm going to try that. So I tried their approach, right, of trying to sound extroverted, trying to play golf, trying to learn sports. None of that worked for me. So I was like, you know what, this is not what I'm going to do. So there was a moment where I decided I'm so bad at what others are doing so naturally, so let me do what comes naturally for me.

And for me, I was analytical, I was a deep thinker, I liked businesses. I was curious about people's businesses, people's careers. And so I said, you know what, I'm going to really be the kind of person who asks deep questions about the company and their business and what they want to accomplish. So that was a big shift and I started enjoying it because it was tapping into what I was naturally inclined to versus trying to find someone else's playbook. And pretty early in my career I said, you know what, I need to stand out as myself authentically versus trying to fit into this room, fit into what others are doing. And I think it was a huge lesson. I've taken it forward.

I still feel it. I go into some rooms and I'm like, can I do this? And that is natural. And I think that it's healthy even because it actually pushes you not to just sit in the doubt and uncertainty, but to find a path forward. And the way I found it works is instead of saying can I do this, you know, can I crack this particular project or initiative or role or a new company that I'm part of, I always start by looking at the future and create the future that I want. So I always think like three years from now and I say, okay, what should I be really happy to have accomplished and let me work backwards from that. So then it stops this feeling of can I do it and really focuses you on exactly what you're trying to accomplish. Then you map all your actions and where you spend time and what you are really prioritizing towards those actions and then all the doubts kind of go away. But you know, the thing is it never goes away.

Comparing or feeling like your past. You know, the biggest learning for me was don't look at your past to predict what you want to do in the future. Look at the future to create the kind of patterns that you want right now.

Yes. But sometimes, you know, things that got us here are not enough for us to get to our path forward. So there are times when if you just look at your past playbook and things that have worked for you, it's not enough. It's not enough to where you're going. And so there are times when past is just limiting. There are times when past will just, you know, only add doubts to your capabilities, not energy towards something that you want to create. And so for me, it's, I don't lose lessons from the past, but I also don't just bank on the past for my future success. You just create it. You just create it and you put your intent and the set of actions. And to me, it's super practical, Marina. I do have what I want to accomplish, you know, in three years and I update it every year. At the end of the year, I'm kind of like reflecting on where I made progress and I write it and I have like top three goals and mostly during the year I'm looking at those goals on a weekly basis and, you know, does my calendar reflect those priorities? Am I actually spending the time improving my skill set to get to those priorities? So it's actually very practical in terms of where I'm looking to go and, you know, really puts away all this doubt and, you know, the way we get limited by just kind of what we have accomplished in the past.

Yeah. I think I had doubts like any 20-something, 30-something would have. I had like a lot of doubts. I started in sales and I did that for almost a decade. Marina, then I had two kids and both of them were under three and we had two careers in the family, both crazy, and I'm like, this is not sustainable. So what can I do with my skill set of what I have done in the last like decade? Then it was like strategy and operations because I understand, you know, being in front of customers, I understand how customers think, negotiate, buy, and now I can use that to kind of like help companies scale and where do you put in the right resources, how do you support salespeople. I can do all of those. And so that pitch was easy once I did that. Then I found that connecting the dots was just exceptionally important as a skill. And what I mean by that is a lot of people think functionally. I started in sales, now I'm going to become a senior manager and then I'll become a director and then I'll become a senior director and they're kind of like going through that. That is great if you want to be just in a function. What is also fascinating is if you can connect the dots across multiple functions. In strategy and operations, I learned how important marketing and sales interlocking on their strategies was. And so I helped marketing teams, you know, talk to sales teams to come up with common strategies. So I think later in my career I was able to like connect the dots and bring insights that teams were generally missing being in silos. And the ability to connect dots and, you know, I call it the T-zone leader: go deep in a couple of functions and go broad across multiple functions. And you have to have some functional orientation to have depth, but then later on in your career it's all about being a T-zone leader, connecting the dots across multiple functions. Really solving first for the customer, you know, not even for your function or your company, first for the customer, then for the company, then for your function, and then for yourself. And if you have that mental model, then new roles open up and new opportunities open up.

Yes, of course.

I mean, we all have doubts. I mean, you know, looking back, you can see the things that worked and the things that didn't work.

Oh, yeah. But at that time, I was like, why is it that I am the one who has to, you know, take a backseat? Why is it maybe like these people who are just, you know, still doing sales, they're going to like progress and, you know, you're trying to figure your life and you don't know if all of the decisions you make are actually going to add up to something good. And this is the thing about being in your 20s and 30s is that you have to have a certain set of principles of what you want to do. I do think that I wanted to be there for my family. I wanted to be there for my kids and be part of the time that I was spending in front with them. At the same time, I didn't know it was going to play out. And I had regrets along the way of, am I doing the right thing? You know, is this the right move for me? And you don't know. And a little bit of uncertainty is what you'll have to live with as a mom, as a career professional, navigating multiple careers and multiple kids. You just have to navigate that and it's hard. Don't assume that people know exactly what they're doing. It's kind of okay if you don't know every bet that you make. As long as you know what your priorities are at any given point and you have a way of sorting through what those priorities are, that can ground you. But you don't know if it's all going to lead to anything. You know,

I don't know. But here's what I will give you about that journey. So I joined HubSpot in January 2020 and initially Brian Halligan, who was the CEO at that point, he's the co-founder of the company, incredible mentor, initially he was like, take all your time, you know, take your time, talk to customers, you don't need to make any changes. March 2020 hit. You know what March 2020 was? It was obviously the world shutdown, but also for small-medium businesses, that is our customer base that we were serving, so much uncertainty and so much churn. And we started seeing customers like didn't know what to do, so they were like stopping their businesses, businesses went bankrupt, all of this stuff. And he looked at me and he's like, do something, you know, and I need something that we can go and talk to our board about. I pulled our team together. We had a great leadership team within the go-to-market organization, that's the team that I was leading, and I said, okay, we're going to meet every day for a couple of times a day, morning and evening. And I want all of your best ideas and any crazy idea that you would never have done before because it was not the time or we couldn't have pushed it, let's just do it. And so we started making all these crazy ideas and the list was, Marina, really crazy. It was take your product and cut the price by 75% and give it away to customers because they all need digital tools.

Take features that were pretty expensive and move it to free because now customers needed to use digital marketing. They needed to do inside sales and they needed to support digitally. So we did all of that. So we went to the board and we said, we're going to cut the price by 75%. We're going to take a lot of features and move it to free tier and then we're going to create a fund for customers and call it the customer relief fund. And anybody who feels like they cannot pay for the next six to nine months, we're just going to give them the benefit of doubt and we're going to use this customer relief fund to help support them. And the board said, "Okay, how are you going to get this money back?" I literally said to them, "I don't know." Yeah, this is the first time. But I'll tell you what, we've always said our north star is solving for the customer. Our customers are really at this point where they don't know what to do. And we're just going to help. And we hope that goodwill will pay something forward. And it did. So March was terrible, April was terrible, May was terrible. Towards the end of May, people started buying and then June, second half of 2020, everybody wanted to get digital tools to market, sell, support, and reach their customers. People who didn't have websites needed websites. 2020 and 2021, it was just massive acceleration. And so you asked this question. So Brian did have, you know, an unfortunate snowmobile accident in March 2021.

And he called me from the hospital and he was like, look, I need time to recover, so just run the company. And I was like, really? What do I do? And he's like, don't screw it up. Oh, no pressure. Just don't screw it up and don't call me because I really need to recover. And he did need the time. And frankly, I think that doing the right thing for customers and making some bold calls where you don't know the answer, but you have high conviction on the path, I think that worked. And so by the time Brian came back in August, I'd done this for a little while. And I would say that if I asked him now, if I asked the board, they would say that you took bold actions and those actions turned out to be the right thing for the customer and was the right thing for HubSpot. And so we built enough confidence that you can continue to execute. And so, yeah, it comes down to do you have a north star priority principle? Yes, a set of principles that you can count on yourself to make the decisions and can you do it, you know, if you need to make a decision five minutes, five days, you know, quickly, can you use those first principles to make the decisions and then can you take a little bit of risk to, you know, have a point of view and then really make that happen. And if you can do those, then opportunities do open up. I'm super grateful. It's just a privilege to lead a company like HubSpot. Since then, it's again like going back to your principles, having a north star, having a big goal in mind and acting from it.

I do think that because of AI we are building things differently. We are selling and providing services to customers differently and we are working differently. This year, and we're talking in 2025, this year, you know, 95% of the code that our engineering teams have committed came with AI assistance. So compare that to 2023, we were actually writing code. So it requires a pretty big shift, both a cultural shift and a technology shift in terms of how we build products and that is the shift that we have made. And then how do we market, sell, and support customers? A lot of the prospecting that we do is with intent data as well as AI intelligence. Our reps, when they go and talk to our customers, they have intelligence of the past 100 conversations they've had with similar customers, what objections they should expect, who they're talking to, all of that is within their fingertips. And so we've really changed how we interact with customers and then how we work internally. When we think about work, we think about what can be automated with AI, what can augment the productivity of teams, and how can we do things better. And so look, I think, you know, somewhere last year there was just this debate of AI is all about efficiency. It's going to like cut jobs and it's all about efficiency. We at HubSpot had a very different view. We said this is the way of the future, which means that every HubSpotter needs to learn and we need to use these tools ourselves. We need to experiment with a lot of these tools so that we can have high conviction when we communicate with customers. So it was more of a let's inspire the team to learn.

And therefore serve customers better. And I tell you, like, the people send me Slacks with, here's what I created and here's a demo, and they're actually excited about learning. And when you create that culture of learning and growing and experimenting, then you get the AI-first or AI-native. You've really changed the way you work and that is what is important right now.

Context, but I haven't seen a job end to end without me having to check or having my team like totally.

I have. It's less, right? It's less. And now, you know, our perspective has been the future is hybrid. It's going to be humans and agents in the loop, taking all the intelligence that agents and AI can deliver, making ourselves much more productive and doing higher value work. And when we do that, the overall productivity within the organization goes up, but we're also able to translate that into wins for customers. And so we're believers in the future is hybrid with humans and AI in the loop.