Yamini Rangan: How to Build an AI-First Company

When you are not in it for the deal, when you are actually in it to understand the motivation of the buyer, what they are staking in terms of their reputation within the organization. And if you can get really aligned with their goals and help them accomplish that, then it was not just the deal you're winning, you're winning the relationship over a very long period of time. That insight has helped me and shaped my thinking and my decision-making for multiple decades now.

So great to be here, Amy and Mag. Thanks for having me.

Oh my god. You're starting with the nerdy me. Yes, totally. I especially during summer vacations, you know, while people had like all kinds of other hobbies outside, I was literally this bookworm. I was at home and I had like, I'd go to the library, pick up like 10 books and literally was reading one book a day, I think. And I even was so lazy, I would not leave the house. So I would give my mom the list of the next 10 books to pick. And so one time she came back, and this was after many years of course, but she came back and she said the librarian said that you've read every book in the library. Your name is on every back cover. And I was like, we need to move to a different town.

You know, I was like particularly into Nancy Drew, Hardy Boys, like that whole genre of, you know, something to uncover. And, you know, my whole thing reading the book was like, can I uncover before, you know, I got to that, right? Like, it was like, can I guess it? Can I figure it out? And it was like this whole thing about that genre I absolutely loved. And it still continues. It's all like leadership is a lot about uncovering something before, you know, someone else makes it obvious to you.

Absolutely, absolutely. My mom, I mean, I grew up in the 80s and my mom really raised me and my sister. I have an elder sister who's two years older and she raised us to have big dreams and it didn't fit the place that we were growing up. It didn't fit the societal expectations of us, but I felt like she had a very different expectation of us in the house. Later on I had to like, you know, reconcile between the societal expectations and what I had been raised. But we had big dreams. We had like big conversations. It was always about what are you going to do when you grow up? Are you going to become a lawyer or an engineer or a doctor? She preferred that I became a doctor but I didn't, you know, concede with that plan. But yeah, it was always big dreams and how to get to those big dreams that, you know, you can like work towards something that was big, motivating and inspiring.

No, I actually moved for a master's in engineering. So I grew up in India, small town. We did end up moving, not because of the library, but because we didn't have a high school that went all the way up to 12th. And so my mom moved and I went to a bigger city with a better library and a high school which was in English, an English-medium school. And then I finished high school and went to undergrad in electronics engineering back then. And then as soon as I got done, and even before I got done, I was like, I want to do a master's. So I came here originally for a master's in computer engineering. I got that in Clemson, South Carolina, and then I started my career as an infrastructure engineer. And this was like the late 90s. There was this thing called the internet boom. We were building, you know, a lot of like capacity, router switches, and that was my first job, is actually infrastructure engineering. And I did that for a few years and then I was kind of not happy being in the data center and I wanted to like talk to people and really understand the value of technology. So I went to business school in Berkeley and then, you know, started my career in the go-to-market side of technology after that.

You know, it was exciting, terrifying, defining all at the same time. The good news was that my mom had always talked about, oh, you're going to go to the US and you're going to get like a higher education and you're going to make your life there. And so there was just a part of the expectation that she had set for both me and my sister. So we had talked about this for almost a decade in dinner table conversations about going. So I knew that was kind of something that I wanted. But at the same time I grew up in a small town and my parents were fantastic. They supported us. They gave us, you know, everything in that little cocooned life. And here I was on a one-way ticket and, you know, a trip where I got to Atlanta. That's the airport that I got to and I was like, 'Yeah, someone from the school will come and pick me up.' And I waited for like four or five hours and then they finally came and grabbed a bunch of us who had, who just like came in. And I was like, 'Yep, someone is going to come.' It was like a terrifying moment of waiting in the airport hoping that I had like a, literally made a name card and I was like, you know, randomly walking around with this name card hoping that someone didn't miss me. And so it's part exciting and part terrifying and then trying to figure out a whole new system and a whole way of life from, you know, the language. And even though I'd studied in English, I found the accent to be very different. And then trying to contribute and trying to understand the societal norms and expectations and being in a college and doing like part-time work so I could pay off, you know, for my grad school. All of that was terrifying. And the defining parts were honestly the very different expectations. Like in India as a student in engineering, you, and especially as a female student in engineering, you kind of like was, you wanted to be under the radar. You literally didn't open and pretty much I felt like I was on mute. And, you know, anytime I tried to contribute there would be some snickering remarks about this woman who is an engineer who was trying to do something. So I tried to be on mute and I think it was literally the opposite in the first year in, you know, a master's degree here. Half of my class, where 50% participation, and I was like, wait, I got to unmute myself and I need to learn how to like contribute. And then I didn't get that right for the first, you know, few quarters and then trying to figure it out. And then, you know, being an engineer even when I first got my job and I moved to the Bay Area in 1996 and I was the only female engineer. How was I, you know, I still am trying to figure out the societal expectations, but I'm also trying to figure out what is my place in a room where I'm the only one that looks like me. And so, yeah, there was just a lot of like figuring things out. But, you know, you then fall back on some defining first principles. I wanted to be authentic to who I was. I had to find my voice, not in a 'I want to participate to earn points' way, but I need to contribute in a certain way. How was I going to stand out? I mean, I have to say that in late '90s and even through the 2000s, I worked twice as hard as everybody else. I don't know if I would recommend that path for leaders now and women that are trying to set their mark, but that was the only path that I knew that I was like, I'm just going to be better than everybody else. I had to work harder than anybody else and I had to have answers faster. And so that was at least the initial playbook. And those were all defining decisions of how you're going to navigate your career but also your life in a very different environment.

That was pre-internet. That was like, you know, the early forms of ARPANET and...

Yeah, there was like the hint of email. Hint of email only in campuses if there was like a very clear LAN connection with an Ethernet cable that was wired.

I wrote a letter to someone and I said, this is the day, this is the time, here's the shirt I'd be wearing and I carry my name, please come find me. And they wrote me a letter back saying, okay. And I got that letter and I had the letter and I had my name and, you know, we got business done.

Yeah. I mean, I think it's the, I would say that it was still thrilling and exciting. Even the wait was thrilling and exciting. I was just like people watching and learning and, you know, and you are right, the 10-year dinner table conversations were all what is typical of a first-gen immigrant. That is kind of what you do. You dream of a better place and dream of a better education and dream of a better opportunity and it is pretty exciting and I still love like my whole journey. Parts of it was really, really hard and much more difficult than I expected but the whole of it is still like super exciting. I would do it all over again, you know.

In feeling both comfortable and ready for this moment that we're experiencing right now because we're in a moment where no one knows. And most people are like, 'Oh my god, I've always known. I've always seen a pattern. I've always had somebody to follow.' And, you know, my experiences are sort of like, well, I went to a place and I started paying attention like more than most people and I just did my best to find my way through and eventually that worked.

So yeah, I could not agree with you more. I think this moment certainly calls for it. But when you've navigated that path, you begin to trust yourself even when you have no answers, you know, and that level of grit and that level of like trying to figure it out. It helps in almost every path within your life, you know.

Oh yeah. When I first met Amy in 2011 when we were both at Workday, I was like, I want to be like Amy when I grow up.

The poise, the clarity of communication and just the ability to command respect in the room. I was like, 'Yeah, I want to be like her.'

Yeah.

I mean, so the decade before I got to Workday, after I had graduated from business school, I was at Siebel and SAP. And, you know, when I joined Siebel, I joined the go-to-market organization. They were creating this new, you know, new function called value-based selling. Now we have like value engineers and value-based sales and, you know, everybody knows this, but back then it was just kind of getting newly created. And over that decade I spent a lot of time in that function across multiple companies and I got to talk to customers over and over again, sometimes when they were prospects, sometimes, you know, post-value. So we were going to try to get like value realization studies done. And in like hundreds of those conversations, you know, I got like very curious. Like on one hand, they became a bit predictable and I would sometimes, you know, I was traveling a lot Monday through Thursday talking to customers and I would sometimes get confused which customer I was like with because it would sound very similar to the conversation that I had the previous week or the previous month. And so, you know, I was like, okay, this is a pattern. The reason I feel this way is because there's a pattern. And what are the patterns that I'm beginning to hear that's not related to that particular deal or winning that particular cycle? What are the patterns? And the patterns were much more interesting to me than the deal. And the patterns were, you know, everybody in the roles that we were talking to, they were trying to bet on technology to do something bigger for them and their organization. And everybody had some kind of goal that was not just that project or signing a deal or something. It was a goal that they wanted to accomplish that would certainly help their companies, but that would also get them promoted. And they were putting their name, their reputation, their career on the line sometimes to make these really big decisions. And that pattern became like so much more interesting for me to observe that when you are not in it for the deal, when you are actually in it to understand the motivation of the buyer, what they are staking in terms of their reputation within the organization. And if you can get really aligned with their goals and help them accomplish that, then it was not just the deal, you're winning, you're winning the relationship over a very long period of time. And that was kind of like what I learned through hundreds of these conversations. And that was super interesting. And that's been like this core tenet. You know, I still carry that pattern of not winning the deal but actually helping people in their careers and that makes for a much better relationship. So, you know, it's paid, you know, that insight has helped me and shaped my thinking and my decision-making for multiple decades now.

Yeah, I've not heard of the ascension test. I'm going to go and read up on that, but I think the concept is definitely the same thing. And, you know, there's a longer arc for everything. It's not the initial buy or the initial value of the product. It's the longer arc. So I like that a lot.

Yeah. Actually, like I'll rewind a little bit. I joined HubSpot January 2020 and...

Timing. Little did I know. And it was like first year and actually the first couple of months I was going through my onboarding and I had conversations with Brian who was at that time our CEO, who was the co-founder of the company, and he was like, don't, don't, don't go, don't rush in your onboarding, just keep it slower and easy. And I was like going through it and then he calls me March first week and he's like, go now, like I need a plan in five days and we are going to go and talk to the board. And we all know what happened. I think March, everybody saw this massive upheaval in, you know, in the world across humanity. Like we were all trying to figure out what are we going to do with our lives. But in business context, it was also everybody in small, medium businesses just going out of business, you know, really quickly and changing the way we operate. And so I do think that that first year was very foundational because we made a bunch of changes. And, you know, think about those whole like customer-centric approach that we were talking about. That was my reason to operate the way I did. But when we got to this point of customers have so much uncertainty, they have no idea what they're going to do, how their businesses are going to operate, and how they're going to even continue given what humanity was going through. For us, it became like super easy. You could have given me one day, I'd have said the same thing, which is like give a lot of customer value. So we cut the prices of the product, we moved a lot of our features into free, we gave value, we created a fund for customers, we said we're just going to help them in the time of need and at some point maybe it'll pay off, but it was not about the payoff, it was like doing the right thing when there was so much uncertainty. You know, fast forward to end of 2020, you know, Brian was like, okay, if something happens, if I get hit by a bus, then, you know, you're on my succession plan. We had like a very short conversation about that. And then March 2021 happened and unfortunately Brian did meet with a snowmobile accident and he called me from, you know, his hospital bed and he said, 'I need to recover.' And of course we were like, of course you have to recover. And he said just, you know, step up, run, you know, and don't screw anything up till I come back. I was like, okay, great plan. I'll not screw anything up till you come back. And I literally had like a, you know, list of when Brian comes back, like, you know, here are like 20 things that he needs to, you know, he needs to fix, I can offer to fix, I can help him. And there was a when Brian comes back list which was pretty long. And then he did come back. He's fully recovered. He's doing great. But he did come back in August and he said, 'Okay, you're doing a good job. We want you to continue to do that.' And yeah.

I know. I was like, 'Okay, the list is long here.' But I think Brian was like very convincing and I also think that these are moments that as any human being, but certainly as women leaders, you know, there's just a lot of questioning, you know, am I ready? Have I done all of this? Have I checked my box in everything that was on my list that I could actually do a reasonable job of that? And we just go into these moments of questioning if I can do everything on that list given I didn't, you know, have the experience of doing everything on the list. And, you know, those are one of those moments where you, I've now come to realize that in points like that, there's no point looking at your past to predict the future. You literally have to go to the future, create the future you want, and then take actions to get to the future. So I changed my perspective and, you know, came out of that period saying I could sit here, question myself, question the shoes I was filling and all of that, or I could define what I wanted to do in the next few years and how I was going to go about doing it. And so this, the working backwards principle, everybody in the industry has talked about it, but it worked really well for me. And I still do like a three-year plan every year where I look three years into the future and what would I want that would give me the deepest level of fulfillment, you know, at work and in life to have accomplished and then set out, you know, taking actions to get to that point.

Yeah, I mean, I literally called up Lorie Norrington, who is now, you know, an awesome mentor for me, is the chair of our board right now. At that time she was an independent chair and literally the conversation after I talked to Brian was, 'Lori, tell me everything. Tell me how you all came to this decision. The good, the bad, the ugly. I want to know it all and I want to know what you think before I even give my answer.' And, you know, you have to have people who will tell you the truth. And Lori is one of those mentors for me where she will tell me the truth and she was like, 'Yep, these are the conversations. This is why we have confidence. These are the areas that we think you still need to like prove and here's how I will, you know, support you in that process.' And I think that gave me just a lot of confidence. And I felt that, you know, both from Lori as well as the board across the many years. And we've had to navigate a lot. Of course, 2020 and 2021 were just, you know, post-pandemic and it was just crazy. But we've had to navigate that, you know, and then we've had to navigate a bit of a downturn macroeconomically where most companies including HubSpot had to do layoffs and then we've had to navigate AI. And when you do all of that, you need to know that there are strong supporters for you, that you can have open, honest conversations and you have the trust that they will tell you the truth.

I, you know, it's a great question. I'll have to go to Brian, ask him for the answer of why he thought so and the board thought so. But maybe the simplistic thing is that I've learned in my career you have to first solve for the customer and then you have to solve for the company, like no politics, no self-preservation, no self-interest can show up. That's how you become a leader. You know, I think over the years I've connected the dots across teams. So it was, you know, not the fact that we were navigating through, you know, this pandemic, but it was like how do you connect the different dots? How do you make decisive moves that you can bet, you know, your career and, you know, your team on to get things accomplished? And how do you do it where it's just not for your self-interest or how you're going to show up in your career? You're doing it because it's the right thing for the company. You know, I bet if I asked, and I will go ask Brian, if I asked, he'd probably say that I focused on the customer and I focused on the company and that built a level of trust. And certainly the fact that we focused on the customer, we made a bunch of moves in 2020 like we said, and second half of 2020, all of those moves like paid off. The goodwill that we had generated with customers actually showed up with customers coming back to us and saying, 'We trust you to help us navigate. We are going to now for the first time have a digital sales team or a digital marketing team.' And they came back and trusted. And so I think part of the results of the moves that we made in 2020 probably also added to the confidence. It comes back to the customer, you know, pretty much.

Not playing politics.

That's right, that's right. I think you said this earlier, Mag, which I want to go to. You know, some of these are fashionable to say during some parts of your career, but really it comes down to the sincerity and authenticity with which you execute over a period of time that people can count on you for that. It has to show up. You can't just use fashionable words, you know, now I'm talking about customer centricity and like two years later you go and talk about something else that is fashionable at that time. It doesn't work that way. You just have to, you know, walk the walk in your career.