Silicon Valley GirlFrom India to $30Bn CEO in the USA | Yamini Rangan, CEO Hubspot
EVERY SPOKEN WORD
40 min read · 7,779 words- 0:00 – 1:13
Teaser
- YRYamini Rangan
Today, with AI, there is no map, so you have to get comfortable with being an explorer.
- MMMarina Mogilko
This is Yamini, CEO of HubSpot, a $30 billion company. She arrived in the US in her 20s with a few hundred dollars in her pocket, and now she's running one of the most powerful tech companies in the world. Now, you land in Silicon Valley, which is mostly male, right?
- YRYamini Rangan
I still feel it! I go into some rooms, and I'm like, "Can I do this?"
- MMMarina Mogilko
She navigated her way in a dot-com crash.
- YRYamini Rangan
First day of my job, they laid off half the class.
- MMMarina Mogilko
Years later, she joined HubSpot, and almost immediately, everything breaks at once. COVID hits, and a year later, the founder and CEO, Brian Halligan, had a snowmobile accident. [audio glitching]
- YRYamini Rangan
And he called me from the hospital, and he was like, "Look, I need time to recover, so just run the company." I, I was like, "Really? What, what do I do?" And he's like, "Don't screw it up."
- MMMarina Mogilko
She steps in to run the company.
- YRYamini Rangan
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
- 1:13 – 5:56
From $200 to Running a $30B Company: Yamini's Journey
- YRYamini Rangan
path forward.
- MMMarina Mogilko
Can you give advice to someone who feel like they've plateaued in their career? What is the one thing that they should change right now to start growing?
- YRYamini Rangan
Okay, first off-
- MMMarina Mogilko
[upbeat music] This video is sponsored by HubSpot. Yamini, you have an amazing story. You arrived in the US in your 20s with a few hundred dollars in your pocket.
- YRYamini Rangan
Yep.
- MMMarina Mogilko
Now you're running a multibillion-dollar company as a CEO. For anyone who doesn't know you, can you talk about your background and career shortly?
- YRYamini Rangan
Yeah, I grew up in India, and a family of, uh, you know, two girls. I know you have two girls.
- MMMarina Mogilko
Yeah.
- YRYamini Rangan
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, uh, helped us think beyond our little town, our little school. The school didn't go all the way till, you know, 12, 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-
- MMMarina Mogilko
Mm
- YRYamini Rangan
... 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... 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. [chuckles]
- MMMarina Mogilko
Oh, yeah. [chuckles]
- YRYamini Rangan
And I went to business school here in Berkeley, and, um, I graduated literally at the worst time, uh, because it was right after dot-com bust.
- MMMarina Mogilko
Mm.
- YRYamini Rangan
My first job after business school was Siebel Systems. The first day of my job, they laid off half the class-
- MMMarina Mogilko
[chuckles]
- YRYamini Rangan
... and then they said, [chuckles] they somehow looked at me and said, "You should be in sales." And I was like, "Sales? Okay."
- MMMarina Mogilko
[chuckles]
- YRYamini Rangan
"I have no idea what I will be doing," but that's how I got started in sales. And then, the next decade was, uh, 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 [chuckles] crazy times. But I will tell you that that's 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.
- MMMarina Mogilko
I love it. I love that you changed so many roles and positions-
- YRYamini Rangan
Yeah
- MMMarina Mogilko
... in companies, uh, especially as an immigrant. Can you walk me through, like, one of the hardest transitions that you had to make, and what was your mindset back then? Like, "Yeah, I'm gonna quit this company and do this."
- YRYamini Rangan
Well, um, 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, uh, initially, I kind of like looked at that, and I said, uh, "Who's the successful person here, and how do I kind of become them?" Turns out they were all men playing golf.
- MMMarina Mogilko
[chuckles]
- YRYamini Rangan
And, uh, 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 a engineer, introverted, Asian woman," and I'm like, "I'm gonna try that." So I tried the- their approach, right, of trying to sound extroverted, not... You know, 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 gonna do." So I... There was a moment where I, I decided, "I'm so bad at what others are doing so naturally, so let me do what comes naturally for me."
- MMMarina Mogilko
Mm.
- YRYamini Rangan
And for me, I was analytical. I was a deep thinker. You know, 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, 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 where 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."
- MMMarina Mogilko
Mm-hmm.
- YRYamini Rangan
... I think it was a huge lesson. I've taken
- 5:56 – 7:15
I Still Walk Into Rooms and Think: Can I Do This?
- YRYamini Rangan
it forward.
- SPSpeaker
Uh, it's amazing, and it's such a great lesson for everyone listening, 'cause happened to me as well.
- YRYamini Rangan
Right?
- SPSpeaker
You know, you land in Silicon Valley, which is mostly male, right? Still mostly male.
- YRYamini Rangan
Yes!
- SPSpeaker
And you're like, "Do I fit- can I do it-
- YRYamini Rangan
Right
- SPSpeaker
... like them?" Do you still get this feeling ever, like when you walk in the water?
- YRYamini Rangan
Always. I still feel it. I go into some rooms, and I'm like, "Can I do this?" And that is natural. Uh, and I think that it's, 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've found it works is instead of saying, "Can I do this?" You know, "Can I crack this particular project or initiative or role or new company that I'm part of?" I always start about, look at the future and create the future that I want. So I always think, like, three years, you know, 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
- 7:15 – 9:14
Your Past Will Limit Your Future — Here's Why
- YRYamini Rangan
away.
- SPSpeaker
Yeah. It's just basically focusing on your long-term goals and focusing on them-
- YRYamini Rangan
Yes
- SPSpeaker
... versus comparing yourself constantly.
- YRYamini Rangan
Comparing or feeling like your past. You know, the biggest learning for me was don't look at your past to predict what you wanna do in the future.
- SPSpeaker
Mm.
- YRYamini Rangan
Look at the future to create the kind of patterns that you want right now.
- SPSpeaker
Interesting. Do you ever have a feeling like, "Oh, my past is what got me here?"
- YRYamini Rangan
Yeah.
- SPSpeaker
"So if I change, I might not be as successful," because I... I don't know, like, I grinded, I did this-
- YRYamini Rangan
Yeah
- SPSpeaker
... this and that.
- YRYamini Rangan
Yes. Uh, 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. Um, there are times when past will just, you know, only add doubts to your capabilities, not energy towards something that you-
- SPSpeaker
Mm
- YRYamini Rangan
... wanna create. And so for me, it's, 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.
- SPSpeaker
Mm.
- YRYamini Rangan
You just create it, and you put your intent and the set of actions. And to me, it's super practical, Marina. Uh, I do have what I wanna 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 the, 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
- 9:14 – 11:55
How to Switch Careers Without Experience
- YRYamini Rangan
in the past.
- SPSpeaker
That's amazing. I think that's a great tip for a lot of immigrants-
- YRYamini Rangan
Yes
- SPSpeaker
... who are like, "I've done this in my country-
- YRYamini Rangan
Yes
- SPSpeaker
... but it's not gonna work here-
- YRYamini Rangan
Yes
- SPSpeaker
... 'cause it's different." And then, Yamini, you've done so many different things. You've done sales. You've done strategy, customer success. How do you convince someone you're good at something you haven't done before? Like with sales, right?
- YRYamini Rangan
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-
- SPSpeaker
Mm
- YRYamini Rangan
... two careers in the family, both crazy, and I'm like, "This is not sustainable."
- SPSpeaker
Mm-hmm.
- YRYamini Rangan
Uh, so what can I do with my skill set of what I have done in the last, like, decade? Then I 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, uh, help companies scale. And where do you put in the right resources? How do you support salespeople? I can do all of that, those.
- SPSpeaker
Mm.
- YRYamini Rangan
And so that pitch was easy. Once I did that, uh, 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 wanna 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, um, 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.
- SPSpeaker
Mm-hmm.
- YRYamini Rangan
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, and 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
- 11:55 – 13:51
Navigating Uncertainty: The Skill No One Talks About
- YRYamini Rangan
new opportunities open up.
- SPSpeaker
This is fascinating, the shift you talked about, like how-
- MMMarina Mogilko
... you thought, "Okay, I want a sustainable career to have a family." Did you ever have regrets that because you're now a mom-
- YRYamini Rangan
Yes
- MMMarina Mogilko
-you have to go through this change?
- YRYamini Rangan
Yes.
- MMMarina Mogilko
How-
- YRYamini Rangan
Of course!
- MMMarina Mogilko
So that transition didn't happen easily, right?
- YRYamini Rangan
I mean, it, it- we all have doubts.
- MMMarina Mogilko
Yeah.
- YRYamini Rangan
I mean, you know, looking back, you can see the things that worked and the things that didn't work.
- MMMarina Mogilko
Yeah, for now, it looks like such a good strategic move, right?
- YRYamini Rangan
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, you're trying to figure your life.
- MMMarina Mogilko
Mm-hmm.
- YRYamini Rangan
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 in- about being in your 20s and 30s, is that, um, you have to have a certain set of principles of what you wanna do. I do think that, um, I wanted to be there for my family. I wanted to be there for, uh, my kids and be part of the time that I was spending in front and with them. At the same time, I didn't know it was going to play out.
- MMMarina Mogilko
Mm.
- YRYamini Rangan
And I had regrets along the way of, "Am I doing this right thing? You know, is this the right move for me?" And you don't know. And, um, 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.
- MMMarina Mogilko
Mm.
- YRYamini Rangan
And it's hard. Don't assume that people know exactly what they're doing.
- MMMarina Mogilko
Oh, yeah.
- YRYamini Rangan
It's kind of okay-
- MMMarina Mogilko
Yeah
- YRYamini Rangan
... if you don't know every bet that you make. Um, 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. Uh, but you don't know if it's all going to lead to anything,
- 13:51 – 15:30
FREE AI Toolkit: The Big 3 LLMs at Work
- YRYamini Rangan
you know?
- MMMarina Mogilko
Yamini is talking about the importance of reinvention and navigating uncertainty in your career. And let's be real, the biggest source of uncertainty right now is AI. If you want to reinvent yourself for this new era and ensure you thrive as an AI operator rather than getting left behind, you need to check out this e-book bundle named Inside HubSpot's AI Stack: The Big Three LLMs at Work. It's basically a practical guide to the three major models right now: ChatGPT, Claude, and Google Gemini. I've put it in the description for you to download for free. This bundle is your toolkit for income and business growth. It helps you move from just playing around with AI to building true operational leverage. You'll learn how to turn AI into your personal executive assistant, visualize complex data to make better decisions, and solve strategic problems faster. I personally found two sections to be real game-changers. The AI as Your Executive Assistant section shows how to automate your busy work, like tracking meeting follow-ups, so you can focus on high-level strategy. And the interactive dashboard sections show you how to turn raw data into visual insights without needing a data science degree. This e-book bundle was made by HubSpot, who's obviously the perfect partner for this conversation. A big shout-out to them for this free resource. And now let's get back to Yamini on how she led HubSpot through the crisis. And it all played out well for you, right? Um, so you became the CEO of HubSpot, first interim, then permanent CEO. What do you think made the board say,
- 15:30 – 20:18
How She Became CEO: Leading Through COVID Crisis
- MMMarina Mogilko
"She's the one"?
- YRYamini Rangan
I don't know. Uh [laughing]
- MMMarina Mogilko
[laughing]
- YRYamini Rangan
But, but here's, here's what I will give you about that journey. So I joined, uh, HubSpot in January 2020, and, uh, initially, Brian Halligan, who was, was the, uh, CEO at that point, he's the co-founder of the company, incredible mentor. He di- initially, he was like, "Take all your time, you know. Take your time. Talk to customers. Y- you don't need to make any changes." March 2020 hit. You know what March 2020 was.
- MMMarina Mogilko
Yeah.
- YRYamini Rangan
It was... Obviously, the world shut down, but also for small, medium businesses, that is, uh, the- 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 bent out, bankruptcy, all of this stuff. And he looked at me, and he's like, "Do something," you know.
- MMMarina Mogilko
Yeah.
- YRYamini Rangan
"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, I said, "Okay, we're gonna meet every day for a couple 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."
- MMMarina Mogilko
Mm-hmm.
- YRYamini Rangan
"Take features that were pretty expensive and move it to free because now customers needed to use digital marketing."
- MMMarina Mogilko
Yeah.
- YRYamini Rangan
"They needed to do inside sales, and they needed to support digitally." Uh, so we did all of that. So we went to the board, and we said, uh, "We're going to cut the price by 75%. We're gonna 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."
- MMMarina Mogilko
Wow.
- YRYamini Rangan
And the board said, "Okay. [laughing]
- MMMarina Mogilko
[laughing]
- YRYamini Rangan
How are you gonna get this money back?" I literally said to them, "I don't know."
- MMMarina Mogilko
Yeah.
- YRYamini Rangan
"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 the 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.
- SPSpeaker
Yeah.
- YRYamini Rangan
And so you asked this question, so Brian did have, um, 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, uh, I was like, "Really? What, what do I do?" And he's like, "Don't screw it up." [laughing]
- SPSpeaker
[laughing] Oh, no pressure-
- YRYamini Rangan
No pressure
- SPSpeaker
... just don't screw it up. [laughing]
- YRYamini Rangan
Don't screw it up, and, and don't call me, because I really need to recover.
- SPSpeaker
I'm recovering. [laughing]
- YRYamini Rangan
And he-
- SPSpeaker
Wow
- YRYamini Rangan
... he did need the time.
- SPSpeaker
Mm-hmm.
- YRYamini Rangan
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-
- 20:18 – 22:56
What It Means to Be an AI-First Company
- YRYamini Rangan
since then.
- SPSpeaker
It's, again, like going back to your principles-
- YRYamini Rangan
Yeah
- SPSpeaker
... having a North Star, having big goal in mind, and acting from it.
- YRYamini Rangan
Yep.
- SPSpeaker
So from the operational standpoint, being this AI-first company-
- YRYamini Rangan
Yeah
- SPSpeaker
... what does it mean from- for your day-to-day?
- YRYamini Rangan
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 codes that our engineering teams have committed came with AI assistant. So compare that to 2023-
- SPSpeaker
Yeah
- YRYamini Rangan
... 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, similar customers they've talked to, w- 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 gonna, 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-
- SPSpeaker
Yeah
- YRYamini Rangan
... and therefore serve customers better." And I will tell you, like, the, people send me Slacks with, uh, "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, uh, experimenting, then get the AI-first or AI-native, you've really changed the way you work.
- SPSpeaker
Yeah.
- YRYamini Rangan
And that is what is important right now.
- SPSpeaker
Yeah, and I like how you noted that, and I'm feeling this
- 22:56 – 24:30
Is AI Really Taking Your Job? The Truth
- SPSpeaker
now. Like, last year, all the headlines were like, "AI is taking your job." Now, we're like, we've used the tools, right?
- YRYamini Rangan
Yeah.
- SPSpeaker
It's not really taking our job. It's making it easier.
- YRYamini Rangan
Yes.
- SPSpeaker
It's making us more effective-
- YRYamini Rangan
Yes
- SPSpeaker
... gives us more context.
- YRYamini Rangan
Yes.
- SPSpeaker
But I haven't seen a tool that does the job end-to-end without me having to check or having my team, like, in a meeting.
- YRYamini Rangan
Totally, totally. I mean, two years ago, I, you know, come from San Francisco Airport all the way to home, they'd be like, "Hire AI agent."
- SPSpeaker
I think it's still somewhere around, but less. Have you... I, I have-
- YRYamini Rangan
I know.
- SPSpeaker
Yeah.
- YRYamini Rangan
It's less-
- SPSpeaker
Yeah
- YRYamini Rangan
... right?
- SPSpeaker
It's crazy. [laughing]
- YRYamini Rangan
It's less. And now, you know, our perspective has been, future is hybrid.
- SPSpeaker
Yeah.
- YRYamini Rangan
It's going to be humans and agents in the loop-
- SPSpeaker
Yeah
- YRYamini Rangan
... 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 are 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.
- SPSpeaker
100%, yeah.
- YRYamini Rangan
Yeah.
- SPSpeaker
And I remember the, the billboards say, uh, said, um, "Stop hiring humans. Hire..." something like that.
- YRYamini Rangan
Exactly.
- SPSpeaker
That startup. I was like, "Oh!"
- YRYamini Rangan
I have a picture of it.
- SPSpeaker
Interesting.
- YRYamini Rangan
I took the picture.
- 24:30 – 26:17
The #1 Mistake Entrepreneurs Make with AI
- YRYamini Rangan
feature.
- SPSpeaker
Mm.
- YRYamini Rangan
... start with your business.
- SPSpeaker
Mm-hmm.
- YRYamini Rangan
What is the biggest problem that you're trying to solve? Start with that, and why have you not been able to solve it? And when you start with that, then you identify the right use cases to leverage AI. What is happening in- is that people are like, "Oh, use AI for this-
- SPSpeaker
Mm.
- YRYamini Rangan
-and use AI for that." And when I have customer conversations, I always ask them, um, "Next year, you're looking to grow, what is the biggest obstacle for you to grow?" And they will say something like, "We don't have enough top-of-funnel leads." Great. Use AI-
- SPSpeaker
That's your prompt [chuckles]
- YRYamini Rangan
... to generate-
- SPSpeaker
Yeah
- YRYamini Rangan
... top-of-funnel leads with better personalization. That's the place to start. Or they'll say, "I have hired enough salespeople, they're just not productive, and I wanna make them efficient, and the deal process is broken. I don't have enough visibility." Start there. Use prospecting to be able to improve the level of intent information you can get, so that your reps can reach out to more accounts at the right time. So my push is, if you're an entrepreneur, if you're a builder, if you are, you know, driving a company strategy, start with the biggest problems, and then look for AI features-
- SPSpeaker
For tools, right
- YRYamini Rangan
... and opportunities.
- SPSpeaker
Yeah.
- YRYamini Rangan
Don't do it the other way.
- SPSpeaker
Yeah, 'cause otherwise, you just spend hours and hours trying different tools without really understanding what the, the KPI should be, right?
- YRYamini Rangan
Yeah.
- SPSpeaker
What's the metric?
- YRYamini Rangan
Yeah.
- SPSpeaker
What makes this tool successful-
- YRYamini Rangan
Exactly
- SPSpeaker
... if it's not solving a real problem?
- YRYamini Rangan
Exactly.
- SPSpeaker
So start with a problem.
- YRYamini Rangan
Yep.
- SPSpeaker
Love that. So when you're hiring these days-
- YRYamini Rangan
Mm-hmm
- SPSpeaker
... in the AI era-
- YRYamini Rangan
Yeah
- SPSpeaker
... what are the two to three skills that you're looking for in a candidate?
- 26:17 – 29:00
The 3 Skills Every Hire Needs in the AI Era
- YRYamini Rangan
the way I would frame it, we are looking for explorers, and I'll tell you what that means. You know, I think there's a fundamental shift that's happening with AI, where not everybody knows exactly how to go from point A to point B. You know, if you knew exactly... And think about them as map readers, right? You know exactly what point A is, point B is. You read the map because someone has figured out the path, and you follow the directions, and you get there. That is what we were doing because you had playbooks that worked, and you were, you know, really clear about following the playbook. Today, with AI, there is no map.
- SPSpeaker
No.
- YRYamini Rangan
So you have to get comfortable with being an explorer, and there are a few skill sets that are important. The first one is that you have to have almost a scientist mindset, and I look for people who are comfortable experimenting and having a hypothesis, proving if the hypothesis is right or wrong, versus saying, "There's a set path," right?
- SPSpeaker
Mm.
- YRYamini Rangan
Like, experimentation, moving quickly, having a hypothesis, and proving whether you're right or wrong, that is, like, skill number one, and I look for examples of when they have done it or how they have comfort around it. That's, like, number one thing that I look for.
- SPSpeaker
Yeah.
- YRYamini Rangan
The second is just this passion and curiosity to go deep in the work. What is happening is that in order for AI to be effective, you've gotta be close to the ground. You have to know what parts of the workflow are broken, what parts of the workflow can actually get value from AI, and you've gotta get, like, really close to the ground, you know? And I talk to customers, but we also do a Gemba walks. We look at, like, how people are using different technology. I'm looking for people like that, who are very close to the ground, close to the process, who can actually make changes. That's the second one, and then the third is really what, you know, I would say, um, as just curiosity and customer orientation. Again, my focus has been, "Don't- forget about AI. Use it to solve something for your customers." So can you be super curious and ask-
- SPSpeaker
Yeah
- YRYamini Rangan
... the right questions of, you know, your customers to get the right thing? And if you have the ability to experiment, the ability to stay close to work, the ability to stay curious, then you're actually gonna thrive in the world of AI. If you are stuck with your playbook, if you are very comfortable with going from point A to point B in a path that someone else has prescribed, then you're just not gonna be successful in the world of AI. That's what I'm looking for.
- SPSpeaker
Yeah, totally. Do, do you feel like you're still looking at their education, or-
- YRYamini Rangan
Um
- SPSpeaker
... it's less important now?
- YRYamini Rangan
I mean, no, I, I don't think I have ever looked
- 29:00 – 31:14
Should You Still Go to College in 2025?
- YRYamini Rangan
at just education, because that's just one thing, right? And it is... It's important to be, like, technically qualified. You know-
- SPSpeaker
Mm-hmm
- YRYamini Rangan
... if you're building product, you need to have the, the basic capacity and everything, but education is just part of the picture. It's all of these intangibles that I'm looking for.
- SPSpeaker
Yeah. Do you still feel people should pursue higher education, or-
- YRYamini Rangan
I- you know what? This is a very controversial topic.
- SPSpeaker
Yeah, yeah.
- YRYamini Rangan
I'm all in on education.
- SPSpeaker
Yeah.
- YRYamini Rangan
And so I just dropped my son in freshman in college.
- SPSpeaker
Mm-hmm.
- YRYamini Rangan
As he was about to go, about, like, four years ago, he said, "I wanna do computer science and math," and he stuck to it, and so he's studying computer science and math. And all of our friends were like, "That is such a wrong, you know, thing. You shouldn't be sending him to study computer science, and coding is gone." And I was like, "Yeah, but who said computer science or math or any of this is about-
- SPSpeaker
Coding
- YRYamini Rangan
... a skill of coding?"
- SPSpeaker
Yeah.
- YRYamini Rangan
It is how you think.
- SPSpeaker
Yeah.
- YRYamini Rangan
It is how you learn. It's how you break down problems. And, you know, interestingly, when I graduated from business school, now I'm dating myself multiple decades ago, there was no job called chief customer officer. That's what I eventually ended up becoming. There was no job. So every decade, as things evolve, new jobs will evolve. You can't even plan for a job that's going to be there 10 years from now, 20 years from now.
- SPSpeaker
Even two years. [chuckles]
- YRYamini Rangan
But two years from now-
- SPSpeaker
Yeah
- YRYamini Rangan
... but what you can is learn how to think-... learn how to break down problems and solve problems, and learn how to ask questions. And if you can do those things, then, you know, education is really worthwhile, and that's kind of like I told my son, "Yep, you, you should do all of this, whatever you want, b- but also go deep." If he ends up wanting to do, like, a graduate program or even go deeper, uh, I'd be all in for that. Just go deeper into an area rather than spread yourself thin.
- MMMarina Mogilko
Yeah, just go explore-
- YRYamini Rangan
Yeah!
- MMMarina Mogilko
... and learn how to learn.
- YRYamini Rangan
Exactly.
- MMMarina Mogilko
Yeah.
- YRYamini Rangan
Exactly.
- MMMarina Mogilko
[whooshing sound] Quick pause here. If you're enjoying this podcast, you will absolutely love my Inner Circle newsletter. So what I basically do is I take all the tips from these podcasts, and I apply them to my personal life, to my investment portfolio,
- 31:14 – 32:42
The Decision-Making Framework of a $30B CEO
- MMMarina Mogilko
and to my businesses, this media company and my language teaching business. Sometimes we get amazing results, and I share our real tactics. Sometimes we don't, and I share that, too. Think of it as an insider version of this podcast. The link is in the description. Join my free newsletter to stay ahead. [whooshing sound] Is there a decision-making rule that you follow as a CEO that someone could learn from you?
- YRYamini Rangan
That's a difficult one. It really, um... First of all, in, in a role as a CEO, in a role as a, you know, C-suite leader, only the most difficult decisions come to you. Sometimes people who are, like, early in their, you know, leadership career or m- you know, in, in the C-suite, they're like, "Oh, my God, these are all tough problems," and, like, guess what? Yes.
- MMMarina Mogilko
Yeah, [chuckles] that's your job.
- YRYamini Rangan
Only tough problems-
- MMMarina Mogilko
Yeah
- YRYamini Rangan
... come to, come to you. I do think that you have to have some set of principles that you kind of look for. In, in our case, at HubSpot, and certainly in my personal philosophy, it's always having a north star for the customer. That has been one. Um, I think the second probably is, you know, balancing short term versus long term, which a lot of leaders find exceptionally hard to do, and you have to be able to, like, balance short-term versus, like, long-term decision-making, and you have to be able to set a vision for slightly long term. And there is... It's a balance. I don't think it's an easy decision-making framework. It is a balance of, uh, some things you have to do that
- 32:42 – 34:36
How to Make Better Decisions Under Pressure
- YRYamini Rangan
give results immediately, some things you have to have the foresight to see how it'll play out over the next couple of years, and your job is to balance both.
- MMMarina Mogilko
It's, it's interesting, but also, like, making decisions where when there's so much fear, right?
- YRYamini Rangan
Yeah.
- MMMarina Mogilko
When it came to COVID, right?
- YRYamini Rangan
Yeah.
- MMMarina Mogilko
The, the lockdown and then AI. Any- anything that, like, calms you down, or, like, is, is that the north star, you'd say?
- YRYamini Rangan
Yeah. First of all, operating from fear is never a good place to operate from. You will make poor decisions. Um, operating from principles, being grounded, you know, in certain set of principles, but also certain ways in which you operate with, you know, enough peaks and valleys, that is important. So I think, like, for me, I do think that clear breaks where I'm thinking about something else is important. You know how they talk about peak performance-
- MMMarina Mogilko
Yeah
- YRYamini Rangan
... of athletes, when you are in flow, when you are in peak performance? The thing that people don't talk about is that they have a period of deep rest, and you can't operate in peak performance, you cannot be operating in a peak decision-making skill set without having clear ways of grounding. For me, it is like rituals that I have. Like, you know, every evening between 5:30 and 6:30, I take an hour off, and I listen to music, I listen to podcasts, I listen to something that is not related directly to my work, and that disconnects.
- MMMarina Mogilko
Yeah.
- YRYamini Rangan
And then I do take, you know, clear breaks, you know, whether it is vacations with family or something, but I think we underestimate the impact of things that ground.
- MMMarina Mogilko
We do-
- YRYamini Rangan
And-
- MMMarina Mogilko
... especially as immigrants. [chuckles]
- YRYamini Rangan
Uh, because we all want to work harder-
- MMMarina Mogilko
Yeah
- YRYamini Rangan
... and get to the next thing, and-
- MMMarina Mogilko
That's how we were raised. Yeah.
- YRYamini Rangan
But you gotta recognize that peak performance comes through peak valleys
- 34:36 – 37:52
The Questions You Need to Ask to Build Your Principles
- YRYamini Rangan
of rest, and-
- MMMarina Mogilko
Mm-hmm
- YRYamini Rangan
... you know, and you have to be able to do both, and for me, those practices have grounded myself. I mean, I make better decisions when I get seven hours of sleep.
- MMMarina Mogilko
Yeah.
- YRYamini Rangan
You know, I, I make better decisions when I've had some level of clarity after I do yoga or meditation, and those are as important as the days that I spend grinding, you know? [chuckles]
- MMMarina Mogilko
I love it. Yeah. When... If someone listened to this and is also like, "I wanna ask you this question," 'cause you talked a lot about principles, how do you come up with them? What questions do you ask yourself? Do you have, like, any, any questions in mind that you should ask yourself to come up with a set of principles to make those decisions better?
- YRYamini Rangan
It's a, it's a really good question. I think for me, practice of reflection has worked, where over the years I've always been introspective, um, somewhat critical of myself, probably the most critical of myself, and as I reflect and, you know, I'm super critical of myself, I always am like, "What did I learn from this, and what would I do differently?" And I use every year as a reflection period to say: What did I learn, and what would I take away? And over a period, if there's a pattern emerging that every decision, if you put your customer at the top, it's always going to be the right one. That comes because you're reflecting on things that worked and things that didn't work. And for me, having a practice of introspection and really thinking about what did I learn from this year's experience, what worked, what didn't work, what would I take forward from here, that has revealed, you know, patterns, uh, both small in terms of, like, making, you know, quick decisions within the business, but also fairly large principled-... you know, decisions.
- SPSpeaker
I love it. That's, that's awesome. Uh, and I feel like you can u- also use AI for that. I've been using AI to just-
- YRYamini Rangan
Have you?
- SPSpeaker
I've, I've been brainstorming a lot of decisions with AI.
- YRYamini Rangan
Yeah.
- SPSpeaker
And now I can just ask questions, "If you could give me advice, uh, six months ago-
- YRYamini Rangan
Yeah
- SPSpeaker
... what would it be?" Based on all of the problems that I experienced-
- YRYamini Rangan
Yeah
- SPSpeaker
... and tried to solve with you.
- YRYamini Rangan
Yeah.
- SPSpeaker
And it was super clear.
- YRYamini Rangan
That's awesome!
- SPSpeaker
Like, this is what you prioritize, this is what you struggle with-
- YRYamini Rangan
Yeah
- SPSpeaker
... this is what you should be doing.
- YRYamini Rangan
There you go.
- SPSpeaker
Uh, so-
- YRYamini Rangan
I have a... You know, I've kind of created a personal style, n- you know, for AI, where I talk about the tone and what my values are. Uh, even when I write, I'm like, "You know, I don't want any fluff. I want direct, candid communication." The communication needs to feel human, you know? No offense, AI, I don't want like- [chuckles]
- SPSpeaker
Mm-hmm. No offense
- YRYamini Rangan
... random fluffy words.
- SPSpeaker
Yeah, yeah.
- YRYamini Rangan
And I give all of that, and I think over time it learns. But, you know, now I'm curious. I'm gonna try and use a lot more of my principles as we make through- make decisions. [chuckles]
- SPSpeaker
Yeah, I learned this from Mustafa Suleyman.
- 37:52 – 39:39
Advice to Your 21-Year-Old Self in the AI Era
- SPSpeaker
I think it's genius. [chuckles]
- YRYamini Rangan
I love it.
- SPSpeaker
It's like-
- YRYamini Rangan
I love it
- SPSpeaker
... very cyclical. [chuckles]
- YRYamini Rangan
I, I try and do the reflections, but not daily. That's a great practice.
- SPSpeaker
Yeah.
- YRYamini Rangan
And you could probably do it in, like, five minutes even.
- SPSpeaker
Hey, even if it's weekly, right?
- YRYamini Rangan
Yes.
- SPSpeaker
If, if it's some decision-making with AI-
- YRYamini Rangan
Yeah
- SPSpeaker
... I think it's, it's a great practice.
- YRYamini Rangan
I love it.
- SPSpeaker
Can you give advice to someone, or to yourself-
- YRYamini Rangan
Yes
- SPSpeaker
... a 21-year-old self arriving in the US, but in the AI era?
- YRYamini Rangan
Okay, first off, I'm happy- [chuckles]
- SPSpeaker
Good
- YRYamini Rangan
... that I arrived [chuckles] when I did-
- SPSpeaker
[laughs] Love it
- YRYamini Rangan
... because there is a lot to sort through right now. Which careers are going to survive? Which ones are not? What jobs? What should I study? And, you know, is- are the entry-level jobs going to go away? There's just a lot of uncertainty right now. So I'm actually glad that I came here in, uh, in the '90s, when I did, and I've learned so much. And but on the, on the advice, like, you know, I do think that we started the conversation, Marina, about feeling uncertain about decisions and carrying a lot of anxiety about the future. I mean, you come here as a first-generation immigrant, and you come here as a woman, and you look at the rooms that you're in, and there's just a tremendous amount of, "Am I going to make it?" You know, "Is this decision right? Uh, am I headed in the right way?" There's just daily anxiety, and I would calm myself down, if I could, to go back and be like, "You will have some level of anxiety, but just, like, you know, enjoy the journey a lot more. And if you have certain principles that you use in your decision-making process, you're going to be fine."
- SPSpeaker
Yeah.
- YRYamini Rangan
And I think there was just a lot more anxiety in me, you know, uh, early in my career, and I would say, "You know what?
- 39:39 – 42:08
Ask Yourself 5 Whys: How to Break Through Any Plateau
- YRYamini Rangan
Life will work it, work itself out."
- SPSpeaker
Yeah, yeah, trust yourself, basically-
- YRYamini Rangan
Yes
- SPSpeaker
... right?
- YRYamini Rangan
Yes.
- SPSpeaker
'Cause we don't have a lot of trust in ourselves, especially in our 20s.
- YRYamini Rangan
That's right.
- SPSpeaker
Yeah.
- YRYamini Rangan
That's right.
- SPSpeaker
My last question would be-
- YRYamini Rangan
Okay
- SPSpeaker
... can you talk to people who feel like they've plateaued in their career or in their business? What is the one thing that they should change right now to start growing?
- YRYamini Rangan
Ask yourself five whys. Why have you plateaued? Why is something not working for you? Why... Ask five questions of, you know, why, why, why, and be curious about what is the reason.
- SPSpeaker
Mm-hmm.
- YRYamini Rangan
And that is what is going to lead you to something, you know, uh, incremental from where you are. A lot of times people take superficial answers, both of themselves and of our business, and they wallow in, you know, where they are stuck at, instead of really digging deep and trying to get to the bottom of, "Why am I in this plateau? Well, because, uh, I don't know what to do with my job." Why, you know, is that job feeling like you're stuck? "Well, because I'm not learning as much."
- SPSpeaker
Mm-hmm.
- YRYamini Rangan
Why am I not learning as much? "Uh, because I don't have the right problems to focus on." Why do you not have the right problems to focus on? Something... Like, go deeper and deeper into the why, and the answer will be right there, and the answer is going to be part of you digging deep and understanding why you are stuck, and being honest about those answers. Sometimes we don't want to hear the answers. You might be running a business which it's probably going nowhere because there is no market. Sometimes we don't wanna take that honest answer that we know in our mind, we know in our gut is the honest answer, we don't wanna take it, but you gotta have the stomach to take that-
- SPSpeaker
Yeah
- YRYamini Rangan
... and then make the change that, that is needed, whether it's personally or for your business.
- SPSpeaker
Yeah, and maybe you dig deeper, and you realize your career has nothing to do with your principles or your North Star.
- YRYamini Rangan
Yes, exactly.
- SPSpeaker
Yeah.
- YRYamini Rangan
Exactly.
- SPSpeaker
Thank you so much, Yamini. This was so insightful. I feel like I've learned a lot. The thing that I'm gonna do after this interview-
- YRYamini Rangan
Yeah
- SPSpeaker
... I'm gonna talk to my AI about my principles. We need to figure them out and, like, set the goals for the next three years.
- YRYamini Rangan
There you go.
- SPSpeaker
Love it.
- YRYamini Rangan
Thank you so much.
- SPSpeaker
Thank you, Marina.
Episode duration: 42:08
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