When Yamini Rangan graduated from business school, she wanted a job in consulting, but the market was shaky. So she took a sales role at a tech company instead.
The move was a blow to her Indian parents, “who were already disappointed that I was not a doctor,” Rangan said. But it turned out to be a smart decision. Today, she is the CEO of HubSpot, a software company with $1.7 billion in 2022 revenue that was founded by MIT alumni and Dharmesh Shah.
In a keynote talk at the 2023 annual conference of the MIT Initiative on the Digital Economy, Rangan reflected on the intentional decisions that altered the course of her career.
“I made a choice to be an engineer back in India, where we had less than 8% of women joining an engineering class,” she said. “I made a choice to leave my country and come here when I was 21 years old, with a lot of hopes and dreams but not much else.”
Rangan believes that becoming a great leader likewise is intentional. She spoke with Andrew McAfee, co-director of the IDE, about six choices she made on her way to the C-suite.
Choose to go far rather than fast
When Rangan was promoted to a sales manager position from an individual salesperson role, she initially made the mistake of moving too fast with her team. She expected them to work both swiftly and accurately — the way she had — and realized that she needed to let her team come up with the answers, not tell them what to do.
“It was all about changing my own mindset from not being the fastest runner on the team but really thinking of becoming a cross-country coach — someone who gets everybody on the team to win,” she said.
“I would say that this is probably one of the biggest learnings I've had in my journey. Whenever I move companies or take on a bigger role within a company, I remind myself that I need to slow down in order to go far with the team, and that’s helped,” Rangan said.
Choose to stand out rather than fit in
In sales, networking is essential. But casual banter over a game of golf with customers wasn’t Rangan’s thing, especially with two young children at home. An analytical person by nature, she instead delved into companies’ 10K and 10Q financial statements and asked customers insightful questions about their business.
“I was genuinely curious about why customers were buying software and what the value was for their company and for their own careers,” she said. Armed with that knowledge, she notched more wins and gained more confidence. “And that was how I got credibility in the room.”
To Rangan, it’s a question of authenticity — in her case, seeking out conflicting viewpoints and both listening to and acting on feedback.
“Authentic leaders say exactly what they mean, and because of that, they stand out,” Rangan said. “There are tons of studies that will tell you that authenticity wins.”
Choose the “invisible path” when it appears
There are two paths toward advancement that you can take in an organization, Rangan said. The first is a visible path; you join a particular function at an organization and rise through the ranks. The second is an invisible path, where the route is less clear.
Rangan took the latter. She had started at Dropbox as a functional leader but found that she enjoyed connecting the dots across functions, which eventually led to an appointment as chief operating officer. Being company-focused rather than functionally focused paid off for her.
“An invisible path opened up, not because I was a great functional leader but because I was a good and credible company leader,” she said. “I didn’t know that path existed, but that was an exceptionally important path toward my leadership roles.”
Choose to “work backwards from the future”
Rangan was named temporary CEO of HubSpot under stressful conditions in 2021, when Halligan needed time off to recover from a serious snowmobile accident.
Stepping into the CEO role permanently later that year was a huge achievement for her, Rangan said, but one that came with self-doubt and imposter syndrome. To get through it, it helped her to think of the future she wanted to create.
“But I made a choice that I was going to work backwards from the future that I was going to create, not from that past [and] the fact that I didn’t know half the functions or that I’d never done this job before,” Rangan said.
Choose to say no
How does Rangan choose where to focus her attention? She looks at her priorities regularly and adds up the amount of time she spends on each of them. Doing so gives her “clarity to say no to a whole bunch of things,” she said.
“If you’re trying to do the things that others are good at or others are capable of becoming good at, then you’re prioritizing your time wrong,” she said. “We have a wonderful team. My job is to coach our leaders and our team to become even better at their jobs, not to try and do their jobs for them.”
Choose to show vulnerability
Instead of embracing a win-above-all mindset, Rangan leans into vulnerability. It’s a stance that flies in the face of the kind of career advice that was offered to women executives when Rangan was starting out.
“I think the whole idea from 20 years ago — ‘Don’t ever show weakness; act like you have armor on all the time’ — I don’t think it builds team strength,” she said. “I don’t think it builds what you want within your executive leadership team or across the company.”
Rangan said she considers herself a “work in progress.” She even shares her performance review with her team because she wants them “to know that as much as I’m pushing them to get better, I’m also pushing myself to get better.”
“You can’t have a growth mindset without being vulnerable about what you need to grow it,” Rangan said.