Leela Srinivasan — The winding path to CMO

Leela Srinivasan took a meandering path to her role as Chief Marketing Officer at fintech decacorn Checkout.com—pivoting from receptionist at a newswire service, to salesperson, to banker and consultant, and finally to marketing. We talk about the benefits of a nonlinear career path and how knowing your authentic self will point you in the right direction.

Q&A

Tell me about your early career.  

I grew up in Scotland and went to a great university where companies came right onto campus to hire graduates. But then I decided to move to the US and that knocked me off my path. I moved to Florida with a highfalutin degree, but my career options were different. I took a job at a consumer goods startup as a receptionist. Once they realized I could write and had other skills, I got pulled into marketing work. After 18 months I went to work for Business Wire, the commercial newswire service, in a sales role. Then, I moved to Boston for a sales management role with the same company. 

When I was working in Boston, I was always in rooms with people with advanced degrees. But I didn’t have one. I started to feel like I hadn’t done myself justice with my education. And coming from a long line of Indian accountants and finance people, I felt like I must have more skills that I should be building. I consulted a few different people and thought—I’ll go get an MBA. 

I don't think I really understood how transformational it would be for me in terms of reopening doors. After I fell out of the traditional recruiting process at University, doors into top tier management consulting firms or banks had closed off to me. I didn’t go to business school specifically looking for that door, but there it was.

What did you hope to do after business school?

Before business school I worked at Business Wire, where my customers were heads of Corporate Communications or Investor Relations. I thought Investor Relations was fascinating. I thought, Wow I’d like to build the skills to be able to go and do that. My plan to get into IR was to spend a couple of years doing equity research at an investment bank. If I could think like an analyst on Wall Street, then I would really understand my customer when I crossed back into investor relations.

Well – within 48 hours of joining an investment bank, I realized I was in the wrong place. In the summer of 2005, Lehman Brothers was “the place to be.” But for me I found it was not a fit. I struggled to find meaning in the work. I didn’t feel comfortable in the environment. The work was not inspiring or exciting. I also realized that I do better work when I’m passionate about the work. I put more of myself in and I bring out more in the people around me.

So your internship blew up your plan. You knew you had to make a new plan. How did you land in consulting at Bain?

In business school I went to Consultant Club meetings and I thought it was fun cracking the practice interview cases. I liked puzzles and intellectual stimulation. Also, I realized that I came to business school with mostly soft skills. In University, I studied history and English literature. No statistics, no accounting, no math. My goal in going to business school was to build those skills so that I could go into a career that would leverage both sides of my brain.

I knew in my heart of hearts that I needed to get more practical experience. I wanted to challenge myself to spend a lot of time in spreadsheets. Consulting was the sweet spot of something that I was intellectually interested in and also was “good” for my career growth.

You worked at Bain — where I also worked. In my personal experience, I worried that consulting was setting me up to be the jack of all trades but the master of none. How did you navigate Bain and where to go next after consulting?

On balance, I really enjoyed my time at Bain—but in consulting there is extraordinary variability in terms of your experience. There were cases where I loved the client, the work, the problem the company was solving, and the impact they were having. I loved it so much I thought, Maybe I’ll go work for this company. And then that would be followed by a case that was the polar opposite. The company industry was not something I could get excited about, the company culture didn't speak to me, or the client didn’t even want us there. Like any consultant, I had some great cases and some less great cases.

After I had my first child, I reflected on returning to work. I wanted to see if I could find a job where I was more consistently passionate and fired up. I know how I operate when I can find connection and meaning to work. On maternity leave, I got clarity on wanting to find a job with consistent purpose and meaning. I started opening messages in my inbox from former colleagues who every once in a while would say hello and send job postings. 

One of these messages was an opportunity for Product Marketing at LinkedIn. It sounded amazing, but I didn’t feel qualified for it. I had never done “real” Marketing. In hindsight, I didn’t even know what Product Marketing was. I went ahead and interviewed for the role and, luckily, the skill set I built in consulting was on the money for the work LinkedIn needed at the time. 

And that was the beginning of my marketing career.

Would you have guessed you’d end up in marketing?

When I think back to business school and the classes that I aced with ease and real passion – Marketing featured prominently. I got good marks in my other classes, but the level of effort I needed to put in to do well was different.

In my first marketing class we did a project with Procter & Gamble. The project was on Pampers diapers. I was not yet a parent and I knew nothing about diapers. But I got really inspired. My team and I were thinking about how to redesign Pampers packaging, differentiate from competitors – it was ridiculous how inspired I got. My passion was so evident that the Procter & Gamble team asked my professor if I was interested in an internship.

I ignored the internship offer because I thought I already had my career path. I was on a track to go into finance and Investor Relations. I told myself that’s what I had come to business school to do. However, looking back, it was obvious to people around me that I should have been considering marketing. Compared to other things, marketing has many elements that feel natural for me.

Do you wish you’d worked in Marketing from day one?

Early in your life, every year feels like it matters. I was 31 when I started business school, while the average student age was 28. I felt late to the game. I felt ashamed that I had meandered through a hodgepodge of jobs and things like sales. Sales was almost a dirty word, no one went to business school with that background. When I got to business school, I realized how valuable a sales background was. Recruiters were doing backflips over the fact that I had sales experience. Because sales and the skills you build as a salesperson—selling, negotiating, listening, tenacity, relationship-building—are really important.

I stopped beating myself up for not taking the most direct, fastest path. Sure, sometimes there is benefit to taking the fastest path. But you also miss out on the journey that builds different muscles and skills, and you don’t know when those are going to be valuable. I am a much better Head of Marketing because I spent five years in sales. I am much better because I spent time in consulting. 

I stopped regretting the meandering. 

What advice do you have for other women who want to make a career change?

What has always helped me make transitions is to look for the common threads so that each pivot is not starting from scratch. When you pivot, try to find a sweet spot of work that you excel in and are comfortable doing, alongside work you don’t know how to do. That helps you fill in the transition. When I took my first Chief Marketing Officer job I was not versed in all the aspects of being CMO, but I purposefully took a job in an industry that I knew well. When I moved from consulting to product marketing, it felt like a chasm but, in hindsight, the skillset was similar. 

Pivoting is all about storytelling. Figuring out how your past experiences are relevant for the thing you're hoping to do. Even if you can’t make that leap directly, you’re building relevant experiences that can over time parlay into a story.

Also—I’ve never felt fully qualified for any job I've taken. Not one. You have to be comfortable with the fact that there will be some unknowns. It’s very rare that somebody will check every single box. If there aren’t unknowns, then you’re not making a jump.

Thank you, Leela! You can learn more about Leela and Checkout.com here.

*Q&A has been edited for brevity and clarity.