- Shama Keskar is the cofounder and CTO of adtech company Nickelytics.
- She spent years working at major tech companies and learned a lot about being a leader.
- She became fearless and customer-focused. Here’s her story, as told to Perri Ormont Blumberg.
This as-told-to essay is based on a conversation with Shama Keskar, a 42-year-old CTO from Mumbai, India, about her career. It has been edited for length and clarity.
I’m the chief technology officer and cofounder of Nickelytics, an adtech company based in Tampa, Florida. I grew up in Mumbai, India, and was raised in a conservative family where women’s education was not especially desired. I give a lot of credit to my parents, who went against all odds to provide me with the best education possible.
In 1998, I graduated from Mumbai University with a bachelor’s in physics, mathematics, and education before moving to the US to pursue a master’s in information systems.
As a graduate student, I took a job as a cashier at a sporting-goods company. I only worked for a couple of months before I got a breakthrough career opportunity at Google.
I was originally searching for employment with Yahoo!, but they rejected me, so when I heard through some friends that Google was looking for software engineers, I applied online and got the job.
My new position gave me the rare opportunity to attend a few meetings with the founders and observe their work processes. I ended up working at Google for the next five years and was promoted to several tech leadership positions.
Every Googler learns to release early and release often (RERO), which is a phrase meant to promote faster, higher software quality
“Iterate, iterate, iterate” is always the motto, so I quickly learned the importance of speed and stability.
For instance, if a piece of software was not working right, the developer kept at it until the flaws were worked out or the project was dropped. At Nickelytics, we definitely value this lesson with every initiative so that none of our products are complete until they achieve a significant amount of speed and stability, which has earned us significant trust with our brands and advertisers.
My fellow Googlers taught me to believe in myself and that my ideas were valid
When I got involved in the Xoogler network, a group of Google alumni and current Googlers who help each other advance their ambitions in the startup ecosystem, I met many ex-colleagues who went on to become successful entrepreneurs and whose stories inspired me to take calculated risks.
Google’s transparent culture encouraged me to initiate a cultural event with my peer, Sudha, to celebrate India’s Independence Day at the campus in Mountain View — a first for the company in 2006. This event was full of Bollywood music, Bollywood and Indian classical dance performances, and mouthwatering Indian food, which was entirely sponsored and supported by Google. Their top executives like former SVP of Google Ads Jeff Huber, former SVP of Google engineering Bill Coughran, and former Google VP and executive director Larry Brilliant even attended.
When I left to join LinkedIn in 2009, I took a four-month break to try launching an adtech idea that ultimately didn’t come to fruition
Similarly, in 2012, I attempted another startup called Novena+, a solution for mobile-app testing, but after gaining a couple of clients, we ultimately struggled to raise funds.
While at LinkedIn, I was fortunate to work on their mobile experience revamp, and we were working under a tight deadline to deliver the product and under a great leader, Kiran Prasad, the former VP of product and engineering. When we were close to completion, it was handed off to CEO Jeff Weiner to play with the product prior to the public announcement.
I remember our entire team was seated in a meeting when Jeff walked in to share his thoughts. At the time, I was the product quality leader and was super anxious to know Jeff’s experience.
When Jeff walked in with a great smile and shared positive feedback, I was super relieved. One of the product leaders even jokingly mentioned, “Jeff, when you walked in, Shama almost had a heart attack.” We were working tirelessly on this product, and getting positive feedback from our leadership for the baby we believed in was super encouraging. Like most experiences at LinkedIn, it taught me to be customer-obsessed and always focus on offering compelling value to the end user.
My time at LinkedIn helped me realize there are kind people at the top who are willing to laugh off innocent missteps
When I first joined LinkedIn as their senior engineering manager, I hadn’t yet met Jeff. One fine morning, I badged into one of the LinkedIn building entrances when suddenly a man came running behind me rushing to get in. Since his badge wasn’t visible, I stopped him and asked him to show me his credentials before entering. It turned out to be Jeff, and I apologized profusely. He kept reassuring me that I did the right thing and said he appreciated my due diligence. This incident helped me become a fearless leader down the line.
In January 2016, I founded a startup called SpringSeattle with a few friends that provided small businesses with access and training for tools and platforms that larger businesses use, but it closed by the end of the year.
From 2017 to 2020, I worked at Amazon as a senior engineering leader, where I specialized in the early days of Alexa for physical store organizations
In my role as a senior quality engineer, I was accountable to create solutions that influence several hundreds of engineering decisions. I loved that Amazon gave engineers a high degree of autonomy and ownership over the implementation details of the features they build, rather than a top-down approach.
In my initial days at Amazon, I was part of a game-changing product team where I was the only female leader in a group of more than eight male leaders with varied personalities. Oftentimes, I wouldn’t get included in critical meetings or decision-making events, so I began setting up one-on-ones with every male leader around me.
Then I started drafting my thoughts in a document and shared them with these colleagues. From then on, I made sure to speak up and voice my opinion in meetings and brainstorming sessions and even started challenging some of their decisions when I referenced our customer metrics and data.
After doing this for a while, my manager would make a point to ask me for my opinion and began to value my suggestions. Eventually, I was able to break the glass ceiling and be one of the leaders in this crew.
In 2021, I connected with Nickelytics CEO Judah Longgrear on LinkedIn who was looking for a CTO to help scale
I started my career working at Google in the ads department and contributed to their platform growth by launching initiatives like TV ads, print ads, and radio ads. This is where my interest developed in the adtech world, which eventually led me to join Nickelytics.
I ended my journey with Amazon in October 2020 and initially joined Nickelytics on a trial period in January 2021. I was hired full time in February. Longgrear and I shared great chemistry, and it quickly became a no-brainer for me to join officially to help evolve the outdoor advertising business.
Here’s my advice to other entrepreneurs making the transition out of tech to working for themselves
Focus on solving one problem at a time. Oftentimes, entrepreneurs attempt to launch multiple initiatives simultaneously to ensure at least one of them will be successful. If you need more feedback on your idea, ask your friends and family.
If you’re unsure of your business, start with a minimal viable product (MVP) instead of the burden that comes with building the entire product. Launch it quickly to receive early feedback and then work backward from that same feedback.
Back in 2009 when I had a startup idea in the adtech space, I spent a lot of time discussing the idea rather than focusing on outlining a business plan, building a proof of concept, or launching in beta to receive early feedback from customers. I just kept on refining this idea and correcting it without any real supporting data from customers, and the ideation phase never turned into reality. This was a great lesson to learn early on in my entrepreneurial career and now at Nickelytics, we believe in launching pilots first and correcting from our customer needs.
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