How I went from flunking programming courses to leading products in a billion dollar startup
My personal journey from a nobody to a tech leader
Welcome to Future of Work, Future of You. I bring insightful content on the accelerating trends for a next generation workplace. It is great to have you here. Today, I will be sharing how I went from flunking programming courses to leading products in a billion-dollar startup. I hope it helps you navigate career pivots, lead in tough times and inspire teams.
As technology & software continues to eat the world, people in other industries often wonder what lies behind the curtain. How do these seemingly successful techies make it big? Did they all drink some cool aid that isn’t available to others? Is there a playbook that we can follow to the tee? Or it is just luck meets opportunity?
I don’t have an answer so I will do the next best thing & let my story be known. Readers can decide for themselves what makes a successful tech leader.
Humble Beginnings
In my 1st year of college, I flunked the only 2 computer courses that I ever took - C & OOPS. I hated computer science. My friends labeled me “Technically Backward” aka TB. During the job placement year in 2009, I was one of the handful of students to not sit in any software company for tests or interviews.
Recession hit us real bad post Lehman Brothers. Most jobs dried up & offers were reneged. But I still chose not to take a software engineering job and join the country’s largest automobile firm.
In 2009, when Google was fast becoming the buzzy search engine everyone wanted to work for, I was starting out on my grunt operations job that made me manage union workers, grease engine oil & wear metal reinforced safety shoes. Couldn’t be farther from my software friends who clanked away at keyboards making decent pay checks.
I just did not think that I had it in me to even think of joining a tech company. Not even as a janitor let alone a white-collar employee.
Taking up the Gauntlet
In 2012, I decided to join an MBA course & try my luck at the “business side” of things. Again, I saw that 25% of jobs came from the tech sector which I had no clue about. So, I told myself, what will be the simplest job I can pick in a tech company? An Executive Assistant to the CEO! It will give me the inner workings of how a tech company operates. So, I joined a tier-3 (only one I managed to crack!) IT company hoping they wouldn’t fire me in a week.
As you can imagine, I wasn’t terribly good in the beginning, so I started hanging out with developers & analysts to figure out what they do. Endless Lines of code would make me blurry eyed but I stuck through the math, & logic till I understood how & what. I scoured algorithms & codebase that powered social media analytics software, enterprise systems. I would ask the head of digital business to explain to me the product deck over & over again till I got a hang of what we build & how it benefits our customers.
Twist of Fate
In July 2014, I got a job referral for an upcoming Indian startup, InMobi, that was making waves in the mobile advertising technology ecosystem. There was an opening for an analyst position.
I asked myself if joining a new company in an entry-level role after 5 years of work experience plus MBA is the smartest thing to do?
Yes, came the answer! I wanted to go where the puck will be in 10 years.
Best decision of my whole damn life!
Shit scared that they hired the wrong guy, I joined them a full two weeks before my official joining date doing double duty across my current & to-be job. I wanted to learn the ropes, so they don’t fire me in a month seeing how I sucked at the job. I found a fantastic peer-mentor who taught me a ton about digital advertising. I spent an insane amount of time hanging back in the office after hours with product & engineering folks to get under the hood of the tech stack. I climbed a few ladders & did decent work in the business organization to get noticed. I was generally good with numbers & deft with customers.
And then one fine day, my bosses conspired to land me a dream-but-challenging role in the heart of Silicon Valley. I was to run the entire US operations & build a team. I asked them - “Are you sure I am the best guy?”
Happy ending? Wrong. I was about to discover some of my darkest days ahead.
Gladiator Times
How hard could it be? I spoke with my outgoing leader, functional leads & existing employees to figure out a game plan. By this time, I was pretty good as an individual contributor so the plan was to replicate my skills in my new team & we will be on our way. We struggled through our initial few hires but eventually did 6 hires in a couple of months. Voila! As a first-time manager, I felt proud but nervous leading others.
Reality struck.
Five out of my first six hires left within six months.
Shock. Anger. Dejection.
Later, I realized we tweaked our job requirements to hire people too smart for the actual job & as a manager I only set expectations but never built aspiration for my team. So, they didn’t see their future, only the present with the work.
Rightly so, I was constantly quizzed by leadership on why we can’t hire or retain people for this seemingly innocuous customer success team.
Deep within, I was fearful as a first time manager. I was afraid to ask tough questions, seek accountability, take hard decisions & demand high standards.
Why?
Because I wanted to play nice & safe. I wanted to be likable at the expense of being spineless. Ouch! Bitter pill to swallow but the truth. With every resignation, this profound truth became more apparent.
There is no playbook to being a successful manager. However, certain guiding principles have stayed with me ever since my disastrous & humble beginnings.
Stay & keep accountable: Work is not charity so build a two-way street of accountability
Be open & seek guidance: Very few get it right the first time so learn from others.
Your actions & cues matter: Your team will dig & dissect every little act of yours so behave accordingly.
Take swift decisions like you mean it: Indecision is the only real bad decision.
Collect blame & distribute credit: Make your team look good & they will do the same.
Own up when you screw up: Managing others is part-science and part-art but your character is absolute.
Loyalty is good but growth is better: Invest in your team not for the job but their careers.
Inspire & engage: Seek purpose, manage ambitions, instill motivation in your team and you will never have to manage them.
Scent of Success
I went on to run many successful teams & businesses that drove several hundred million dollars revenue for my company. I led customer success, revenue operations, product & partnership teams across multiple countries & continents. I rose from an analyst to a Vice-President in a span of seven years all while being a relative outsider to the tech industry.
I never thought I will make it this far.
Remember I knew nothing about software, technology or products till I joined this company. The only skills I brought was common sense, intuition, motivation and an appetite for learning.
In the end, I guess they were enough with a dose of good fortune.
So next time, when you think you aren’t succeeding enough or are not sure if that course, project or job is for you, remember this guy who went from flunking software courses to leading products at a billion $ software startup.
I almost messed it up & then messed it a little less before I got better.
And believe it or not, I eventually got great at it.
If I could do it, so can you.
If you have a co-worker, founder, product manager or even an entrepreneurial dreamer who needs to see this, please share. You may be helping them more than you realize.
Feel inspired to share your “flunking to leading” story? Just like mine, your story may inspire others to go that extra mile. Drop in your comments below.
Reach me at Tejaswi Gautam and let me know what you think about this issue. Are you ready for the future of work? See you next week!