My HERO's journey

Here’s my story.

After a month at NC State I knew deep down that I’d picked the wrong major: civil engineering—you know, doing stuff with bridges, highways, and surveys. I felt trapped and stuck (barely passing with a GPA of 2.1). But, my parents and mentors advised me that an engineering degree would “hold up better” than a business degree.

As the months turned into semesters, I knew I had to figure out what I wanted to do. My dissatisfaction with my major, combined with the clock counting down to graduation, led me to accelerate my exploration of jobs, internships, and life experiences, all in an attempt at finding the career path that was right for me.

Real estate agent, civil engineer, loan officer, entrepreneur—I tried on all these hats. Some I wore for longer than others. I even went overseas to see how a CEO lived. I moved to the Canary Islands and worked as a day trader and poker player.

By my final semester of college—I’d made it … nowhere. I’d been fired from two different places: Audi and a local digital agency. The real estate flipping company I’d started went under. Two of my business plans went unused. And the cherry on top: it was 2010, just two years after the great financial crisis of 2008.

Time was up.

And even with my beloved engineering degree—you know, the one that would “hold up” above all others—I couldn’t get hired.

After pouring out my struggles to a friend, he suggested I look into technology.

My first response: “I have no tech background. I have no computer science degree.” Frankly, I’d never even looked at that world because it just seemed too complex. Too technical, for me at least.

His response: “You know, Irwin, there are a lot of entry-level roles that don’t require any prior tech experience. You’ll get on-the-job training. If you have the drive, the hunger to learn, and the humility to take coaching, you have shot!”

It took me a total of five months, but with a lot of persistence, trial and error, and caffeine, I finally broke into tech! I managed to get my foot in the door, and I was determined to see where this journey would lead me.

What was that tech job I landed? I started as a sales development representative at BMC Software. And that was the start of my career in tech sales. I was tasked with calling into the largest West Coast companies—Disney, PayPal/Ebay, 21st Century Fox, MGM Resorts—and I was paired with the enterprise account executives who were tasked with selling huge software contracts to the IT buyers in the largest companies in the world. I’m talking multimillion-dollar deals.

In my first week, when I sat down with my manager, he asked, “Do you realize the opportunity at hand here? I was at dinner with the top four reps from the previous year. Every single one of them had made over $1 million in commission.”

WOW! That’s when I realized—there’s a huge opportunity here—in tech—for me.

It was at BMC that I met Adam Aarons who became my mentor. Adam eventually left BMC to join a San Francisco startup called OKTA. He and the executive team then hired me, at 24 years old, to build and manage the newly-created sales development representative (SDR) team.

After much discussion with my girlfriend (then turned fiancée), we moved our entire lives across the country, from North Carolina to San Francisco, CA.  

Over my first year I hired many SDRs from very different backgrounds. One had worked at Macy’s, another at a Sprint store, another selling persian rugs, someone had been at a radio station, another had worked at Enterprise Rent-A-Car, as well as a lot of recent graduates. I hired history, business, and English majors. (Notice: these hires didn’t have CS, math, or tech backgrounds.)

That’s when I had my first of many breakthroughs: SDR is a great entry-level position into the technology business. There is no correlation between college majors or gender when it comes to being a successful SDR. If a person is hungry and willing to learn, work hard, and align to the corporate culture—that’s it. They’ll only climb higher in their sector of tech.

When my wife, who hadn’t graduated from college, went from working the front desk at a chiropractor's office to becoming a recruiter at a small company in Menlo Park called Facebook :) —I’ll be giving you the details of her successful break into tech later in the book—that’s when I had my second insight: there are entry-level jobs (what I call gateway jobs) in every department in every tech company. At first glance there are seem humble and others seem unapproachable. They are unlike entry level jobs at most company as these gateway jobs leads to many different career paths across different companies!

And again, as my wife showed if a person is hungry and willing to learn, put in the work, and align to the corporate culture—that’s it. They’ll only climb higher in their sector of tech.

Then I had an ah-ha moment! I realized that every job segment had to have a gateway role. For me it was my first job as a sales development rep. From my wife it was first getting experience as an office manager, then the gateway job was a recruiting coordinator position. So I took some time and mapped out what are the different segments of business. I wrote down sales, marketing, operations, finance, product management, developer, people (HR), customer support, IT, and legal. Then I asked myself, “What are there other gateway roles for each of the business segments?”

Then I realized there was nothing like this on the internet. It was all tribal knowledge. That’s when I became obsessed with decoding every “gateway” job into tech.


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