Breaking Into Sales: From Rideshare to President’s Club, How Kendrick Trotter Conquered the Tech Industry

If you knew my background, you’d probably never peg me as the CEO of a growing tech company. I grew up in the hoods of the Bay Area in California, the son of a single mother. I survived my first drive-by shooting at the age of 8. The homes on both sides of us got hit. I still remember playing outside in the days afterward, my small fingers tracing the bullet holes in the cars out front. My mother, who worked two jobs, saved her money and moved my brother, sister and me out of Richmond as quickly as she could.

Three years ago when I started my company, Us In Technology—with a mission to help diversify the technology industry by training and placing minorities and historically excluded individuals in sales, marketing, coding, engineering and revenue roles with top tech companies—I gave a lot of thought to social determinants and “barriers to access,” a term that’s prevalent in health care. Common in health, as well as social care, are physical, psychological, financial, geographical, cultural/language and resource barriers.

People from disadvantaged backgrounds typically experience many of these barriers when it comes to getting a leg up in life. But have you ever considered how once (and if) you’re able to get beyond some of these initial blocks, a lack of access to the right kind of personal and professional exposure can contribute to your experience of continually “rolling the ball uphill?”

I experienced these barriers firsthand when breaking into the tech sales industry, and that is what drives Us In Technology’s mission today. Here’s the story of my journey into tech, what drove me to start Us In Technology, and my top three pieces of advice for other aspiring sales and tech professionals—particularly those from underrepresented groups.

Starting a career in tech sales 

While I eventually made it out of the hood and went to college—even becoming a Division 1 football player at the University of Idaho before I graduated in 2016—I still tripped and fell over myself professionally on the road to where I am today. I was fortunate enough to first learn about, apply for and almost immediately land my first job in the tech industry after striking up a conversation a few years ago with the man I was driving for a rideshare company. He was a VP of sales for a small tech startup then; now he’s a sales VP with a major corporation. But, getting my foot in the door with an entry-level cybersecurity sales position was just the beginning.

My biggest gaps were related to the social adjustments I needed to make to transition mentally and physically from the tough areas I’d grown up in, along with the football field, into a corporate environment. 

During my first few months as a sales development representative, I struggled greatly with my sense of identity. Stepping into a corporate work environment where no one resembled me, the first thing I tried to do in order to fit in was to mimic other people. This was a horrible idea: I was different from them, and they were different from me. I remember asking my manager for help on how to make prospects feel more comfortable with me when I cold-call them and she told me, “talk to them like you’re talking to your friends.” That didn’t work because my friends were mostly from the hood I grew up in, not corporate America. That same manager also told me to “talk to current customers like you are talking to your father at the dinner table,” which I knew nothing about because I did not grow up with a father. In both situations, instead of speaking up I just took the feedback, smiled and did my best to find my own solutions to the problems I faced. 

Stepping into the sales industry not knowing anything about sales, and certainly not software sales, I assumed a good salesperson was someone who could convince someone to buy something they didn’t need. But I quickly gleaned that’s not the case—I learned that a typical character trait of a good salesperson is great listening skills, which came naturally to me. Once I learned the value of proving to clients and potential prospects that I was a great listener versus someone trying to trick them, the conversations I had with leads became much more open and transparent, and, not so coincidentally, the sales came rolling in.

I went on to become successful in my field by prioritizing hard work and high output—making President’s Club with the company I was with by 24, and being promoted to account executive within one year. What I now know is that the experience of climbing the corporate ladder would have been a whole lot less painful had I been mentored by people who saw all of me, not just a tech industry newbie.

Launching Us In Technology

My personal journey through the tech world, as well as the journeys of those I’ve met and mentored, informs why one of Us In Technology’s major offerings this year is the launch of a tech starter program and boot camp via its new mobile app. Available to users this fall via Apple iOS and Android, UIT created this version of its already popular academy for people on the go, predominantly in entry-level sales positions, to help them climb the corporate tech ladder, with a goal of helping to stack the pipeline with future tech sales leaders. 

In addition to there being fewer than 100 sales programs in the nation available to future and current salespeople, let alone a program with an emphasis on sales specific to the tech world, there are hardly any that help minorities conquer typical barrier points to access when it comes to succeeding in tech sales. Thus, the academy was also created with the intention of preventing other underrepresented people from having the same experiences I had breaking into the tech industry. 

Our goal is to fill a much-needed education gap, considering very few universities in the world offer courses that prepare individuals for entry-level SaaS positions. Our intent is to help our candidates know they belong in these roles regardless of how they arrived at them. This is crucial because underrepresented people churn at a 35% higher rate than others in their first year of being in a tech role. In assisting our hires with these training resources pre- and post-hire (UIT places talent each year with companies ranging from Radware to ServiceTitan) we have found our retention rate after Year One was 92%, with 86% of our hires promoted or the recipient of a pay increase within their first 15 months on the job. 

You could look at our sales academy kind of like we’re playing team sports— me and others coaching new players not only on what we’ve learned about how to successfully navigate the world of sales as practitioners, but as people of diverse backgrounds and diverse learning styles. 

3 tips to drive success

Us In Tech has trained hundreds of people from all professional backgrounds—from teachers and administrative assistants, to social workers—placing them with tech giants such as ServiceTitan, Seismic and ZScaler, many of them with no college degree.

The biggest keys to their success? 

Coachability, drive, integrity and intelligence.

You show up to the free sales academy with those skills and intentions and we’ll take it from there. Here are a few tips I’ve learned along the way that can contribute significantly to a tech newcomer’s success. 

1. Seek mentors

If you want to get somewhere quickly, surround yourself with people who have already accomplished what you aspire to accomplish. This is a sure-fire shortcut to success. Mentors can teach you things and share lessons with you that may have cost them a ton of time and/or money. 

One of the first big wins I had with a mentor came when I was offered a promotion. The option was potentially accepting a role with another company that offered me more money initially, but would keep me in the same role I was previously in—meaning less money over the long haul. My mentor used this dilemma as an example, teaching me that early in your career you should always value “Learnings over Earnings.” Meaning, go (or stay) where you’re given the most room to learn and grow your skill set. Then, when you’ve gotten the experience, you can call the shots regarding compensation. 

With his help, I chose to stay with the company and accept a title change and modest pay bump, which I was then able to capitalize on eight months later when I left. Many of my most transformative experiences were driven by my mentors—one of the main reasons we offer such a strong mentorship program at Us In Technology. 

2. Stay humble

As I build my company, I intentionally surrounded myself with people who are smarter than me. Although this may sound like a very simple concept it constantly challenges me because it forces me to be vulnerable as a leader, admit when I am wrong, and empower others to make critical decisions. Sometimes the best way to lead is by being a great follower. 

An example: I was in a rush recently to launch our mobile app, but some members of my team, more experienced in product development, decided it was best for the company to launch a month later. We needed more time to work out the bugs and kinks, and they were right. As a result of waiting, we are more prepared to provide value to our customers and meet the anticipated demand more fluidly. 

3. Define your personal brand

What I have learned as both an employee and a founder is that customers and clients “buy” into people, not companies. That means you are your own best ambassador from a business standpoint. That said, do you have a clear personal brand? What do people say or believe about you? Are you personable, easy to work with, and a great communicator, or do you need a little help in these areas or others? 

To arrive at what your personal brand is, recruit people you trust to give you feedback: Ask them to share three or four professional characteristics they think of when they think of you. Then, ask yourself if their perceptions match how you see yourself. Where is there room for growth or improvement? How do you wish to be perceived? Work backward from there, investing in personal development through self-help books and/or enlisting the help of a business coach or mentor is a great place to start.

At just 27 years old Kendrick Trotter is the founder and CEO of Us In Technology (UIT), a virtual community, job placement, mentoring and training platform aimed at bridging the gap between hiring companies and qualified underrepresented talent. Before launching UIT in 2019, Trotter was an award-winning sales manager operating primarily within the cybersecurity space. Trotter has held executive or management positions at, among others, Radware and Agari, where he made President’s Club and was a finalist for the memoryBlue Phenom Award, which recognizes the former employee off to the hottest sales career start. 

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  • Originally published October 21, 2022