Sales Impact on My Life & Purpose

Childhood Dreams

Growing up, my only goal in life was to play in the NBA. Basketball was my entire life and purpose.

I was raised as an only child by two working class parents who didn’t have much, but poured every bit of energy and money they did have into supporting me pursuing my dream. Basketball, eat, sleep, repeat was my daily agenda from the age of six. It became my identity and saved me from trouble in a middle school filled with the gangs, drugs and violence that I certainly would have been an easy target for had I not been dubbed “the best white basketball player since Larry Bird” by some of the ring leaders (clearly a far too generous assessment, but it kept me safe so I gladly took it).

I love everything about the game:the competition, dedication, perseverance, work ethic, teamwork, integrity, being coachable, strategy, execution, recruiting, leadership, winning (more-so hating losing), learning from failures, and most importantly, the camaraderie and special bonds formed with a diverse group of coaches and teammates that last a lifetime. In my mind and my heart, I could play forever at the highest level.

Unfortunately, it turns out I’m 5'11" and slow enough that no amount of skill, intelligence or leadership was going to put me on a trajectory to make it to the NBA. When I finished playing in high school, I realized my dream was dead.

Quitting basketball cold turkey was out of the question, so I figured I would get into coaching. From the time I was 12 years old, I coached basketball camps all summer, every summer and I found as much joy in coaching as I did in playing.

I called Nate McMillan, Head Coach of the NBA’s Seattle Sonics at the time, who was a friend and mentor to me and had a significant influence on my life, to ask him for advice. Nate was a fan of me as a player so I secretly hoped that by calling him, he would tell me I had a shot to make it to the NBA. No such luck, but instead he offered me a job to work for the Sonics! I spent the next five years with the team, responsible for helping players warm up before games and running through drills at practices and individual workouts. The friendships, experiences and stories from those years are memories I will never forget and participating in the NBA in a small way fulfilled some part of my childhood dream.

Aside from the amazing experience, the decision to work for the Sonics rather than pursue a college basketball career changed my life in so many ways.

First, instead of having an educational criteria of “any school that would give me a starting point guard opportunity”, I earned a business degree from the University of Washington.

Second, I met the love of my life three weeks before my 21st birthday and we’ve been happily married for eleven years with two kids (aged 9 and 6).

Third, the Sonics moved from Seattle and became the Oklahoma City Thunder the year I graduated from college (2008). My career plans hadn’t evolved much by this point as I only dreamt of coaching or having a front office position for an NBA team. Losing the Sonics to OKC was like ripping my heart out of my chest and for the second time in five years, my dream was dead. It was time to get a “real job.”

Filling a Void

With a business degree and no specific plan for what I wanted to do, I had no idea where to start. After a dozen interviews for a completely random and diverse assortment of jobs, I ended up with one offer, and one opportunity that my instinct told me seemed interesting. Luckily, they were for the same role, something called a “Market Development Representative.” I didn’t quite know what that meant, but I really liked the people I met in the interview process and they seemed to like my background in sports. Deep down inside, I was just relieved to have a job so I didn’t have to move back in with my parents. That relief turned into shame and sheer terror on my third day when they handed me a phone and explained that “Market Development Representative” meant cold calling strangers to get them to evaluate buying software.

How was it possible that I was tricked into a sales job? I had every negative stereotype about sales that you could imagine. I didn’t particularly like talking to my friends and family on the phone and I was being asked to call people I didn’t even know and convince them to schedule time to consider purchasing our product. I can tell you with the utmost confidence that I would have absolutely turned down the offer had I realized that was the job!

After some serious coaxing and pep talks from my manager and teammates, I picked up the phone and gave it a shot, and I’m proud to say that my first cold call should be nominated to the Guinness Book of World Records as the Worst Cold Call In History. Luckily for me, and I’m certain it was out of sheer sympathy, the person on the other end of the line agreed to schedule a call and, when I hung up the phone, I was informed that I would be paid $50 every time I was able to do that successfully.

Growing up in a modest financial situation while also having exposure to rich people and professional athletes gave me a combination of gratitude, hustle and ambition. While I was incredibly grateful for all that I was given from my parents, I knew providing a different lifestyle for my family was a top priority in my life and I quickly saw sales as a way to do that.

From that moment forward, I was in the office at 5 am and out at 7 pm and I took coaching from all the people who were gracious enough to help me (although I’m certain my eagerness was obnoxious), and I did everything I could to be a great teammate in return. I was determined to be the absolute best I could possibly be and help others around me. Three things quickly became clear to me as I went through this journey:

  1. Sales (done correctly) is about genuinely caring for your customers and finding ways to add value that help them personally and professionally. Basically the opposite of every stereotype I had coming in.
  2. Sales is a vehicle to provide the type of life that I want for my family, and leadership roles create the opportunity for you to do that for others simultaneously.
  3. Everything about sales and sales leadership is absolutely synonymous with basketball and team sports. I was back in my zone with a new dream.

Player vs. Coach vs. Leader

As my basketball dreams progressed from playing in the NBA, to coaching, to becoming a General Manager responsible for the entire basketball operation and organization, my professional interests have followed a similar progression.

I really enjoy selling. It’s the closest you can get to the customer and you are in full control of your destiny. If you put in the right inputs, it’s a matter of when, not if, you will be successful.

I like coaching more than selling. Helping others achieve success is far more rewarding (assists > scoring) and you learn from all of your players how to make everyone on the team better. Besides, accepting responsibility and deflecting praise are much more in my comfort zone than having to accept recognition for simply doing my job.

Being a GM is what I enjoy most. Assembling the absolute best talent with the best coaches, putting people in the right positions to succeed individually and collectively, creating a culture of winning and accountability, managing the salary cap and aligning everyone in the organization towards a common goal is the perfect combination of responsibilities for me.

The Power of Mentors & Picking the Right Opportunities

I attribute the majority of my professional success to two primary factors:

  1. Working for an amazing mentor at early stage startups in roles I was not qualified for, learning by doing and wearing lots of hats with guidance and support, then applying what I learned to do the same in leading others.
  2. Seeing what great looks like across multiple disciplines through three highly successful software IPOs over the last decade:
  • Tableau Software — later acquired by Salesforce for $16B
  • MongoDB —$30B market cap
  • Snowflake — $100B market cap(largest software IPO in history)

Every decision I’ve made professionally is based on a few simple evaluations:

  1. Do I wake up in the morning excited to work? Do I love what I do and who I do it with?
  2. How can I increase my market value (defined as learning and earning skills, experience, network, accomplishments, and reputation) and create opportunities for others to do the same?

So much in life is luck and timing, but the framework above has been helpful in increasing the odds of sustainable success.

Reflection, Finding Balance & Your True Purpose

I am humbled and grateful for the endless list of people who have contributed to my growth professionally and personally. A career in sales has changed my life in a way I would have never imagined.

Financial freedom means different things to different people, but to me it means the opportunity to choose how you spend your time. Here’s what I’ve concluded are the ways that I want to spend mine, in no particular order other than #1.

  1. My family is my #1 priority in life.
  2. My greatest joy is helping others create career and life changing outcomes.
  3. I love working, learning and growing.
  4. I love leading, coaching, and teaching.
  5. I love helping early stage companies.
  6. I love giving back.
  7. I still love basketball.

In addition to my role at Snowflake serving a group of people who I absolutely love and respect, I’ve been giving a lot of thought about how to shape my future and took on a few additional responsibilities in 2021 to focus on the priorities above.

  1. I am coaching both of my kids’ basketball teams, which has been my purest form of joy (#1 & #7).
  2. I became an Instructor at the University of Washington, teaching the Sales Certificate Program, which gave an amazing group of students meaningful opportunity and education to take their careers and lives forward (#2, #4 & #6).
  3. I became a Limited Partner at Stage 2 Capital, where the opportunity to learn from Mark Roberge, Jay Po and the entire S2C team, LP network and portfolio companies has been nothing short of exhilarating (#3 & #5).

These experiences highlighted a few glaringly obvious takeaways that stood out to me.

  1. There is a massive gap in supply and demand of GTM talent. No shortage of brilliant technical founders, but every company on the planet is looking to grow and up-level their sales team.
  2. Revenue, growth and sales efficiency are the primary factors that are driving the company valuation and failed GTM execution is a primary reason why most companies fail.
  3. There is very little education available at any level about sales. How on earth is it possible that one of the world’s largest professions and most universally applicable life skills is not taught in grade school or middle school, much less high school, or as a major in college?
  4. There are millions of people in the world currently in the GTM profession who are forced to learn on the job (every time they are promoted) under the pressure of always being a few months from being fired, and have minimal quality education available. It’s some cruel combination of luck of the draw meets survival of the fittest.
  5. There are also millions of people in the world who would make outstanding sales people, but have no clue the profession exists or access to it, have misconceptions about what it means, or realize how they can apply the characteristics they may already have or learn skills to turn it into a life changing career (like a 22 year old me).

My Next Chapter & Beyond

Over the last year, I built a three pillar vision under the umbrella of YNOT Growth (my name spelled backwards, which my daughter helped me with), that would focus my energy where I both provide the biggest impact, and receive the most fulfillment and return on my time.

  1. YNOT Ventures — a powerful network of world class GTM operating partners to help early stage companies bridge GTM strategy with hands-on execution across all aspects of GTM.
  2. YNOT Sports Academy — focused on teaching children how to apply lessons learned in team sports to achieving success in life, relationships, finances, and career (with an emphasis on underrepresented communities).
  3. YNOT Growth Foundation — a non-profit whose mission is TBD but will focus on children and teachers.

Over the last 4 years at Snowflake, I have been beyond blessed with an amazing culture, team, product, customers, market, and all that comes with it. Given Snowflake’s success, I’ve consistently been recruited externally, but expressed no interest in what would otherwise be wildly attractive leadership opportunities, purely based on the fact that Snowflake is such an amazing company. I’ve consistently told people the earliest I would even consider something different was 2023 and it’s likely that my life after Snowflake would be focused on some combination of entrepreneurship, investing, and advising tied to the priorities I outlined earlier.

I am thrilled to announce that I’ve decided to change course. As of today, I’ve officially joined Sales Impact Academy, the world’s leading GTM learning platform, serving in the role of Chief Revenue Officer.

Having been through three outstanding IPOs, SIA hits on all of the things I look for in a company with potential to be elite.

  • Massive market
  • The makings of a truly differentiated product
  • The makings of a great leadership team
  • Outstanding investors
  • Great people and culture
  • Early momentum w/ fantastic customer success & value

On top of that, the primary drivers for me personally include:

  • SIA’s mission — I’ve seen first hand what quality education does for people through teaching at The University of Washington. Scaling that impact to millions of people is a thrilling prospect and resonates deeply with me.
  • SIA’s culture — human-centered culture and values, executing rapid scaling with a foundation of kindness, empathy, and respect.
  • The opportunity to create a world-class GTM team. As a function of what we do, we better have the best GTM team on planet earth and drink our own champagne.
  • The opportunity to create a generational company that will create life changing outcomes for our employees and customers.
  • The opportunity to interface with elite GTM leaders all day, every day and learn from the best.

I’d like to express sincere gratitude to anyone reading this (my very first blog post) who has helped me along my journey. To list you all by name would be nearly impossible but you know who you are and I thank you for the impact you’ve had on my life.

If you want to pursue a career in sales, improve your selling skills, or differentiate your company through an elite GTM team, I hope this serves as a small piece of inspiration to help you.




Dad, husband, basketball coach, sales leader, advisor and investor.

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Tony Jackson

Tony Jackson

Dad, husband, basketball coach, sales leader, advisor and investor.

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