In my final four years of corporate sales, I closed over $50 million in strategic accounts, leading AI-enabled transformation deals with brands such as Delta, Chipotle, and UnitedHealthcare.
In my second year as a Strategic Account Director, I joined the seven-figure annual earnings club, averaging $1.1 million for three consecutive years before stepping away from corporate life at age 42.
This is not to boast. It’s both a warning and an invitation.
That type of success wasn't always the case.
Like many competitive (and insecure) overachievers, I bought into hustle culture earlier in my career. The constant pressure eventually led to severe burnout, including a hospital visit due to a stroke in my early 30s—all from chasing “more” and overworking. Even after that health scare and despite increased efforts, my earnings stalled at around $200K per year.
I felt like either I was broken or the game was rigged.
But everything changed and started to click into place when I adopted a Human First, Professional Second philosophy. I combined systems thinking and intentional performance design.
Instead of pushing harder, I redesigned my approach. The result wasn’t just higher income. It was sustainability—and more importantly, gaining authentic autonomy.
The outcomes:
High performance while averaging ~7 hours of sleep
$27.3M+ in ARR generated with a 78% win rate
$3.8M+ in personal income in under 4 years
Corporate retirement 10 years ahead of plan
My journey from chaos and burnout to living an autonomous life wasn’t quick, easy, or linear. And yours won’t be either.
What I know for certain: It isn’t about just perfecting a POV deck, applying the right sales methodology, or learning specific tactics. It’s about transforming yourself into a thoughtful designer—someone capable of architecting a career and life you know deep down you’re capable of living.
That transformation unfolds through three universal stages every tech seller must navigate: Learn, Earn, and Evolve. I like to think of these macro phases as levels:
Level I — Learn: You step into the workforce to build skills and knowledge. You say “yes” more than “no.” Your calendar is mostly controlled by others. This is the on-the-job apprenticeship that pays for life.
Level II — Earn: You start to apply your skills more strategically. You deliberately say “no” more than “yes,” and as a result, you earn asymmetric income—the kind that, if managed wisely, can fund options and independence on your terms. Sadly, this is where most get trapped before it’s too late to pivot and build what they truly desire.
Level III — Evolve: You now fully own your calendar. You design your life around your mission, values, and purpose. No boss, no board of directors, no permission. You make bold bets without financial return as the primary driver. You’re more motivated by impact and by helping others. You work at the pace or intensity you choose, and this work starts to feel more like “art.”
Progress through the levels can be measured across these four core components:
Time & Mastery: It takes time, mistakes, experience, iterations, and innovation to move from beginner to expert. The aim is to upgrade your mindset and improve your abilities so you can make significant progress.
Calendar Ownership: Simple—move from 0% → 100% as quickly as possible without losing control, missing opportunities, sacrificing your values, or lowering your standards.
Financial Runway: The goal is to keep your costs in check while you expand your financial powers, measured in how many years of current annual expenses are covered by your net worth. Money becomes a tool, not a status symbol.
Optionality: This is about transforming from limited options, where you’re tethered to one employer/one income stream, to generating multiple options of interest that you can act on from anywhere in the world.
The tech sales arena, especially in enterprise and strategic accounts, gives you a unique advantage to take control and accelerate this journey—more than any other corporate role.
In fact, I’d venture to say you’re already an entrepreneur at heart, and that’s why you landed in sales in the first place. Now is the time to finally spread your wings.
The Purposeful Performer helps you systematically work through this journey so you can achieve Level III Autonomy ahead of schedule, equipped with the right capabilities and financial engine, to finally pursue your passion projects without stress or regret.
It’s not easy, and it’s certainly not for everyone.
Along the way, there are jobs to be done, traps to avoid, skills to develop, and missions to complete. That all starts with understanding where you are, so you can get crystal-clear on where to go next—embarking on your very own hero’s journey.
To give you a roadmap, it starts with a brief assessment.
This will help you get tactical on exactly what needs to be improved with the help of The Purposeful Performer and one-on-one coaching with me, and ultimately allow you to “choose your own adventure” so you get the right content at the right time at the right cadence that makes sense for where you are in your career right now.
