A Letter from My Future Self
April 17, 2026
Dear Bill,
It’s April 2016. You just made the leap to AWS. You’re excited. You’re nervous. You have no idea what the next ten years will actually require of you.
Let me tell you.
The First Chapter: Learning to Obsess
You’ll spend your first years in San Francisco managing a portfolio as wide as any you’ve ever seen. A public utility. A data storage company. A vision care provider, a global bank, a payments network, a semiconductor leader, a genomics pioneer, a cancer detection company, a global law firm, and an automotive logistics firm. Each account will teach you something no previous role ever could.
The public utility will file for bankruptcy in January 2019. You’ll want to pull back. Don’t. Call the CIO. Tell her you’re not walking away. That decision will define your reputation more than any deal you ever close.
In October of that same year, the same utility will face the largest Public Safety Power Shutoff event California has ever seen, impacting millions of customers. Their systems will crash. You’ll mobilize over sixty people within hours, working war rooms at 2 AM because that’s when customers need you most.
That experience will teach you the first and most important lesson of your career. Customer obsession isn’t about choosing easy accounts or celebrating wins during good times. It’s about showing up when it’s difficult, especially when it’s difficult.
You’ll spend the first five years mastering enterprise sales. You’ll think that’s the destination. It isn’t. It’s the foundation.
The Rejection That Refines You
In January 2019, you’ll interview for your first leadership role. The feedback will be two words: Not Inclined.
It will sting more than you expect.
Don’t quit. That rejection is not a verdict. It’s a roadmap. Your first leadership mentor will tell you that your interview answers need work, your customer portfolio needs broadening, and you need more management experience. Listen to every word. He’s giving you a gift.
You’ll spend the next few years preparing, not waiting. You’ll interview dozens of AWS leaders. You’ll join the Emerging Leaders Cohort. You’ll become a Bar Raiser in October 2022. You’ll mentor Enterprise Account Managers, Inside Sales Representatives, and new Amazonians.
“If I were sitting in a debrief, I would say Bill has over twenty years of experience in a broad set of customers and has been really successful. But where do we see evidence of him collectively raising the bar on the organization, whether that’s through hiring, bar raising, mentoring, coaching?”
The question will land. Be more intentional. Not just mentoring informally, but creating mechanisms to develop others at scale.
Three Months That Changed Everything
In October 2021, you’ll briefly step into Healthcare and Life Sciences. You’ll become the Global Account Manager for both the genomics pioneer and the cancer detection company. Two companies. One industry you know nothing about.
You could pretend you know more than you do. Don’t.
Instead, turn to online learning. Courses on biology, life science consulting, and AI for life sciences. Within weeks, you’ll hold your own in rooms you had no business being in. That curiosity is the engine. It is one of your superpowers. You walk into unfamiliar rooms ready to absorb, and you always leave knowing more than when you arrived.
In the first thirty days, you’ll inherit an urgent priority: a multi-million dollar agreement stuck in limbo for over a year. You’ll work through the weekend to close it.
That experience will teach you something fundamental. Sometimes, the most important work is finishing what others started. Execution matters as much as strategy. Learn and Be Curious isn’t just an AWS Leadership Principle. It’s a survival strategy.
The Semiconductor Sector: Two Years of Strategic Patience
In December 2021, you’ll transition to semiconductors. This will become your focal point.
Complex contract negotiations will last nearly two years. Multiple stakeholders. Evolving requirements. Competing priorities. You’ll target six products for SaaS deployments and work toward making your customer the first EDA supplier to sign such an agreement with AWS.
The partnership will teach you that complex deals don’t close quickly. Customer obsession at the strategic level means staying committed to a customer’s long-term transformation even when the path forward is unclear.
The Hardest Year
In September 2023, you’ll step into your first AWS leadership role, leading a greenfield cross-industry team.
“Your first year is going to be hard, really hard. You’ll wake up every day questioning yourself, and you’ll want to quit.”
They’re right.
Around month four, you hit the trough of despair. The operational complexity is relentless. Your calendar is no longer yours. Fire drills cascade and build on one another. But the complexity is not the worst part.
The doubt builds slowly, then all at once. Do you belong here? The question follows you into every meeting, every call, every room where you feel one step behind everyone else. The imposter feeling does not knock. It just shows up and stays. Before long, you are drafting the message to your manager in your head, already rehearsing the exit before you have given yourself a real shot.
That’s when you’ll remember the Gartner Hype Cycle.
You’ll stand at the whiteboard in your home office and sketch the curve. Five phases. Then you’ll mark where you are: deep in the trough, exactly where the framework predicted you would be.
You’re not failing. You’re in phase three of a five-phase journey. The trough is real, but it’s temporary. The path forward is through, not back.
You’ll keep that sketch visible for months. On the hardest days, you’ll look at it and tell yourself: Still in the trough. Still normal. Still temporary. Keep becoming.
What Leadership Means
You’ll sell vision instead of products. Possibility instead of services. Growth instead of solutions.
A mentor from the gaming division will teach you that you work for your team, not the other way around. That perspective shift will change everything.
Another trusted advisor will show you how to build flywheels. People development. Executive engagement. Operational excellence. Cross-functional collaboration. While a flywheel requires effort to start, once it moves, it sustains itself.
A peer leader who has walked the path before you will warn you about the temptation to solve problems for your team rather than developing their capability to solve problems themselves. That advice will save you from the trap of heroic leadership.
And your direct Area Sales Leader will coach you on psychological safety. She’ll tell you it’s the secret sauce of high-performing teams. She’ll challenge you to lead as the General Manager of your business, with a focus on the entire cross-functional team. She’ll warn you that there will be things you’ll have to land messages on that you have no control over. The key will be learning to control what you can control, to influence what you can influence, and to let go of what you cannot.
She’ll be right about everything.
Numbers Are Important. But Not Everything.
By the end of 2025, your cross-industry team will exceed its revenue attainment with impressive year-over-year growth. You’ll complete hundreds of Bar Raiser interviews and mentor an equal number of members across the organization.
But here’s what will matter more. Your peers will say you have an infectious can-do attitude even when the cards are stacked against you. They’ll say your superpower is coaching. That you make daunting goals feel attainable. That you get people to rally around a common objective.
That’s the legacy.
What You’ll Learn About Yourself
Curiosity is a competitive advantage. When you step into unfamiliar territory, you don’t pretend. You learn. That investment pays immediate dividends every single time. Credibility increases. Executive conversations deepen.
Rejection does not diminish you. It refines you. You’ll come to welcome it as proof that you’re pushing far enough. You’ll come back sharper. That’s the growth mindset in practice. You don’t run from the hard moments. You run toward them. Because you know that’s where the real development lives.
Leadership is recursive, not linear. You don’t graduate from one level and master it. You spiral upward, revisiting the same challenges at higher complexity. The trough comes again. Lean into it.
You’re now ten years in. You’re an L7 leader. You’re writing a memoir called Becoming the Builder. You’re thinking about speaking and teaching about finding your why and helping others manage their careers.
Your core philosophy is clear: I build people and teams through challenge, trust, and example, so that they rise into their fullest potential.
You’re not done. You’re just getting started.
One last thing. Your wife and children are your foundation. They’ve stood shoulder to shoulder with you through every chapter of this journey. Don’t forget that. The beehives, the lacrosse sidelines, the trips to Ireland, Scotland, France, and Italy. Those moments matter as much as any deal you close or team you build.
Remember when you asked your father how long it takes to raise a child. He answered the only way he could: “I’ll let you know when I’m done.” He was still in it. Leadership works the same way. You are never done. The journey is not a destination. It’s an ongoing process of growth and learning.
The best is yet to come.