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From Fired Twice to Amazon VP: Leadership Lessons and Career Insights with Ethan Evans

Ethan Evans’ career journey is a compelling story of resilience, growth, and strategic leadership. From being fired twice during the dot-com bust to becoming a Vice President at Amazon, leading over 800 engineers, his experience offers invaluable lessons for professionals navigating the tech industry and corporate leadership.

Early Career: Embracing High Growth Startups

Ethan's career began with a clear passion for engineering, spurred by the early days of home computing. Despite not getting into MIT, he pursued a master's degree at Purdue and dove into the startup world, largely influenced by friends and the allure of stock options. His early roles were diverse, ranging from networking startups to internet search and streaming audio, with most of these ventures ultimately failing or flaring out during the dot-com crash.

He attributes his initial setbacks—including two layoffs—to his abrasive personality and confrontational style. Ethan candidly describes himself as a "loose cannon," often clashing with peers and managers due to his combative approach and unwillingness to accept dissenting views.

The Power of Soft Skills and Strategic Annoyance

Ethan’s turning point came after his second layoff, when he took a hard look at himself and recognized that technical skills alone weren't enough. He began focusing heavily on soft skills—learning how to ask questions, listen, and build relationships rather than escalate conflicts. His concept of being "strategically annoying" emerged: maintaining a strong, clear opinion and pushing for what you believe in, but doing so in a way that invites collaboration rather than confrontation.

This shift was key to his later success, illustrating how combining technical expertise with emotional intelligence is critical in leadership.

Navigating Corporate Politics and Building Alliances

Ethan shares that one of his biggest mistakes early on was failing to build enough alliances within organizations. Being overly confrontational led some colleagues to exclude him from important conversations and even push for his removal. His advice to leaders and aspiring leaders is to focus not only on being right but also on cultivating relationships that foster mutual respect and inclusion.

Joining Amazon: Stability Meets Opportunity

Ethan’s move to Amazon came after he had been working at various startups, some struggling with funding and product-market fit. A prior role involving a partnership with Barnes & Noble exposed him to Amazon's innovative approach and competitive edge, making Amazon an attractive next step. Despite Amazon being much larger than his previous employers, it still felt like a high-growth, fast-moving company—an "escalator" that allowed him to grow as the company expanded exponentially.

Climbing the Leadership Ladder: Risk and Relationship Management

Ethan’s promotions at Amazon—from senior manager to director and eventually VP—were fueled by a combination of demonstrated leadership, taking calculated risks, and strategic communication with his superiors. He shares a telling story about pushing forward a high-risk project despite management’s reservations, which ultimately succeeded and became a pivotal point in his promotion.

He emphasizes the importance of "the magic loop"—a partnership between a leader and their manager where the leader commits to delivering exceptional results, and the manager commits to advocating for their advancement.

Managing Promotions and the Reality of Corporate Life

Ethan is refreshingly honest about the realities of promotions and performance management. He acknowledges that sometimes, those who advocate for themselves and "threaten to leave" get promoted over quieter, collaborative employees. While it may seem unfair, this reflects the pragmatic challenges managers face balancing team dynamics and organizational goals.

He also recounts a painful lesson when a promising engineer on his team missed a promotion due to his own ignorance of Amazon’s formal promotion cycles—a reminder that understanding and navigating corporate processes is crucial for career advancement.

Leading Through Integration: The Twitch Acquisition Experience

As the integration liaison for Amazon’s $970 million acquisition of Twitch, Ethan faced the unique challenge of influencing a young, fast-growing company without direct authority. His role required diplomacy, patience, and soft skills to align Twitch’s culture and priorities with Amazon’s expectations, especially around profitability—a concept initially foreign to Twitch’s venture-funded mindset.

Insights on Leadership Styles: Jeff Bezos vs. Andy Jassy

Having worked with both Jeff Bezos and Andy Jassy, Ethan notes distinct leadership styles:

• Jeff Bezos: The founder’s style is bold and risk-taking. Bezos viewed the company as his "toy," willing to gamble resources aggressively. He was emotionally supportive of leaders and inspiring, often pushing boundaries with confidence.

• Andy Jassy: More traditional and measured, Jassy focuses on partnership and accountability, expecting leaders to own their plans and deliver results without as much emotional backing. Ethan describes this style as less inspiring but pragmatic.

Performance Management and the Harsh Realities of PIPs

Ethan offers a candid critique of Amazon’s performance management system, particularly the use of stack ranking and Performance Improvement Plans (PIPs). He explains how the pressure to meet attrition goals forces managers to put underperformers on PIPs, often with a predetermined outcome of termination. Despite good intentions in some cases, the system is psychologically biased and difficult to overcome.

He warns employees that once on a PIP, the best strategy is often to start looking for a new job, given the low success rate of recovery.

The Power (and Risk) of Managerial Authority

One of the more sobering revelations Ethan shares is that managers at Amazon can effectively end an employee’s career with little intervention from HR. Since managers frame the narrative about an employee’s performance, they hold significant power, which can be abused or misused. Employees must navigate this reality carefully, building relationships and avoiding conflicts with vindictive bosses.

Final Career Advice: Growth, Relationships, and Reputation

Looking back, Ethan would advise his younger self to:

• Prioritize high-growth environments: Being part of rapidly expanding companies accelerates career progression.

• Invest in relationships and soft skills: Technical expertise is necessary but insufficient without the ability to connect and influence others.

• Build a reputation proactively: Use tools like LinkedIn to establish your professional brand and network, even if you are an introvert.

Closing Thoughts

Ethan Evans’ story is a testament to the complex interplay between technical skill, interpersonal savvy, risk-taking, and political navigation in building a successful tech leadership career. His transparency about failures, personality flaws, and the realities of corporate life provides a rare and valuable window into what it takes to thrive at the highest levels of companies like Amazon.

For more insights and guidance on leadership and career growth, Ethan can be found on LinkedIn as Ethan EvansVP or at his website, EthanEvans.com, where he offers coaching and courses on career advancement.

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