Career from Engineer to CEO & EVP with Ethan Evans & Ameesh Paleja
Chat with Ameesh Paleja (EVP at Capital One, ex-Google VP, ex-OfferUp CTO, Atom Tickets CoFounder & CEO, ex-Amazon Director)
Welcome to this week’s free article of Level Up: Your source for executive insights, high performance habits, and specific career growth actions.
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15 years ago I told Ameesh Paleja, then an Amazon Sr. Manager (L7) on my team, that I could see he would surpass me.
Now Ameesh is an EVP at Capital One (ex-Google VP, ex-OfferUp CTO, Atom Tickets Cofounder & CEO, and ex-Amazon Director) and has clearly done so.
Ameesh’s successful recipe (from my perspective):
Absolutely relentless hard work.
Stellar ownership and delivery.
Non-stop self-advocacy (pushing for bigger opportunities).
Willing to make deals to grow (I will over deliver but I want X in return).
Confident enough to repeatedly leave good jobs for bigger opportunities. He was never static nor satisfied.
Watch our fireside chat below, we discussed:
Each step in his career, how he saw his decisions, and how I saw them as his manager for 8 years from mid-level SDE to high-level Director.
Ameesh has a model career you can study and learn from. He switched majors from engineering to CS facing classic family pressure to become an engineer. Then he worked at Microsoft before coming to Amazon. After Amazon, he raised money and founded his startup Atom Tickets (serving as CEO).
At the same time, he has had some struggles and sideways moves before ultimately becoming a VP at Google and then an EVP at Capital One.
Note: Live attendance was exclusive to paid newsletter members.
I hope this advice helps you plan ahead for your career. If you’re looking for help growing in your organization and leveling up your career, consider my course, Stuck at Senior Manager - How to Break Through to Executive. For the first time, Maven is offering 25% off, this is the biggest discount offered for my course and it ends June 9 (Sunday) at 10 PM EST. Enroll now and use the code MAVEN100 to get 25% off.
If you’re already in executive roles (e.g. Director, Sr. Director, VP) and want to optimize performance or move up further, consider my course, Cracking the C-suite 'How to Get and Master Key Executive Roles' which I co-teach with Sue Bethanis (Executive Coach & CEO/Founder of Mariposa Leadership) who has coached 400+ tech executives.
On June 18 (Tuesday) Sue and I will host a live fireside chat with Q&A on how to get support for an Executive Coach and make the most of it. Level Up newsletter paid members and the Mariposa Leadership Community are invited to join live (we will share the recorded version at a later date). Members, RSVP here.
Takeaways
(1) “Your job is to stretch muscles you don’t have.”
Every career move Ameesh made (e.g. leaving Microsoft for Amazon) was predicated on that plus holistic ownership over larger areas/systems/businesses.
Ameesh attributes his career growth to: “Being comfortable being unsafe.”
(2) Ask yourself “What gives you energy and motivation.”
If you get energy from helping others be successful and driving a larger impact through others, then management may be your path (but you must take the good with the bad).
Know that management is not always pleasant (usually, there is no playbook to reference). There is a lot of bureaucracy. If that makes you unhappy, think deeply.
(3) Get critical feedback, fix it, and deliver.
In Ameesh’s first year as a manager, 7 of his 8 reports (as part of the Amazon 360 review process) wrote “Ameesh blows off our 1:1s.” Ethan delivered the feedback, and Ameesh replied: “Ok, I got it.” He immediately fixed it and Ethan never saw that feedback again.
Ameesh credits being open to feedback, able to take it, incorporate it, and not having to be told multiple times as a top reason why executives were willing to take a bet on him. As Ameesh said: “It will just be done.”
If you want to build a win/win relationship with your manager or direct reports, read my article The Magic Loop: A framework for rapid career growth (5th most popular article in Lenny’s Newsletter).
(4) Develop “I have your back” trust.
To be a bar-raising leader, create “I have your back” trust with your team and your own muscle to navigate EQ problems.
Three actions to build your EQ:
Start by assuming and demonstrating positive intent.
Remember that communication delivery matters. People hear your remarks in different ways.
Pick your battles. Know when it is appropriate to argue the point and when it is okay to let go.
“People don't care how much you know until they know how much you care”
― President Theodore Roosevelt.
If you want to go in-depth on how to manage up successfully and create effective relationships with your boss and senior peers, consider my on-demand course, Managing Up Successfully.
(5) Don’t be afraid to take on the ugliest problem in the room.
If you are in or are coming into a fast-growing company, take on the problems nobody wants and deliver high-quality results. This quickly builds your credibility and hits the turbo button on your ability to ask for larger scope roles such as being a GM.
(6) “It’s the loneliest job in the world” — being an early stage startup Founder/CEO.
Nobody cares if you are sad or upset.
You are constantly worried about payroll and every decision.
Much of the gray in Ameesh’s beard is from those years. Any semblance of work/life balance was destroyed.
Do not do this casually. You have to truly want it otherwise you will not succeed.
(7) Always strengthen the weakest part of your portfolio.
Elevate what you are weak at to balance yourself as an executive. This helps you be in contention for “all-around athlete” executive roles, not just specialized ones.
For example, most engineering leaders are unable to deeply walkthrough a P&L.
Follow Ameesh on LinkedIn.
In my chat with Ameesh, a consistent theme was the power of networking.
If you want to learn how to be a high-value connector and networker, Level Up newsletter paid members are invited to join live (we will share the recorded version at a later date) our next fireside chat where Jason Yoong (my operating partner) will speak with Andrew Yeung, former Google and Meta product leader turned tech and hospitality entrepreneur and investor. Andrew hosts some of the most in-demand events with executives, founders, and media personalities.
Business Insider dubbed him the "Gatsby of Silicon Alley."
Don’t miss this one, a strong network is your most powerful and portable long-term career asset.
*UPDATE* Video recording and takeaways here.
Connect With Ethan & Jason
Follow Ethan on LinkedIn.
Get Ethan’s career advice on YouTube.
Connect with Jason (Ethan’s operating partner) on LinkedIn.
Learn more about Ethan’s live online courses and on-demand courses.
Contact us for corporate training, speaking, podcast appearances, and more.
Many subscribers expense this newsletter to their Learning & Development budget, use this email template to send to your manager.
This is a fantastic roadmap. Ameesh's playbook is legit.
The point about taking the ugliest problems is the ultimate cheat code. It's how you skip the line. But the hidden lesson here is the psychological price of being "comfortable being unsafe". You end up living in a state of constant calculation. Every relationship can feel like a variable in your growth equation.
It’s incredibly effective. It's also exactly why he says being a founder is the loneliest job. You trade comfort for leverage. A brutal but necessary deal for that level of success. Great chat!