I Joined AWS
Sometimes people can see things in you that you do not see yourself. That was the case with my friend Nelson who said the following to me:
“I can see you in the role.”
It was the beginning of February when he shared a link over LinkedIn about an open role at AWS. He had recently joined Amazon Web Services from a bank and seemed pretty happy. While I was grateful for the consideration though, I enjoyed the freedom of startups. What could AWS possibly offer?
Ironically, jumping into the startup world was not something I had expected over a decade ago. I had been comfortable working in bigger, established firms doing management consulting and enterprise sales. I had gotten progressively more senior roles, better salary, and the work was relatively interesting and intellectually stimulating.
Something always gnawed at me though, the desire to experiment and test crazy ideas. I had some of that freedom in my consulting days, crafting several new service offerings and collaborating with customers on new solutions. Even at places like Siebel, thinking big often lead me to better outcomes.
Eventually my quest for more money and bigger roles led me to a “big enterprise tech” company. There was the promise of autonomy, authority, and visibility. What I walked into instead was the relentless and soulless machine of a bureaucracy that crushed all joy from my working life.
Every single thing was a chore. The deal reviews for even the most minimal of deals took forever and always elicited endless rounds of questions. Every decision was second-guessed. Every email was an ongoing chain of CYA* replies and deflections. Every meeting required a busload of people that added nothing to the agenda.
The most frustrating thing to experience though were the endless choruses of no. In my conversations with CTO’s and CIO’s, we would often talk about ways of accelerating value to the business. Out of these discussions emerged many ideas, some tactical and immediately actionable and others audacious in scope and scale. When I brought these back to “big enterprise tech” firm, I would be met with either stone cold silence or “that’s not what we do”.
After drowning in the bureaucracy and inability to innovate, I had reached the tipping point. I pursued my own path with one of the ideas that “big enterprise tech” company had no interest in. With that move, I leapt into the world of startups, never to return to the big corporate world, or so I thought.
Nothing notable ever happened with my startup. It didn’t help that enterprise HR tech was not a hot segment during the financial crisis of 2008. To be fair though, I made plenty of appallingly bad errors that limited any chance for success. Instead of going back to the corporate world in defeat though, I doubled down and turned what I learned into opportunity to help founders avoid the same mistakes.
I mostly spent this time investing in startups, advising founders, and working as a part-time head of sales. It was during this time that I saw themes emerge in the typical stumbling blocks encountered as startups progressed from launch to scale. Sales was top of the list.
Sales was a profound mystery for most of the founders I was supporting. However, I was spending an exorbitant amount of time in one-on-one sessions coaching founders on rudimentary sales skills. Doing these over coffee also meant that I would get raging coffee headaches by evening. I needed a more scalable way of supporting founders. Reflecting on these conversations then, I worked backwards to find a more scalable and impactful way to help them.
What emerged was the Enterprise Sales Forum, a place to bring founders and salespeople together so they could network and help each other. It was my way of inventing and simplifying; bringing relevant and useful content on a regular basis about modern sales skills to people that needed the most help. When people in other cities started inquiring about the Enterprise Sales Forum, I knew the need was even more widespread than I had imagined.
I never fashioned myself as a community builder. At the time, I was simply taking a model I started in New York and expanded it elsewhere. Revenue was tight early on, so travel was extremely frugal. When opportunities to partner on a new city launch came up, my bias was to move quickly and act. As I added chapter leaders and sponsors, I had to earn their trust that I would support them and deliver results. I made plenty of mistakes along the way, but insisting on the highest standards for content, speakers, and event experience meant my instincts were right most of the time.
The skills I learned in building a community and running events at scale would prove critical in building the enterprise business for Stack Overflow. While beloved by developers, I had to build trust, credibility, and rapport with buyers that were not as familiar with Stack Overflow, that being CIO’s and CTO’s. The cornerstone of that strategy was insightful content, which later turned into speaking invitations and hosting live forums for senior IT and engineering leaders to meet and learn from each other.
As I read the AWS job description my friend had sent, I felt I was reading the synopsis of my playbook at Stack Overflow. The difference was that it was with a company that valued the importance of being a trusted advocate for founders, executives, and startups. AWS understands and appreciates the long term view and the value of obsessing about customers over short term considerations.
Still I was skeptical. Someone once made the off-hand remark in the Stack Overflow lunchroom saying, “I’m glad I don’t work at AWS’. I brushed it off but could not shake how successful AWS had been over the past decade. Nearly every startup I knew launched on AWS. Plenty of people I respected had joined AWS and seemed quite satisfied. Could the culture really be as bad as “big enterprise tech” company?
It is remarkable how opinions can form on the slimmest and most threadbare of “evidence”. It is easy to assume that all big companies are bureaucratic and unfeeling. You might assume that people are just there for the paycheck. You could be excused thinking that all the talk of “Day One” culture is more marketing spin than reality.
What I found however during the interview process and in speaking with folks familiar with AWS was a picture of a very different company. There was a genuine respect for AWS and the people. Despite the success of AWS, they still managed to keep things humble. They are truly customer obsessed.
Amazon’s culture rests on their fourteen Leadership Principles. These principles come through in conversations, underpin “6 page narratives” and other documents, and are threaded into Amazon’s framework for decision making.
Thinking back to that lunchroom conversation, what I realize is that AWS embodies all the things I had hoped for at Stack Overflow. While this would seem obvious, having a set of principles helps align how everyone in a company operates. Since joining, I have already experienced the principles in action with the speed of decision making, the thoughtful approach to hiring, the way people take ownership, and how customer obsession drives much of the roadmap for the services AWS creates.
If there is one addition to Amazon’s Leadership Principles I might suggest though, it would be “Help Each Other”. That was one aspect of Stack Overflow that I most appreciated and was glad to see at AWS. Maybe you could call it an unwritten rule or maybe place under “Ownership”. Whatever the case, the willingness to help others across teams is palpable. That people have been so open to spending time to speak with me has helped me immensely given my onboarding has been entirely virtual.
So you might be wondering what exactly I am doing at AWS? My title is Principal Startup Advocate for APJ and I will be based in Singapore. In the role, I focus on startups and the startup ecosystems across the region. Most of my work will be speaking at events, creating content, and developing stories of startups using AWS to build and scale.
While similar to my work at Stack Overflow, there are a few differences. First, I am focused on startups primarily whereas before I spent more of my time with larger enterprises. Second, instead of being in sales, I sit in marketing with the Developer Advocate team. Third, I have much greater support, reach, and impact to help founders and startup leaders. AWS provides a platform to truly be customer obsessed on a wider scale.
For most community builders, helping people is the key motivation. This is why they do what they do despite the challenges. This is what guides me as well and joining AWS finally gives me the ability to help as many people as we can. It is the natural evolution from my journey from the Enterprise Sales Forum to Stack Overflow to DEVBIZOPS.
What does that mean for DEVBIZOPS? I will still publish the weekly newsletter and blog (which I am moving to Substack). I am also in the process of writing and publishing longer form content such as my upcoming book Community-in-a-Box.
How about yourself? What is new with you, would love to hear from you and what you are working on!
* CYA means “Cover Your Ass”, or in other words the opposite of accountability and ownership
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