Journey of 15+ Years: Unzipping the Archive at WSO2.

Asanka Abeysinghe
architect2architect
13 min readJun 4, 2023

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Sitting down at my home office desk this morning, sipping my cup of tea, I’m overwhelmed with memories. Today isn’t just another work day — it marks a significant milestone. Today, I’m celebrating 15 great years at WSO2, a journey that has profoundly shaped me professionally and personally. 15 years! That’s a long time to spend anywhere, and it’s surreal to think that over a decade and a half have passed since I first stepped into this exciting role. Yet, here we are, and as someone who cherishes the power of the written word, I couldn’t think of a better way to commemorate this anniversary than by sharing my experiences through a blog post. It’s a heartfelt, sleeves-rolled-up account filled with highs and lows, life lessons, and, of course, a myriad of indelible memories. So, let’s start this journey together, rewinding back to where it all began…

The Genesis — Discovering My Path

It was the Fall of 2008. I was the Chief Architect (jointly assumed CTO responsibilities with the CEO) at a FinTech startup, deeply engrossed in finding the right Enterprise Service Bus (ESB) for the portfolio management tool we were developing. Our top contenders were Apache Synapse and Apache Camel, both excellent choices, but we needed to decide to best fit our needs.

Amidst this search, there was another quest that ran parallel to my professional life — my search for a basketball court. As a die-hard basketball player, my evenings were incomplete without the swish of the net and the rhythm of dribbling echoing through the air. After a long day of wrestling with code and architectural decisions, the basketball court was my sanctuary, where my mind could roam free, away from lines of code and system architectures.

#59 Flower Road Colombo 3

One evening, while walking down Flower Road in Colombo 3, Sri Lanka, my eyes fell upon a welcoming sight — a basketball court. Next to it, the name #59, “WSO2,” shone on a signboard. A strange coincidence, I thought, recalling that Apache Synapse, the open-source software we had been considering, was driven by the very same company. I remember standing there, looking at the signboard, and feeling an inexplicable connection. Little did I know, this was my first hint of the incredible journey ahead. It was just the beginning, the first dot in a constellation yet to reveal itself.

Seeing that WSO2 sign next to the basketball court was not just a coincidence for me; it was a serendipitous hint at what was coming. I had known about WSO2 and its significant contributions to the open-source world, and standing there in front of their name, I was reminded of the man behind it all — Sanjiva Weerawarana, the founder and CEO.

I had crossed paths with Sanjiva a few times before that day. I first met him at an AMCHAM event, where we talked with Brian Behlendorf. My admiration for Sanjiva deepened when I attended ApacheCon Asia in 2006. He delivered a keynote titled “The World is Flat in Apache,” I was in the audience, hanging on to his every word. His insightful discourse resonated with me.

With these experiences in mind, I decided to reach out to him. So, that evening, I sat down at my desk and emailed Sanjiva. It was a simple message expressing my interest in joining WSO2. Sanjiva’s prompt reply led us to meet at “Commons,” a cozy local restaurant near the WSO2 office. It was a non-business chat, a refreshing break from the tech talk.

Further casual meetings with senior leads, Samisa and Sanjaya K followed at the same locale. I also had an exciting encounter with Paul Fremantle, the former CTO and co-founder of WSO2, at the stylish Cinnamon Grand Lobby. More about Paul later.

Soon enough, a door opened that I had not anticipated. I received an offer from WSO2 to join their team as an Architect. The role was described as follows: “Your role will be to help architect and engineer WSO2’s products to better suit the financial services market as well as to liaise directly with customers and work with them to build innovative solutions using our technology, especially in the financial services domain.

Embracing this opportunity, I embarked on this new journey on June 2nd, 2008. And so, my adventure at WSO2 officially commenced…

Day One — The Immersion Begins

Stepping into WSO2 on my first day was a delightful whirl of excitement. I was welcomed into the OxygenTank (OT) room, a lively space with diverse teams and job roles. Nestled within this energetic crowd, I was in a prime spot to absorb and learn about the unique WSO2 culture. At that time, the company was a hive of around 50 dedicated individuals, each deeply engrossed in their work, a testament to their shared mission. Despite the general buzz, I found camaraderie among my immediate OT roommates, Devaka Randeniya, the lone ranger managing sales, and Hasmin, the solitary force steering marketing, who took the time amidst their bustling schedules to welcome me into the WSO2 fold.

The Rookies’ Chronicles — Learning the Ropes

In the early days at WSO2, I found myself navigating unfamiliar waters. Concepts like SOA, web services, WS-* standards, SOAP, and more were new to me. Undaunted, I dove headfirst into learning, contributing numerous samples to WSO2 ESB, specifically on FIX and AMQP.
Within three months, my efforts were recognized with an Apache committership — a notable milestone. But the learning didn’t stop there. I was appointed as the Architect/Project Manager for our largest customer at the time, based in Long Island, NY. This presented a fantastic opportunity to travel to the US, further expanding my horizons.

Guiding Lights — The Impact of Mentorship

Sanjiva: I’ve touched upon Sanjiva previously, so I’ll keep this brief. His approach to business and technology was always rooted in first principles, ensuring a solid foundation for any endeavor. His influence was instrumental as a fervent protector of WSO2’s unique culture and an exceptional mentor. Not only did he guide me through challenges, but he also created massive opportunities for my growth — he continues to do so to this day. His guidance has been a significant factor in my extended tenure with WSO2. He is, without a doubt, one of the best mentors I’ve encountered. Despite his position as the ‘big boss’, he always remained open for any discussion. Whether it was a technical dilemma or a personal concern, he was there as a friend, not just a CEO.

Standing with giants — Jonathan and Sanjiva

Paul: One cannot discuss my time at WSO2 without mentioning Paul’s tremendous impact on my career. Even after he departs from the company, I still turn to him for advice. As the former CTO, he set an exceptionally high bar, creating a standard that was not easy to fill.
I’ve had the privilege of working with Paul for over twelve years, and he stands out as an extraordinary technologist, leader, and mentor. But more than that, he is incredibly kind and person-oriented. Paul’s grasp of technology is deep and wide, with a unique ability to delve into a complex subject, then distill and explain it in simpler terms. This skill also makes him an outstanding public speaker. His foresight and opinionated views on technology have been instrumental in shaping the vision, architecture, and functionality of WSO2 products.

Paul with my family in 2010

Throughout his tenure at WSO2, I reported directly to Paul. More than a conventional manager, he was my coach, mentor, and good friend. We shared many firsts together: my first webinar, my first customer visit to Long Island, NY, and the first workshop in downtown NYC. In addition, we collaborated on some significant projects that I will explain later.

Jonathan Marsh: Another vital name in my mentorship constellation is Jonathan, renowned as the father of XSLT. To this day, Jonathan remains one of the most impressive coders I’ve ever worked with.
Jonathan’s influence extended beyond the technical sphere; he provided valuable guidance on business and go-to-market strategies. But perhaps his most personal impact was aiding my transition to life in the United States. His support was invaluable during that significant period of change.
His unique blend of technical acumen, strategic thinking, and personal support has impacted my career at WSO2. Even today, I continue to benefit from Jonathan’s mentorship, a testament to his enduring impact.

Lavi de Silva: If one person epitomizes the spirit of salesmanship, storytelling, and networking at WSO2, it’s Lavi de Silva. With an incredible network extending from Colombo’s celebrities to India’s major cities, Lavi has always been our connective tissue to the broader world.
Lavi was instrumental in honing my public relations skills, teaching me how to interact effectively with customers and gain their trust. From the basics like self-introduction to the nuances of trust-building, he patiently walked me through it all.
I made my fair share of pronunciation errors as a non-native English speaker. While many found humor in those mistakes, Lavi took a different approach. He helped me correct them, enhancing my confidence in external-facing technical tasks. His influence has substantially shaped my approach to customer interactions and public speaking. His mentorship, a potent combination of technical savvy and interpersonal skills, has been invaluable in my career at WSO2.

Numerous others have also been instrumental in my journey, offering unique wisdom and guidance. I would be remiss not to mention Udeshika, who equipped me with invaluable management insights; Puny, who consistently guided me on matters of intellectual property and professionalism; and last but not least, Katie, who was the driving force that encouraged me to create and cultivate my personal brand.

The Dream Team — Colleagues Turned Family

My journey at WSO2 was not a solitary one. I was fortunate to be part of a dream team — colleagues who became family. They were there to lift me during challenging times and celebrate the victories. While some of them have since moved on, our bond continues to endure.

Few members from the dream team with Paul (Sumedha and Srinath are missing, Sanjaya K featuring)

Our group, fondly known as SENGL (Senior Engineering Leadership), comprised Selvaratnam Uthaiyashankar, Srinath Perera, Prabath Siriwardena, Sumedha Rubasinghe, and Afkam Azeez. Under the coaching of Sanjiva and Paul, with Samisa providing administrative and logistical support, we took on remarkable projects together.
One notable achievement that stands out is the architecture and implementation of Carbon, a testament to our collective dedication and teamwork. The memories of our time working together are embedded in my mind. A heartfelt tribute to this dream team — their impact on my professional journey and personal growth at WSO2 is immeasurable.

Just like the legendary 1992 Dream Team in basketball, our SENGL collective at WSO2 had its own unique magic. Yet, I was doubly fortunate. I had the privilege to also participate in the creation of our “Dream Team: Redux”, a force to match the 2012 USA Olympic basketball squad. This second dream team was none other than the Solutions Architecture team, which I proudly built and nurtured from the ground up. Kudos to Nuwan Bandara, Chintana Wilamuna, Dakshitha Ratnayake, Mifan Careem, Senaka Fernando, Chathura Kulasinghe, Shiroshica Kulatilake and Nadeesha Gamage, each invaluable members of my Dream Team: Redux.

Most of the members from Dream Team: Redux

Yearbook — Highlights and Milestones

The path I’ve traversed over these 15 years at WSO2 is packed with professional milestones and personal achievements. While it would be impossible to list them all, there are a few that shine exceptionally bright:
On the technical front, I’m proud to have written the first eventing (pub/sub) implementation in Carbon using Java generics and introducing FIX and HL7 protocols to the Carbon stack. These were significant contributions to our technological prowess at WSO2.

Journey continues

I also initiated and led the solutions architecture function for a decade, a role that allowed me to shape our approach to creating comprehensive solutions for our clients. Furthermore, I introduced the concept of a ‘digital double,’ a strategy that has since become integral to our CIAM stack.
In collaboration with Paul, we authored Cell-based Architecture, an innovative approach to designing and implementing cloud native applications. This work remains a cornerstone of our architectural strategies at Choreo application development suite. Serving as the Program Committee Chair for WSO2Con, our user conference, I had the privilege of contributing and overseeing numerous world-class events.

First interhouse basketball tournament — a reverse layup

Outside the realms of work, I’ve also contributed to creating a culture of camaraderie and sportsmanship. Together with Heshan, we kick-started the inter-house basketball tournament. With Bryce, we took our passion for the game further and represented our company in the Mercantile Basketball Tournament.

The Heartbeat of WSO2 — Embracing Our Unique Culture

Sanjiva, once perfectly encapsulated what culture means to us at WSO2: “Culture is what you do, who you are, the way you act. Every day, on the ground, for real.
To visually convey the essence of our culture, I’d point you to the following two diagrams (borrowed from his slides):

What does open culture mean?
Culture is all about people

These images encapsulate the principles, values, and behaviors that make WSO2’s culture unique. This vibrant and embedded culture in our day-to-day operations is the second primary reason, next to Sanjiva, that I’ve remained at WSO2 for so long. It is the backbone of our organization, the heartbeat that keeps us moving forward together.

One personal story (from many) that captures our culture’s essence happened in February 2009. I had just returned from a customer engagement in Boston, MA, and found that my seat had been moved from the OT room to a product team. Confused, I sought out Sanjiva, who was enjoying bila music with his feet on the table in his typical morning routine. He seemed to anticipate my query and closed the door for a private conversation.
He informed me that the product manager for Product X was leaving to pursue a Ph.D., and they thought I could fill the role. But that wasn’t the path I had envisioned. I declined the offer. Unfazed, Sanjiva simply asked, “So, what do you want to do?”
I replied that I wanted to work across all products, aiding customers in utilizing them with proper architecture and assisting Devaka in selling the products from a technical perspective. He responded with laughter and tossed a book from his collection my way. It was “SOA Architecture Patterns.” He told me to read it and come back with a proposal for my desired role.
That’s how Solutions Architecture began as a function at WSO2, and I became the first solutions architect. It was a turning point that dramatically shifted my career trajectory, steering me in the direction I was meant to go.

After that personal anecdote, it’s fitting to underscore how this incident reflects the culture of Mastery, Autonomy, and Purpose (MAP) ingrained at WSO2.

Journey Beyond Borders: Embracing the World and Settling in the U.S.

I recount a journey that spanned the globe. Throughout my career, I’ve traveled 1,398,338 miles, spent 1,515 days on the road, embarked on 188 trips, visited 20 unique countries, and set foot in 123 distinctive cities (based on Tripit). In essence, airports and terminals became my second home before the pandemic. My colleague and friend, Devaka, was my travel buddy for most of these trips. Between us, we have enough adventures to fill a book! These experiences, rich in diverse cultures and perspectives, have shaped me professionally and personally.

Picture credit: https://www.eurasiareview.com/

An opportunity then emerged that led to a significant change in my life — the chance to move to the United States with my family. We initially settled in the heart of Silicon Valley, the San Francisco Bay Area, a vibrant hub of technology and innovation. We later moved to Folsom, an emerging tech city in the Great Sacramento. Today, I am proud to identify myself as a Sri Lankan American, cherishing the cultural roots that nurtured me while embracing the opportunities and experiences of my new home.

Stargazing — Envisioning the Future

As the CTO of WSO2, my dedication is unwavering. I am committed to our mission of transforming the world by “revolutionizing the creation of digital experiences by offering powerful and intuitive abstractions.” Armed with lessons gathered over a 15-year journey with WSO2, I am excited to guide us towards a future filled with promise and innovation.

Though I haven’t elaborated on the exceptional technology we’ve developed and the global transformation it’s spurring — already well-proven in the marketplace — I’ll refrain from extending this blog entry any further.

The business world can be unpredictable, and who knows, I might not hold this position tomorrow. Regardless, this blog will remain a testament written in good faith to my journey and experiences thus far.

With passion as our compass and agility as our guide, we continue to innovate, touch lives, and shape culture — one line of code at a time.

Celebrating a culture of Mastery, Autonomy, and Purpose (I’m repeating this), WSO2 is constantly evolving. If you’re inspired by my journey and keen to become part of this family, I encourage you to explore WSO2 career page.

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Humanizing Technology | Architecting Transformation | CTO at WSO2, Inc. | @asankama | Infodoodler