On the origin of Darwin CX and the end of dead letters

Omri Tintpulver
Evolve CX
Published in
8 min readMay 19, 2020


Unhappy fortune! By my brotherhood,
The letter was not nice but full of charge,
Of dear import, and the neglecting it
May do much danger.
- Shakespeare’s Romeo and Juliet, Act 5 Scene 1

The idea for a startup surely begins long before incorporation. Darwin CX was formed on November 22, 2017, yet my personal journey to co-found it began two decades and two regrets earlier. Co-founders each have their own origin story. This one is mine, which I share now on the eve of the company being acquired.

Dead letters are messages that, for whatever reason, don’t reach their intended destination — a tragic symbol of failed communication and disconnection. Postal systems have dedicated dead letter rooms to process undeliverable mail. Many of Shakespeare’s plays pivot on a dead letter, the most famous being the ill-fated one that led to tragedy in Romeo and Juliet. Friar John was unable to deliver the letter because (all too familiar to us in the time of Covid) he was quarantined at home due to the plague. Since my early reading days, these missed connections have drawn my attention — a fifth business often off to the side and out of sight — yet critical to the outcome.

If we measured the number of dead letters from the start of letter writing and postal delivery to just before the modern internet, we would see a steady and predictable climb. Today, the dreaded dead letter extends into the digital realm. There’s more data than ever and more of that data is sent and received without humans involved, from one system to another system, sine hominum. Due to the internet, digital disruption and AI, the annual increase of dead letters is exponential.

From society to commerce to our personal lives, how we confront and mitigate dead letters is paramount to our success. Charles Darwin’s On the Origin of Species makes this existential observation at the genetic level. Genes that fail to transfer from one generation to the next are a form of dead letter. Successfully preventing dead letter disconnections is the difference between a species’ evolution or extinction; between a literary comedy or tragedy. This is why one of the core elements of the Darwin CX platform is a dead letter queue.

Software systems generate an incredible amount of intra and inter communication. Take a simple online order, for example. From the moment the customer hits the submit button, tiny messages are sent to the payment processor, to the databases that store the details, back to the customer to say thank you, as well as to various forms of tracking, logging, etc. If any one of these messages fail to deliver, various degrees of deficiency can occur, from poor customer experiences to preventable and expensive calls to the call centre.

A dead letter queue is a catch-all for the tiny messages that fail to deliver. In the best cases, an automatic retry achieves delivery. And in the worst cases, a human reviews, triages and resolves the misfire. Either way, a disconnection is prevented and, like Lazarus, the dead letter is reborn.

The concept of dead letter queues, however, goes beyond tools that function as message brokers, such as Amazon’s Simple Queue Service, Apache’s Kafka, RabbitMQ, Sidekiq, or similar. Fundamentally, ending dead letters starts with a mindset — shared by each person on a team — that adds rigor and hardened processes across the entire company, including operations and the tech stack. The proper mindset begins with seeking and anticipating dead letters, everywhere.

Three years into my first job after grad school, I was fortunate enough to work for an owner who despised dead letters. Jim Shenkman taught me how to identify disconnections in all things business — especially the ones that lived in the periphery, the hardest to see. This is a drawing we worked on one inspirational Winter weekend at his cottage, a map that would be the foundation of a corporate connection system we’d spend the next many years building with some incredible developers (Eddie Ting, Bing Jiang, Farhan Quadri, Rob Chamberland, Adam Prime and others).

After a company-wide vote, this system was christened the Matrix. Its aim was to bridge disparate data systems into a single browser view and by doing so transform the company’s ability to make informed and timely decisions. Sounds pedestrian these days, but in 1999 it was rare and risky. Bill Gates had just published Business @ the Speed of Thought: Using a Digital Nervous System and it prophetically matched our intent. Incidentally, this was also the year that Salesforce was born.

Which brings me to my first regret. It was the dotcom boom and we had the ingredients to become our own Salesforce. Sadly, I wasn’t aware of the dotcom potential until many years later, looking back. And in that 2008 reflection, the regret fueled a redemptive effort to extend the Matrix to other companies.

Luckily, the new owner, Russell Goldstein, had acquired the company partly because of the Matrix, and, like Jim before him, felt the same way about dead letters. Is it possible that all successful media owners despise dead letters? There must be a Harvard study that confirms the point.

Together, in no time at all, Russell and I sold the Matrix. To one other company. And it was essentially and almost immediately an operational bust. The Matrix — though still utilized and valued two decades later — had been so customized for its original company, that there were no economies of scale and, sadly, no margins.

Our frustration was compounded by the fact that the market was ripe for the taking. The gorilla incumbent, CDS Global, had yet to develop a browser front-end and their database architecture was sufficiently hampered by its legacy roots that a couple of years earlier, only a month into trying to integrate their circulation system into the Matrix, we spent not an insignificant sum to terminate. Instead we built our own circulation system.

By 2010 it was clear where we’d erred with trying to extend the Matrix to other companies. This called for a reset. We needed to start over, raise capital and invest heavily to build a truly multi-tenant SaaS equivalent. Thus, I crafted my first pitch deck, delivered my first pitch, and impressively flopped. Regret number two.

As this slide demonstrates, NewCo was attempting to be too many things to too many people. It wasn’t until five years later, in 2015, that two pivotal lunch meetings would begin the journey to a truer understanding of the problem that NewCo could solve.

The first meeting was with Laas Turnbull, a forward-thinking media exec and born leader. The second was with Michael Smith, a successful entrepreneur and technologist.

Laas Turnbull and Michael Smith

We did not realize then that two years later, while working together at ZoomerMedia, we would found Darwin CX (coined by Laas, as he so often finds the right word at exactly the right moment) and finally, what had been missing in the first pitch would come into focus: a roadmap for the end of dead letters and the beginning of customer experience orchestration.

Customer experience (“CX” for short) is the zeitgeist of marketing circles, and rightly so, putting the customer at the center makes a lot of sense. The hardest part, however, is coordinating or orchestrating the customer’s experience from one part of your organization to the next. The goal of CX is to manage customer information so that it’s available to the right person or system at precisely the right time. Dead letters are the misinformation between customers, staff and systems. They exist in an inverse relationship to the goal of CX.

If you’ve ever been on hold with your cell phone company as they pass you from one well-meaning but unhelpful group to another that then requires you to start from the beginning — for the third infuriating time — then you understand poor orchestration, and worse, poor CX. That singular, though expansive, problem is what we zeroed in on.

The second pitch, seven years after the first, was to the ZoomerMedia Board and to its iconic CEO, Moses Znaimer. Unsurprisingly, Moses, having gone to Harvard, did not deviate from the imagined study on dead letters. But remarkably, he is also a master of letters. It took his trailblazing creativity and capacity for risk, along with the Board’s support, as well as a rare and lucky trifecta of co-founders, to sign the deal on November 22, 2017. And thus Darwin CX was born.

Moses Znaimer and me on November 22, 2017, signing the deal with Laas and Michael to start Darwin CX

Not six months from birth, our largest competitor, CDS Global, announced they were abandoning Canada. The upside/downside was that this forced us to evolve, quickly.

To help us, we received some invaluable guidance from veterans Scott Ray and Peter Allemang that resulted in, among other things, a methodology for prioritizing and staying focused. They presented a baseball diamond analogy: first base was “Real,” second base was “Cool,” and third base was “Strong.” Our job was to defer cool and strong until we were real. Although the path is never quite how you envision it, the company is now rounding third on its way to “Victory.”

Success begins and ends with the talent on your bus. The cliche is true. And for Darwin CX it was one incredible hire after another: Damir Lutvic, Ashlynn Whalley, Reena Rai, Adam Borg, Dave Garon, Zian Zhang (best interview, he came with handwritten notes upon notes and an app already built, we hired him on the spot), Sarath Madayil, Gavin Chen, Nathalie Halevi, Jonathan Kok, Jason Patterson, Praveen Lobo, Tina Nikou, Ethan Wallace, and Scott Montreuil. The team now stands fifteen strong, ready to take on the next stage in Darwin’s evolution, the next run around the bases.

And yet, we’re only in the second inning of customer experience orchestration — the plague of dead letters persists. Thankfully, it’s a great time to build, and perhaps, in concert with AI, their inexorable end is nigh.

Darwin CX is a Toronto technology company that develops enterprise software-as-a-service (SaaS) applications for publishers and membership-based organizations. Designed to replace the legacy technology that serves these industries, the Darwin platform supercharges acquisition and retention through customer experience orchestration, the conductor that keeps various departments and systems aligned on customer intelligence management. As customer expectations continue to change due to digital disruption, the subscription economy is expanding rapidly, doubling between 2000 and 2015 to $480 billion in the U.S. and Canada. Darwin has seized on this opportunity through three design principles that form the heart of the platform: user-centricity, seamless integration, and AI-powered expertise. Supporting that are a suite of tools for marketing (digital experience, customer insights, personalized marketing), commerce (omni-channel, order and data management, financial reporting), and fulfillment (customer support, direct mailings, data integrity).



Omri Tintpulver
Evolve CX

product + software architect | media exec @ Zoomer cofounder DarwinCX meshMD | cryptopunk #3390 | blockchain | gen art | shakespeare | golf