Essays

Long-form pieces to help me make sense of and shape the world.

Redefining the Digital Value Chain for Multi-Brand Retail

Published on December 4, 2024 · 11 mins
Over the last couple of years, a lot has been written about the rise and fall of Digitally-Native Vertical Brands (DNVBs). These players vowed to eliminate the middleman and sell their products exclusively online, seizing an incredibly profitable arbitrage opportunity that revolved around cheap advertising and meager interest rates.

Digital Product Passports and Retail’s New Growth Opportunity

Published on July 24, 2024 · 6 mins
With the Ecodesign for Sustainable Products Regulation (ESPR) becoming effective on July 18, 2024, Digital Product Passports (DPPs) are now set to become a reality in the European Union within the next 2-3 years.

Span of control

Published on June 10, 2024 · 5 mins
If you’re a Dune fan, you’ll probably be familiar with the Bene Gesserit’s agony box. If you’re not, here’s a primer: early in the story, a young Paul Atreides is forced to choose between death or sticking his hand into a mysterious box—a box which, as he quickly discovers, causes excruciating pain, but will at least allow him to live. It’s a powerful scene, and one of those rare cases in which the movie lives up to the book.

Holding the space

Published on April 18, 2024 · 6 mins
(Today, we’re starting with a bit of a detour. I promise we’re still going to talk about commerce eventually. I just need to set the scene before getting there.)

The Ultimate Guide to E-Commerce Loyalty Programs

Published on March 20, 2024 · 15 mins
In the last few years, customer acquisition has become more challenging and expensive for direct-to-consumer (DTC) brands due to App Tracking Transparency, increased competition, and inflationary pressure. With Chrome deprecating third-party cookies in late 2024/early 2025 and the resulting “signal loss,” marketers expect campaign performance to take another hit, driving Customer Acquisition Cost (CAC) further up.

The collapse of commerce

Published on March 20, 2024 · 5 mins
I am sending this to you on the fifth day of a hayfever case that’s not serious enough to keep me in bed, and yet serious enough to annoy me beyond measure. In any case, it did put me in a very reflective mood. So much so, in fact, that the thought I want to dissect today is more of a meta-analysis than a thing in and of itself.

The Web3 rightshifting

Published on February 21, 2024 · 8 mins
The last time I wrote about retail x Web3 in this newsletter was almost a year ago. Back then, my thesis was that there are only two types of retail brands that can successfully build in Web3:

Maslow and brands

Published on January 24, 2024 · 6 mins
Those among you who’ve been following this newsletter for a while know it’s more of a brainstorming exercise than a “grownup” marketing initiative. I often use these emails to chip away at rough concepts until they start to make sense—or until they fade away in the endless void of things that sound very exciting in my head but utterly idiotic when I spell them out loud.

Agency, deconstruct thyself

Published on January 10, 2024 · 6 mins
I’m not usually one for predictions, but here’s something I’m bullish on: over the next four to five years, the e-commerce agency blueprint as we know it today will become obsolete, at least for the majority of small-to-midsized brands—let’s say anyone doing less than $150M/year.

Apology of the regulator

Published on December 13, 2023 · 6 mins
Three things that I love, in no particular order: countries that are both very cold and very sunny, Donald Duck impressions (especially if there’s a puppet involved), and e-commerce regulation.

The curation opportunity

Published on November 29, 2023 · 6 mins
In systems theory, a balancing feedback loop can be found wherever two mechanisms compensate each other. The classic example is a thermostat: when the temperature in the room drops below or above a certain level, your thermostat kicks in and brings the temperature back to your desired target.

Outage outrage

Published on November 15, 2023 · 5 mins
If you’ve been following us for a while, you know that we’re not the ones to sing Shopify’s praises when they’re undeserved. In fact, we have been quite critical of Shopify’s strategy in the past—back when that strategy implied the existence of a single, obviously correct way of doing things, and that anyone who ran their business differently didn’t know any better.

All hail the superapp

Published on November 2, 2023 · 5 mins
In case you’re not familiar with the term, a superapp is pretty much what it sounds like: an app that does it all. The concept of a superapp was theorized a long time ago, when a handful of tech startups started eating the Internet, M&As were abundant, and perhaps we were all more optimistic about the future.

Rise of the cultural brand

Published on October 18, 2023 · 3 mins
Lately, we’ve been chatting with a few current and potential clients about the role and future of DTC in a world that’s increasingly omnichannel and, dare we say, not DTC-centric anymore.

Beauty and the Beast

Published on October 4, 2023 · 3 mins
It’s time to get weird.

The eCommerce rat race

Published on September 6, 2023 · 2 mins
If you’ve been following e-commerce news lately and your head is spinning, you should know it’s not you—it’s them. The stack of press releases keeps growing by the day. So, just like we spent the last newsletter talking about Shopify’s SMB-vs-enterprise strategy, we’re spending today’s newsletter looking at the broader e-commerce technology landscape.

The Shopify play

Published on August 23, 2023 · 4 mins
Over the past weeks and months, we’ve had many interesting chats with clients and industry practitioners about Shopify’s strategic direction. There seems to be a lot of curiosity on the topic, so we felt this would be a good time to publish our thoughts and try to draw some conclusions together. Lay back and get your coffee, because there’s a lot to say here.

Members only

Published on August 9, 2023 · 2 mins
When it comes to customer loyalty, most brands have a very transactional mindset: whether it’s through cashback loyalty programs or discounts, the default approach is to buy your way out of the problem. That shouldn’t come as a surprise in an industry where paid social was—for a very, very long time—the one and only channel for customer acquisition.

Why Memberships Are The Future of Customer Loyalty

Published on August 2, 2023 · 12 mins
When it comes to customer loyalty in DTC, two strategies dominate the industry: subscription business models, where a consumer commits to a recurring payment, typically in exchange for a discount, and loyalty programs, where a consumer receives rewards–most often in the form of cashback–in exchange for performing specific actions, such as completing an order, referring a friend, or talking about a brand on social media.

Media x commerce

Published on July 10, 2023 · 3 mins
Last week, Liquid Death launched Greatest Hates, Vol. 3, a full-length album produced entirely out of hater comments. The tunes are available on streaming services and vinyl and, for one song in particular, the Liquid Death team went so far as producing a music video. Some of our team have been listening to the songs on repeat for a whole week now.

Building Content Infrastructures for eCommerce Brands

Published on June 26, 2023 · 12 mins
With unlimited digital estate, DTC brands can tell their stories, announce, entertain, educate, and keep their name front and center in customers’ minds, all of which is very hard to do in the limited shelf space afforded by wholesale partners. Now that even die-hard digitally-native brands are going omnichannel in pursuit of reach and profitability, it’s paramount to double down on the exclusive capabilities of each channel to create complementary experiences—for DTC, content is one of the most obvious levers to pull.

The playbook delusion

Published on June 26, 2023 · 3 mins
A few days ago, some of our team had the pleasure of chatting with the CIO of a large European brand—large, as in, a little short of €1B in revenue last year. We ended up talking about technological innovation in retail and how the narrative has changed over the previous years—a change that was most definitely accelerated by the sharp increase in OpEx for most brands. The conclusion was that we’re an industry that loves a good playbook.

Supercharge Your DTC Growth with Product Management

Published on May 24, 2023 · 10 mins
The modern direct-to-consumer brand has potential access to a plethora of information about their customers: post-purchase surveys, CSAT scores, site analytics, A/B testing, market research… Often, it can all be a bit too much, with brands not being sure how to use this information in a structured and strategic way to scale their business.

Scaling DTC Brands Through Product-Led Growth

Published on April 27, 2023 · 9 mins
With the rising cost of advertising and inflationary pressures making it hard to acquire, activate, and retain customers profitably, direct-to-consumer (DTC) brands are increasingly looking for ways to lower operating costs and scale more efficiently. This often takes the form of wholesale partnerships or marketplace expansions, which allow brands to tap into existing audiences and offload last-mile distribution.

How to Make Your E-Commerce A/B Tests Useless

Published on March 29, 2023 · 13 mins
In our latest article, we wrote about the value of A/B testing (also referred to as “split testing”) and how eCommerce brands can set up and scale an effective A/B testing strategy. By getting the fundamentals right, brands can use A/B testing to generate unbiased, data-informed market insights. Large brands often run tens of experiments at any given time and use the results to directly inform their product strategy.

eCommerce A/B Testing: Strategies for Success

Published on March 7, 2023 · 13 mins
eCommerce brands have a variety of techniques at their disposal for understanding their customers and optimizing their KPIs: most of these techniques have been borrowed from modern product management practices and can be directly applied to eCommerce–A/B testing is one of these.

The GTDT Model for Intentional eCommerce Personalization

Published on January 3, 2023 · 10 mins
With 9 out of 10 online shoppers stating that they want retailers to offer recommendations based on their interests, and considering the vast amount of data and technology brands now have, there are few excuses not to have a personalization strategy in place. eCommerce personalization is proven to increase conversion rates, customer retention, and lifetime value, creating a virtuous cycle that can turn your visitors into loyal customers.

The Feedback-Centric Organization

Published on November 16, 2020 · 9 mins
Let’s consider two engineering managers, John and Jane. They have the same seniority, they both work on similar projects in similar conditions and their teams are both terribly smart.

The Transformative Nature of Ownership in Engineering Orgs

Published on April 30, 2020 · 12 mins
During my career, I’ve had the honor of observing and being part of tens of engineering teams as a consultant, IC and manager.

Using RFCs to Drive Organizational Change

Published on January 9, 2020 · 9 mins
Once the number of decision-makers in a company increases, it becomes increasingly more difficult to gather feedback and get stakeholder buy-in on organization-wide changes and policies.

Coach Them Until It Hurts

Published on September 29, 2019 · 4 mins
“I think I can run the demo on my own, you don’t need to be there.”

Evolution Techniques for RESTful APIs

Published on February 27, 2019 · 6 mins
This is a follow-up to UIs for Machines: Design Principles for HTTP APIs. One of the principles outlined in the original article is Evolution, and it suggests that developers should strive to keep their API relevant and up to date without sacrificing usability and backwards compatibility.

6 Design Principles for Your HTTP APIs

Published on February 13, 2019 · 8 mins
There’s no debate around the fact that good API design is an art. When we stumble into a properly designed API, we can feel it. Just like good visual UIs, good APIs are not just beautiful, it’s functional and it saves everyone’s time. With this mind, it’s not a stretch to say that APIs are, in fact, UIs. They’re not just meant for machines either: since there are people programming and using those machines, creating an API that users are delighted to interact with is a deliberate choice of its development team, and one we ought to make.

Fail Better: Turning Software Errors into Documentation

Published on January 21, 2019 · 7 mins
The open-source community has done a great job of promoting good documentation as a necessary trait for the success of a software project, whether it be a utility library, a larger framework or a standalone program.

My 2018 Annual Review

Published on January 7, 2019 · 7 mins
2018 has had lots of ups and lots of downs for me. I’ve never published an annual review before, but I thought it would be fun to try.

March Reflection

Published on August 20, 2018 · 7 mins
I have not written anything for the past three months. There are various reasons for this, but mostly I’ve just been completely out of energy. A lot of stuff has happened which I was absolutely unprepared to deal with.

The Three Tenets of API Design (3/3): Respect REST

Published on January 22, 2018 · 10 mins
This is an extract from my book “API on Rails”.

The Three Tenets of API Design (2/3): Embrace HTTP

Published on January 15, 2018 · 11 mins
This is an extract from my book “API on Rails”.

The Three Tenets of API Design (1/3): Be Boring

Published on January 8, 2018 · 4 mins
This is an extract from my book “API on Rails”.

People vs Process

Published on December 25, 2017 · 8 mins
When you think of a startup, processes are not exactly the first thing that comes to mind. Instead, you envision an environment where people are trusted to always do the right thing, where checklists are scoffed at in favor of a natural feeling for what needs to be done, where failure is viewed as something that happens every day because that’s how things work.

The One Skill You Need in Order to Thrive in Life, at Work and Everywhere

Published on December 18, 2017 · 11 mins
Do you know the difference between the top players and those who gave up? I can tell you it’s not talent — how many people do you know who are extremely talented and waste every single day they spend on this Earth? It’s not access to opportunities, either — how many masters have made it despite coming from a poor household, or even a poor country?

The Changelog-Versioning Revolution

Published on December 11, 2017 · 8 mins
At Batteries911, the BE team has the responsibility of maintaining an API that is consumed by 3 (soon 4) different clients: two iOS applications and a SPA. This means that, whenever we introduce a change, we need to be absolutely sure that the change is either non-disruptive or, if it is, that it was communicated properly and coordinated with all the FE teams.

In Defense of Human Testing

Published on December 4, 2017 · 8 mins
Developers are hackers — good developers are, at least.

The Hype Cycle: What It Is and How to Game It

Published on November 27, 2017 · 8 mins
As a CTO, one of my responsibilities is to constantly research technologies that will enable my company to stay ahead of the competition. It might then come as a surprise that, for the longest time, I’ve had a lot of trouble studying and understanding new tools and languages.

Everything Is an Investment

Published on November 20, 2017 · 6 mins
Managing money is hard, everyone knows that. It doesn’t help that no one ever teaches you how to manage money, which leaves you with few ways to learn. One of them is squandering your entire first year of earnings — that makes you realize that you need a crash course in money management.

I Want to Quit

Published on November 13, 2017 · 3 mins
I want to quit. For the past two weeks, every morning I have woken up with the same thought in my head. “I want to quit.” Every. Damn. Morning.

The No-Bullshit Guide to Hiring

Published on October 11, 2017 · 21 mins
When I started on my first position as a manager, I had no idea that one of the most complex, fascinating and intimidating things I would ever do was going to be hiring people. Then again, this was but one of the many surprises.

Leadership: Five Lessons in Five Months

Published on September 5, 2017 · 8 mins
I spent the first five years of my professional career working as a software developer and deriving great joy from it. Sometimes I worked on my own, sometimes I worked in teams, but I had never considered moving into a leadership position. In my mind, a leader was someone who delegated work to others while reaping the benefits.

The CTO Manifesto

Published on May 5, 2017 · 2 mins
I published my personal manifesto in 2014. I put a lot of work into it, so much so that, three years later, I am still living by those values.

The Superhero

Published on May 1, 2017 · 5 mins
Today’s story is about awesome customer support and how it can make someone’s day (mine, in this particular case) awesome.

BSBS: Building Solid Billing Systems

Published on November 29, 2016 · 9 mins
One of my first tasks at InterConn was to set up a billing system. We did not have many requirements, so we evaluated a lot of SaaS options. Now, there’s no shortage of billing SaaS — unfortunately, though, none of them could handle our particular rated billing process, except for JBilling, which was awesome but definitely out of our budget’s reach (in retrospect, Stripe might have been a good solution — I just didn’t know about it at the time).

Composizione

Published on February 2, 2016 · 2 mins
Il mare.

25 Things I Learned on Software Development

Published on September 20, 2014 · 15 mins
I wanted to put together some tips about software development, customer relationships and learning in general, so I wrote this in the hope that it might prove useful to someone else. Very little of what’s written here is new stuff, but I liked the idea of having it all in one place, along with the reasoning that led me to accept it and make it a part of my methodology.

Executing Sidekiq Jobs Immediately

Published on September 13, 2014 · 2 mins
When you’re working on a side project and you don’t expect to get a cent out of it, you want to keep operational costs to a minimum.

Testing Active Record Concerns with RSpec and Temping

Published on August 23, 2014 · 3 mins
I won’t even attempt to discuss the utility of concerns. To some people, they’re a dangerous way of hiding dependency and just syntactic sugar for include/extend. To others, they should be used whenever possible. To me, concerns are just a tool. I try not to use them too much, but I don’t freak out when I see them either.

:extend’s Gotchas

Published on July 5, 2014 · 5 mins
LESS has a useful feature called :extend. Basically, it extends (d’oh!) the given CSS selector to match the current element.

Do Reinvent the Wheel

Published on April 17, 2014 · 3 mins
“Don’t reinvent the wheel.” If you’re a developer, chances are you’ve heard this a hundred times. It’s one of the foundations of the hacker culture. You shouldn’t waste your time and energy building what already exists—instead, it’s much better to improve it (if possible).

Meditate with Purpose

Published on April 6, 2014 · 3 mins
I started meditating for a practical purpose: it had been quite a long time since I was able to get a full night’s sleep. Without any apparent reason, I would keep rolling in the bed, worrying about how I’d feel in the morning. I was exhausted, falling asleep on the bus and, in general, whenever I was able to sit. I became nervous and aggressive towards other people—people who were trying to help me.

Be Childish

Published on April 3, 2014 · 2 mins
Everybody starts to seek a meaning for their life at some point. It’s an instinctive and natural research: we need to know if there’s a reason for our existence, we need a path to follow, we need an object to accomplish.

The Imperative Manifesto

Published on March 19, 2014 · 2 mins
A few months ago I read somewhere that it’s important to have a personal manifesto, so that you never forget who you are. Personally, I think it’d be quite hard to forget who I am, but the idea was fun so I did it anyway. This is what I came up with.

The Evolution of an Introvert

Published on March 16, 2014 · 6 mins
I’ve been an introvert for the past sixteen years. As a kid, I was shy and self-centered. Eventually I outgrew my shyness, but I’ve never had any need for human interaction. I’m not a misanthropist — most people find me quite funny and approachable, actually—but still, I’ve always preferred machines to humans. Not because they’re more predictable or because they don’t judge me or whatever. I just do.

UI Components in Rails

Published on December 24, 2013 · 5 mins
In the process of developing my CRUD application, I eventually decided that I needed to DRY up my code and build a set of reusable UI components. Those would be things like toolbars, attributes lists and similar.
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© 2025 Alessandro Desantis