Building Bollingen Tower

Why Stitch Fix style curation can help make distributed work actually work.

In an era of endless choice, curation reigns supreme.

Almost a decade ago, I tried Trunk Club on the recommendation of a friend and loved the experience. In the years since, the market for trusted personal style support has exploded, highlighted by Stitch Fix who has paired data science with expert human curation to build a publicly traded company worth well over $2b.

There is an powerful “always on” feedback loop to the Stitch Fix experience. With each successful match, the client spends more time in Stitch Fix curated clothing and is constantly generating positive associations with the service — each glance in the mirror or comment from a friend. Pair that client-side feedback loop with the data loops Stitch Fix benefits from by combining client provided preference and size information with merchandise data and the service becomes highly personalized and more successful over time.

This graphic from the company’s S-1 conveys this value loop nicely.

This type of curated experience, enabled by empowering trusted experts with data and technical tools to amplify their impact, has spread effectively to other areas., who raised its Series A round from Kleiner Perkins, Khosla Ventures, and other top firms is providing a similar experience for health and wellness — giving each member a dedicated trainer who is able to leverage the data and content provided by the user (via videos, chat, and an Apple Watch) along with trainer-facing tools provided by Future to maximize effectiveness.

While both fashion and fitness represent large areas of consumer spend from a time, attention, and money perspective, many important parts of life remain unimpacted by this form of curated empowerment.

One area that stands out, and is currently top of mind as fears of pandemic permeate the global psyche is distributed work, where the millions of people who are now spending at least a part of their time away from a co-located office are vastly under-equipped to deal with the different emotional and physical requirements posed by working in a remote setup.

As you continue reading through the post, I’d love to discuss with you here in this thread on Twitter — your experience with remote work, what you’re optimistic about, what’s lacking.

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Building Bollingen Tower

When Karl Jung, the Swiss psychologist, needed to get deep work done, he would go out to Bollingen Tower, a stone house without electricity or running water he built by the lakeside outside of a small village in the countryside beyond Zurich.

For J.K. Rowling, it was the Balmoral Hotel. And for Mark Twain, it was a physically isolated cabin on the other side of his large property.

This is according to author Cal Newport, who talked about the value specific physical spaces have as enablers of deep work in this great podcast from NPR — but the lessons about the impact of physical space on our effectiveness goes well beyond deep work.

A well-designed co-located office (of which there also seem to be exceedingly few…but that’s for a different post) offers workers spaces to get all sorts of work done — collaborative space, deep work space, task focused space.

Distributed work takes this to the next level and creates the opportunity for individuals to curate a set of physical environments perfectly tailored to maximize their own effectiveness.

In Stitch Fix terms, it can be like going from shopping at a lowest common denominator department store to having the perfect outfit pressed and ready every day of the week.

Of course, this is generally not the case.

The current distributed work paradigm assumes that everyone is their own Stitch Fix expert and is able to decide for themselves how they work best — when, where, how they should be working in order to cope with the entirely different set of emotional and physical challenges posed by remote work.

It requires us to be part psychologist, part real estate agent, part architect, and part personal assistant. I’m certainly not all of those things and I’d wager most other people aren’t either.

Stitch Fix for Distributed Work

One valid criticism that the distributed work trend often receives is that there are too many companies focused on the “easy” stuff — building a new collaboration product, for example — and not enough time laying down the difficult infrastructure needed to make the situation workable for a significant enough number of people. This lack of infrastructure will likely rear its head over the coming months as more and more companies struggle to maintaining employee productivity and happiness in a shift to a new remote paradigm.

Designing personalized plans for how we access, design, and utilize physical spaces to make ourselves happier and more productive workers is a foundational piece of the distributed work puzzle — alongside things like benefits (ex. Catch) and insurance (ex. Alan) — that has the potential to accelerate adoption and drive real business value for companies who will be much better equipped to attract and retain talented people.

This is the Stitch Fix client journey as described in a recent investor presentation.

..and this is how they visualize their personalization model.

It is reasonable to think that the journey and model employed in the distributed work context would look similar.

Workers provide a broad set of data points that help their “Distributed Designer” understand their personality, how they like to work, and how different work related habits and environments have helped or hindered them in the past. Also taken into account would be the person’s role at the company. Are they a developer mostly focused in individual work or a salesperson who is often on the phone?

That data could then be paired with information about the space available at that worker’s home and could also incorporate a local database of partners — coworking spaces, libraries, cafes, parks — to help the worker understand additional options available to them. In addition, the data would be used to best match the individual with the tools necessary to get their job done most effectively.

And to wrap up the experience — similar to Stitch Fix — a worker could have the ability to test out multiple options, both for their at-home setup and how they work around the city they live in before selecting a final arrangement.

Building Distributed Company Culture (in Real Time!)

I’ll conclude by pulling things up a level, as any company hoping to successfully implement a new tool focused on distributed work — whether a new chat app or something akin to what I described above — must first get its foundations right.

Making sure those cultural foundations are solid when making a transition to distributed work on the fly — as many companies are being forced to do now as a result of COVID-19 — is especially challenging.

A company’s strategy and the tactics it deploys in support, no matter how well conceived, are useless without an aligned culture through which to implement said strategy. Company culture is the bridge between theory and action. It is the operationalization of a company’s values and it expresses itself as a set of frameworks that a company uses to make decisions under uncertainty.

While every company must be intentional about the culture it is developing from the outset, companies starting out with a distributed team (or forced into a rapid transition into one) must pay extra attention to developing a company culture that fosters transparency and collaboration.

For any company looking for resources to get started, I can’t recommend this syllabus on remote work from Holloway enough.

And to better understand the way that an effective distributed work culture maps to strategy, I recommend any company evaluating full or partial distributed team setups spend time learning about Gitlab and Zapier — who were both recently included in Wing VC’s Enterprise Tech 30, showing that the right alignment between strategy and (remote) culture can create truly venture scale companies.

Both companies have invested heavily in equipping their employees with the resources necessary to succeed in a distributed environment — from tools to information — and have seen that flow through to business results.

Zapier’s Jobs page provides an abundance of great information that can serve as a starting point for any company looking to make the leap. My favorite post from Zapier, to bring it back to the initial topic of this article, is this one sharing photos of the remote setups of various team members.

And the Gitlab “Guide for Starting Remote Work” is perhaps the best holistic primer for both companies and employees pushing forward with a distributed arrangement.

Backing Bien-Être

As someone has now spent around half of my career in remote work settings or in companies with distributed teams, I have first hand experience with the challenges of finding the right physical environment for success and managing one’s own productivity (and that of a team) without the benefit of in-person context and feedback loops.

Yet despite the despite these challenges, I am a firm believer that one of the key drivers of improved health, happiness, and opportunity will be the embrace of remote work by more and more companies of all sizes and look forward to meeting more companies building the “hard” solutions to elevate the remote work experience.

I’d love to discuss this post with you here in this thread on Twitter — your experience with remote work, what you’re optimistic about, what’s lacking.

Discuss on Twitter →