Remote First — This is Water

tjmahony
The Startup
Published in
6 min readFeb 14, 2020

You are probably reading this from a desk, in an office, in close physical proximity to colleagues who, like you, will spend ~54.2 minutes getting to and from work today.

Photo by Iwona Castiello d'Antonio on Unsplash

However, in the very real and near future, this will not be the case for 20%+ knowledge workers, because they’ll be working remotely from somewhere that isn’t called HQ.

I’m eager to see what new big companies spawn out of the problems remote companies, workers, and general society will face.

In 2017, the US Census reported that 5.2% of US workers were remote. When that increases 20% and beyond, it will fundamentally impact company management, talent mentorship, retail markets, real estate, and a number of ancillary markets that have historically relied on humans traveling to commercial centers to go to work.

“The remote movement might invent a new form of community centers or coffeeshops, drive population growth to rural areas, evolve into the savior of the retail apocalypse or even reinvent offices as show-rooms instead of places of work.” Andreas Klinger, Remote First Capital

Before we get into refactoring our commercial infrastructure, there is one key milestone: we have to get more comfortable with scaling remote companies.

Plenty of literature exists on why companies are going remote, and a healthy trove of remote how-to guides are available to help companies learn from one another. So it’s no surprise that we have seen an influx of companies that are committing to building remote-first teams — we at Accomplice have even funded a few (Postscript.io, User Interviews, Creative Market). And, in our market checks, there is an NPS of (roughly) 99 for those who have chosen to go remote.

The BIG BUT…..

BUT, from my (non-exhaustive) market checks, the only material transactions of remote-first companies have been GitHub->MSFT and the Elastic IPO. Moreover, to date, there have been no material transactions of “fully remote” companies.

One would assume I’d be nervous that no one is buying remote companies when three of my most recent investments are fully remote, but fear not: soon, we realize ‘this is water’.

“Humans currently don’t know how to do remote work. We don’t. We grew up in classrooms. Remote is unnatural to our instincts — our need to see and be close to people. Thus, this can’t be approached by thinking about how to make horses run faster. Instead, we should focus on ‘what is an automobile’. -Hiten Shah, CEO & Co-Founder, Fyi

Solved and Unsolved

Liv Benger and I spent the last month interviewing key figures and Head People Officers from companies across the remote spectrum. Far from an exhaustive sample, but directionally sound for our purposes.

Participants: GitHub, InVision, Webflow, UserInterviews, Zapier, Close, HelpScout, Postscript, Fyi, Creative Market, BuySellAds, Remote First Capital

We compiled our notes and summarized the key takeaways.

The communication stack is generally solved

Between chat (Slack), email, video (Zoom), documentation (Notion et al.), storage (Dropbox et al.), collaboration (Airtable, cloud docs, etc), prototyping (InVision et al.), repos (Github et al.) and project management (Trello et al.), there isn’t a material gap in the stack.

Companies will leverage and manage these tools in different ways. Some require everyone to always be on video (“one face, one voice”). Others have strict rules around notifications and status settings. Ultimately, the gap is less in the tooling and more in the human behaviors that surround the tooling.

“Success in life is highly dependent on strong communication skills. Multiply that by 20x in a remote company.” Sam Tilney, Director of Operations, BuySellAds

Loneliness is not solved

It’s real. The top brass do not feel it that much, but the rank-and-file do. Culture apps like Donut help, but they don’t fully resolve the lost dynamics of physical proximity. Software can’t solve everything.

Remote onboarding is a challenge

Preparing someone to jump in to a remote org and feel like they i) belong ii) know what’s going on iii) can contribute in a reasonable timeframe, is a different challenge compared to on-prem.

Onboarding is a pain. For every hire, you need to have every minute of the first four weeks fully booked, coordinated between team members, explicit instructions and check-ins.” Ryan Burke, SVP International, InVision

There are some new solutions focusing on this (ex. Ahoy), but for the most part, it remains a bespoke endeavor that is critically important and under resourced.

Recruiting is more than solved

When pressed about the challenges of recruiting, there seem to be few. The quality of life benefits and unrestricted geo fence is consistently highlighted as a core asset.

“By creating remote work opportunities, companies give themselves a unique advantage to attract and retain the best, most diverse talent in the world.” Leah Knobler, Director of Talent, Help Scout

“Requiring proximity to a physical location inherently conflicts with a commitment to the best and the brightest — not to mention diversity and inclusion.” Merritt Quisumbing Anderson, Fmr. Employment Counsel and VP of Employee Experience & Engagement, GitHub

Most recruiting managers cite traditional resources (eg. LinkedIn, AngelList, etc.) as their primary sourcing platforms. Most have tried ‘remote centric’ marketplaces with varying degrees of success. WeWorkRemotely and Remotive were specifically highlighted as impactful resources.

When it came to recruiting, the priority was more on qualifying candidates versus sourcing. In fact, more than half of the participants noted the willingness to pay for a mini project. All of which was conducted…. wait for it… remotely.

“If the timeline allows, we often try to find a way to host a two week, paid trial period for both parties to confirm it’s a match. At a minimum, during the interview process every candidate works through a take home exercise that simulates a real life work project.” Mary Hartberg, Director of People Ops, Close

Visibility, at scale, is not solved

All orgs go through growing pains. The code base grows out of control. Roles and responsibilities get fragmented. Old guard vs. new guard. Politics emerge. And so on. These challenges are arguably more difficult to manage in a remote environment.

“Remote is tricky to scale. You have to be continuously mindful that what you’re doing now, might have started breaking three months ago. ” Mark Frein, CPO Lambda School & Fmr Chief People Officer, InVision

It’s above my pay grade to decouple the complexity of organizational management at scale, but when boiled down, ‘visibility’ is the core challenge. Who is doing what? What’s expected of me, him, her, us, them? Where are we, as an organization? What’s the priority? What did we kill? And so on.

“Everything must be intentional. The default status of remote culture is erosion, so you must continuously tend to the garden.” Heather Doshay, VP of People, Webflow

Software alone will never fix organizational complexity, remote nor on-prem, but it will help. Stripe Home has been a well documented tool that helps Stripe centralize organizational visibility. We imagine someone will productize this concept to power internal communications, horizontal information exchange, social engagement and, of course, people finders.

Fyi* provides another interesting angle on visibility. Focusing on the status of active team documents begins to create a team member’s “work news feed”. We consume social feeds and news feeds, but beyond our inbox and endless Slack channels, we don’t have an organized, intentional, work feed.

*Disclosure: I’m an angel investor in Fyi.

What we know:

  • Remote work will continue to grow in popularity.
  • New solutions will find their way to market.
  • We will get better and more comfortable at scaling remote first teams.
  • Increasingly larger remote companies will IPO or be acquired and this will feel like water.

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tjmahony
The Startup

Founder+Partner @Vinyl Capital | Board Partner @Accomplice | CEO/Founder @FlipKey | Original @Compete | Friend to many | Dad of 2 | Husband of 1