High Output Remote Management: What Works — and What Doesn’t

Each month at General Catalyst we host functional leaders from high-growth startups for a working session on an industry theme or shared challenge. Through an exchange of creative practices among New York’s most innovative technology executives, our goal is to move the collective ecosystem knowledge forward.

For our most recent session, Pascal-Louis Perez, former Engineering Lead at Square in New York, joined us in hosting CTOs and VPs of Engineering from local startups for a conversation around building and scaling remote engineering teams.

A self-described “entrepreneur and ‘type nerd,’” Perez is a Stanford CS grad, hailing from Switzerland who quickly has emerged as a rising star within the technology community. In his four years leading Square’s engineering efforts, he helped scale the company from 120 San Francisco-based employees to 1,500 employees across eight global offices, about a third of which were engineers. Perez was a key driver in this expansion, overseeing the opening of the company’s New York and Atlanta offices. Before Square, he was the founding Chief Technology Officer (CTO) of robo-advisor Wealthfront, one of the more recognizable FinTech companies of the decade.

Perez’s experience was complemented by a roster of prominent CTOs including Paperless Post CTO Tatum Lade, Meetup CTO Yvette Pasqua, ClassPass VP of Engineering Paul Twohey, Foursquare Head of Engineering Jon Hoffman, WayUp co-founder and CTO J.J. Fliegelman, former Tumblr VP of Product & Engineering Derek Gottfrid, former Birchbox CTO Liz Crawford, former Rent The Runway CTO Camille Fournier, Cymbal CTO Amadou Crookes, and SumALL CTO Todd Sundsted.

Here’s what these seasoned pros have found works — and what doesn’t — when building distributed teams:

  1. Some of the biggest challenges are logistical

The irony of a room full of CTOs complaining about the WiFi was not lost upon them, but it’s a real point of tension for a lot of companies. Dropping video calls, confusing audio bridge dial-ins, and kludgy screen sharing set-ups were familiar challenges among the group.

Understanding time zones is often one of the most overlooked challenges of managing a bi-coastal team, Perez says. It effectively cuts out three hours from the day, so you have a pretty short window for coast-to-coast meetings. Be sure to take local meetings in the morning or evening, and reserve this window for collaboration.

2. “Culture” isn’t just a buzzword, it creates cohesion.

To avoid a “second-class” citizen sentiment among the smaller offices, focus on cultivating an office-agnostic culture from the get-go, Hoffman (Foursquare) said. Of course, this easier said than done.

Source: Giphy (http://gph.is/1K43i8P)

Here are some of the ways the group recreates serendipity in remote offices: At ClassPass, nearly all meeting rooms have two displays so participants can screen presentations on one, and see the other meeting room on the second. At Square, the office has robots to effectively teleport remote employees to the office. In some ways, robots add to the serendipity. What’s cooler: Having your boss walk into a meeting? Or — Having your your boss walk into a meeting, as a robot?

3. Culture goes beyond hallway talk

Of course, there some cultural challenges not even a robot can fix. Some differences are simply unavoidable, like the lower growth ceiling for employees working in satellite offices, as Fournier (Rent The Runway) highlights. This matter of fact can affect the caliber of talent each office can attract. For companies that value internal mobility, prioritize making growth opportunities transparent and accessible across offices.

4. Embrace cultural and educational exchanges across offices

When the office headquarters has 600 employees and a remote office has 30, distinct cultures inevitably arise.

In an effort to embrace these differences, Square launched an ambassador program, which each week allowed an employee from any level or department to work in another office. The goal was to build awareness and empathy across offices. After a week in the New York office, an SF-based employee may realize ‘Conference room x isn’t good for scheduling web meetings because of the street noise’ or ‘everyone in the New York office sits at the communal desk, so it’s better to IM them than call their work line,’ Perez explained.

While the program embraced no-special-purpose travel, there was some loose structure around the trip. As part of the trip, ambassadors were expected to:

  • Hold court for 1 hour — Ambassadors were required to host a one-hour working session on a topic relevant to furthering Square’s business mission. This could take the form of a Q & A, a brainstorming session, or a presentation showcasing their team’s work.
  • Have fun — To encourage ambassadors to get to get to know their colleagues on different teams and offices, ambassadors were encouraged to organize a dinner or social event with co-workers.
  • Write a trip report — At the end of the trip, ambassadors had to write a report reflecting on what they learned during the trip. While the report itself wasn’t the most useful, it encouraged ambassadors to be thoughtful and proactive throughout the trip, Perez says.

5. As soon as one person is remote, treat the whole company like it is

“As soon as one person is remote, you have to treat the whole company like it is,” Pasqua (Meetup) says. Echoing this point, Gottfrid (Tumblr) stressed the importance of establishing structured processes from the start in order to maintain cohesion in the company. “You have to drop the ad-hoc really fast,” he says.

To provide structure to distributed teams, Fliegelman (WayUp) suggests clearly defining your company’s processes and values and making this information accessible to all employees. He points to GitLab as an example of a remote-only company that has uniquely leveraged transparency to build a culture. GitLab’s handbook is completely public (even to you and me!) and open-sourced, and includes everything from the company’s vacation policy to what makes a good blog post.

Other hacks the group have found effective include routine weekly reporting, encouraging video conferences over phone calls, and moving standing meetings to Slack.

5. Either make a commitment to be results-driven… or don’t.

If someone is productive but watches soccer half the day, is that okay?” Sundsted of SumALL asked. While the group laughed, it’s a valid question: Should an employee’s success be measured by only the results of their work?

This question becomes increasingly important when teams are distributed across offices, as a manager isn’t on the ground to oversee employees. While some managers adopted a “what-you-can’t-see-can’t-hurt-you” philosophy, others felt that having work-style policies are important to company culture.

What matters more is that you commit to having a results-driven-policy, or you don’t. Pasqua (Meetup) says. Clear expectations are one of the most important attributes of a productive organization.

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