3 rules for working remote, from Pleo's Jessie Scheepers

Lundie Strom, Wednesday April 3rd 2019

Last week on Tuesday, March 26, MEST Cape Town welcomed members of the community to join us for coffee and the first Community Conversation of 2019. We were excited to have Jessie Scheepers, Head of People at Pleo, in town from Copenhagen to lead an interactive discussion titled “Keeping Talent in South Africa: How to work internationally, from here.”

Jessie is a South African who has lived and worked across Europe, the Middle East, and Africa for several hyper-growth tech companies. Most recently, Jessie has been working with fintech company Pleo, building it from 50 to 170 people this year alone. She is passionate about finding and nurturing some of the world's top talent.

The Community Conversation began with some surprising statistics: 56% of startups globally outsource their work [source], and 30% of Silicon Valley jobs are done remotely [source]. It's clear that many companies around the world have begun to expand recruitment beyond their local talent pool.

With employees spanning nine different countries, Pleo is one of the startups adopting a remote-first mindset. “The way we work today is quite outdated," Jessie began, "And we need to be more progressive... You want to work with the best people in the world, but the reality is that the best people in the world might not be in your city. There are markets with a lot of opportunity and growth, that just might not have the right people.”

Keep reading for three of Jessie's key tips surrounding remote-work mindsets and how to make working remotely work for you!

1.Be honest with yourself. Is remote work right for you, or are you even right for it?

Working remotely looks pretty idyllic from the outside looking in, as it usually appears to involve a laptop and some palm trees. There's no doubt that the pros for remote work include flexible location (working from home, the beach, coffee shops, you name it), fewer interruptions, less time spent in traffic, more sleep, lunch with friends, the list goes on.

The perks sound ideal on paper, but it's also important to consider the drawbacks of the work-from-home lifestyle. Jessie pointed out that these can include underworking and overworking (do you have trouble staying focused, or often lose track of time?), FOMO of the office, no quick on-site communication, and the frustration that comes with communicating across different timezones. If you're someone who enjoys water cooler catch-ups, a long-distance relationship with your company might be a deal breaker.

2. Are you qualified? Employers are looking for people they can trust to get the job done without oversight.

Jessie says that unless your former employers or schools include one of the big players (hi Google, how's it going Ivy Leagues), "Chances are, people won’t know the name of your past company or university. So you have to bring across the significance of your work experience and achievements in another way to impress employers.”

There are some things you simply can't change, like your passport, people's biases, and the fact that some positions just aren't conducive to remote work. Jessie told us that you can oftentimes tweak some of these seemingly 'negative' things to work in your favour during the hiring process, however. Are you bringing knowledge from an emerging market to an established one? Do you help fill one of those controversial minority quotas (women of colour software engineers, we're looking at you)? Use these to your advantage!

Invariant factors aside, Jessie says there are also several things you can be proactive about to help make yourself the most attractive candidate for those limited remote positions.

"Skill yourself up, via academics or learning by doing. Get involved in the community or ecosystem to become relevant in the industry. And work on building your own personal brand… Become an expert in one domain, so that people trust your expertise and trust you to work remotely.”

3. Do you and the employer want the same things? Remote work shouldn't come at the expense of feeling like a 'real' employee at the company.

Working remotely is typically not the same as freelancing, and you should never feel like disposable, outsourced labour. Be sure to ask how the companies you are considering take steps to ensure you still feel like part of the team, even when you're not present in person. For example, Pleo makes a point of having remote workers train at their HQ in Copenhagen for at least three months, to ensure they feel aligned with the company values and their on-site coworkers before relocating elsewhere.

Jessie also told us that compromising in some areas in order to achieve a remote-work lifestyle is okay, depending on what your priorities are. "You may need to take a step back before you take a step forward," she says. "What I mean by that is, you may need to make a sacrifice. If lifestyle, location or flexible work is most important to you, then that might come at a cost to your career ambition… When looking at hyper-growth companies, it’s okay to start in a role that isn’t necessarily at the top. You can prove your worth, and grow internally. If a company has shown that it is on an upward trajectory, you’ll likely end up in a higher position just based on necessity - but you don’t need to start there!”

To sum it up, when considering whether to adopt the WFH lifestyle, first ask yourself if working remotely will also work for you. Once you've done that, Jessie concluded, then it's simply about finding the right fit and landing the job. "Demand for remote work is high, and the markets are adjusting slowly but surely. So just be the best, and get the job. Easy, right?"


To access the Community Conversation audio and presentation slides, click here.