How to Retain Top Talent in Your Remote Teams from C-Levels execs

Ho Yin Cheung
The Startup
8 min readApr 8, 2019

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It’s not what you thought you knew

Let’s face it, we’re living in the generation of Instagram, Twitter and Tinder. There’s no argument that people’s behaviors are changing due to the rapid pace of technology and instant gratification of the internet. The question is, how do you continue to retain top talent when your employees aren’t in front of you every single day? How do you keep your team interested without 24/7 motivation and pep talks in a shared kitchen? How do you inspire people to want to work with you and stay loyal to your company despite heavy poaching and aggressive rival compensation you may not be able to compete with?

I know from personal experience, and from speaking with dozens of the top employers - that people’s expectations for their career have changed.

That means that companies must not only be competitive when it comes to compensation; they must be creative and resourceful when it comes to satisfying the needs of their workforce, and remote teams are no different.

Through conversations with the CEO’s of a number of remote companies, I’ve been able to gather tips from executives who feel they’ve been successful in addressing the problem within their own companies and distributed teams. Here’s some of the insight I’ve learned, and some initiatives you can put into practice starting today.

Allow Your Employees to Contribute to the Bigger Picture

Shivani Thakur Daxini, the co-founder and General Manager at Kiprosh a software services and product development firm talked with me about the challenges and successes of running a distributed team. Interestingly enough, her firm hasn’t always been distributed. Kiprosh started at an office and shifted into remote working to try and overcome the frustration of long commutes and traffic — a transition that was met with a few bumps.

“To me, success is good synergy within teams and within the company. That the environment is healthy and the overall growth is healthy. Not just in numbers, but that everyone in the company is growing.”

Daxini understands that success is about recognition, that individuals recognize that they are making a mark and they are recognized in the company for their achievements and hard work.

Quinten de Graaf

After transitioning to a remote environment, Daxini realized that the sudden shift was met by her team with some confusion and a lack of structure and communication. There was a missing step between shifting from the office space and preparing the proper tools and systems for her team to be successful in being fully remote.

To resolve this, and in order to ensure her employees were motivated, she focused on creating an open environment and KPIs that could be used as a marker for individuals to know how they were performing.

“Every employee or associate should feel they are valued, and they can come up with suggestions and new ideas — and if everyone is in agreement then we can implement those ideas.”

She spoke about increasing employee engagement. “They have the possibility of learning new technologies based on their projects and how long they’ve been working on them. It gives them comfort knowing that they can grow in the company and feel they are valued and motivated to work. Otherwise, people aren’t passionate and don’t feel the need to work hard.”

Allowing her team to contribute to product development and reinforcing their hard work through sharing performance metrics allowed employees to feel confident in their own abilities. This also allowed them to feel certain about where they stood in comparison to their peers and in the company overall.

Treat Each of Your Employees Like They’re Sitting in the C-Suite

There are two ways to be a remote company, either to shift from centralized to distributed or to begin as remote from day one. Hotjar is a company that started as the latter. Hotjar, the website optimization tool for understanding your users was developed by CEO and founder David Darminin. From the very beginning, he determined that he wanted to share the lifestyle of creating an environment you don’t need to escape from.

“With Hotjar I think the key is to embrace being fully remote. You can’t see it as a way to do things better, it’s just a way of being. And we take it to the extreme — like everyone in the company gets their Hotjar credit card, everyone gets allowances and budgets so they spend it, they don’t need to get it approved. So the way we think about it, it’s about freedom — the freedom to reach your potential and to live how you want to live.”

Not only are employees able to work from wherever they want, but they’re also offered a budget to spend on workspace every month. Darminin believes in autonomy and empowering his teams to make decisions as much as they can. He believes in keeping a weekly rhythm and structure and celebrating accomplishments, but also complete transparency.

Admittedly the company determined they would hold off on hiring leadership roles, in the beginning, to really focus on people and growing the teams and wait to see the need later on. There’s no C-suite at Hotjar and only one VP. That being said Darminin entrusts his people to be a part of the larger conversations and to understand the details of the business.

“Making sure we’re on the same page of where we’re going — we’ve always believed in this principle of work with the team to create a strategy that is completely visible, so we are super transparent. Our financials are available, leadership calls, exec calls everything is available that anyone can join.”

For Darminin it’s not about finding one or two people to get a real look into the company, it’s about empowering your team to work as though they’re all running the business.

Join a Digital Office Space for Employees to Build Great Relationships with One Another

Sondre Rasch saw the trend early on. While he was working with social and labor policy he started seeing the shift in work styles “that young people are more and more becoming freelancers and more mobile and loosely connected to the labor market.”

His company, SafetyWing was actually created to solve a huge gap in the market. The lack of benefits, and social safety net that remote workers and freelancers are faced with when choosing to work outside of a full-time office, 9–6 job. His company offers insurance for digital nomads for a low monthly rate to ensure that they’re protected worldwide.

Zach Reiner

“We wanted to get benefits for freelancers but no one offered it, so we decided to build it ourselves” Rasch’s business and team have been growing rapidly as people start to discover the solution. As it’s grown a challenge he’s faced is figuring out how to strengthen employee to employee relationships. His solution turned out to be quite simple, an 8-hour digital hangout. He would leave Skype/Zoom/Google Hangout call on for a full 8 hours while they were working, and this made everyone feel like they were working together.

In my experience, (talk about needing to strengthen team bonds). Like Rasch, I saw a huge gap in the market, that video technology hasn’t been updated in years. I started Remo a digital hangout space for remote teams to solve for exactly that problem. Our software allows businesses to communicate with their teams as if they’re in an office, they can talk about their weekend from the comfort of a private room, host a Monday meeting through the ease of a large video call in a digital conference space and simply get comfortable seeing that their coworkers are also all online.

For Rasch and his team, working on a digital hangout was “similar to being in an office, where you can message remote workers, but you can still be anywhere in the world, so it incorporates time zones, you can move around, you can sit at home, you can be in a coworking space”

The idea was freedom and flexibility while building relationships with people you’re not in physical proximity to. A resolution that has worked quite well for SafetyWing.

Get Your Sales Team Behind a Single Story & Assign a Mentor to Junior Recruits to Help Them Learn

For Tim Vandecasteele of Silverfin, hiring junior employees for remote work proved challenging. Silverfin, the software platform for finance professionals, recruits for distributed and centralized teams in certain cities. The problem they faced with remote working, Vandecasteele mentioned, was training junior employees on the extensive knowledge they would need to have without an office space to collaborate in.

“We feel it’s very hard to educate them, especially if they’re in separate time zones.” noted Vandecasteele, “but when someone new joins the team, we assign a mentor to them, and I think that’s much easier.”

Vandecasteele admits that it can be challenging to provide a mentor in a remote environment which is why having the proper tools, setup and frequent touch bases are critical in the junior employee's success. Furthermore, he stresses the importance of sharing the story of your application, features and advantages of your technology with your sales team. When selling a platform like Silverfin, “what you can do is limitless” this makes it difficult to get on the same page with the entire workforce. It makes understanding the customer even more crucial to the success of the company. “You really need to understand the ecosystem that the client works with, to know what to pitch them. It’s not a pull off the shelf and deploy tool, someone is going to be implementing it, which means you really need to have some domain knowledge to apply it to their situation”

Getting on the same page requires some Facetime, in our startup, we’ve hosted all-hands meetings and sales discussions through a large digital room setting online using Remo, where everyone has the opportunity to split up after the discussion and debrief on information they either found handy or had more questions on.

The key to Vandecasteele’s team success is keeping customer focused and revolving the entire sales process around the customer’s needs, from educating and training employees to constantly sharing fireside chats about the real world usage of the application, Silverfin has done everything to ensure their people, and customers around the globe are taken care of.

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Ho Yin Cheung
The Startup

Founder of Riotly, Founder & Creator of Remo: a virtual office that fosters social collaboration & connections for remote teams. Try for free: www.remo.co