Starting and Managing a Remote-First Startup by@jwolinsky

Starting and Managing a Remote-First Startup

More than 4.3 million Americans are currently working from home or on a hybrid basis. Microsoft reported more than 145 million daily active users during the second quarter of 2021, up 30 million from the end of 2020. Remote working is now more common today than it was a few years ago, and companies of all sizes are making use of high-tech platforms to help make the virtual workplace more accessible and productive. Here are some things we’ve learned along the way that makes starting a remote-first startup a lot easier and straightforward.
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Jacob Wolinsky

Jacob Wolinsky is the founder and CEO of ValueWalk.


The early months of the pandemic were a catalyst for entrepreneurs, a time where innovators, thinkers, and doers were able to combine their skills and knowledge, leading the next generation of business and work into the virtual future.


Now, more than two years since the pandemic took hold, entrepreneurs are taking advantage of the tools and software that’s helped businesses transition from brick-and-mortar to virtual offices.


Remote work and working from home have completely changed the business landscape, allowing companies to increase their talent pool during recruitment, and allowing startups to grow an impact-driven strategy during a time of crisis and market volatility.


The advent of the remote work culture has seen more than 4.3 million Americans currently working from home or on a hybrid basis. The virtual office has grown exponentially, Microsoft reported more than 145 million daily active users during the second quarter of 2021, up 30 million from the end of 2020.


The transition has seen some companies looking to remain fully remote or implement a hybrid business model, even as the pandemic starts to wane.

The plethora of digital remote working tools and software programs has given birth to a new era of remote-first startups, and entrepreneurs can now leverage these tools to help them get their businesses off the ground.


But in the remote-first startup world, how are entrepreneurs able to cultivate a digital work culture from scratch, keeping team members engaged, productive and motivated?

Here are some things we’ve learned along the way that makes starting a lot easier and straightforward.

Hiring the Right Person for the Job

Finding the right people for the job, and building a team that you can trust in the virtual workplace is a challenge many businesses had to overcome in the last few years.

As a startup owner, you have an idea of who you want on your team, and what they can contribute both to the business and the overall company culture. In the virtual workplace, recruiting and hiring, both short and long-term means you will need to be meticulous about who you’re interviewing, and the type of conversation you’re looking to drive.


During the interview, it’s important for you as a business owner and entrepreneur to ask the right questions and focus on any particular cues you might be able to pick up during the call.

The risk of interviewing candidates virtually means you’re unable to get to know them in person, and it makes it a bit more challenging to see whether they are the right people for the job.

Additionally, as a remote-first startup, you will be requiring a range of different skills from your employees, so make sure you have a list of skills you would like your new hires to already have before starting.

Some of the skills to include, outside of technical and job-related skills are:

  • High-level of tech proficiency
  • Reliable and Independent
  • Self-starter and motivated
  • Organized
  • Effective time management skills
  • Easy communicator
  • Ability to collaborate on projects
  • High-level of worth ethic
  • Team player

These skills are crucial in the remote workplace, and for a startup, it could mean that having the right people for the job can make the job load a lot more bearable.


Being more proactive during the recruiting and hiring process helps you eliminate candidates that might not be suitable for the position, and ensure you bring the right set of people on board.

Implementing the right digital tools and management platforms

Today, a plethora of digital working tools and management platforms exist to help drive remote working processes and ensure a more streamlined virtual workplace.

Remote working is now more common today than it was a few years ago, and companies of all sizes are making use of high-tech platforms to help make the virtual workplace more accessible and productive.


In the case of a remote-first startup, technology will be crucial to your business, and without it, you’ll have a hard time making a success out of your business and driving meaningful change.

While looking for the right tools and software to use, and the people who will be using it, there’s a bit of background you need to consider first.

Implement tools everyone can use

When starting, you might want to consider who will be using these tools. Even though being tech-savvy is a prerequisite for your business, you might have the perfect candidate for the job, but they’ve never worked with virtual remote working software or platforms.

Spend time getting to know the tools

In some cases, it might be a good idea to choose a few tools you’re familiar with and take the time to know the ins and outs of each. There’s a chance you might be using a few different tools for your startup, depending on your business requirements. If you’re able to grasp how these tools work, it’ll be easier for you to share with teams any notable features you’d like them to make use of or things they should avoid to make any errors.

Give employees a chance to master tools

A big part of your business will be conducted using these tools, and if employees are not completely comfortable with the ins and outs, it could become a drag on your startup's productivity.

Spend time during the onboarding process to help employees get comfortable with the software and the layout. Make sure they’re aware of the features you’d like them to use, and answer any queries they might have. The quicker an employee can master the digital tools, the easier you’ll be able to get your startup running.

Offer Technical Support

It’s one thing to teach employees how to work effectively, but offering technical support, even after the onboarding could mean you’re open to assisting employees who aren’t as tech-savvy as you thought.


The key here is to be patient and allow enough time for staff to get comfortable, especially for those who haven’t necessarily worked with these tools before.


If you notice someone is struggling, or you come across errors in the system, address these issues immediately to avoid any potential long-term problems that can reduce productivity.

It’s one thing to have the right set of tools, but making sure that teams can effectively utilize aspects of the software and platforms can help drive faster company development, and initiate better communication efforts between members.

Get to Know the Virtual Employee

In the traditional office, human resource managers and office leaders tend to initiate an onboarding process, allowing new hires to get to know their colleagues and help them settle into their new job.


While virtual offices might not have the perks that come with working in-office, it’s still possible to ensure that new staff members can settle in comfortably.


For startup entrepreneurs, company culture, or virtual office culture can help improve team morale and motivate those who are working from home. The proverbial water cooler can still be a place where employees can share ideas, or talk about personal events.


There should be a firm understanding that communication is part of the business model and strategy, and having open channels through which employees can do this can help drive up team motivation, creativity, and inclusivity.


Conduct a mandatory check-up every day, even if this means you’re simply checking in to see if employees are coping, or how their work progress is going. You can also do a weekly round-up, either at the start or end of the week, and create time for employees to share their high and low points.


In team meetings, whether it’s related to a certain project or client, think of ways employees can engage in active conversation, during and after the meeting. The more frequently people engage, the easier it is to spark new ideas and generate note-worthy concepts.

Make sure you know your staff, who they are, and what they enjoy doing when they’re not working. Even in the digital office, it’s possible to foster relationships with your staff, without having them feel disconnected from the company or other team members.


Provoke small talk, especially during weekly roundups. Remember that proverbial water cooler I mentioned earlier? This is where employees can chat about upcoming events or things they did over the weekend. Of course don’t let the small talk allow you to veer off from topic, but giving employees space where they can get to know one another can help create a better connection with the company and the culture you’re looking to establish.

Celebrate the Big and Small Wins

As a remote-first startup, you want your employees to remain motivated, and during times when team members succeed in reaching a specific target or achieving a specific company goal - it’s good to celebrate those wins.


Don’t think of it as handing out (virtual) participation trophies, because that’s perhaps something completely different. Rather consider how even the smallest wins can help team members feel more motivated to complete challenging projects and tasks.

In the startup environment, where you still have the capacity to celebrate everyone’s achievements and success, it’s easy for you to pop a message on a group chat, or perhaps a private message.


If you think the opportunity is right, hold a virtual conference call where you can publicly celebrate these wins and achievements.


When teams see their work and personal achievements being rewarded, even if it’s through small gestures of goodwill, they’re more likely to remain loyal employees of your company.

The virtual office space can be a cold place sometimes and having employees share their victories can be a place where one will motivate others, share ideas, and increase overall team morale to help achieve better long-term success.

Lead By Example

To finish off, it’s important for you as a startup entrepreneur to lead by example, from the very first day.


Employees tend to have better relationships with their employers or managers if they’re able to see them as a leader, or someone that they can trust and learn from.


Show your employees why they should trust you, and be loyal to the company. Create an environment of inclusivity and channels where employees can talk with one another. Eliminate the feeling of disconnectivity, especially in a remote-only workplace.


There’s a lot you need to have to lead a remote-first startup, but making sure you hire the right people for the job and establish an online office culture could see your business taking flight, and your employees remain loyal throughout the startup journey.

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