Remote Work’s Top Challenge and Opportunity

Everyone started working remotely in 2020, including the Uprise team, and it became immediately clear that this new style of working came with a new set of challenges. Two main concerns emerged: how best to deal with increased cybersecurity risks and how best to motivate a remote team.

Brian, our CTO, and I recently participated in a discussion on navigating the remote business world of 2022 and beyond, hosted by the Institute of Family-Owned Businesses (IFOB). The Institute for Family-Owned Business (IFOB) is a non-profit organization committed to empowering family-owned businesses throughout the state of Maine with a range of education programs and consulting services.

A lot of great points were brought up and you can watch the full webinar on YouTube. But what I want to highlight in this post is the way remote work has impacted us and our offerings, and how we’ve been able to optimize WFH life.  

To Remote Work and Beyond

Our commitment to providing businesses with tools to protect their data and keep teams productive propelled the creation of Uprise Partners in late 2017. Having worked with a huge number of Fortune 500 companies prior to starting this organization. It was clear that smaller businesses were not being afforded the same variety of technological support typically reserved for these massive companies.  

Interestingly, the pandemic lockdowns happened while we were looking to further evolve Uprise’s technology offerings. We saw a clear need for a more comprehensive tech support, so we decided to launch a full-service IT offering in January 2020. (We had been offering this service previously but hadn’t made a lot of noise about it publicly to that point.)  Looking back, the shift to remote work and upsurge in business tech demand seems obvious, but at the start of the pandemic it was scary because we were all navigating unknown territory. Like many, we had those difficult discussions about how best to handle this new situation, and luckily, we were able to rise to the challenge and help our clients in the ways they needed it most. Our clients were changing the way they operated, and they needed a reliable IT partner that didn’t just know tech but also knew how to grow and operate a business.

The entire industry (really the world) had changed.  

Everyone started going remote, including the Uprise team, and it became immediately clear that this new style of working came with a new set of challenges. Two main concerns emerged: how best to deal with increased cybersecurity risks and how best to motivate a remote team.  

Dealing With Cybersecurity Risk

Many small businesses in the US believe they’re too small for a cyberattack. But what we have seen time and time again is that half of all cyberattacks happen to small businesses. And it’s not because the business in question was irresponsible with their data--just this last month we’ve had companies come to us seeking help after suffering a ransomware attack. Almost all forms of cyberattacks are destructive, with ransomware, the loss of data can be crippling (especially for a software startup), and often paying the ransom itself can be quite devastating, sometimes forcing these businesses to close.

As cybercrime continues to rise, employing good IT security is crucial. There are plenty of quick security enhancements that can be implemented ASAP so that your business is much harder to hack. It can even be as simple as updating your software and changing your computer password.

Managing a Remote Team

Keeping a remote team engaged and productive can be a bit harder than installing antivirus software. Tech solutions are important here as well, but in terms of team-building, the conversations themselves should always take precedence over whatever platform they’re happening on.  

What has been working very well here at Uprise is having regularly scheduled structured meetings as well as informal meetings. We try to strike the balance of having enough structure to keep the team connected, but never want to overburden team members with too many meetings to clog up their calendars and keep them from focusing.

Here are our standing meetings that help us stay connected and are key to nurturing our strong culture.

Daily Stand-Ups - This comes from agile software development methodology, but it can be applied to any kind of business. These are daily 15-minute meetings where the team shares what they accomplished in the last 24 hours, what they plan to accomplish in the next 24 hours, and whether there are any blockers preventing progress. If something comes up and discussions need to happen, that gets recorded and dealt with after the meeting. The goal is to keep this “stand-up” as quick and structured as possible. It’s a check-in to make sure everyone is on the same page and able to help each other if needed.  

All Hands Meetings - This is a strategic, big-picture meeting. We have our All Hands weekly, but it could be monthly or bi-monthly depending on the organization. We look at what the company as a whole has accomplished and give any updates like new clients coming onboard, a 10 min training on a new best practice, or announcing new team members who are joining.

Celebrations and Lessons Learned - We hold a very informal meeting every Friday where team members share what they learned that week and what they’re celebrating. This can be related to work or not, like a birthday or a new puppy. It’s been such a nice way of reflecting on the week and being able to celebrate everyone’s accomplishments. There are usually lots of laughs – and often some profound reflections as well.  

These kinds of meetings all serve distinct purposes and provide important touch points. So even working remotely, team members have these weekly anchor points, so to speak, to keep them connected to the rest of the team.  

Two years in and it doesn’t look like remote working is going to end anytime soon. Despite calls from big corporations to get employees back in the office, remote work will forever remain a new norm. Even with the new cybersecurity threats inherent to working virtually, by letting our employees work remotely, we’ve been able to get the best out of everybody, and those kinds of benefits will far outweigh the cons.


The content for this post was derived from part of an on-going webinar series exploring the challenges and opportunities of operating in a remote world. See IFOB’s website for more information.

Malinda Gagnon

Malinda is CEO at Uprise and has more than 20 years of experience in business strategy and technology at companies including Google and WPP, and has advised clients such as Procter & Gamble, General Electric, VW, BlackRock, and Walmart.

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