Remote Work Enablement in 3 Days | Where’s The Any Key? Podcast Episode 1

Above is a podcast led by JumpCloud’s IT team that tells the story of how they guided our company through the sudden transition to entirely remote work in response to the global COVID-19 pandemic. 

Below we have also presented this episode in written form. Feel free to submit any additional questions you have that may have been left unanswered. You can find our show on Apple Podcasts, Spotify, and wherever podcasts are available.

Welcome to Where’s the Any Key? The podcast where we talk about anything IT related and even some topics that are IT adjacent. I’m your host Ryan Bacon, the IT Support Engineer at JumpCloud Directory Platform. 

Who We Are and What We Do

Ryan: Hello everyone and welcome to our little chat about how JumpCloud® transitioned from an in-office work model to a work from home (WFH) model in a very short period of time. Joining me is Noah Rosen, he’s the IT Support Technician at JumpCloud. Together we are the internal IT team.

What’s This All About?

Ryan: With the COVID-19 pandemic and with everybody taking precautions and doing their best to flatten the curve, a lot of organizations (including JumpCloud) have seen the need to transition to a WFH model for social distancing to help slow the spread of this pandemic. 

As the IT team of JumpCloud, we would like to share our experiences with other people in the IT industry to show what we did, what helped us, and what challenges we had. We’re doing this because we know there are a number of organizations who have either rarely or never had their employees work remotely and we’re just doing what we can to help. There’s a lot of information out there, some good some bad, and it’s our hope to add to that good and helpful information.

Noah: Yeah, we’re trying to cut down on the chaos of an immediate switch to working from home, not a gradual switch. For a lot of companies like ours, it was literally days. One day we were told, “Yep, we might go to WFH model,” and the day after that everyone’s working from home. 

Ryan: Exactly. And that leads into our timeline. 

The Timeline

Ryan:  On March 10, 2020 we started planning for the mandatory WFH days to test for business continuity. We were looking at it as pretty much one day a week for a few weeks. The idea was to try mandatory WFH to test that everything would work, and that business operations would not suffer. 

The very next day, we received updates of positive tests for COVID-19 in our area. It was getting too close for comfort, and things changed quickly. It was decided that we needed to make that move immediately.

So we started planning in the middle of the day on March 10 for our first test WFH day to be on March 12. But on the 11th we knew we were going to be working from home for the foreseeable future. There was a lot of stuff that Noah and I had to plan for in order to get everybody ready to WFH. 

Where We Started

Ryan: Let’s put things into perspective. We are a fairly young company. So there’s a few things to keep in mind when looking at the profile of JumpCloud as an IT organization: 

  • We are a cloud-native organization, which means we use a lot of SaaS applications
  • We use AWS® and we have very few on-premises resources
  • We’ve allowed our workforce to be a little bit more mobile; everybody’s workstation is a laptop and it’s managed by the JumpCloud platform
  • We already make heavy use of Slack® for internal communications
  • We already have VPNs set up
  • We have an IT asset management system in place so we can log who has what asset and so on
  • Over the course of the past year or so, we have heavily automated our new hire onboarding
  • We have processes in place for remote work contractors

So that’s where we started.

Remote System and User Management

Noah: I’d say that we were lucky as a company that we were already set up in a way that a WFH transition was relatively smooth for us because we had a pretty automated setup in general. And a huge part of that is JumpCloud itself enabled us to transition our workforce to a WFH model without any changes to our existing protocol. 

Ryan: That’s very true. Both Noah and I are very hesitant and try to avoid sounding salesy if at all possible because we’re IT people: that’s what we do. We’re not out there to push our product but I’d be remiss if I didn’t give credit where credit’s due. 

So I think one of the main reasons why we were able to quickly transition to this remote model is that we do heavily rely on our own product. We “drink our own champagne” or “eat our own dog food,” as they say. In other words: we use the JumpCloud Directory-as-a-Service® platform internally.

These remote working environments, as well as really dynamic working environments (i.e. having to switch from in-office to remote), are places where the JumpCloud platform really does shine. It’s referred to as supporting a domainless enterprise:

I do honestly feel that it is because of this platform we were able to make this transition quickly.

Noah: I’m just going to add a few examples of how we use our own product to ease the transition to working from home:

  • We have to provision a user account in any service that we support SSO with. It’s much easier for that user to just go to their JumpCloud User Portal and click on the application, as opposed to us having to share credentials with them over potentially unsecured networks.
  • When we need to make a change to a user’s system we use the command runner to run commands directly on their system as the administrator without giving that user administrative access to that system.
  • We use JumpCloud’s RADIUS service to authenticate the VPN. So when users connect to our remote VPN, or an internal VPN they use their RADIUS credentials which are managed by JumpCloud so they don’t have to remember, say, the official password anywhere. 

Ryan: You could also use LDAP to authenticate VPNs.

What We Did

Making Sure We Are Available 

Ryan: It was critical that we made ourselves more available than normal to help people get set up for remote working. Normally we would only be quick to respond for emergencies or vital things during after hours. But with this shift it was and continues to be very important that we make ourselves available even later in the day or on weekends so that we can make sure that people are up and ready to go.

Noah: It really boils down to easing the transition for users. We’re here for making it as simple a transition as possible without creating a huge amount of transition work. We want users to quickly move to a WFH environment without making them fill out a number of forms or having them learn new processes and protocols. We’d rather just basically stay out of the way as much as possible and simplify the process of provisioning IT equipment and getting people software. This way there’s as little friction as possible during such a large change and people aren’t slowed down getting back into the flow of work. 

Ryan: As internal IT support it is our job to help other people do their job. Especially in a case like this, we need to make sure that we’re doing that; we’re being as efficient and as helpful as possible. I think that’s key to a smooth and quick transition. 

Making Sure They Have The Right Equipment

Ryan: We did have to reassess our policy on previously not providing equipment for people’s home offices. The decision changed to allow for inexpensive peripherals like mics, keyboards, and laptop stands. It ended up being a decision to allow people to be as effective and efficient as we can. It was just opened up to say, “Okay, you can take anything from your workstation home as long as you report it to us so we can keep track of things.” 

We did this in two parts: 

  1. We created a Google™ Form that we sent out to everybody that asked on the Slack channel. 
  2. For the stuff we needed to track in our asset management system — such as monitors — we asked that they please provide the serial number for the device. 

Then, we could take that serial number and make sure it’s updated and accurate in our system. We were in the middle of doing a full inventory to get our asset management system up to date. This kind of threw a wrench in that, but then again, it helped us get a head start on doing such an extensive inventory count. 

Also, we were letting people back into the office to pick these things up. So what we had to do is get extra assets like keyboards, mice, cables, power strips, etc. ready for people to take home. 

Normally we have a shelf in the office that’s kind of a “help yourself” to IT stuff that has things like batteries, various adaptors, cables, and mouse pads. Little stuff like that is more efficient to let people go and grab stuff than go through the process of making a ticket and to hand out a mousepad or a keyboard. That shelf was already there, but we did expand our “help yourself” policy to allow our users to easily grab other things as well.

In a way, this sudden need for at-home equipment helped us out. We had a bunch of old equipment leftover from our old offices that we were getting ready to purge because we didn’t need it in the new office. So this transition helped us get rid of our huge stockpile of cables and powerstrips that we had.

The Challenges

Testing in Production

Noah: Like a lot of companies, this was a pretty unexpected change. Under normal circumstances, when an organization starts hiring remote workers, they have months to practice, get all their processes set up, get all the tools distributed to users, and teach users how to use those tools. But like most organizations suddenly moving to WFH in response to COVID-19, we had maybe 24 hours notice before transitioning to a fully remote model for every user. 

So it was definitely a “test in production” situation; we had to start rolling out tools for remote workers while they’re already remote. There was no time for testing.

This is not an ideal scenario, but if you have your tools set up in advance (i.e. good vpns distributed to all your users, the right software available to them, and identity/system management in place) then you can make that transition less painful. 

Complicated Communication

Also, communication with users has been challenging. Most companies, especially most companies in the tech world, use some form of team messaging like Microsoft Teams® or Slack. We personally use Slack, but even with a communication platform like that the process of communicating with people is made more difficult.  

For example, you can’t just stop by somebody’s desk if something’s hard to explain over Slack. Or, if a user has an issue that you have to resolve and you don’t quite understand what they’re explaining — it may be too hard to verbalize in messaging — you don’t have the option to just walk up to someone and ask them.

Troubleshooting hardware remotely can be incredibly difficult. If someone’s computer doesn’t turn on, or their microphone isn’t working, and you don’t see anything wrong from a configuration point of view there’s very little you can do without having the user themselves do some troubleshooting. Finding documentation for them to go over to do their own diagnosis is a huge part of moving to a remote environment. 

Troubleshooting Home Networks

Home networks are challenging as well. When everyone works from a central office, we have a controlled network that we set up all of the tagging on. We give people access to the resources they need, both external and internal, from a relatively reliable setup. 

But when people are working from home, many don’t have fast or reliable internet. Additionally, they may not have access to the routers if they’re in an apartment building. So anything that goes wrong on those networks may be out of our hands, requiring some of the user’s own troubleshooting work. Essentially they’re taking over the role of network administrator for their own network. 

An Increase in Demand for IT Support 

Underlying issues that weren’t a problem when people were in the office have started to become problems. For example, people have VPN configurations that aren’t working. Many don’t use these very frequently so as soon as they moved to a remote environment, they started to realize all these underlying problems are bubbling up. 

This rapid shift puts a lot of pressure on an IT department to resolve problems that would have normally been spread out over a long period of time. They’re all consolidated into a very short little burst of tickets. 

Ryan: I was thinking we would be getting things ready and establishing processes. We were able to deal with this smoothly because we did have a lot already in place. We had already been giving the option for people to WFH from time to time, so it was just a matter of scaling the existing procedure and adjusting to a full-time model. 

Helpful Resources and Tips

Ryan: So today at JumpCloud, business is going on as usual pretty much across all departments – other than the fact, of course, that every single employee is working remotely. It’s going really well. 

Now we want to highlight some of the tools and resources that helped us get to where we are now. 

Google’s G Suite Platform

There have been several companies and products that we either started leaning on in 

different ways or that have expanded their services to help with this pandemic. We use G Suite™ for our email, Google Docs™ for various projects, and we use Google Hangouts for our conference room meetings. 

Usually the ability to record on a Google Meet is restricted to Google Enterprise accounts, but Google has opened up the ability to record and livestream meetings.

They have also increased participant caps on meetings, which has been critical for company-wide events. Previously, we were set up for all-hands meetings where we’d expect half of our people to be either at the meeting in person or gathered in conference rooms at remote sites. Now, everybody’s joining these meetings from their systems. Everyone is a single participant and we can’t really group them together. So that increased our participant number, and if it weren’t for Google increasing the participant cap temporarily, we wouldn’t be able to have everybody join our meetings (unless we upgraded to a G Suite Enterprise account).

So for those interested, meeting recordings and live streams can be enabled in your G Suite settings, and the participant cap has been automatically applied. So if you use Google Meet you can now have up to 250 participants joining your meeting, and you can livestream out to 100,000 users.


There are certain features in Slack that we didn’t start using until now. Instead of trying to distribute everybody’s phone numbers, Slack actually has a call feature built into it. So in Slack you can make a call or enable screen sharing to other people in your workspace. We’ve started using those features for instances where things may be difficult to describe in text so users can have more real-time communication with their coworkers.


If you are looking for ways to do these remote meetings where you normally jot down notes or illustrations on a whiteboard, there are various virtual platforms to help with remote collaboration. You can use Jamboard™, which is included in several of the G Suite packages, or Zoom for their whiteboarding features.

Halp in Slack

Something that really helped us process-wise was having a user-friendly ticketing system that simplified interacting with IT. We already had processes in place to make working with IT easy and they didn’t really change when we moved to remote work. 

We use Halp’s Slack-based ticketing system. People still Slack us and we can convert their inquiries into tickets if needed; it’s a very streamlined workflow. It’s important now more than ever that the process of asking for assistance from IT is easy to use for remote workers. You need to have people comfortable with your ticketing system so they can reach out to you when they need help and that you can respond quickly and effectively.

FAQ For Remote Work

Our management team created an FAQ for remote work. In it, they went over policies on why we’re doing certain procedures and what expectations should be moving forward. 

Communication is going to be vital from you to your end users; they need to know what you’re expecting and what you need from them. Be on top of this communication and make sure you’re clearly setting standards. If you’re needing to get serial numbers from hundreds of people make sure to be assertive to get the information that you need. You letting them take stuff home to help them work is a responsibility, not a right. Users have a responsibility to work with you to make sure they get what they need. 


As we mentioned before, the JumpCloud platform has also been a huge help. We do have free trials for up to 10 users and 10 systems that’s free forever. If you stay under those numbers it’s a free account for as long as you have it. Just reach out to us and we can work with you on getting a free trial setup that has unlimited users and unlimited systems with full feature access. Feel free to take a look.

Questions? Just Ask

Ryan: Thank you everyone for taking the time to listen to us share our experiences. 

Be healthy. Stay safe. Please let us know if there’s anything we can do to help you. Check us out at our website. You can email us at [email protected] or [email protected] and we will do what we can to help you guys out. 

Thanks For Tuning In!

Thank you for listening to Where’s the Any Key? If you like what you heard, please feel free to subscribe. Again, my name is Ryan Bacon and I work for JumpCloud Directory-as-a-Service, where the team here is building a cloud-based platform for system and identity management. You can learn more and even set up a free account at

So until next time, keep looking for that any key. If you find it, please let us know. 

About JumpCloud

The JumpCloud Directory Platform provides secure, frictionless user access from any device to any resource, regardless of location. Get started, or contact us at 855.212.3122.