9 Chicago Tech Companies Share Their Experiences With Remote Onboarding

Michael Hines
November 16, 2020

As companies reenter the hiring market, people teams are being asked to design remote onboarding plans that ensure new hires hit the ground running and feel welcome.

Going from an onboarding process predicated on in-person office interactions to one dominated by Zoom calls and Slack messages requires thinking critically about the needs of new employees and how to best meet those through digital tools. 

Remote onboarding isn’t easy, but some of Chicago’s tech companies have designed a playbook of sorts to help companies navigate the process. Built In Chicago recently spoke with nine companies that have dealt with remote onboarding in recent months to learn more about how their processes have changed and the challenges they’ve had to overcome along the way.

 

Stephen Popp
Senior Director of Sales, Learning and Development

Designing a remote onboarding program is as much an opportunity as it is a challenge. Stephen Popp, senior director of sales, learning and development at Epsilon, and his team focused their efforts on providing new hires meaningful experiences and resources. According to Popp, their efforts have led to a more streamlined onboarding process that has helped cut costs and bring the team together.

 

What’s the biggest challenge you’ve faced onboarding new employees remotely?

The biggest challenge to onboarding new employees remotely is providing global, regional and local new hires meaningful engagements. Without meaningful engagements, associates may feel lost, disengaged or frustrated.
 

We created a welcome page to provide insight into the onboarding experience and minimize uncertainty around the first day and week.


How have you overcome this challenge?

First, we defined what meaningful engagements looked like and broke them down into three stages: pre-hire communication, new hire onboarding and associate development. For pre-hire communication, we created a welcome page to provide insight into the onboarding experience and minimize uncertainty around the first day and week.

With new hire onboarding, we evolved our existing content to create a week of virtual sessions that explored our company history, products and solutions, global organization, teams and benefits. We explain how teams work together so new hires immediately understand their role in our company’s success. We also added meet and greets with HR and senior leaders, icebreakers and work-from-home best practices. We utilize Zoom and Mentimeter quizzes to create additional engagement opportunities and set up a new hire portal and a networking page for finding tools and resources.

Our approach to continued associate development was to create meaningful engagements beyond the first week. We added virtual onboarding deep dives to reinforce and deepen their product and solution knowledge, curated content for our learning management system, created department and role-specific 90-day development plans, and designed and implemented a career discussion guide.

 

How have you used the lessons you’ve learned about remote onboarding to improve your overall onboarding process? What are some specific changes you’ve made?

Moving to remote onboarding and a unified program has allowed us to streamline our communications, control quality and consistency of global content and messaging, reduce travel expenses and improve engagement. We’ve brought together teams that would traditionally be limited in their connection due to time zones and geography.

 

The Screencastify team kayaking on the Chicago River
PHOTO VIA SCREENCASTIFY

Caitlin Cuesta knows all too well how challenging remote onboarding can be. She’s the people operations manager at Screencastify, a company that has more than tripled in size since the start of 2020. Cuesta said that when it comes to remote onboarding, one of the biggest lessons her team has learned is to not overload new hires with video meetings.

 

What’s the biggest challenge you've faced onboarding new employees remotely?

We were a team of fewer than 10 at the beginning of 2020 and have more than tripled in size since going fully remote and are on track to hit 50 employees by year’s end. All of our new team members have been onboarded remotely, which has been a challenge. In an office environment, a large part of onboarding happens simply by osmosis — observing how people behave and communicate, the norms they follow, etc. 

That’s easily lost in a remote context. Video meetings are great, but as soon as you exit Google Meet, you’re completely alone. We’ve had to quickly learn what works and what doesn’t when onboarding new employees to ensure our culture of kindness, generosity and collaboration is felt throughout every aspect of a new employee’s journey.
 

We’ve had to quickly learn what works and what doesn’t when onboarding new employees.


How have you overcome this challenge? 

Before an employee’s first day, we send them a virtual welcome card signed by all of their new coworkers. We also pair them with a “Screencastify Buddy” who sends an email to the team on their first day to introduce them. Their buddy will meet with them a couple of times per week to check-in and make sure they’re feeling supported and included. We treat their calendar as a virtual compass, pre-populating it with both onboarding-related meetings and suggested times for tasks as well as reminders to take a breather.

 

How have you used the lessons you’ve learned about remote onboarding to improve your overall onboarding process? What are some specific changes you’ve made?

Initially, we thought putting a lot of meetings on a new employee’s calendar would make them feel connected to the team and help with the feeling of being “lost” after leaving a meeting. However, after asking for feedback, we realized the toll video call fatigue took. Now, we only schedule a couple of video calls per day and instead check-in via Slack and offer a checklist to give new hires more autonomy over their first days.

We tell every new employee, “Your feedback on our onboarding process will directly impact future employees’ onboarding,” and we mean it!

 

Shari Hinnen
Manager End User Computing

Effective remote onboarding programs don’t just focus on communicating intangible aspects of a company. They also need to focus on more practical issues, like ensuring people have the equipment and login info they need for day one before day one. Shari Hinnen, manager of end user computing at Paylocity, said working with Kristen Krefting-Sprecker and other members of the HR team has helped her iron out those practical kinks from the remote onboarding process.

 

What’s the biggest challenge you’ve faced onboarding new employees remotely?

Our goal is to get laptops to new hires the Friday before they start so that they can get everything set up before their first day. They are now ordering their own equipment and know when it’ll arrive, which means they can set it up ahead of time and just plug it all in and go when their laptop arrives.
 

I have never worked closer with the HR group and talent acquisition team, and the collaboration has created a better onboarding experience.


How have you overcome this challenge?

Other than the hardware issue, that first day for new hires is tough as people are getting logged in and changing their passwords. We have complex requirements for passwords, and people inevitably forget them, which means New Employee Orientation Mondays — or NEO — are always a busy day for the IT service desk. 

 

How have you used the lessons you’ve learned about remote onboarding to improve your overall onboarding process? What are some specific changes you’ve made?

During NEO, one person will present and the other will run the chat and answer questions. This allows my team to focus on questions and the presentation instead of both at the same time. Also, we now send videos along with laptops to show new team members how to set up their equipment and dock items correctly. We are always trying to improve based on what we are seeing and the tools that we have access to make the onboarding process even better. 

I have found that there is so much more collaboration happening around things like this since we went remotely. I have never worked closer with the HR group and talent acquisition team, and the collaboration has created a better onboarding experience.

 

The Black Spectacles team on a video call
PHOTO VIA BLACK SPECTACLES

Black Spectacles has made it a priority to bring a human touch to its remote onboarding process. According to Jenni Schwaner, executive assistant and office manager, this has required the company to pivot from hand-signed welcome cards and in-person lunches and meetings to more virtual-friendly offerings. In addition to moving its welcome week activities online, Schwaner said the move to remote onboarding has created a paper trail that her team uses to refine the process with each new hire.

 

What’s the biggest challenge you’ve faced onboarding new employees remotely?

The greatest challenge has been preserving the personal touch, that human element we want all new hires to experience. We’re not just managers and coworkers but warm, funny people with rich personal lives, interests and hobbies, and communicating that is essential to making new hires feel at home. To that end, we set up informal group lunches and meetings for the entire first week so new hires can learn fun facts about their teammates as well as what each person contributes to the company. We also welcome them with a gift voucher, t-shirt and hand-signed card from the entire team. 

Obviously, doing this in cyberspace may not provide the same sense of camaraderie as it would in person, but we are able to adjust to the virtual platform and, in some cases, make it even more efficient.
 

Our efforts have been so successful that we recently instituted a ‘work from wherever’ policy.


How have you overcome this challenge?

Instead of a hand-signed card, we now compile a welcome video with a greeting from each team member. This is an even better approach, as now the new team member can put faces to the names of the people they’ll be working with. Lunches and meetings are done virtually, and when it comes to tech, the IT company we work with sets up and ships laptops directly to our new teammates and ensures everything works properly. We also make sure we’re available to answer questions via email, phone and Slack. 

 

How have you used the lessons you’ve learned about remote onboarding to improve your overall onboarding process? What are some specific changes you’ve made?

We have discovered that by following our usual procedures and making minor adjustments, we have not needed to make many changes to facilitate an experience that is similar to our in-person onboarding. In fact, there are many small details that can be missed without an email and message trail to refer to, and we’ve actually been able to add to our onboarding checklist and improve it with each new hire.

Nothing can replace the personal satisfaction of in-person gatherings and face-to-face interaction, but we do our best to schedule fun online events and team-building exercises, such as virtual escape rooms, photo-based “scavenger hunts” and a weekly happy hour we have called “Quarantini Time” that everyone is strongly encouraged to attend. In these ways, we are able to keep our new hires engaged, involved and informed. Our efforts have been so successful that we recently instituted a “work from wherever” policy that not only encourages safety but expands our hiring pool to the national level.

 

remote onboarding perkspot
photo via shutterstock

Instead of making tweaks to their existing onboarding program to make it more suitable for remote work, PerkSpot decided to do something more radical. Lauren Willett, marketing manager, said the company instituted a new 90-day onboarding program designed specifically for remote work. Along with the new onboarding plan, the team also introduced new perks to make the work-from-home transition easier.

 

What’s the biggest challenge you’ve faced onboarding new employees remotely?

As a company, we are passionate about making every place a great place to work, starting with our own, and as we’ve shifted to remote onboarding our focus on culture hasn’t wavered. However, remote onboarding has presented us with additional challenges. At PerkSpot, company culture can be found in every meeting room and gathering space in our office. Without that physical presence, we’ve had to get more creative and innovative to demonstrate what our culture is and how it works within our company. 

Onboarding a new employee at PerkSpot means introducing them to various coworkers outside of their own department, as our culture highly values the importance of teamwork throughout the entire company. The absence of casual run-ins, hallway “hellos” and monthly themed companywide events have been a challenge for us and remained top of mind during our virtual onboarding process.
 

We provide a generous home office stipend and regularly check in with employees during their first few months via a series of surveys.


How have you overcome this challenge?

We’ve implemented a number of new programs and processes. The first is our new 90-day onboarding program, which picks up where our in-person onboarding left off and emphasizes the importance of understanding and learning the business while reenvisioning how remote employees can gain easy access to various resources.

During their first 90 days, we also facilitate regular meetings between new hires and members of each PerkSpot team so that they can get to know fellow PerkSpotters outside of their own team and those they’ll interact with on a regular basis. This leads to a deeper understanding of the different functions here at PerkSpot and provides a more holistic view of our company. 

 

How have you used the lessons you’ve learned about remote onboarding to improve your overall onboarding process? What are some specific changes you’ve made?

We have implemented smaller processes to help employees hit the ground running. We provide a generous home office stipend and regularly check in with employees during their first few months via a series of surveys, which allow us to continuously evaluate and improve our own onboarding experience. At PerkSpot, we have a people-first mentality that helps ensure new employees gain exposure to our culture just as they would if we were in the office, from new employee introductions by our CEO during companywide Zoom meetings to leaning on new remote cultural events that encourage participation and inject a bit of levity into our day-to-day routines.

 

The SpotHero team volunteering
PHOTO VIA SPOTHERO

Alexandra Christou said the people team at SpotHero has doubled down on communication since moving their onboarding process online. The HR generalist said her team has increased its communication with new hires in the weeks before their start date to make sure they’re feeling at ease, and each new hire works with their individual managers to ensure they have everything they need to hit the ground running.

 

What’s the biggest challenge you’ve faced onboarding new employees remotely?

Our teams are very close-knit, which made the shift from an open-concept office to our own homes difficult to navigate at first. SpotHero’s inviting culture and collaborative office setup made it simple for teams to engage with new employees, specifically in casual day-to-day interactions. These informal conversations allowed new team members to get to know not just their own teams but also colleagues who they may not work with often or at all.

In our fully remote setting, these relaxed chats are less organic and rely on deliberate scheduling to happen. As a result, the biggest challenge has been ensuring that our new employees feel welcome and part of the larger collective team, and are learning about our company’s culture and values.
 

For more than seven months, we have learned just how valuable it is to maintain a consistent dialogue ahead of a new hire’s official start date.


How have you overcome this challenge?

While impromptu conversations cannot happen as easily while we’re remote, we are able to coordinate our efforts to foster similar environments. We’ve focused on promoting participation in our employee resource groups, setting up virtual brown bag lunches and outdoor volunteer events where social distancing and other health guidelines can be followed. We have also increased the number of SpotHero Spirit Weeks, themed weeks where employees wear different attire each day and share photos of themselves on Slack. The team has a lot of fun with those, and it really shows new employees how creative, fun and welcoming SpotHero is.  

Additionally, we felt that having more companywide meetings would allow new employees to get a sense of where they fit into the greater organization and learn more about other teams at SpotHero. To that end, we host biweekly all-team meetings and AMAs where our CEO Mark Lawrence and exec team answer questions submitted by our employees.

 

How have you used the lessons you’ve learned about remote onboarding to improve your overall onboarding process? What are some specific changes you’ve made?

One of SpotHero’s core values is “remember to signal,” meaning each of us strives to communicate openly and honestly about issues and concerns big or small. For more than seven months, we have learned just how valuable it is to maintain a consistent dialogue ahead of a new hire’s official start date. This has led us to be extra communicative in the weeks before a hire’s start date to ensure their initial onboarding goes as smoothly as possible. 

The people team also works closely with managers on thoughtful onboarding plans and welcome initiatives. Managers craft personalized onboarding documents and support new hire success by coordinating meetings with individuals across the company. We also send SpotHero swag packs to each new hire’s home before their start date to generate excitement and welcome them to the team. This approach to communication has improved our onboarding process so much so that we plan to maintain these best practices once we return to the office.

 

A stock photo of a team video call
photo via shutterstock

Onboarding is about more than making sure new employees have everything they need to do their job — it’s also about putting them in the best position to be successful and achieve their career goals. Terry Lyons, VP of sales at Silkroad, said she ensures this element is incorporated into her team’s remote onboarding strategy by setting up weekly meetings between new hires and those who can help them succeed.

 

What’s the biggest challenge you’ve faced onboarding new employees remotely?

Salespeople are generally very social and relationship-driven, which makes hiring and onboarding remotely quite difficult — and a bit of a leap of faith for both parties. When hiring a senior sales executive, I want to get a sense of how they present themselves in-person and how they command attention in a room. Video meetings are relatively new to many and can be awkward for some. 

Typically, new team members meet with their teammates and colleagues for an intensive one-to-two week immersion into the culture, product and processes of the organization. This incredibly important timeframe can make or break the success of a new employee.
 

In a remote environment, giving new hires a buddy helps them to understand the culture.


How have you overcome this challenge?

I’ve made sure to establish connections early and often for new team members to put them “in front” of the right people at the right time during their first few weeks. I have weekly cadences set up for new team members with those internal colleagues who are going to be the most influential and the greatest resources for their success. 

In order to avoid video meeting fatigue, I set up information meetings in bite-sized sessions. Continuous check-ins and an open line of communication have been critical. It’s best to engineer out any ambiguity in the new hire process wherever possible. Setting expectations as part of the onboarding experience also helps to ensure that new hires are successful and have defined goalposts to aim for.

 

How have you used the lessons you’ve learned about remote onboarding to improve your overall onboarding process? What are some specific changes you’ve made?

It’s really important to be intentional when designing the onboarding experience to help new hires foster connections with pertinent stakeholders within the organization. In a remote environment, these connections to people and strategy have to be made intentionally as there are no hallway run-ins or random desk visits. In a remote environment, giving new hires a buddy helps them to understand the culture and how to navigate within, which is critical to their success and longevity. 

It’s equally as important to include an element of strategy immersion so that new hires understand their role and how it impacts the organization’s goals as well as what other facets of the organization do and how we all work together. These things aren’t going to happen on their own: We have to deliver these components at the right time to the right people with personalized and relevant content as they move through their first year.

 

One of the most attractive elements of remote onboarding is the ability to train as many new hires as can fit in a Zoom room. However, Craig Burke, sales trainer at HomeAdvisor, said that his team has learned more isn’t necessarily better. Instead of packing training sessions full of people, Burke said his team has focused on smaller groups that provide new hires with more one-on-one interactions.

 

What’s the biggest challenge you’ve faced onboarding new employees remotely?

The biggest challenge has been making new hires feel at home. It’s definitely difficult to give them a true feel of what the company is like when they can’t be in our office. Video calls, no matter how effective they are, cannot replace the face-to-face interaction our sales teams have at each office site. Our company has a specific culture and it’s definitely difficult to instill it while working remotely.
 

Having smaller groups with one to two trainers makes it much easier to identify any technical issues new employees may be having.


How have you overcome this challenge?

We broke down our sales training classes into small groups, with one to two trainers responsible for each class. This helps provide more one-on-one interaction in regard to getting them set up and logged into our system and helps us address any issues with their equipment much faster. New employees also have the ability to interact more with one another and to discuss the material being reviewed.

 

How have you used the lessons you’ve learned about remote onboarding to improve your overall onboarding process? What are some specific changes you’ve made?

We have started using designated Zoom rooms for technical issues. Having smaller groups with one to two trainers makes it much easier to identify any technical issues new employees may be having. This helps us to resolve issues much more quickly than when we first started working fully remotely. Finding out if a new hire has a legitimate issue, or if it’s just a user error, helps training run smoothly.

 

Bernt Olausson
North America Country Manager

As a company with a team spread across the United States and Canada, Palette Software is extremely familiar with remote onboarding. According to Bernt Olausson, North America country manager, bringing on new employees entirely online isn’t as scary as it might seem.

 

What’s the biggest challenge you’ve faced onboarding new employees remotely?

We have a team that is dispersed all over the United States and Canada, so we’re used to working remotely and use regular team meetings to keep up to date and individual meetings for more specific issues. So hiring a new person to work remotely with a team spread across different time zones is something we are used to. 
 

I would prefer to meet someone in person, of course, but finding the best talent might mean getting outside of the city you’re in.


How have you overcome this challenge?

We use both Built In and other platforms to reach out to prospective hires. Obviously a Zoom call or meeting online works well in this context. I would prefer to meet someone in person, of course, but finding the best talent might mean getting outside of the city you’re in.

 

How have you used the lessons you’ve learned about remote onboarding to improve your overall onboarding process? What are some specific changes you’ve made?

With online contracts and regular meetings, it can be a fairly seamless process. Once the employee is hired and becomes accustomed to our meeting structures, they seem to settle in. We supplement our remote working environment with biannual meetings in someplace warm, like Miami, to catch up on any issues, plan for the future and have some social time together.

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