Introducing Sure’s 2024 State of Digital Insurance Report

By Allison Stewart, Head of Recruiting at Sure

You’ve conquered the obstacles of the remote hiring process and found the perfect candidate. They’ve happily accepted the position with your company and are ready to start contributing immediately. A well thought out plan — executed properly — will make all the difference fostering new employee productivity and their integration into your company culture without ever stepping foot in a shared office space. 

Here are five things that are critical for a smooth onboarding experience of remote team members.

1. Be prepared for day one long before day one

A smooth remote onboarding requires stakeholders across multiple departments to be in the know and ready to take action at any given moment. From shipping the right IT equipment and providing relevant software access, to ensuring the completion of benefits paperwork and onboarding training, the list of team members involved to get one new hire setup for success can be quite extensive.

We have a remote hire checklist that works wonders for us, but it’s not just any checklist - it’s the ultimate checklist. Not just because of what’s on it, but because of the respect we give it to ensure onboarding tasks are completed correctly and in a timely manner. We leverage a work management platform to bring our checklist to life, share updates in real time, and automate processes wherever possible. This ensures priorities are set, dependencies are addressed in the correct order, and deadlines are met within the required timeframe.

If a step is missed, we know exactly where it went off course and can correct so that on day one, our new hires have everything they need to be successful.

2. Provide a comprehensive remote onboarding guide

One of the most common mistakes made during remote onboarding is failing to provide all necessary information - that includes the things that you, as a seasoned company employee - think of as common knowledge. Don’t forget to put yourself in a remote employee’s shoes. New hires come from every experience level and there’s no guarantee that the last company they worked for used the same equipment, shared the same values, or had access to the same software as your company.

Take full advantage of setup wizards and widgets, but also have the information needed to sign into their computer and communication channels readily available. We abide by the motto, “don’t make assumptions.” This applies to everything from logging into a laptop for the first time to new hire projects that warm up our newest edition to the suite of tools and applications used by our team.

While specifics for each company are different, Sure provides an overview of what to expect each day of the first week of employment. Here’s a taste of what we include in our guide:

Computer setup - This includes everything from first login to Two-Factor Authentication, and more.

Registration for the tax and payroll system - Make sure the registration processes for taxes and payroll is documented and shared.

Email and calendar setup - Don’t forget to provide instructions on how to correctly add the company-approved email signature.

Links to company information stored in our internal wiki including the employee handbook - Provide your new hire with the resources they'll need for all company information and employee expectations.

Onboarding and information security trainings - Document and share all the security info that any new hire will need to follow and complete as they get onboarded.

Insurance 101 course - We highly recommend a baseline training specific to your industry. Getting everyone on the same page from the get-go is incredibly valuable.

Communication channel setup - At Sure, we use Slack to communicate with team members throughout the work day. It’s also a tremendous resource for remote culture building (you’ll see more details related to this in the next tip). Because we’re remote, we have a backup ready to go in case our primary tools are down. We provide login information for each of the tools on day one so no one is left in the dark.

Video conferencing - Like many companies, we use Zoom day-in and day-out. We provide Zoom conferencing info, directions on how to reserve our internal and external Zoom rooms, and clearly state that using your camera is expected for all team members. New hires can rest easy knowing what’s expected and not left wondering what the protocol is for communicating virtually.

Work hours - Be sure to publish work hours for all central office locations. For example, our West Coast team members typically work between 8:30am to 5pm PT. To allow for a greater amount of overlap, our East Coast teams work from 9:30am to 6pm ET. We also accommodate for international time zones to foster as much collaboration as possible.

3. Culture building communication

I can’t stress the importance of ongoing communication enough in a remote workforce. It’s so easy for everyone to put their heads down, finish the items on their task list, and close their computer without interacting with their teammates on a social level. We put a lot of effort into hiring the best-of-the-best — not only in skill level, but also by hiring individuals whose values align with ours. We hire people who are motivated by creating and building collaboratively and who voice their opinions non-judgmentally and without ego. We believe people do their best work when they are fulfilled as humans. That requires a sense of belonging and camaraderie — something that is hard to achieve as a new remote hire.

At Sure, we use Slack channels to communicate around shared interests, local happenings, and more. Our team has created channels to celebrate their love of dogs, plants, tv, books, cooking, restaurants, and more unique interests, like Settlers of Catan. New employees are brought into the mix on day one when they are introduced to the entire company via Slack. They answer a few fun questions and a flurry of welcome messages come in with recommendations on which Slack channels to follow.

We also hold monthly coffee chats — Zoom meetings where a group of individuals are randomly selected to get together. Conversation captains lead the discussion so there’s no awkward silence and employees can interact with those they may not work with every day. These chats are also a great way for new remote employees to learn more about their fellow co-workers, and the tone and personality of the company itself.

4. A single source of truth

There’s nothing more frustrating to a new employee than feeling like they are on a treasure hunt for information. Having a single — and shared — source of truth is critical to new employee productivity and satisfaction. I mentioned our internal wiki previously. This is where we house everything from internal team documentation to brand guidelines to holiday schedules. Everyone in the company knows from day one to check the wiki and the information is likely to be there.

5. Prioritize inclusion

Working remotely has become commonplace for many organizations. This makes it more important than ever to instill valuable habits that make inclusion a daily practice — beginning on day one. Working from home has made us all more vulnerable. Every day, our teammates enter our home on video. They may see what our kitchen or living room looks like, they may hear our children playing (or crying), they may witness the dog pooping on the floor in the background. Things that were once easily compartmentalized — work life vs. home life — are now one.

This past year has brought a great sense of awareness to employees throughout the organization. We’ve all experienced ups and downs and it’s opened our eyes to just how important it is to be there for one another. We do our best to invest in the well-being and fair treatment of one another as a standard enabling employees to contribute their best thinking. We may be far in physical distance from our peers, but we do our very best to remain close in mind.

While the hiring process may be your first impression, the remote onboarding process provides a lasting impression. It sets the tone for the first 90 days and beyond. By giving it the attention it deserves, your new hires will be set up for success, not feel like the train left the station without them.

Visit Sure's Careers page to view current job openings.