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How to automate and personalize your employee onboarding process

First impressions matter, which is why creating a welcoming experience for new hires has always been important. But for fast-growth companies in today’s talent market, thoughtful and intentional employee onboarding has become mission-critical. Let’s explore some of the ways onboarding is transforming and what that might mean for your own approach.

What is employee onboarding?

Employee onboarding is the process of setting new hires up for success in their roles. While it might sound simple, it’s actually a complex process that involves several dimensions, departments, and people. In broad strokes, onboarding involves:

  • Making sure new hires have all the tools and equipment they’ll need to do their job (which can involve teams like IT and facilities)
  • Building the foundation for good working relationships (which will likely involve the new hire’s direct manager, team members, and cross-functional coworkers)
  • Establishing expectations for the role and working norms in your company (which might involve the new hire’s direct manager as well as other company leaders or members of the HR/People team)
  • Emphasizing the importance of belonging (which might involve employee resource groups, an onboarding buddy, and other new hires who are onboarding at the same time)

When you consider the fact that each of these bullet points can potentially contain multiple action items (and involve several individuals or departments), it’s easy to see how unwieldy onboarding can be. There are so many moving pieces it can be incredibly hard to keep track of, especially when you’re working with distributed or global teams. Perhaps this is why only 12% of employees strongly agree that their company does a great job of onboarding new employees.

In fast-growth companies in particular, there’s a greater risk that onboarding will suffer. When a company is small or growing at a slower pace, HR/People teams might treat onboarding as a one-off or ad hoc process. This works when you’re only onboarding a handful of people each quarter. But when you’re scaling rapidly, a manual onboarding process becomes increasingly difficult and time consuming. In these cases, HR/People teams may find themselves in “firefighting” mode—just trying to stay on top of all of the tasks involved with onboarding. Once this happens, it can be challenging to look at the big picture and try to improve processes. 

Why the future of onboarding is automated and personalized 

In the past, workers might have been more willing to accept a sub-par or rocky onboarding experience, but talent professionals are finding that’s no longer the case. Alex Duell, VP of People at Cutover says, “We’ve seen a few folks who have come out of relatively short tenures—1 month, 3 months, 6 months—at companies where they’re still onboarding because they’re not being impressed with what they’re seeing.” Yikes! So how can you ensure your onboarding program retains the talent you’ve worked so hard to recruit? It comes down to two key concepts: automation and personalization.

Automation supports fast-growth companies 

There are several advantages to automating your onboarding processes rather than doing them manually each time. Automation means:

  • You won’t forget any steps or leave anyone out
  • You’re reducing (if not eliminating) the risk of human error like inputting someone’s name or start date incorrectly
  • You can focus on more meaningful work and communication rather than repetitive tasks
  • You can more easily collect data on what’s working (and what’s not)

Wondering what this looks like in practice? Insurance comparison company EverQuote recently experienced a surge in hiring and their biggest pain point was around managing their pre-onboarding and onboarding communications. The team used to have to look through BambooHR to find the start date of every new hire, reach out to the managers of new hires to gather information before they started, and manually create a list of new hires and their email addresses to send them pre-boarding and onboarding information.

“Think about all of the emails we send every single day of our lives when we’re working,” says Kailee Heffler, Employee Brand and Marketing Associate at EverQuote. “How much of that can be bundled into a really deliberate and thoughtful series of communications, instead of hitting people with messages randomly? The more we can bundle, the more time and energy we’re saving our employees.” 

Read more about how EverQuote automated their onboarding communications here.

Personalization builds belonging

Successful new hire onboarding today is about more than tools and processes. Workers want to feel a sense of belonging in their new workplace (whether they’re sharing an office with their coworkers or not). Luckily, many HR professionals already understand this—69% believe inclusive hiring and onboarding practices have a positive impact on a company’s brand and contribute to greater employee wellbeing. 

At first glance, it might seem like you have to choose between automation and personalization in your onboarding processes, but this is not necessarily the case. At EverQuote, Manager of Employee Development Emily Nissensohn used to have to tailor messages for each office and send them out through a BCC format, which didn’t allow for personalization. By working with Pyn to automate onboarding communication, she can now give hiring managers the ability to personalize messages as needed. 

Besides personalizing message content, they can also personalize how a message goes out. Emily says, “We use email for our two-weeks-out message and Slack for our one-week-out message for new hires. Some people love email, and some people love Slack, so now we can customize how we communicate with people.”

Emily finds that automation can actually lead to more personalization. She explains, “Automating communications doesn't make me afraid of losing my job. It makes me more excited for the things I can do with my extra time. I see Pyn as a huge catalyst for allowing us to do the really important, strategic people-centric work, rather than the monotonous, burdensome work that we would happily give to a robot.”

What you should include in your employee onboarding checklist 

If you’d like to create both an automated and personalized employee onboarding experience, it can help to start with a checklist (or a series of checklists). What needs to happen in order for you to consider an employee successfully onboarded? We’ve included a basic checklist here that outlines tasks for both HR and hiring managers. Looking for a template you can edit directly? You can find one here! We also have a template for onboarding new managers here.


What HR is doing: 

  • Alert the manager when the offer is officially accepted
  • Send a welcome package to the new hire

What the manager is doing:

  • Announce the new hire’s acceptance to the rest of the team
  • Coordinate welcome emails or phone call to new hire


What HR is doing:

  • Provide the manager with a 60-day plan template (A good way to structure this is with Day 1-20 focused on learning, Day 20-40 focused on contributing, and day 40-60 focused on Independence and ownership. See our Pyn on How to create a 60-day plan for your new hire for more details on what to include.)

What the manager is doing:


What HR is doing:

  • Prepare and send paperwork to the new hire
  • Address any questions from the new hire
  • Follow up to ensure paperwork is completed before Day One


What HR is doing:

  • Remind the manager to send a welcome email

What the manager is doing:

  • Send out a welcome note via email or Slack to welcome the new hire
  • Encourage employees to send the new hire welcome messages (if remote)
  • Encourage employees to stop by the hire’s desk to say hello (if in office)

For an even more detailed checklist (including a free customizable template), check out our Comprehensive Employee Onboarding Checklist and Template for Hybrid Work.  

Employee onboarding communications from Pyn

Below you will find links to our Pyns related to employee onboarding. You can use these messages for free via the Open Library, or you can automate and personalize these communications as a Pyn customer.

We also have topical guides on How to build an onboarding buddy program and Pre-onboarding: How to support new hires before day one.

Employee onboarding communications for new hires

Employee onboarding communications for managers

Pre-onboarding employee communications

Onboarding buddy employee communications