The first person hired to a People Ops role at a startup has the unique challenge of building programs from scratch.
As a one-person People team at Checkly — a Series A startup distributed across Europe and America — Kaylie Boogaerts is responsible for everything People-related. She runs onboarding, performance, culture, team events, and offboarding. What’s more, she’s still spending 50% of her day recruiting and managing an external recruiter to double headcount by the end of the year.
The very first program Kaylie tackled on the job was onboarding. She wanted to ensure that the great people she was recruiting had everything they needed to be successful on the job.
We interviewed Kaylie about the onboarding process she designed with limited resources. In this post, we break down her program to look at what happens in pre-boarding, on day one, and during the first six months.
When it comes to pre-boarding, Kaylie’s currently (mostly) European-based team has an operational advantage over their American counterparts — more time. Since European employees usually have a longer notice period, Kaylie has about a month between receiving a signed contract and a new joiner’s first day. The extra time allows for better communication and setting clear expectations both with the new joiner and with the rest of the team.
Onboarding kicks off when the candidate signs the employment contract. Soon after, Kaylie quickly talks logistics with the new joiner. In these back-and-forth emails, she finalizes the start date, informs the new joiner about the pre-boarding timeline, and obtains the info she needs to order a laptop — which often takes a few weeks to arrive.
At this point, Kaylie syncs with leaders at the company and compiles basic information about the person (like their title and place in the org chart). She informs the whole company about the new hire and what their job will entail.
Kaylie also assigns an onboarding buddy, who will be the new joiner’s first point of contact besides their manager.
Kaylie sends a ‘welcome aboard’ email about two weeks before the first day. This communication introduces the manager and onboarding buddy (who are also cc’d), answers some frequently asked questions, and shares information about the first week’s schedule.
The manager and onboarding buddy are encouraged to follow up on that email with a message about how excited they are for the new team member.
In the week before the new joiner arrives, Kaylie sets up a shared onboarding document that includes the information from the email in addition to tasks for each of the first four weeks. Kaylie and the line manager spend significant time coordinating with one another to craft this overview of the first four weeks, but it’s important work. The document is a critical piece of communication for setting the right expectations with the new joiner.
While she creates this document during the pre-boarding period, Kaylie won’t share it with the new joiner until their first day. Kaylie wants to show respect for her new hire’s time from the beginning. She notes, “if they have access to the document and our Notion, they tend to really dive into our documentation. I don’t want them to spend too much time on that before they’re actually being paid to onboard.”
At a remote company like Checkly, it’s critical to get the first day right. Kaylie has three main objectives for the new joiner on the first day:
In practice, that looks like this:
In a remote environment, the first day of work is marked by access to accounts. On day one, the new hire gets access to their Google Account, which gives them access to a host of other software including Slack.
Once the new joiner is on Slack, Kaylie invites them to the #welcome-to-checkly Slack channel which includes the new joiner, their manager, the onboarding buddy, herself, and other new joiners.
“This channel is for us sharing things with [the new joiner], giving the new joiner a place where they can easily ask us questions, [and] training [the new joiner] a little bit on asking questions in public because a lot of people are not used to it,” says Kaylie.
Once the new joiner has signed into Slack, Kaylie gives them access to the shared document with the information that she compiled during the previous period.
On the first day, the new joiner has 1:1s with some of the most important people:
The last of these talks focuses on high-level culture items including the company history, values, and mission.
For the team at Checkly, the onboarding process extends through the first six months of the employee’s tenure at the company. Kaylie, the manager, and the onboarding buddy all continue to have check-ins and tasks throughout this period to ensure the new hire is settling in smoothly and meeting expectations.
Kaylie has scheduled check-ins with the new joiner at the end of the first and second months.
These check-ins are informal. The goal is to make sure everything is going well and that the new hire’s relationship with the manager is off to a good start. Check-ins provide a space for raising concerns and getting a pulse on what’s tough and what’s enjoyable.
At the one month check-in, Kaylie also goes over the onboarding survey that the new joiner fills out a week after they join in case there are any pieces of feedback she wants to clarify or dig a little deeper into. This feedback helps to continuously improve the onboarding process.
At the quarter and half year mark, Kaylie hosts more formal check-ins with the new joiner and their manager. Kaylie and the manager hold a 360 feedback session that includes a self-review, a manager review and pre-collected reviews from several other people that have worked closely with the new joiner.
From these sessions, the new joiner should have a good understanding of how they are matching up against expectations. If they are not meeting expectations, they should come away knowing what they need to be doing differently.
After the six-month session is complete, onboarding is officially over for the new joiner.
Kaylie collects feedback from the new joiner on the process and is already looking forward to phase two of the program (which includes improving product education and delivering a company swag on Day One).
Given her immense time constraints as a one-person team, Kaylie knows she will have to find ways to eliminate some of the manual coordination and reminders to free up time to continue to design her programs.
Very soon, she’ll be looking to tools like Gather to eliminate her manual pain points and scale her programs.