Remote onboarding: can it be as good as the ‘real’ thing?

Sarah Ruth Boyer joined Octopus Ventures on Day One of the lockdown. Her job? To support the US portfolio and help build out our talent function. So what can her professional experience (at Alphabet’s Sidewalk Labs and Oscar Health) as well as her recent personal adventure in remote onboarding into Octopus, teach us?

Be intentional

A remote onboarding experience, while materially different, need not diverge too far from a regular onboarding process. But integrating a new employee onto the team, whether remotely or at the office, will benefit from clear forethought and intention to make them welcomed and valued. Intention plus forethought is the magic formula.

Prepare and Plan

Set up your new hire’s email and calendar ASAP, so you can begin to build out their schedule for the first few weeks on the team. If you think you’ve put too much on your new hire’s calendar, you’re probably on the right track.  When I arrived at OV, I had Trello board with a checklist to work through a 30/60/90 day guide, complete with OKR’s, expectations, and an onboarding meeting plan emailed to my inbox to open when I arrived.

If your new employee needs a computer, install all the tools and programs they need. Ship it out to arrive before they join. (NYC was shutdown the evening before my first day at Octopus, but I was lucky enough to have a local colleague bring my laptop all the way from the London office so we could coordinate a pickup.) Create a list of required apps and tools the new hire will need and work with IT to give them access. See that they’re connected with HR before they start to enroll in the company’s payroll, savings plan, and insurance. Send out an email to their personal account to let them know what to expect from their first day on the job: how to log into their computer, what time to join the first call, and any other instructions.

I was added to a Team NYC WhatsApp group which was informal enough that I felt comfortable to ask questions and join the banter about the going price of an ounce of hand sanitizer.

Welcome and Integrate

The new hire’s first interaction should be with you (their manager) that morning. Show up on time! Introduce them to your onboarding plan, standing meetings, and give them a general overview of what you expect from that first week. By then, your new hire should understand who is who on your team, the tools and systems they need to do their work, and standing meetings. They should also be acquainted with your team’s norms and have met several folks outside of their immediate team.

Make sure they know what systems you use, and how you use them, as soon as possible. Do you use hangouts to communicate, or is slack the better place for quick pings and questions that need immediate answers? Is email the holy grail?

Send out a company-wide welcome email announcing your new team member’s arrival. Include a photo (this is especially important for remote hires) and some fun facts, then cc the new hire and encourage team members to introduce themselves and say hello.

Taking a Step Back

Putting together an onboarding process sounds pretty easy, but take it a level deeper: assign onboarding tasks to immediate team members. These meetings have an agenda and they introduce your new hire to more people on the team. Play to your team’s strengths: who’s best suited to walk through systems? What about introducing the investment workflow? Team documents and tools? A history of the company? An intro to the sales process?  A walk through your company values and what they look like in the workplace?

“The message to the new arrival must be ‘we value you’”


Does your organization have a standard onboarding process? Perhaps your department heads already host deep-dive conversations to introduce new hires to each of the groups. If so, keep these up and make sure they’re scheduled before the new hire begins. Are there other new team members joining around the same day as yours? Set up time for them to connect and share their experiences as a cohort.

Don’t scramble to navigate calendars once they arrive. The message to the new arrival must be “we value you” but lack of planning contradicts this – as well as making you and the company look disorganised.

On my first Friday on the job, I joined the London team’s end-of-the-week Quarantini drinks over Zoom (lunchtime NYC time) with my sparkling water and sandwich. I didn’t know everyone on the call, but I gained a lot of information and insight just watching the team interact with one another!

If you are the new hire

Take initiative and put yourself out there to meet your colleagues. Your team may not have a robust onboarding in place, but you can still make the most of your first few weeks on the job – especially if you’re remote:

  • Schedule conversations with your team members over video chat. Don’t be afraid to ask for introductions or to introduce yourself to others.
  • Create a list of colleagues you’re most likely to interact with when back in the office. Start scheduling conversations with those folks first, then work your way through other parts of the company.
  • Does your company use slack? Join the #donut-coffee channel and you’ll be connected regularly with a random set of colleagues from across the business.
  • Is there a company-wide event or activity? Join and participate!



Remote onboarding, like its face-to-face twin, speaks more of how your company values its employees than your written values do. You have the opportunity to set the tone for their career within your organization. Be intentional about how you do it.

Do you have remote onboarding advice you’d like to share? Send Sarah Ruth an email (

** Here’s a great resource from Halloway on onboarding Remote Employees and a really useful timeline from First Round Capital

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