Table of Content
  1. Why remote “first-ish”?
  2. But really, why remote?
  3. What are the challenges?
  4. I am ready, where do I start?

"We Are Remote First-ish, and You Should Be Too!" - a case study by CareMessage

This article is first published on the CareMessage blog by Cecilia Corral, co-founder and VP of Product at CaraeMessage.

Why remote “first-ish”?

To get a few key points out of the way, over 50% of our company is remote. As I’ve learned, the terminology you use when referring to remote work is really important. We refrain from using “remote friendly” because it has a negative connotation signaling you are simply accommodating remote employees. However, we are also not “remote first” because being remote is not yet the default for all employees. For the purposes of this blog post, I will use the term “remote first-ish,” even though remote people are slowly taking over CareMessage!

But really, why remote?

As a first-time founder, my first years were focused on getting the product out the door and in the hands of users. I knew nothing about building or managing teams.

The following years I actually learned a thing or two about hiring and building a team, including my favorite benefit of remote work: building a diverse team.

As a San Francisco-based tech startup, building a diverse team is much easier when you open yourself up to people outside of the Bay Area. We’ve been able to hire people from all around the U.S. and the world who are extremely talented but do not want to live here. This gives people who may be older, have children, or who have a life outside of work the opportunity to have flexibility. It is also common for San Francisco-based employees to work from home regularly, or take a trip and work from anywhere in the world. We believe we don’t need someone physically sitting in San Francisco to get stuff done.

What are the challenges?

Remote work is definitely not for everyone, and there are some very real culture challenges you will face if you do not actively prepare your company for remote work.

The first is more of a mindset on you and your employees because remote teams are not the same as “outsourced” teams. If employees see themselves as an “outsourced” team then they will almost expect micromanaging, which is personally not my preferred managing style. As a manager, you should set clear metrics for success and define responsibilities clearly that will, in turn, allow you to measure people’s performance. We use the OKR framework to structure goal setting across the company and getting teams to align with our company goals. We combine that with our career ladders to give everyone guidance on how they are doing.

The second challenge is that without a physical space to share, you need to create virtual places for people to share experiences and feel they are a part of your company and culture. For us, we use Slack to have “water cooler” chats, so sometimes we may be physically sitting next to each other in the office and will be chatting in a public channel so our remote employees can be a part of the conversation. We also use a slack bot to randomly pair people every 2 weeks for real or virtual coffee. This allows remote people to meet people in our office and other remote employees.

The last challenge is related to various aspects of communication, but as with measuring performance, this really isn’t only a challenge for remote employees. We use Slack to centralize real-time communication and email for asynchronous communication. We make a concentrated effort to write everything down and put it in public Confluence spaces, ensuring people can be self-sufficient in finding any information they need. For video-conferencing, we recently started to ask everyone to join a meeting “remotely” if one person is remote. This ensures everyone feels they can contribute equally to a conversation.

I am ready, where do I start?

If no one on your team is remote, it may be harder to make a drastic change. I would suggest starting with a single role or function, ideally with a team that is interested in testing things before a company-wide roll out. It is also critical to make sure you bring in people that understand remote work to help you build a remote team the right way.

For us, our test bed for most company changes is engineering. (Sidenote: I’m super grateful that they go along with us when we test new things!) Our whole engineering team is remote, and it has worked because the team has been intentional in making it work. Being a few time zones ahead is also really helpful for doing database migrations at crazy hours like 3 am PST (9 am in Brazil, where many of our engineers live).

Within our hiring process, we tend to look for people that have worked remotely in the past. This is mainly because working remotely is not for everyone. For example, some people who were on our remote team in the past found they really missed physically sitting next to colleagues. Now we test for it in the interview process and look for people who are self-aware of challenges and benefits of working remotely.

Over time, we’ve opened up other teams to remote roles. This has made it easier to onboard remote employees and makes sure everyone knows how to work well together. Today over 50% of our company is remote and includes people from Sales and Operations. Some people started remote and others have moved out of the Bay Area over time. Both are welcome at CareMessage!


There are a few companies we admire who have great remote cultures and write about it including Basecamp, Automattic, and Invision. When you’re ready, try hiring on WeWorkRemotely, WFH, Remotive or Working Nomads.

It is really a team effort to make a remote work environment successful, and we’d love to hear from you on what you have seen work or fail. Feel free to comment below and look out for our next post in this series, where we will cover the biggest benefits of remote work for employees.

Cecilia Corral
Cecilia Corral is the co-founder and VP of Product at CareMessage where she leads all aspects of product design, development and evaluation. CareMessage is a nonprofit organization using mobile technology to make underserved populations healthier. Healthcare organizations use the CareMessage patient engagement platform to remind, inform and educate over 1 million patients about primary care appointments, preventive care screenings, and disease self-management.