It has been over 10 months since I joined Customer.io as a member of their Customer Success team based in Colombo, Sri Lanka. Here is my review working for this fully remote and distributed SaaS company!
The Company
Customer.io is a software company specializing in automated omnichannel messaging that organizations and brands (including Codecademy, Segment, and IFTTT) can use to reach their customers. The company was co-founded 8 years ago by Colin Nederkoon and John Allison who are both still at Customer.io serving as its CEO and CTO respectively. Colin and John first started working on Customer.io in New York City but decided to move the company headquarters to Portland, Oregon in 2014 to pursue a better work/life balance where continues to thrive today.
What attracted me to apply for a position with the company was the fact that it is a fully remote and distributed team in addition to awkwardness being touted as one of the company’s core values. Thanks to the coronavirus, companies of all kinds and sizes have been forced to become remote, but years of remote and work from home experience meant that Customer.io had to do little to nothing to adjust to operating and serving its customers in the middle of a pandemic.
In fairness, empathy, transparency, and responsibility are Customer.io’s other core values but those seemed rather boilerplate, while awkwardness, on the other hand, was a little more unique. As of this writing, approximately 75% of the company’s employees are located in North American timezones with the remainder scattered all over the world between London, England, and Auckland, New Zealand.

Application Process To Day 1
I focused my job search on a remote customer-facing position with a SaaS (software as a service) company which lead me to WeWorkRemotely, arguably one of the biggest online job boards for remote positions.
Since I didn’t live in the US anymore, I had to comb through scores of listings on the site to find ones that didn’t have geography or timezone restrictions. These kinds of positions are harder to come by but they are out there. Patience and a bit of luck will go a long way, I promise!
Speaking of luck, I came across a posting for a Customer Success Manager (CSM) at Customer.io. The job posting accepted applications from anywhere in the world and a cursory look at the company’s website ticked all of my boxes, so I went for it.
Here is the timeline from my successful application to my first day on the job:
Coincidentally, I was actually in the United States when I was going through the interview rounds which made coordinating interview times much easier since the hiring team was based there. In the grand scheme of things, the whole process was rather quick with the first interview to the job offer only taking 3 weeks. I really appreciated that they were quick to make a decision and didn’t leave me hanging with an agonizingly long wait.
To add to the fortuitousness of it all, I just happened to be in Portland, OR visiting friends so I was able to spend my first day at Customer.io at HQ in downtown Portland before leaving the next day for Austin, TX.

Benefits At A Glance For Non-US/Canada Employees
- Competitive monthly salary paid in USD
- 20 days paid time off (only after 3 months of service) with the option for a few more at the discretion of your manager
- Up to 13 public holidays in your local area/country
- Your birthday is a paid holiday
- Flexible working hours, no time tracking
- Company issued laptop and generous home office allowance for a desk, chair, cables, external monitor, etc.
- Monthly stipend for home internet and cellphone plans
- Monthly stipend for coworking rentals
- Monthly stipend for healthy lifestyle activities (yoga, gym, massages, running shoes)
- Monthly stipend for healthcare reimbursements (insurance premiums, doctor visits, etc)
- Annual stipend to celebrate company anniversary
- Annual stipend for professional development (conferences, courses, books)
- 1 month paid sabbatical for every 4 years of service
- 2 week-long in-person company retreats annually (our last one in April was virtual due to the coronavirus pandemic)
- Complimentary personal subscription to 1Password Families ($4.99/month value)
- Employee pricing plan for Customer.io
I had to pause after putting that list together because it is certainly a very nice list of benefits that put to shame all the benefits I received from the previous companies I have worked for in the past quite easily.
Since I was in Portland a few days before my first day on the job, I popped over to the headquarters to meet the Director of Operations, Sonja Beardsley, and pick up my company-issued laptop (a brand new 2017 13″ MacBook Pro) and my welcome kit which included some really neat Customer.io swag. My favorite piece of swag has to be the company branded socks. They’re super comfortable!

While I was there, I even snagged a webcam and trackpad that was laying around unused to add to my home office setup. Employees are expected to have a working headset for video calls but we are free to decide what other accessories we needed to perform our roles. I ended up getting a protective laptop clip-on hard case, wireless Bluetooth headset, wireless keyboard, and various USB-C cables and dongles for the new laptop to add to the desk, chair, and external monitor in my home office.
Customer.io HQ in downtown Portland, OR, USA
My Typical Work Day As A Customer Success Manager
As a customer-facing role in the company, I spend the majority of my day interfacing and supporting Premium customers (high paying clients who sign a 12-month agreement) in Europe, Africa, Asia, and Australasia. When I was being interviewed, I was asked if I was willing to work later hours so I could support European based customers and I gladly agreed since I work better in the afternoons and nights anyways.
An average day for me looks like the following but can vary wildly depending on my workload at the time, meetings I have to attend, or if I am working from somewhere else other than my home office. Here goes (all times are in India Standard Time GMT +5.5):
1:00pm – 1:30pm Boot Up Sequence
Starting a workday at 1 pm will not suit everyone but it works really well for me. I am able to do errands or personal projects in the morning with a fresh mind which I kick into high gear in the afternoon for Customer.io. In addition, being able to start work later in the day means that I am able to cover clients in European, African, and Asian timezones with a lot of overlap. This symbiosis is a win-win for Customer.io and me.
In the first hour of my day, I log into Slack to catch up on messages across out various company channels. Next, it’s over to my email where I read new emails that came in after I had logged off the day before as well as respond to emails I didn’t get around to replying to the previous day.
1:30pm – 3:30pm Power Session 1
After I am all caught up on internal and external messages on Slack and email, I spend the next 2 hours troubleshooting customer issues or speaking to customers on Zoom calls.
3:30pm – 4:00pm Coffee Break
I schedule a 30-minute break on my calendar every workday to force myself to leave my desk. I usually leave my home office and make a fresh cup of iced coffee and hang out with my wife for about 30 minutes. I try to minimize screen time during this time but we usually end up having something playing on the TV.
4:00pm – 5:00pm Power Hour 1
If I don’t have any customer calls during this time or need to finish some troubleshooting for a customer, I like to spend this hour finishing some “admin” tasks such as writing up call notes, organizing my calendar, posting information to our Customer Success and Product Slack channels, or reviewing my customer portfolio.
5:00pm – 6:00pm Gym (3x a week)
Three times a week, I schedule some time to head to the gym in my apartment building and break a sweat. I’m really fortunate that I have access to a well-equipped gym very close by which means I can get in a quick workout and be back at my desk in no time.
For days when I don’t work out, I usually extend the power hour for another 50ish minutes with a 10-minute break before the next session.
6:00pm – 7:30pm Power Session 2
The back half of my day is when my colleagues in North America start coming online and they usually start responding to messages I posted on Slack from earlier in my day. By this time, the whole Customer Success team is now online so I usually have weekly team meetings and 1:1s with my manager around this time.
7:30pm – 8:00pm Dinner Break
I’m usually gassed by this time of the day so I take a break to have dinner. Eating some delicious food helps take me over the home stretch and finish my day strong.
8:00pm – 9:00pm Power Hour 2
After getting some food, I spend an hour replying to as many customer emails as possible during this hour. Since I will be logging off soon, I also nudge colleagues over Slack who I am still waiting for responses from.
9:00pm – 9:30pm Shut Down Sequence
To end my day, I reflect on the day I just had and also mentally prepare myself for the coming day. I will also take this time to block off my calendar for things I need focused time to work on the following day. I also make sure to respond to everything that needs my input and also let my colleagues know to keep an eye on things that I need help with while I am out for the night.

Positives & Challenges Working At Customer.io
After being here for over 10 months (pandemic and all!), I think it is fair to say that the honeymoon period has come and gone and I have a fairly good idea of what it is like to work at Customer.io. It is not perfect (I doubt a perfect workspace even exists) but working here does has a lot of positives going for it!
Allow me to break it down into pros and cons:
Positives

Challenges
The good news is that points (1) and (3) under Challenges are being worked on by our People Operations team whose goal it is to improve the onboarding experience and establish career trajectories for current and incoming Amis.
To Be Determined
There you have it. I hope my account as a Customer Success Manager at Customer.io painted a clear picture of what it is like to work here!

Speaking of which, we are currently looking for a new member of the Customer Success team! If you would like to join our remote, worldwide team as our newest CSM, click here or the button below to apply on or before June 1, 2020. FYI, strong preference will be given to applicants who are in US Pacific timezones (GMT -7) for this role.
If you have any questions about the position or the company as a whole, feel free to contact me or leave a comment below.
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ABOUT THE AUTHOR

Nico Atienza
Chief Storyteller
An expat remote worker based in Colombo, Sri Lanka with a penchant for window seats on planes, travel, and technology that makes everyone’s lives easier.