IRL Remote Work

10+ Months Review Of Working At As A Customer Success Manager (+We’re Hiring A New CSM!)

It has been over 10 months since I joined 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 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 serving as its CEO and CTO respectively. Colin and John first started working on 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 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’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.

In our most recent all-hands meeting, we watched while our colleague sliced some freshly baked bread. Riveting stuff in these pandemic times!

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 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:

May 7, 2019

Submitted online application

May 7, 2019
May 18, 2019

Received an invitation to schedule a first-round interview

May 18, 2019
May 23, 2019

First round 1:1 interview over Zoom

May 23, 2019
May 28, 2019

Second round group interview over Zoom

May 28, 2019
June 4, 2019

Final round group interview/homework assignment over Zoom

June 4, 2019
June 13, 2019

Call with job offer and explanation of benefits with a start date of July 8, 2019

June 13, 2019
June 14, 2019

Accepted the offer after getting questions answered

June 14, 2019
July 8, 2019

First day on the job!

July 8, 2019

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 at HQ in downtown Portland before leaving the next day for Austin, TX.

I spent my first day at at HQ in Portland, Oregon, USA

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

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 swag. My favorite piece of swag has to be the company branded socks. They’re super comfortable! Employee Welcome Kit

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. 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 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 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.

You get to choose what you want your working setup to be!

Positives & Challenges Working At

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 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:


  • Flexible working hours – Managers and Senior Leadership at the company have made it very clear that our hours are not tracked. We can easily flex our schedule within reason to start or end later or sooner as long as we get our work done and maintain an average of 40 hours per week.
  • Work from anywhere – For the most part, all employees are allowed to work from anywhere they choose as long as there is a strong internet connection and a quiet space to take internal or customer calls. I’ve even worked from different countries while I was traveling with great success!
  • Autonomy – My manager and fellow Success Managers provide really great support when I need it but I am free to look after my customer portfolio independently.
  • Transparency – During my first month, I got an email from our CEO, Colin, with the subject line “FWD: Letter to investors“. The email contained details of the company’s financial health as well as a forecast for the coming year. I thought it was sent to me in error but I quickly learned that everyone in the company is kept up to speed on all aspects of the company’s overall health and invited to provide feedback as much as possible.
  • Quick reimbursements – Reimbursement requests are processed and paid out with the same month’s salary so I am not left waiting for weeks or months to be reimbursed for business-related expenses from previous months.
  • Very employee-focused – The welfare of employees (affectionately known as ‘Amis’) is one of the top priorities for the company and we are encouraged to balance our family and working lives as much as possible. To prevent burnout from the added stress of the pandemic, we were given two extra days off this month which was much needed.
You can even work from a Wifi enabled airplane!


  • Remote onboarding was tough – learning the ins and outs of a powerful tool like is hard to start with, and trying to onboard as a distributed team member made it a lot tougher. The onboarding material largely consisted of large pieces of text and access to a sandbox environment for you to test with. A lot of the learning was from making tons of mistakes.
  • Timezones – this challenge is not unique to but it does make it a rather big obstacle when I need rather urgent help for an emergency. Asynchronous communication does work 95% of the time but there have been quite a few occasions where important issues have fallen through the cracks in Slack leaving a very frustrated customer on the other end for me deal with.
  • No career growth direction – at the moment, career tracks for employees have not been formalized so you really have no idea where and how you can progress within the company. On the flip side, there are few employees in the past who have been promoted or switched roles so it is possible to level up or reinvent yourself.
  • Team silos – again, this problem is not unique to, but even for a small company, don’t expect to know or speak to everyone on a consistent basis. I’m rather surprised that I haven’t met members of our Marketing and Engineering team given our social and extroverted I am. We do use Donut to foster inter-department communication between Amis but I opted out of the program after scheduling woes with teammates on the other side of the world.

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

  • Retreats – I was unable to attend the company’s last in-person retreat in Budapest in October 2019 and was really looking forward to attending the most recent one in Vermont, USA. However, thanks to the pandemic, the retreat went virtual which ended up being a mixed bag for me. Our operations team has never put together a virtual retreat so needing to give them the benefit of a doubt on this one is fair enough.
  • Professional development budget – I haven’t been able to take advantage of this benefit yet so I can’t give an opinion on how useful it is or not. On paper, it sounded great, but after speaking to my manager, she eluded that attending a conference was the only viable option and the current pandemic has put a pin on it for the moment.

There you have it. I hope my account as a Customer Success Manager at painted a clear picture of what it is like to work here!

Hey, that’s me in Ami form!

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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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.