Two Years at TransferWise

Chris Raastad
7 min readNov 13, 2016

November 10th. TransferWise Anniversary. Another year, another post. Why write it? I’m really having a hard time the second time around… It’s that feeling when you go to a festival for the second time. No matter how amazing it is, it just doesn’t have the magic of the first time. A year ago I had many many many emotions, it was a rocky time and the words at 1am just flew off my fingertips in One Year at TransferWise. This year, things are much more stable and calm, eerily approaching business as usual. Finally, Sunday at noon, inspiration hit describing my feelings perfectly.

Track & Field Day 2016 Prize — TransferWise Socks

Together with a capital T. Thinking about the last year, moving into our new Tallinn office, WinterDays, SummerDays, the growth of my team, our interns, that epic day in August when our investors were in town, hosting our hackathons, NYC & Ukraine office visits, the never ending funny messages on slack, our yearly planning last Thursday, the epic afterparty that soon followed, and our awesome Track & Field day where I won these inspiring socks; I’m surrounded by these amazing diverse motivated colleagues now stretching the globe.

We are changing the world Together.

It’s as simple as that. TransferWise is a mission driven lifestyle with your fellow Wisers. We’re making Money Without Borders a reality, starting by eliminating overpriced cross border money transfer. We have massive goals that we will only reach working together. Kristo’s “too small” is engrained in the back of our minds to question ourselves and look into the future never underestimating our potential and growth.

Looking back one year, then comes the so much WOW. So much has changed since then formy team, our company, and myself. We’ve grown into a mature sustainable company. We’re just starting our first steps into adulthood after turning the corner from a teenager one year ago but not losing any bit of our humbleness.

So, how did the last year go?

:)

  • Still keeping up our amazing growth rate. Every chart is moving up and to the right with no end in sight. Anyone with a TransferWise account with us for years could plot their transfer number on a graph for a hint of how we’re doing. On November 2013 I completed transfer #178,600, then November 2014 #1,166,851, then November 2015 #4,860,837, and last week November 2016 transfer #11,675,026. ← This is insane!
  • To add to our global team, we’re planting new seeds with a presence in Budapest, Japan, Singapore, and Australia.
  • Hooray for new happy TransferWise’y offices in Tallinn, London, NYC, and Cherkasy Ukraine (my personal favourite).
  • You haven’t read any news of us having 700+ employees, most of it now says 600+, last year at this time it was ~500. Yes we have been able to increase our efficiency without very heavily increasing our number of employees compared to the year before. This is a huge win.
  • Customer > Team > Ego. For me, this was the year of the team. The forces blessed our tiny team with a Product Manager. I then jumped into the position of Engineering Team Lead. The high point was having 8 people on our team in the summer: 3 devs, 2 analysts, 1 PM, dev intern, and an analyst intern. I can’t thank you guys enough for working hard each and every week.
  • That feeling of anxiety while being on vacation or out of the office is totally gone. I have left the office at 5-6pm many more times this year than the previous one. Of course I will stick around at work as long as I can to try to squeeze every last hour to knock off things from my TODO list.
  • I’ve embraced multiple hats. If I need to write code, I write code. If I need to do team lead stuff, I’ll do team lead stuff. If I need to do product, I’ll do product.
  • AML & Compliance will not be a show stopper for TransferWise. All the pieces there are there and improving each and every week.
  • Our engineering organization is moving towards the land of “take time to build things right.” We need to build for 10x or 100x not to hack stuff too quickly to get it out the door. A very important cultural shift for some of the super exciting stuff we are working on that I certainly can’t tell you about.
  • We’ve made massive progress in modernising our engineering stack, e.g. modularization, performance, release processes, message processing, automated infrastructure, quickly deploying new services, routing, CDN, configuration server. Everything is moving in the right direction and I can’t wait to see where we are in a year.
  • We’re still keeping our openness and autonomy. Team call still happens every two weeks often with founder Q&As and company financial reports. Decisions making still come from the teams. Our quarterly song dance still happens where we get all the playmakers of the company in a room to think long term and reassure the company is moving full speed ahead towards the mission.
  • I have learned a massive amount about leadership, how to run a team, how organizations work, employee lifecycle, helping make sense of product backlogs, hiring, and basically a lot soft skills in tech.
  • Our parties are still nothing short of epic, mostly because of the amazing people attending them. SummerDays was still the best weekend of the summer and the year (despite being at the same time as Positivus and Electronic Family) :)

:(

  • I’ve still struggled to do anything meaningful outside of the company walls. No side projects, no startups on the side, number of books read per month <1, not much outside learning, and no progress on my thesis. This is more of a personal prioritisation struggle and time management more than anything work related. But still, I can’t say the natural tendency to email, slack, and work around the clock helps. Only two more weeks left until my Thesis proposal needs to be submitted… I better get my S*** together here…
  • Balancing Team Lead, part time Product, and actually writing code is super tough. This simply boils down to prioritisation, ignoring distractions, and saying no to meetings. It’s too easy to find things to eat your time and really cool things you want to get involved in! Unfortunately I haven’t made any progress here. There are just too many little things flying around on emails and slack that take a little time here and there. TODO list at the end of the week gets made and never gets completed. This is the side affect of so much information flying around.
  • Working in a company of autonomous teams can be very challenging, especially on a central platform team instead of the more expansion or geographical teams. It feels like you are trying to maintain life in a petri dish planet when the entire universe is changing around you. Although thing are stabilising much more now compared to a year ago.
  • As the company grows it becomes harder and harder to keep your eyes open and pick out that tiny piece of important information relevant for your team. Solution? You are the reason why communication is broken. Long are over the days of reading everyone’s quarterly plans in detail.
  • As the median time an employee has been in the company is between one and two years (gut feeling), it seems that some general participation in company outings, events, and spontaneous gatherings isn’t what it used to be. I think it’s similar to this “second time around” syndrome as opposed to the first time excitement. Our infamous slack channel has been very quiet (except when the Londoners are in town). It could be people are taking more value in personal time and life, which is totally a great thing to do.
  • Our massive office in Tallinn can feel quite empty some days. There are some days when quite a few people working from home or traveling. It could be as simple as moving around the office, but it unfortunately lacks one central place of running into people when you’re busy.
  • Hiring for engineering hasn’t happened fast enough. It’s tough to the right people. I don’t think this point will ever disappear from a retro as long as I still work in Tech.
  • We risk getting comfortable, start working too much in isolated silos, and fall into “business as usual” within our product teams. Innovation is do or die in our space. It’s so important the longer and longer we are in the company we take a step back to look at the big picture, examine where our personal impact can be highest, act on radical ideas, and not be afraid to change teams. This is surely the most important thing to get right moving forward to continue to grow.

Last Thursday during our (legendary) planning afterparty, we had one dinosaur team member celebrate his last day at TransferWise after more than four years of service. The guy is a product rockstar, building the revolution from basically nothing, an absolute #WeGetItDone guy. We’re not happy to see him move on to other opportunities, but the way the old timers sent him off in ceremonial fashion, with a cleverly titled album, was yet another “proud to be a Wiser” moment.

I can’t imagine what I’ll be writing here when I reach that point of moving on. But believe me, it’s not anytime soon, there is just so much left to be done! But I certainly know we’ll have a killer party to celebrate and I’ll have plenty of good things to write about Changing the world Together!

Onwards!

PS: If you like what you see check out our open positions or tech blog.

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