Raymond Mendoza
Inside League
Published in
4 min readApr 16, 2020

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League hosting a room at Web Unleashed

2 years ago, I decided to leave my history of big companies (Amazon, Ebay, BlackBerry) and join a startup. League was around 100 people at the time nearing the closing of series B funding. Today we’re more than 300 people with teams around the world and well into our transition from startup to scale up. My name is Raymond Mendoza and I’m currently Director of Engineering at League.

I have been through scale up periods before in different contexts. At Amazon, we were creating a new “Digital” department which was like a startup within a company. From a team of around 8 that quickly went to 30, 100, 1000, we launched the first versions of Kindle, Video, and Music.

Few people know that Kijiji is an Ebay company and part of a group of companies around the world known as Ebay Classifieds. I was the first developer hired in their new investment in Canada and was a part of the story of making Ebay Classifieds a billion dollar business.

Balloons for celebrating League’s Top 5 Startup status on LinkedIn

There are a lot of parallels to what I’ve seen at League in these past two years, but learnings are more pronounced and important to apply in a truly independent company. These observations can be applied at any company, but especially at scale up companies.

  1. Companies can grow faster than some of its employees. You have to coach for that (the preferred way) or help them transition out. It’s a harsh reality, but if leaders fail to coach those employees to match or exceed the company growth, it’s better for all sides to part ways. My job changes every 4–6 months. As my CEO, Mike Serbinis, references, you need to get used to giving away your Legos.
  2. Silos grow faster than bridges. “Us vs Them” is poison when it happens internally. It’s not intentional, but it is very subtle. When you stop knowing everyone in the company or stop interacting regularly or your KPIs don’t match, it’s easy for departments to inadvertently work against each other. This is a leadership issue. It’s important for leaders to repeat that we are all one team and have and have an endless focus on the customer, not their own metrics.
  3. Lack of investment in fundamentals expose the company. It’s easy to think only about technical debt when scrapping together something to achieve product market fit. When a company starts scaling up, the same things as a small company seem to take longer to achieve or fail completely. Yes, technical debt accumulates, but process and people debt can accumulate even faster. Are workflows adjusting systematically? Are people’s career paths and roles being considered? If not, things fall apart, people leave. As my volleyball coaches used to tell me, the best teams are usually the ones with the best passers, not necessarily the best attackers. The fundamentals count.
  4. Tribal knowledge handcuffs scaling efforts. It was comforting when you knew to go to that one person who could do that super important thing and it would happen quickly. It’s not comfortable when that person goes on vacation or those 30 new hires start or you get a new set of 10 of your biggest customers. Document and train regularly and often.
  5. Diversity matters. The easiest thing to do when you need to hire 20 people yesterday is to hire the same template of people that worked before. You can go from a 100 person company to a 300 person company quickly, but the company lacks the perspectives to produce a truly great product. I’ve benefited and grown a lot from a company like League who has more than 50% women and more than 50% women in leadership positions among other diversity statistics. I am challenged more and am aware of different view points. I am selfishly better because of this. The company is too.

These learnings may appear common sense to most people. They kind of are, but it’s hard to apply common sense in the chaos of customers stretching you to your limits or viruses disrupting the world. Sometimes we need a reminder.

These two years have flown by and as I told my CTO, Dan Galperin, it feels like I’m just getting started.

League swag

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