Inside League
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Inside League

Scaling Engineering Culture

Photo of a laptop with a zoom meeting in the background. In the foreground a leafy green plant.

If you’ve been in the industry for a while, there is a good chance that you’ve seen how culture can change significantly when team composition shifts — whether it’s a period of hypergrowth, a change in executive senior leadership or an acquisition. Unfortunately, in many cases this type of change or growth often means culture — or more explicitly, the way it feels to be a part of the team — changes for the worse. With the market for technical talent hotter than ever before, engineers do not need to settle for a less than ideal work environment.

I have had the pleasure of working on multiple teams over my career that were well-known for “great culture”. Common threads throughout all of these organizations include:

  • Leadership (from management to the C-suite) genuinely cared about fostering a positive and inclusive culture. They felt a sense of ownership around it and considered it a key part of their roles as leaders in the organization.
  • Culture was not just an important focus for existing teams, but rather the entire lifecycle of someone’s tenure at the company — from how we treated our candidates during the interview process to how departures were communicated.
  • The definition of “good culture” meant an environment that was inclusive and fostered psychological safety.

Scaling our team (and culture) at League

There are a lot of awesome things about our current engineering culture at League. We have a great sense of community within our cross-functional scrum teams and the broader platform teams. With biweekly hangs for backend, web and mobile teams, folks are able to share knowledge, demo work in progress and discuss ways to make improvements to our codebase. Additionally, we all have a mentorship program in place and individualized growth plans that are co-authored with managers. It’s not perfect — and there is still plenty of room to improve and grow — but we make a habit of actually listening to our team and continuously trying to improve the way we do things here.

Preserving (and improving upon) this culture as we scale is a hot topic these days in both my 1:1s with team members and interviews with external candidates. Growth isn’t new to League, over the company’s seven-year history the engineering team has experienced 50% growth year over year, growing from a small group of 10 to more than 200 as of this month. Prior to 2020, our team was all Canada/U.S.-based, and since then we’ve added five more countries to the list. Now, on the heels of our exciting Series C announcement, our expansion continues as we hire in more regions around the world. With this, our engineering headcount will significantly increase this year — something that I’m simultaneously excited and nervous about. Luckily, I’m not heading into this challenge alone, but with a fantastic and experienced team of like-minded leaders.

Here’s what our Leaguers had to say on:

Being intentional

“League started with a group of people that care about the mission, company and one another. We have tried to grow that mindset intentionally through the way we hire, celebrate and recognize each other for living our values and making changes when needed. Everything stems from people that care.” — Liam WIlliams, AVP Engineering

“Intentionally revisit the tactics you employed to create your initial culture and re-think how to best sustain that culture given the changes your company has experienced over the last year. What’s changed with the company? Do we have new/more geographic regions? More remote staff? More diverse skills/team members? Does how we instilled our culture translate effectively at scale, given the changes we’ve experienced in the last year? I recommend running a true retrospective on this!” — Howard Chen, Director, Data

Having a vision

If you are constantly filling in seats to just get the work done, but don’t have a real long-term sense of where you’re going, it’s hard to build a team that will be set up for the long-term. Sometimes you need to be building the car while you drive, but you should at least have an idea where you are going, otherwise, you will be driving in circles!” — Kim Beaudin, Engineering Manager

Being agile and iterative

Establish (or re-establish) communication norms and patterns and have leaders and champions model the “right” communications style. Examples: what’s our slackmoji game like? What is our video camera policy in meetings? What’s the general vibe of our team, group and org-level meetings? How do we sustain it?…

It’s also important to understand that culture will drift naturally as your company grows. Determine what values must remain to constrain the drift over time.” — Howard Chen, Director, Data

Paying attention to who Is getting hired and promoted

Tenure does not automatically give you the appropriate skills to do a job. Often people who have been there a long time have more context around a product/client, but this doesn’t mean they are the best person to be in charge of the overall architecture or lead teams. There are very specific skills that need to be learned and that growth needs to be supported by the organization before someone is put into the role.” — Kim Beaudin, Engineering Manager

Make sure all of the opportunities are given out equally, and not going simply to whoever is the loudest in the room, or participates in the most “social events”. Introverts and those who prefer to spend their social time away from work could be overlooked and miss out.” — Daniela Hagen, VP Compliance, Security & Internal Audit

Ensure that culture add is a prominent consideration when making hiring decisions for new staff. Create — and get creative around — scenario-based questions that suss out whether a candidate would be a good culture add to the team.” — Howard Chen, Director, Data

Valuing clear communication and expectation setting

I think the most important thing is overcommunicating, setting clear expectations and defining roles and responsibilities. It sounds so simple, but if you don’t intentionally do that, it can create a lot of political drama.” — Kerry Weinberg, VP Data

Transparency is important. Employees need to be able to see what the pay bands are, what their career options are and have regular opportunities to give and receive feedback through reviews.” — Daniela Hagen, VP Compliance, Security & Internal Audit

Avoiding silos when it comes to planning and decision making

If there is no company planning process, each department and group is on their own to plan for themselves. This inevitably leads to roadmaps collapsing and a product launch taking much longer than it needs to.” — Daniela Hagen, VP Compliance, Security & Internal Audit

“No matter how well thought out team structure is, as the feature surface area and the number of people working on it grows, more people need to be given the opportunity to weigh in on architectural changes. Written communication better facilitates mass discussion than large meetings, is easier to arrange and provides posterity. The ability for folks to put extra effort into refining their responses before putting them out for consideration can also save participants incredible amounts of time. The Linux Kernel and IETF RFCs are examples of very successful engineering efforts that are mostly guided by asynchronous written communications.” — Jack Forrest, Staff Engineer

Remembering ground-up patterns matter

Developers will, for the most part, copy the patterns that are already in front of them. This isn’t just laziness, the resulting consistency has considerable benefits. However, this makes bad patterns a risk, as the institutional knowledge that a given pattern is bad and should not be copied becomes much more expensive to spread with organization size. The quality of code in areas that are likely to be emulated in other parts of the codebase become paramount as the number of people working on it grows.”Jack Forrest, Staff Engineer

Listening to your team and creating a safe space for feedback

“Consider designating an unofficial ombudsperson/ombudspeople or, at a prior company, what we called the “omsbuddies”. When you create a channel for sensitive inter-team communications from staff to trusted peers it can facilitate operations to de-identify and aggregate feedback to leaders/leadership to take action and sustain team culture.” — Howard Chen, Director, Data

In Closing

Every organization is different and will value different things. However, we can see that clarity around vision and values is foundational to establishing a culture that can grow and adapt. Prioritizing thoughtful and clear communication as well as making sure there is a safe forum for team feedback is essential.

While it’s impossible to expect that things can stay the same forever, approaching challenges with a growth mindset; regularly checking in on rewarded behaviors and making changes when needed, gives organizations a fighting chance to preserve what makes being a part of their team great.



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