Can a company culture survive scaling?

At around 500 members, the organization hits a wall and becomes ineffective. Individual autonomy is limited, while control and red-taping inevitably grow. The problem isn’t people, it’s structure. And solving it requires fundamentally evolving how we work. - Seunggun Lee, at the Weekly Alignment Meeting in December 2024

WHAT HAPPENS WHEN A TEAM GROWS BEYOND 500

As Toss grew, team members became hesitant to try new initiatives and even shied away from small challenges. These signs became clear when the team grew beyond 500. (August 2021) When the culture came under strain, three issues stood out in particular.

First, information asymmetry. As the team grew, the amount of information and context became overwhelming, making it impossible for anyone to keep up no matter how hard they tried. When information is insufficient, people start to lose confidence. As a result, people started to look to leaders who have access to more information, and individuals ended up becoming less independent, making fewer decisions on their own.

Second, overburdened leaders. Even the most capable leader running a one-person company can’t tackle all problems by themselves, but dependence on leaders grew, which was a risk in itself. At times, the leader’s authority even instilled unnecessary fear or hesitation in team members.

Third, misaligned interests. As the organization expanded and business models diversified, visibility into what each team is working on and what they aim to achieve became less clear. As a result, decisions sometimes happened to go against the company’s overall interests.

When the same situation kept recurring, we had to make a choice. Are we going to keep the team under 500 people, or evolve into an organization where individuals continue to drive excellence with autonomy? Without hesitation, Toss chose the latter.

THE CORE PRINCIPLE OF ORGANIZATIONAL EVOLUTION

The core principle of organizational evolution at Toss was to grow while protecting its culture. A culture where brilliant individuals can take on challenges without fear. To protect this culture and ensure healthy growth, we established five key premises.

1. Greater access to information

Each team member should feel, “What I know is all I need to get my work done,” without fearing they might take the wrong path for lack of information.

2. Ownership of work

Each member should have full decision-making power over their work. Rather than following one sided instructions, they communicate openly, make their own judgments, and choose the most suitable and effective path forward.

3. Separate but together

When team members set their own goals and act to achieve them, the whole company benefits, and the organization grows stronger.

4. High talent density

We work with colleagues that truly drive success. Every time we solve tough challenges together, we’re reminded that “The best benefit is working with the best people.”

5. Faith in the vision

We believe that our work not only contributes to the survival and growth of the company, but also makes society better and brighter as a whole.

HOW TOSS SOLVES PROBLEMS

Toss solves problems through specific measures, such as information sharing, distributed leadership, and cross-organizational alignment^*. Here are three key examples. *Originally meaning “arrangement in a straight line,” the term is often used in companies to describe the process of aligning goals across organizations, teams, and individuals. When all members understand the company’s objectives and strategies and make decisions accordingly, alignment has been well achieved.

Build an Information-Sharing System

Beyond giving each member open access to company information, we created workflows to ensure the information needed for their tasks flows seamlessly. We also established a cadence so that the leaders can regularly collect, organize, and share updates, and keep everyone on the same page. With the right information in place, team members can make autonomous decisions with confidence.

Q. What does greater access to information mean at Toss?

Greater access to information doesn’t necessarily mean that every individual must know all information in real time. It’s more about whether the information required for decisions reaches the right person at the right time. When each member has the necessary context at hand, they can be confident that they can make the right decision with the information that they have.

Q. How is Toss’ information-sharing system different from other companies?

We have several ways to reduce the information gap. One notable way is to have a dedicated owner responsible for the flow of information. Each major business has a designated strategy leader (mCSO, mini Chief Strategy Officer) and a finance leader (mCFO, mini Chief Financial Officer) who examine how changes in the business affect our financials and share those insights with the leadership and teams. In addition, a monthly Gap Bridging meeting is held to discuss changes in product and business, financial impact, and to align perspectives across organizations. The content covered in these meetings is then made public on the company’s work messenger. Of course, not all team members can know everything, but we continue to improve access and transparency so they can find the information they need to try something new or make a decision.

Q. What impact does this information-sharing system have on individuals?

Team members no longer have to make decisions “in the dark.” Instead of relying on their leaders, they are given the power to act autonomously. This confidence strengthens the ownership of their work and provides them a peace of mind. As a result, individuals can work more efficiently, take initiative, and grow independently.

Become a Company of Many Leaders

As the business expanded and products became more complex, it became clear that one company leader making every decision was no longer sustainable. To address this, we built a leadership group by appointing C-level leaders and heads so they can share the responsibilities of the company leader. These leaders become the DRI (Directly Responsible Individual) of specific problems, directly owning and solving them. However, these efforts go beyond just distributing leadership at the individual level. To tackle the growing complexity of the organization, we utilized our organizational structure, which we call domains and chapters. At Toss Core, for example, the business is divided into domains, each with its own leader. Also, we have chapters, which refers to organizations grouped by job function. Chapter heads manage hiring, performance, and feedback to maintain HR process and talent density.

Q. Doesn’t having too many leaders threaten the flat structure?

In many companies, having too many leaders can slow down decision-making or even create factions. However, we avoid this by expecting C-levels and heads to lead not just through authority, but through expertise and trust. Influence without authority. Only those with strong hands-on skills and people management skills can become leaders at Toss.

Q. Why continue to distribute leadership?

When too much authority is given to the hands of the affiliate leader, side effects follow. At Toss, there were times where the authority of the company leader over-shadowed individuals, blocking criticism and dissent, and making it harder to speak up about problems. As a result, we were no longer able to see diverse perspectives, which led to less opportunities to spot risks or discover better solutions. To address this, we chose to distribute leadership and dilute the company leader’s authority.

Q. What positive impact does this distribution of leadership have on individual team members?

Individual team members are able to get multiple supporters, the company leader, the domain leader, or the head, each offering different perspectives. This allows individuals to avoid being dependent on a single authority and instead turn to the leader best suited for each situation. This structure enhances both autonomy and a sense of psychological safety.

Look to the North Star, Together

When an organization gets bigger, each team develops its own goals and interests, which sometimes lead to conflict. To reduce friction and to ensure that every team moves toward the same direction, we came up with the following. First, we created regular forums to align and retrospect. The overall Toss organization, including all affiliates, is called the Toss Community. Every month, the Toss Community gathers for a Monthly Alignment Meeting to share company-wide priorities and updates. We also hold Alignment Week twice a year, which is a full week dedicated to reflecting on the past six months and setting the direction for the future. As the organization grows, the topics we handle inevitably become more complex and difficult. To keep the meetings more clear and engaging, Toss’ communication experts help connect different functions, encourage active participation, and ensure that everyone fully understands the content.

Q. Why is Alignment Week, held every six months, strategically important to Toss?

The first Alignment Day was held in April 2018. Back then, the entire team consisted of less than 50 people, and the presentations wrapped up in just half a day. In 2021, the event was expanded to Alignment Week, as the organization grew. One day was no longer enough to accommodate all the new affiliates that formed one Toss Community.

An Alignment Week presentation mainly consists of three critical parts:

1. Review the past half-year based on key metrics, share stories of success and failure, and thank team mates who stood together along the way.

2. Present the team’s specific goals and core strategies, highlight upcoming products or campaigns, and energize the community with confidence that their plans will succeed.

3. Outline where achieving these plans will require support from, or have an impact on, other teams, so that everyone can align in advance.

This allows team members to fully understand the current state of the Toss Community, which reduces information asymmetry and provides team members the momentum to continue moving forward toward a single goal. Instead of results and plans coming solely from leaders, all teams and members participate as presenters, questioners, and colleagues.

Q. What is the role of the communication experts that organize the Alignment meetings and events?

At Toss, there is a role called the “Culture Business Partner.” Their job is to create a “forum” where people can freely share their opinions, without hesitation or second-guessing themselves. They design environments where all kinds of stories can be exchanged openly, from challenges and mistakes to successes and lessons learned. It is especially important to bring bold agendas to the table that make people wonder, “Is it even okay to bring this up?” and to openly address the questions people are curious about but hesitant to ask. Especially when leaders open up first, team members can feel a stronger sense of connection and psychological safety to speak up. This culture prevents conversations from being dominated by a handful of leaders or those with the loudest voices, and instead creates a foundation for even the hesitant members to take part, which creates a virtuous cycle. In a culture where anyone can speak up, that entire organization can communicate more honestly and connect on a deeper level.

Q. What about smaller, more specific discussions that are too detailed for company- or community-wide meetings?

Some issues are too detailed or require deeper discussion than a company-wide meeting can cover. That is why organizational units with more than 100 members can hold Domain town hall meetings once a month. In these sessions, teams can openly share their performance and plans, as well as current challenges and concerns and exchange honest feedback. The goal is to maintain a sense of unity even within large organizations, where team members actively raise issues and solve problems together.

Toss culture has evolved through countless trial and error. The solutions we’ve found today are not final, but steps toward a better tomorrow. Built on autonomy and accountability, we are shaping a culture where everyone moves forward together, towards a common goal.

Reference “Challenges and Solutions in Scaling Beyond 500”, Toss internal document

Advisors Kyuin Oh, Toss Pay Leader Jaenee Chun, Toss Culture Business Partner Sungbong Ha, Toss Head of Staff Seonghak Hong, Toss Head of Staff (People)

Writer Jiyoung Lee