What happens when you admit failure?

If I had to sum up this journey in one sentence, it would be, ‘We lost, but we fought well.’ We achieved the greatest results since Toss Insurance was founded. But we weren’t able to build the foundation to further scale. Now, as painful as it is, I believe it’s time to bravely acknowledge this failure. To everyone at Toss Insurance who gave their all, thank you for your hard work. - Kyounghwa Jung, No Ordinary Challenge, Bookstone, 2022, p.315

Byungik Cho, leader of Toss Insurance, spoke with a slight tremor in his voice. It was at the end of 2021, when he made the decision to end, with his own hands, the experiment of hiring full-time Insurance Planners (Analyst Managers). Nearly 100 people left the company, leaving the office almost empty.

In the final chapter of No Ordinary Challenge, a book recounting Toss’ 11-year journey, Toss Insurance was described as a stranded ship, after struggling to find a viable business model. But by 2025, Toss Insurance had transformed into a large general agency (GA) of 2,700 planners. In 2024, it posted its first annual profit, coming closer than ever to the “free navigation” every startup dreams of.

Those who run away in times of hardship become failures, but those who shake it off and rise again become victors. - Kyounghwa Jung, No Ordinary Challenge, Bookstone, 2022, p.136

When a project ends in failure, it may feel as though everything has been for nothing. In reality, that is not the case. Even in the process of dealing with or overcoming failure, countless crossroads of choice appear, what matters is with what attitude you approach the problem and the grace with which you handle it. The decisions made at those crossroads can define an individual, and even become an opportunity to turn the game around. So, what is Toss’ attitude toward failure? Byungik Cho, who had led Toss Insurance for over two years, acknowledged that period as a failure. Yet instead of running away, he chose to move forward step by step. This is his story.

Facing the Wall

Toss Insurance was founded at the end of 2018 as a GA, offering insurance products developed by partner insurers. Its vision was clear: to create a world where people fully understand potential risks in life and for Toss Insurance to provide basic safeguards with insurance.

Among financial products, insurance is one of the most complex, often involving long-term contract terms. The complexity comes from the wide range of variables like illness, accidents, or even death that can affect a person and their family. That is why consumers have little choice but to trust the insurance planners for guidance. However, compensation plans often misalign the planners' incentives with customers’ best interests. Planners earn commissions that vary by product, with higher payouts tied to products favoring insurers over customers. This structure created a paradox. The less favorable the policy was for the customer, the more the planner earned.

When Cho joined Toss Insurance in 2019, he sought to solve the structural problems in the industry by changing the employment model. Sales staff were no longer called planners but “Insurance Analyst Managers.” They were hired as full-time employees on a fixed annual salary, separating individual performance from income. Their success was measured not by the number of contracts they closed, but by net promoter score (NPS), which also determined their incentives. This way, Insurance Analyst Managers could focus solely on what mattered most: the best interests of their customers.

The first obstacle they faced was slow hiring. Skilled insurance planners earned more as commissioned independent contractors, so they had little interest in switching to a fixed-salary position. Cho shifted to mass recruitment for entry-level talent, speeding up the expansion.

Consultations begin with analyzing the customer’s existing coverage. For example, in the case of a male client in their 40s, an agent would calculate the likelihood of major illness, the average duration and cost of treatment, and the potential loss of income to determine the necessary coverage. If the customer is underinsured, products are recommended to increase coverage. But if the customer was already overinsured, they are advised on ways to reduce premiums instead of being sold a new policy.

The hypothesis that consumers were eager for customer-centric insurance planning was quickly validated. Customer satisfaction consistently stayed in the 90s, well above the industry average of 70 to 80. More than 90% of policies purchased through Toss Insurance were still in force after 13 months. Toss Insurance held two rounds of mass recruitment, expanding its team to 100 members.

However, a greater obstacle soon appeared. Recognizing customer-centric planning as the correct approach was one thing, proving it could sustain a business was another. Even customers who were highly satisfied with their consultations rarely returned to Toss Insurance. Insurance policies are long-cycle products. Once a person purchases coverage, they don’t get another one for a while.

In the first half of 2021, the team set out to break even, even if just briefly. With labor and rent making up most of its costs, cutting expenses was difficult, so the focus shifted to boosting revenue. Skipping meals and working late, the team pushed to handle more consultations. The result was a narrow failure. A sense of frustration swept over the team, “We gave it everything, and it still wasn’t enough.”

Toss Insurance’s innovation wasn’t profitable and barely registered in the industry. To make even a small ripple, the team would have needed to be ten times larger. But with monthly losses already mounting, expanding would only multiply losses on the balance sheet by ten fold. Without a clear sales strategy, the added costs were unsustainable, a limit the company struggled to overcome.

Cho watched the team he had personally hired grow weary and lose energy. They were talented and driven, but they still couldn’t break even. Dragging things out any longer would be nothing more than wishful thinking.

It’s Okay to Struggle

That’s when Cho decided to admit failure to his team, rather than hiding the truth.

I saw it as a matter of respect for my team, and also as my duty as a leader. I asked myself, ‘If I were a team member, what kind of openness and attitude would I want?’ The answer was clear: they would want the truth, without embellishment or pretense. There was no need to dress it up. They would just want to hear why we failed and what we plan to do next. Everyone already knew there was nothing more to be done. We had done all we could. If we couldn’t make it, then surely no one else in Korea could. - Kyounghwa Jung, No Ordinary Challenge, Bookstone, 2022, p.320

Of course, Cho also struggled. With the business faltering and team members leaving, he questioned whether he deserved to remain a leader. But then his perspective shifted, “I don’t have time to dwell on this. I barely have enough time to figure out how to make the next model succeed. I won’t let a second chance to tackle the insurance industry’s problems slip away just because I’m feeling discouraged.” Some members who had been working with him on strategy rallied once again.

The next model had to be: 1. financially viable, 2. fast growing, and 3. still offer customers an enhanced experience. A new hypothesis was formed, markets were studied closely, and projections were built accordingly. Finally, Cho began asking a different question:

“What if we seek impact in breadth instead of depth?”

This meant two changes.

First, instead of salaried full-time positions, agents are compensated based on their own consulting performance.

Second, rather than limiting sales to over-the-phone consultations, the company adopts the traditional face to-face approach of meeting customers directly.

In Korea, more than 90% of insurance policies are still sold face-to-face. What if those agents could be encouraged to value the quality of their consultations as much as the number of contracts? And what if Toss could rapidly expand its pool of commissioned planners to scale faster? If the company’s impact is measured in customer satisfaction multiplied by the number of customers, this new model promised to expand that breadth significantly.

Getting Back Up

Toss Insurance launched face-to-face sales in February 2022 with just two commissioned agents, a modest start. Still, it held firm to the belief that in the insurance market, customer experience is defined by the agent. To ensure consultation quality and earn trust from both customers and agents, several safeguards were put in place.

Toss matched customers seeking consultations with agents for free, helping them overcome their biggest challenge: acquiring new clients. It also disclosed commission policies transparently and cut back on layers of managers who typically take a share of the commission. At the same time, it enforced a strict zero-tolerance policy against mis-selling, whether by misleading customers or concealing unfavorable terms. These measures were designed to guarantee high-quality consultations and build credibility in the market.

A new sentence was added to Toss Insurance’s original vision, “to create a world where people fully understand potential risks in life and for Toss Insurance to provide basic safeguards with insurance.” The addition read, “To become the indispensable partner for planners to succeed.”

The new strategy worked. At first, planners were skeptical, but soon they began joining Toss Insurance in growing numbers. Within a year of launching face-to face sales, Toss Insurance surpassed its first milestone of 500 agents. Only then could Cho finally shed the fear of failure: “We’ve reached a safe checkpoint. Now we can accelerate.”

As of July 2025, Toss Insurance now has 2,700 agents. Surpassing the 3,000 mark, the benchmark for a major GA, now seems only a matter of time. Agents crisscross major cities nationwide to meet customers, and the total number of policies sold has exceeded 360,000. Building on this growth, Toss Insurance recorded its first annual profit in 2024.

Cho points to “sales without mis-selling” as the achievement he is proudest of. Even after shifting to face-to-face sales, only three complaints were filed by customers with the Financial Supervisory Service. The once-stranded ship is now sailing smoothly with its sails raised.

If we had compromised on customer experience, we could have made profits faster and on a larger scale. But at every crossroads, we gritted our teeth and held on to our core value of raising the quality of consultations. I believe that’s what helped us weather the crisis and get to where we are today. - Byungik Cho, September 12, 2025

Writer Kyounghwa Jung