How the Toss Team Faces the AI Wave: AI Surf Day

Toss created AI Surf Day, a dedicated weekly time for employees to experiment with AI, share lessons, and redesign their workflows. Running on Fridays from April through June, the initiative aims to reduce the AI gap across technical and nontechnical roles by making experimentation collaborative and accessible. Its broader conclusion is that successful AI transformation depends less on formal programs than on culture, time, and people who actively share what they learn.

AI Surf Day’s Purpose

• Employees focus on their core work Monday through Thursday and reserve Friday for AI experimentation and practical application.
• The program addresses anxiety and knowledge gaps, especially among nondevelopers who may struggle to identify useful AI information or find time to learn it.
• Its concept comes from Jon Kabat-Zinn’s phrase: “You can’t stop the waves, but you can learn to surf.”
• The goal is to help Toss become a company that works with AI as a foundation, not merely a workplace where individuals use AI tools.

AI Surf Club

• Employees can create or join informal groups focused on AI topics; roughly 200 clubs were formed at launch.
• An AI Antipattern Study focused on failures and mistakes, turning participants’ experiences into a practical guide for avoiding common problems.
• An LLM Wiki group explored how to organize scattered organizational knowledge across data engineering, machine learning, and business teams.
• A beginner-focused “Step 0” group helped employees overcome basic technical barriers, such as installing agent tools and asking questions they felt were too fundamental.
• A customer-protection team built an external-complaint monitoring portal in one month, along with automation for complaint-response drafts and classification.
• A marketing team divided AI work into roles such as:
  • Builder: creates AI-powered tools and workflows
  • Curator: collects useful examples and resources
  • Operator: applies AI to repetitive work
  • Scouter: identifies new opportunities
• The clubs emphasized reusable outputs and shared confidence, rather than isolated individual experimentation.

AI Surf Weekly

• Weekly sessions share successful internal AI applications, lessons learned, and current industry insights.
• Toss connected employees with similar needs across different departments, enabling them to solve problems quickly by learning from existing internal examples.
• Rather than prescribing specific tools, the program presents ideas and use cases that encourage employees to adapt solutions to their own work.
• Examples included connecting a sales employee with an HR colleague who had built a similar tool, and pairing a marketer with a designer experienced in AI-powered automation.

AI Surf Evangelists

• Toss selected 142 employees across its affiliated companies and teams to promote AI adoption in their own organizations.
• Evangelists were chosen through peer nominations, recognizing people who already shared useful discoveries and helped colleagues overcome AI-related obstacles.
• Their responsibilities over three months include:
  • Reporting effective AI use cases
  • Sharing useful insights with colleagues
  • Hosting at least one meetup or workshop
• Toss’s Culture team provides workshop templates and facilitation support.
• Many teams have conducted workshops around redesigning their existing workflows with AI.
• The program treats AI adoption as a team-level workflow redesign challenge, rather than simply measuring individual proficiency with AI tools.

OpenAI Collaboration and Mini-Hackathon

• Toss held a special AI Surf Day with OpenAI on May 15.
• Hands-on sessions covered:
  • Codex-based development workflows for developers
  • ChatGPT Agent-based automation for nondevelopers
• A 2.5-hour hackathon produced two notable projects:
  • An iOS workflow where Codex implements features, operates the simulator, tests the result, iterates on problems, and produces verification footage.
  • An agent that classifies thousands of daily Toss Place product records, sends reviewers links, and supports approval or rejection through an admin interface.
• These projects demonstrated how AI can become a reusable agentic workflow rather than a one-time assistant.

Culture Over Programs

• Toss does not claim to have a fixed answer for managing AI’s rapid evolution.
• The lasting value of AI Surf Day is the protected time for learning and experimentation, along with a culture where employees openly share results and failures.
• Successful examples spread naturally across teams, while evangelist-led workshops translate experimentation into concrete changes in how work is performed.

Organizations pursuing AI transformation can take a similar approach: create dedicated experimentation time, encourage peer-led learning, recognize existing champions, and focus on reusable workflow improvements rather than tool adoption alone.