WAY is an investment firm and company builder focused on the Japanese market. Our primary focus for the next several years is our AI-enabled Rollup strategy — acquiring and consolidating companies with untapped potential and radically enhancing them through modern digital transformation and AI integration.
As our Lead Technologist, you will be the technical architect of this strategy. You will work directly with WAY and our portfolio companies to design the next generation of technology-enabled businesses. While you will still support the development of early-stage MVPs for new ventures, your majority focus will be on guiding technical due diligence, modernizing legacy platforms, and leading comprehensive AI transformations across our acquired portfolio to ensure long-term growth.
You’re a hands-on technologist with a strategic mindset who is excited by the possibilities that modern tech stacks and AI enable. You enjoy building, but you also thrive when architecting digital transformations, reviewing complex systems, or helping portfolio companies make high-stakes technical decisions. You’re naturally curious, collaborative, and energized by driving value across a diverse range of companies. Whether your background is in software engineering, product architecture, or systems design, you have both the technical depth and business acumen to translate between legacy systems, modern cloud infrastructure, and the next generation of AI-enabled business models.
At WAY, we believe AI is not just a tool — it’s a competitive edge. Everyone on the team, regardless of role, is expected to:
- Identify and automate parts of your job that can be made more efficient using AI.
- Experiment with AI tools to increase productivity, improve quality, and unlock new ideas.
- Share what you learn with your teammates so we all get better, faster.
Responsibilities
- Lead the digital and AI transformation of portfolio companies, moving them from legacy systems to modern, scalable, and AI-ready architectures.
- Perform technical due diligence on potential acquisitions, assessing tech stacks, security, scalability, and data quality.
- Design technical roadmaps for acquired businesses that prioritize operational efficiency and sustainable growth.
- Architect and oversee AI implementations that provide a clear competitive edge, from automation to data-driven decision-making.
- Collaborate with portfolio leadership to define technical strategy and manage critical build-vs-buy decisions.
- Identify and evaluate external vendors, APIs, and modernization tools to accelerate the transformation of the rollup portfolio.
Requirements
- 5+ years of experience in software engineering, technical leadership, or systems architecture, with a proven track record of scaling or transforming businesses.
- Broad technical fluency across modern cloud infrastructure, platforms, and frameworks, with the ability to navigate and modernize legacy codebases.
- Deep curiosity about the AI ecosystem, including LLMs, automation workflows, and building data foundations.
- Experience in technical due diligence or post-acquisition integration is highly desirable.
- Ability to quickly assess risks, estimate timelines, and advise on resource needs within a portfolio context.
- Strong communication skills; able to translate complex technical transformations into clear business value for investors and stakeholders.
- Strong business-level English required; Japanese fluency is a significant advantage for working with local portfolio and group companies.
- Deep curiosity, strong execution skills, and a long-term mindset focused on building enduring companies.