Lead Technologist

Who you are

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.

Traits we look for:

At WAY, we rely on deep technical insight to inform and accelerate our rollup and company-building strategies. Here's how our values come to life in this role:

Customers are our obsession. You ground technology choices in the real needs of customers. You prioritize usability, scalability, and value creation over technical novelty.

Everything is possible. You help portfolio teams find a way forward — simplifying complex legacy problems, identifying smart trade-offs, and charting pragmatic paths through technical debt toward modern efficiency.

Strength in diversity. You work across different industries, teams, and perspectives. You welcome different ways of thinking and help technical and non-technical people collaborate effectively during post-acquisition integrations.

Grit. You take ownership and follow through. You’re the kind of person who gets into the details when needed, whether performing deep-dive technical due diligence on an acquisition or debugging a high-priority system integration.

Energy and execution. You bring focus, structure, and urgency to everything you touch. You help acquired companies get unblocked and move their digital and AI roadmaps forward with clarity and speed.

Curiosity enables potential. You’re always learning — whether exploring a new LLM framework, refactoring an inherited codebase, or diving deep into a new industry to understand how digital transformation can disrupt its constraints.

Pragmatic about purpose. You’re motivated by impact. You want to do your life’s work by transforming existing businesses and building systems that endure and support people who share that mission.

About the role

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 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.

What you will do

• 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.

• Build or advise on early-stage MVPs for new business models and "future-state" prototypes for acquired companies.

• Contribute to recruiting and vetting technical talent for portfolio companies — from CTOs to specialist engineering hires.

• Act as a coach and high-level advisor to founders and operators across the entire WAY ecosystem.

How we work with AI

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.

Who we’re looking for

• 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; Business-level Japanese for working with local portfolio and group companies.

• Deep curiosity, strong execution skills, and a long-term mindset focused on building enduring companies.