Senior Bilingual Software Engineer – West Coast (U.S.) at Tailor

OVERVIEW We are seeking a highly capable Senior Bilingual Software Engineer to serve as the connective layer between our Forward-Deployed U.S. teams and our Platform Core Engineering team in Japan. This role reports directly to the CTO, reflecting its strategic importance in aligning product direction, platform evolution, and field execution. This role is not about language translation. In an AI-enabled environment, its core responsibility is context alignment and leverage maximization—ensuring both teams operate with a shared understanding of priorities, constraints, urgency, and intent. You will play a critical role in making sure: - The Platform Core team focuses on the highest-impact problems, grounded in real-world usage - The Forward-Deployed teams extract maximum value from the platform, leveraging it effectively and correctly This is a high-impact role at the center of a two-speed organization: fast-moving field execution and a scalable, reusable platform. KEY RESPONSIBILITIES - Act as the primary interface between Forward-Deployed U.S. teams and the Platform Core team in Japan, driving deep, bidirectional context alignment - Continuously synthesize and communicate what is happening on the ground—including priorities, urgency, constraints, and team sentiment (“temperature”) - Translate not just requirements, but intent, trade-offs, and decision rationale across both sides - Influence platform roadmap and product strategy by ensuring decisions are grounded in real-world usage, high-impact opportunities, and evolving field needs - Ensure the Platform Core team is working on the highest-value problems, with clear prioritization informed by field context - Ensure Forward-Deployed teams fully leverage the platform, including understanding its capabilities, constraints, and intended design patterns - Drive cross-regional program execution, including: - Defining and maintaining clear priorities, milestones, and success criteria across teams - Managing dependencies, risks, and trade-offs between Forward-Deployed and Platform Core workstreams - Establishing and enforcing execution cadence (planning, check-ins, reviews) across time zones - Ensuring accountability and follow-through on key initiatives - Facilitate technical discussions, design reviews, and prioritization decisions across regions - Improve internal systems for global collaboration, including documentation, communication cadence, and decision-making frameworks QUALIFICATIONS REQUIRED - Near-native proficiency in both English and Japanese, capable of conveying nuanced context such as priorities, urgency, assumptions, and technical trade-offs. - 7+ years of experience in software engineering, with strong exposure to system design and real-world implementation - 4+ years of prior experience operating as a Software Engineer within a U.S.-based organization, where English was the primary language for technical discussions, design reviews, and deliverables, both orally and in writing. - Strong understanding of modern software architecture (APIs, backend systems, data models) - Proven ability to operate across product, engineering, and implementation contexts - Experience working with distributed or cross-border teams - Strong communication skills with the ability to convey nuanced context, not just information PREFERRED - Experience in platform engineering or building extensible systems - Familiarity with ERP, supply chain systems, or complex business applications - Experience with SaaS integrations or composable/headless architectures - Background in solution architecture or technical program management - Experience in a startup or high-growth environment - Experience or familiarity with modern systems programming languages (e.g., Go, Rust) and/or TypeScript, aligning with the Platform Core team's current or evolving technology stack. WHAT SUCCESS LOOKS LIKE - The Platform Core team consistently prioritizes high-impact work aligned with real field needs - Forward-Deployed teams maximize leverage from the platform, minimizing unnecessary custom work - Reduced rework and friction caused by misalignment in priorities, assumptions, or timing - Clear and shared understanding of technical trade-offs and decision rationale across both teams - Faster feedback loops between field execution and platform evolution - High trust and strong collaboration across U.S. and Japan teams LOCATION & WORKING CONDITIONS - Based on the U.S. West Coast (required) - Hybrid or remote-friendly - Open to working regular hours of 10:00 AM – 7:00 PM PT to maintain meaningful daily overlap with the Japan-based Platform Core team (required) - Willingness to travel (~15%), primarily to strengthen cross-regional collaboration and alignment WHY THIS ROLE MATTERS As organizations scale globally, the challenge is not access to information—it is alignment on context, priorities, and intent. This role ensures that: - The platform evolves in the right direction, focusing on what truly matters - The field operates with maximum leverage, building on the platform instead of around it By synchronizing these two layers, you enable a system where speed and scalability reinforce each other, rather than compete. Salary range: $120K - $200K