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Checkbox is a Series A, Sequoia-backed AI-first legal tech platform transforming how in-house legal teams operate. The company serves leading enterprises including SAP, Coca-Cola, Allianz, BMW, Elastic, and Stryker, providing workflow automation, AI-powered intake, matter management, triage, and work orchestration.
This is a hands-on Principal Engineer role serving as the senior technical authority across Checkbox's product engineering streams. You will own key architecture decisions, including high-consequence "one-way-door" decisions that shape the company's future-state product architecture. The role is technical leadership focused on influence through judgment, clarity, and working code—not people management.
Key responsibilities include: defining and documenting the future-state product architecture; ensuring coherence across product streams, platform, data engineering, QA, and enterprise IT teams; identifying and building force-multiplier initiatives that accelerate engineering velocity; contributing directly to production releases while setting technical standards; driving decisions through data and measurable quality signals; embedding fitness functions and architectural feedback loops; partnering with data engineering on AI and data reference architecture; ensuring tenancy, security, and compliance are designed in from the start; and collaborating with Product, Customer Success, and Sales to align technical decisions with customer and commercial needs.
You will bring significant experience as a Principal Engineer, Staff Engineer, Architect, or senior technical leader in modern SaaS environments. Deep expertise in product engineering, platform architecture, distributed systems, and cloud-native software is essential. You have a proven track record of making and governing high-impact architecture decisions across multiple teams or product areas, and designing force-multiplier initiatives that improve velocity, quality, or reliability. Strong understanding of enterprise SaaS tenancy, security, compliance, and data isolation is required. You are comfortable contributing to production systems while setting broader technical direction, and you influence through credibility, clarity, and working code rather than formal authority. Excellent communication skills and the ability to connect technical decisions to commercial outcomes are critical. You thrive in fast-moving scale-up environments.
Bonus experience includes work on AI-native products, agentic systems, workflow automation, enterprise legal technology, multi-product SaaS ecosystems, systems relying on context/retrieval/eventing/AI workflows, AI and data reference architecture partnerships, and introducing engineering fitness functions and architectural decision records.
