Teams at Checkbox

Lead data strategy and architecture for AI-native SaaS, building secure, tenant-isolated context and retrieval layers, data platform, integrations and eventing. Define data contracts, models, and observability; make buy-vs-build decisions; mentor and grow a small Data team; partner with Product, Engineering, AI and Platform to enable reliable agentic AI features and compliant data access.

Lead and scale Revenue Operations for a B2B SaaS startup: own GTM tech stack and CRM, build processes and playbooks, run data-driven experiments, partner with Finance and GTM Engineering, build AI automations, manage cross-functional projects, and drive measurable revenue outcomes.

The Senior Software Engineer will build AI-powered user experiences, develop frontend and backend services, and integrate AI capabilities into legal workflows, while mentoring engineers and ensuring strong engineering standards.