Teams at Checkbox

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.

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.

The Senior Customer Success Manager will partner with enterprise legal teams, guiding them from adoption to growth, ensuring successful integration of Checkbox into their legal workflows, managing retention and expansion of accounts, and leveraging data for proactive engagement.