Drew Grossman

Background

About Drew Grossman

I’m a strategic and technically fluent Principal Technical Program Manager with 11+ years leading large-scale initiatives across cloud infrastructure, billing platforms, platform engineering, and security. I specialize in aligning cross-functional engineering teams to deliver scalable, reliable systems that directly impact business outcomes.At Toast, I led a multi-phase billing system overhaul supporting $4B+ in annual revenue, resolved a $40M+ MRR revenue leak, and helped re-architect customer lifecycle processes across 120k+ users. I thrive in environments where ambiguity meets complexity—transforming both into structured execution, roadmap clarity, and measurable outcomes.With a strong foundation in SDLC, compliance, cloud-native infrastructure, and data platforms, I excel at embedding program discipline into fast-moving technical organizations. I’m passionate about building systems, processes, and teams that scale—especially in domains like usage-based pricing, observability, and secure development.Let’s connect if you're solving hard infrastructure, platform, or billing problems and looking for someone who can drive clarity, velocity, and impact across engineering.