Drew Grossman
Experienced Technical Program Manager | Driving Scalable Cloud Infrastructure, Billing Systems & Compliance Readiness | Platform Engineering & Security Programs
- Role
- Lead Technical Program Manager at Klaviyo
- Location
- Philadelphia, PA, US
- LinkedIn followers
- 500 followers
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.
Experience
Lead Technical Program Manager
Jul 2025 — Present · Philadelphia, PA, US
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