Senior Operator (ex-Grubhub, GoodRx, 1stdibs) | Fractional Strategy & Ops

Posted .
Hey everyone — I’m Charlotte Caldwell.
After 10+ years leading strategy, revenue operations, and GTM at high-growth companies including Grubhub, GoodRx, and 1stdibs, I’ve launched Caldwell Projects. I provide fractional leadership and advisory for teams that need to bridge the gap between early product success and a high-scale operating model.

I partner with C-suite and leadership teams to:
  • Drive Growth & Revenue Operations: Executing GTM motions across PLG, Partner, and DTC channels while building the underlying infrastructure for scale.
  • Optimize Unit Economics: Reducing OpEx through automation and BPO strategy while expanding customer coverage.
  • Establish Operational Rigor: Designing the business cadence—from strategic planning and KPI/quota setting to OKRs and the WBR/MBR cycles required for high-impact C-suite and Board reporting.

Recent Impact: At Charlie Financial, I led GTM motions that drove 45% growth in funded accounts in under six months. In parallel, I led cost transformation efforts that reduced OpEx by 42% while expanding support coverage by 88%.

I am a first-principles operator who thrives on getting into the technical details to strengthen long-term business health. If you’re looking for a trusted operating partner to help you navigate your next stage of growth, I’d love to connect.

www.caldwellprojects.com | charlotte@caldwellprojects.com

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