Jacob Sinclair

Startup Operator | GTM, Strategy & Operations | 0→1 Builder | DroneDeploy: $500K→$35M+ ARR, acquired by Procore for $845M

IIndependent / Project BasedSex-Silent Circleex-Hudson and Jane

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I’m a startup operator who builds the systems, processes, and GTM motions that help companies move from ambiguity to

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At Silent Circle, I grew from customer support into program management and helped build the company’s enterprise account management function from the ground up, while representing Customer Support on the company-wide PMO team. At DroneDeploy, I joined early and helped build the outbound and enterprise GTM foundation as the company scaled from roughly $500K to $35M+ ARR and ~45 to 150+ employees through Series B–E. I progressed from SDR to Senior SDR to Account Executive, helped establish construction as a key enterprise segment, and ultimately managed a $3M ARR portfolio across construction, energy, mining, and agriculture. At Box, I managed a commercial territory with three accounts worth roughly $1M TAV each, recovering two significant churn risks into six-figure expansions through structured QBRs, automation, and cross-functional Since returning to full-time work, I’ve focused on project-based operating work across GTM, onboarding, and account management. Most recently, I worked directly with the founder of an early-stage AI company as its first GTM hire, building partner onboarding infrastructure from 0→1, creating SOPs and journey maps, setting up CRM workflows, and supporting partner and investor-facing I’m now looking for a high-ownership role at a growing company where I can work across functions, take on ambiguous problems, build what doesn’t exist, and become increasingly useful as the company scales.