Caroline Prettyman
Founder @Jammie Drive
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WORK HISTORY
Founder @Jammie Drive
Richmond, VA, US
Count of PJs Raised + Donated to Children’s Hospital of Richmond at VCU- Year 4 Jammie Drive: 1,052 sets of jammies - Year 3 Jammie Drive: 941 sets of jammies - Year 2 Jammie Drive: 484 sets of jammies- Year 1 Jammie Drive: 228 sets of jammies
EDUCATION
Virginia Commonwealth University
Bachelor of Science (B.S.), Marketing
ABOUT CAROLINE PRETTYMAN
HubSpot + digital nerd, organization enthusiast, problem-solver, wife, boy mama (x2), dog lover, lifelong tomboy, dancing queen, and connecter working to lead with compassionate candor. Personality Types- Myers-Briggs: ENFJ - Protagonist- Enneagram: Type 3 (Achiever) Wing 2 (Helper)- DISC: Id - The Influencer- Predictive Index (PI): CollaboratorI was born and raised in Richmond, VA, and went on to study Marketing at the VCU School of Business. My professional passions and expertise are in HubSpot CRM management, automation, and all things digital marketing, content, and process adoption. I\'m a self-proclaimed digital nomad and thrive working in a remote, collaborative, compassionate, and creative environment. Currently I\'m taking freelance consulting opportunities as a Fractional RevOps & HubSpot Strategy Consultant who partners with scaling companies to transform their HubSpot CRM into a connected, automated, and revenue-driving engine.I support teams across CRM strategy, data governance, pipeline operations, marketing and sales automation, reporting, AI enablement, and process adoption with a deep focus on HubSpot. My work balances analysis and creativity, turning strategy into systems that drive alignment, improve conversions, and unlock smarter GTM execution.I thrive in the fast-moving digital landscape, continuously sharpening my expertise in HubSpot and emerging AI + automation capabilities. I enjoy helping teams build scalable processes, establish clean data foundations, and automation that feels a little bit like magic, all while delivering measurable business impact.
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