Darrin Caldwell
Fractional CMO | AI-Enabled Marketing & RevOps | HubSpot Expert | $3M+ Budget | ex-Zappos I help founders, operators, and mission-driven teams build the AI-powered marketing and RevOps infrastructure that turns scattered effort into scalable, measurable growth. What I actually do: Fractional CMO/CRO + HubSpot expert — part strategist, part operator. I don't just build the playbook. I implement it: strategy, CRM architecture, demand gen, paid media, automation, and website — without you hiring five people. Oh, and then I layer it with AI. Experience that backs it up: • $3M+ annual paid media at Zappos.com, driving a 4:1 ROAS • Stood up Salesforce at NIRVC; HubSpot at iDonate & Roots Management Group • Built HubSpot websites: iDonate.com, RootsMG.com, CatalystDataHub.com + more • 2025 "Trusted to Transform" Core Values Award — RootsMG (Blackstone-backed) — recognized for transforming the marketing, driving occupancy growth across the portfolio, and building cross-functional trust at the executive level • 250+ creative & marketing initiatives annually across multi-brand, distributed portfolios • 1 of 5 certified Simon Sinek WHY Discovery facilitators at Zappos Where I work best: Companies doing $1M-$20M who need executive-level marketing leadership, HubSpot expertise, and AI-enabled systems — without the full-time CMO price tag.
