OpenView's portfolio companies were rapidly adopting AI technologies, but leadership lacked a standardized way to track progress or compare capabilities across the portfolio. Without visibility into which companies were leading versus lagging in AI maturity, it was difficult to allocate resources effectively or identify where strategic support was most needed. I led the design and launch of a comprehensive quarterly AI survey to address this gap. I began by interviewing 5-6 portfolio company CTOs to identify the most meaningful AI metrics to track, ensuring the survey would capture actionable insights. I then built a 20-question survey in Typeform and collaborated closely with our portfolio team to drive adoption, ultimately achieving an 80% response rate across more than 50 companies. To make the data actionable, I created a benchmarking dashboard in Claude that allowed each company to see how they ranked relative to their peers across key AI capabilities. While the survey has not yet produced measurable outcomes, the expected impact is significant. CTOs will use their personalized benchmarking reports to identify capability gaps and prioritize AI investments with greater confidence. Leadership will leverage the aggregate data to make informed decisions about which companies require additional support or resources, enabling more strategic allocation of OpenView's expertise across the portfolio.