How Flatfile uses AI to 6x their prospecting response rates

• Company background: Flatfile is a data platform that helps businesses seamlessly import, clean, and structure customer data, turning messy spreadsheets into ready-to-use, validated formats. It eliminates the manual effort typically required in traditional data prep, making it faster and easier for teams to move data into their systems.

• GTM strategy: Flatfile’s GTM strategy revolves around researching verticals that process a lot of data but still use relatively little software (or legacy software). After finding such a vertical, Flatfile identifies the vendors in each that meet its target firmographic and technographic characteristics and targets them with outbound messaging. Flatfile uses deeply-researched market segmentation to identify niche markets of companies with shared characteristics rather than individual prospecting.

• Motivation for adopting AI: Flatfile’s ideal buyers were difficult to identify. They didn’t have conventional titles and they didn’t exist in standard CRM or enrichment databases, making it difficult to target the right audience. Consequently, Flatfile needed a way to identify hard-to-find personas, generate relevant messaging at scale, and do it all with a leaner team

• AI adoption: Flatfile developed an in-house dashboard called the “Flatfile CIA (Central Intelligence Agency),” which synthesizes AI research from tools like ChatGPT, Exa, Perplexity, and Fire Crawl in a multi-step process. First, after specifying a vertical to research, Flatfile uses ChatGPT’s Deep Research to identify the largest accounts in that vertical and the key market dynamics at play in the industry. Second, with Perplexity, Flatfile generates a detailed summary of an individual account’s background, key objectives and challenges, and financial trajectory. Third, using Exa or similar, the Flatfile team identifies the target personas to reach out to at the account. Finally, leveraging the market- and company-level research they’ve already generated, they write highly-contextualized outreach for those personas, again using AI to take the first draft.

• AI operationalization: Though this all sounds technical, in reality, it took only a couple weeks for a single Flatfile engineer to stand up this process and create the dashboards (the “Flatfile CIA”) the GTM team uses to track it. Flatfile capitalized on their strong engineering culture, taking a technical and deliberate approach to embed AI into their GTM engine.

Results: Flatfile reduced its GTM team from 35 to just 7 people while increasing outbound capacity and improving performance. Their AI-generated outbound emails now achieve 5–6% response rates—compared to ~1% from traditional messaging. They’re able to run thousands of highly personalized outreach messages weekly, with a level of quality that manual prospecting couldn’t match. The AI-powered model has allowed Flatfile to envision a future where a 200-person sales operation can be run by just 20 strategic operators.