Marketers are ‘freaking out’ about AI search. This Seattle startup just raised $2M to help.

Seattle startup vets Todd Sawicki and Patrick O’Donnell are teaming up to solve a critical challenge for marketers: understanding how increasingly popular AI search tools recommend products. Their startup, Gumshoe, just closed a $2 million pre-seed funding round led by Seattle startup studio Pioneer Square Labs. AI tools like ChatGPT and Claude are shaking up the SEO industry as more people switch from traditional search to the new services. There are significant potential e-commerce implications — ChatGPT, for example, announced this week that it is adding shopping features within its search app. Instead of sending users to a list of… Read More

Apr 29, 2025 - 23:33
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Marketers are ‘freaking out’ about AI search. This Seattle startup just raised $2M to help.
Gumshoe co-founders Todd Sawicki (left) and Patrick O’Donnell. (Gumshoe Photo)

Seattle startup vets Todd Sawicki and Patrick O’Donnell are teaming up to solve a critical challenge for marketers: understanding how increasingly popular AI search tools recommend products.

Their startup, Gumshoe, just closed a $2 million pre-seed funding round led by Seattle startup studio Pioneer Square Labs.

AI tools like ChatGPT and Claude are shaking up the SEO industry as more people switch from traditional search to the new services. There are significant potential e-commerce implications — ChatGPT, for example, announced this week that it is adding shopping features within its search app.

Instead of sending users to a list of links, AI can now recommend — and even help buy — a specific product. In the same way marketers once obsessed over Google rankings, the next frontier could be understanding which brands LLMs recommend — and why.

“Every marketer is just freaking out about what’s going on with this new world,” said Sawicki, a longtime revenue leader at companies including media content site Cheezburger and Shopify-focused startup Fantastic.

Gumshoe’s technology generates thousands of conversations with AI models, helping marketers see how their brands are discussed and what sources are cited. This allows them to discover what AI is telling potential customers about their products compared to competitors and whether a company is winning the so-called “share of LLM” — a metric measuring how often brands are mentioned in AI-generated answers.

Gumshoe generates reports that show how often a brand is mentioned in AI search responses — in this case, Microsoft Azure. (Gumshoe screenshot)

Gumshoe’s analytics also reveal trends. For example, AI models are increasingly citing business and product pages over time, with a strong preference for recently published content.

The startup also tracks how different LLM models are evolving month-to-month.

The company’s product shows how AI search is a much different beast than traditional search.

Unlike traditional SEO, which Sawicki describes as a popularity contest similar to “high school prom king and queen,” he said AI search prioritizes the right information rather than the most popular.

“AI search is absolutely trying to find the canonical correct information,” said Sawicki, the former CEO of content marketing platform Zemanta.

Other startups addressing similar challenges include Profound and Evertune, though Sawicki said Gumshoe is more focused on specific brand positioning rather than a mass-market approach.

Gumshoe is currently in public beta with hundreds of companies, and plans to implement a commercial paywall model this summer. Future plans include helping companies make their content more AI-crawler friendly and generating FAQs optimized for AI consumption.

Other investors in the company include Hawke Ventures, a Los Angeles-based firm focused on marketing tech, as well as angels such as ad tech vet Ari Paparo and other former execs from Google, LinkedIn, Meta, and X.

Gumshoe has seven employees. O’Donnell previously co-founded restaurant review company Urbanspoon, AI training startup MightyAI, and local professional platform Fresh Chalk. Gumshoe’s chief revenue officer, Jim Watson, was a senior vice president at Foursquare and Placed. Stan Chang, head of product, was a product lead at Redfin and Moloco.