Pie Raises $23.7M as Small Businesses Chase AI Search Over Google

Pie has raised $23.7 million to help barbershops, gyms and repair shops get recommended by ChatGPT instead of just ranking on Google. The New York startup announced a $19.5 million Series A led by Lightspeed Venture Partners on June 30, its first public funding news since building its product quietly in stealth.

Investors are chasing a market they openly call brutal to serve. And the adoption story used to justify that bet splits wildly depending on whose survey gets quoted, from 8.8% to 89% of small businesses supposedly already using AI.

Pie Steps Out of Stealth With a $23.7 Million War Chest

The Series A, announced in a funding release detailing its product suite, brought Pie’s total funding to $23.7 million, meaning roughly $4.2 million had already been raised while the company built quietly before this round. The financing included Capital One Ventures, PayPal co-founder Max Levchin’s SciFi VC, F-Prime, Commerce Ventures and WEX Venture Capital.

The same announcement marked Pie’s exit from stealth and the launch of Front Desk, an AI product that answers calls for small business owners around the clock, books appointments and fields customer questions. Pie was founded by Syed Ali and Akhil Mantripragada, former operators at payments giant Square and restaurant software company Toast, who say they spent 15 years hearing the same complaint from small business owners: they did not need another piece of software, they needed more customers.

Pie’s pitch rests on three linked products.

• AI Search gets a business recommended when customers ask ChatGPT, Claude or Perplexity instead of typing a Google query.
• Growth runs customer acquisition campaigns across Google Maps, Yelp and Nextdoor.
• Front Desk answers the phone at any hour, books appointments and handles routine customer questions.

“Small business owners have been stuck with expensive, opaque agency models for decades,” said Syed Ali, Pie’s co-founder and chief executive.

The Agency Bill Pie Is Undercutting

Pie’s whole pitch leans on undercutting the marketing agencies that many small merchants have relied on for years, which can charge $2,500 to $5,000 a month, lock owners into long contracts and offer little visibility into results. Pie sells itself as a cheaper, always-on substitute that optimizes business profiles and content across those same discovery channels.

• $359 a month is what one Los Angeles salon owner told Inc she pays for Pie, against the $2,500 to $5,000 a typical agency charges.
• $10,000 to $12,000 in added monthly sales followed, according to Inc, enough for her to hire more staff and add nail tables.
• 100,000-plus phone calls have been driven to small businesses through Pie’s platform since its first product launched in late 2025.
• 15% to 20% is the typical year-over-year sales increase Pie says its customers see.

“Pie has made local marketing incredibly simple to manage across our 65 salons,” said Jason Siska, vice president at Moxie Management Group, a Supercuts franchise operator that uses the platform. “At Tekmetric, we’re focused on helping auto repair shop owners grow their businesses, not just run them,” said Sunil Patel, founder and chief executive of Tekmetric, whose software serves more than 15,000 auto repair shops.

A Historically Hard Market Draws Big Names

Small businesses have a reputation in venture capital for being expensive to reach and slow to pay for software, which makes the roster behind Pie notable. “Small businesses are notoriously hard to build for and even harder to reach,” said Max Levchin, the PayPal co-founder who now runs Affirm and backed the round through his fund SciFi VC.

Julian van Guissen, a senior principal at Capital One Ventures, said Pie’s early traction shows “its potential to be a real growth enabler for small businesses.” Lightspeed partner Aaron Frank called customer acquisition “a powerful entry point” toward a larger goal of supporting small businesses across more of their daily operations over time.

The bet mirrors a broader pattern of outside capital treating Main Street as a fresh frontier, the same logic behind easier retail access to crypto investing this year. It also lines up with research firm Gartner’s projection that 60% of commercial research queries will be AI-assisted by the end of 2026, a shift that has turned showing up inside a chatbot answer into its own discipline, often called answer engine optimization.

The Adoption Numbers Depend on Who’s Counting

Ask how many small businesses actually use AI and the answer changes by as much as 80 percentage points depending on the survey. Deloitte’s State of AI in the Enterprise research found 80% of small businesses already using AI believe it is now standard among their peers, while only about a third of non-users agree that is true.

The its research on small business AI spending found new businesses reached 10% adoption in six months in 2025, versus 77 months for firms started in 2019, a pace it calls unprecedented for any prior technology cycle.

Where Small Business Owners Still Don’t Trust AI

Fast growth numbers sit next to a stubborn trust gap. A Business Owner Success Survey from financial technology company Bluevine, published this week, found 82% of small business owners report at least one barrier to using AI more deeply, and just 22% say they are completely confident AI can handle low-level tasks without human supervision.

Data security concerns among small business owners jumped from 23% to 33% year over year, and 78% said they don’t fully trust AI to work unsupervised even on simple jobs, according to the survey’s trust and security findings. The U.S. Small Business Administration’s own guidance flags a related risk: tools that recognize AI-generated content may mark it as spam, which the agency warns could create customer resistance to future outreach if owners lean on automation too heavily.

Is Showing Up in AI Search a Real Moat?

Nobody can say yet whether ranking inside a chatbot answer becomes as durable as ranking on Google once was. Pie’s lead investor treats customer acquisition as the opening move in a much bigger platform play. Reporters covering the raise flagged the opposite risk, that OpenAI, Google or Anthropic could simply build the same recommendation feature into their own products for free.

• Lightspeed Venture Partners frames customer acquisition as just the first chapter, with partner Aaron Frank describing the broader goal as an AI platform supporting small businesses across daily operations over time.
• Coverage of the raise raised a different question entirely: whether showing up in ChatGPT is a durable business or, as The Next Web put it, “a feature the big platforms simply fold in.”

Pie’s answer, for now, is distribution. The company reaches merchants directly and through embedded partnerships with vertical software platforms serving auto repair, pet care, fitness and beauty businesses, a structure meant to make switching costs higher than a single chatbot feature could ever create.

Washington Is Circling Main Street’s AI Gap Too

Small business owners are not waiting on venture capital alone. A Goldman Sachs survey of 1,256 participants in its 10,000 Small Businesses program, run with Babson College and David Binder Research in early 2026, found 93% report a positive business impact from AI, yet only 14% have fully integrated it into core operations.

That gap is fueling a bipartisan push in Congress. The found only 14% fully integrated AI alongside 85% support for the AI for Main Street Act, a bill from Representatives Mark Alford and Hillary Scholten that already passed the House and would direct the Small Business Administration and Small Business Development Centers to train owners on AI adoption. Senators Todd Young and Maria Cantwell have introduced a companion bill in the Senate.

Pie’s own pitch leans on that same scale argument, calling small businesses one of the largest and most underserved software markets left in the country. Its newest capital is earmarked for reaching more of them through the auto shops, salons, gyms and pet care chains already plugged into its distribution partnerships.

Frequently Asked Questions

What does Pie’s Front Desk product actually include?

Front Desk answers business calls day and night, books appointments straight into a calendar and handles routine customer questions, with a customizable voice among its features. It launched alongside the Series A after Pie’s earlier products, AI Search and Growth, had already built a customer base through referrals and platform partnerships.

How much does Pie cost a small business owner?

Pie does not publish standard pricing and instead sells through a demo or signup, but new customers get their first month free plus a $300 advertising credit on a its no-contract, first-month-free offer. That structure undercuts the $2,500 to $5,000 monthly retainer typical marketing agencies charge.

How big is the market Pie and its backers are chasing?

Small businesses make up 99.9% of all U.S. firms and employ roughly 62.3 million people, according to the SBA Office of Advocacy, and Pie calls the segment one of the largest and most underserved software markets left. That scale is why Lightspeed, Capital One Ventures and Max Levchin all bought into a single Series A.

Why do small business AI adoption surveys disagree so much?

The gap comes down to definitions. Government surveys like the Census Bureau’s count only businesses actively using AI in production, while vendor surveys count anyone who has ever tried a free chatbot for a single task. Both sets of figures are real, they are simply measuring different behavior.

Why do so many small businesses still say AI is not for them?

Among businesses with fewer than five employees that have not adopted AI, 82% say they see no applicable use case for their business, according to the SBA Office of Advocacy. Researchers describe that as a perception gap rather than a real limitation, since similarly sized firms already use the same tools for scheduling and customer replies.