An AI startup making WhatsApp behave like Shopify - and getting paid by Alibaba to do it.
It is a Tuesday morning in São Paulo. A woman tries on a pair of jeans, photographs herself in a fitting-room mirror, and texts the picture to a number she got from an Instagram ad. Three seconds later she gets back a reply: a recommended pair in her size, a discount code, and a link that, when she taps it, drops her two clicks away from checkout. There is no app to install. There is no login. There is, technically, no website. The brand on the other end of the conversation is a Connectly customer, and the friendly voice replying to her is not a person at all. It is Sofia, an AI agent built by a small company headquartered four-and-a-half thousand miles north, in San Francisco. This is what Connectly does for a living. It makes shopping feel like texting a knowledgeable friend - and it makes the brand on the other end of the thread look almost suspiciously good at its job.
For two decades, online retail has been a one-way push. Brands shout. Customers scroll. Conversion rates hover around 2 percent because the medium - a static webpage seen through a browser tab - is, frankly, a terrible place to ask a question. Email open rates linger around 20 percent. SMS does a little better, then dies in a thicket of spam filters. Chatbots, for most of the last decade, were a punchline.
Meanwhile, in the places people actually live online - the inbox of WhatsApp, the DMs of Instagram, the SMS thread with their dentist - a different rhythm prevails. Messages there get opened. They get answered. They feel like life, not like marketing. The trouble is that those channels are gated, rate-limited, and a regulatory minefield. Most retailers stare at them, see the opportunity, and have no idea what to do next.
Stefanos Loukakos spent four years at Facebook running the business side of Messenger and, for a brief stint, its blockchain group. Before that he was country director at Google in Greece, and before that, somehow, CEO of a Greek telco called Hellas Online. The man has a long résumé and a stubborn habit of ending up in places where messaging meets money. In 2020, with Yandong Liu - formerly CTO of Strava and a researcher at Yahoo - he started Connectly with what at the time looked like an oddly narrow bet. The bet: that messaging would eat e-commerce, and that the right way to win was not to build another app but to make every existing chat thread shoppable.
It is the sort of pitch that sounds obvious now and sounded mildly eccentric then. Conversational commerce had been talked about for years and had, with the exception of a few outliers in China and Brazil, mostly produced clippy chatbots and disappointed quarterly reports. Loukakos and Liu argued the difference would be AI - not the kind that answers FAQs, but the kind that can read product catalogs, hold a coherent conversation, and quietly close a sale.
The marquee product is Sofia AI, launched in 2023. Sofia is an AI sales agent that lives inside a retailer's WhatsApp, Instagram and SMS channels. She greets customers, answers questions about the catalog, recommends products, recovers abandoned carts and - when a human really is needed - hands the conversation off to a live agent with the entire history neatly attached. She is the part of Connectly that gets demoed at conferences and screenshots well in pitch decks.
Behind Sofia sits the part that takes longer to explain: a campaign builder for multi-channel messaging, a workflow engine for automating order updates and reminders, a UTM-tracked analytics layer, a no-code template library, and integrations with Shopify, VTEX, HubSpot, Salesforce and Zendesk. None of that is glamorous. All of it is necessary. The hard part of conversational commerce is not the AI. It is the catalog sync, the consent management, the rate-limit handling, the message templates that Meta has to pre-approve. Connectly does the boring parts so that the chat looks magical.
Connectly does not publish a public customer list, and the case studies it does release come with the usual caveats - cherry-picked, retailer-friendly, marketing-team-approved. Still, even discounted, the numbers are interesting. Customers have reported campaign ROI of up to 30x. One unnamed retailer doubled its conversion rate inside Sofia. Connectly itself reportedly doubled revenue and headcount in the year following Sofia's launch. The Series B announcement put valuation at roughly $100 million and total funds raised at just under $40 million - modest by Silicon Valley standards, but unusually capital-efficient for an AI company in 2024.
The investor list is its own quiet argument. Unusual Ventures, Volpe Capital, RX Ventures and Falabella Ventures - the venture arm of the Latin American retail giant - all returned for the Series B. Alibaba led it. That last name is the headline. American AI startups rarely take strategic money from Alibaba; it implies a worldview in which conversational commerce is not a US niche but a global default, and in which Connectly is positioned to ride both the WhatsApp tide and the broader shift in how Asian and Latin American consumers shop.
Read the company's About page and the wording is almost suspiciously plain. Connectly wants businesses to build meaningful, personalized two-way relationships with their customers on the channels customers already use. That is a sentence that could, with very minor edits, sit at the bottom of a thousand SaaS landing pages. The difference is that Connectly seems to mean it in a particular way: relationships, not blasts; replies, not broadcasts; revenue earned in a thread, not in a banner.
The internal culture, by all available signals, matches. The company is small for its reach - about 58 people - and distributed across San Francisco and Latin America. The team ships fast, measures itself in customer revenue lift rather than feature count, and seems to enjoy the slightly unfashionable position of selling AI that does an old-fashioned thing: helps a customer find the right pair of jeans.
The bull case for Connectly is straightforward. Messaging volume keeps rising. WhatsApp keeps opening up its business APIs. Generative AI keeps getting better at the one thing Sofia needs to be good at: holding a coherent, helpful, on-brand conversation about a catalog. If you believe any two of those three things, you probably believe that some company will own conversational commerce the way Shopify owns small-business storefronts. Connectly has spent five years arguing that company should be them.
The bear case is also straightforward. Meta itself could decide to build this in-house. A larger player - Salesforce, Klaviyo, Shopify - could buy a competitor and bundle. Regulators could change the cost of business messaging overnight. Conversational commerce, like most categories named in TechCrunch headlines, may take a decade longer than the optimists think.
Return, for a moment, to the fitting room. The woman buys the jeans. Three days later, a thread on her phone lights up again - a polite check-in, a styling tip, a question about whether she would like the matching jacket she nearly added to her cart. She replies. She buys. She does not, at any point, open the brand's website. She does not download an app. She does not, strictly speaking, know the name of the company on whose plumbing this whole exchange is running. Connectly likes it that way. The best infrastructure tends to disappear into the experience it powers.
A chat thread became a checkout lane. A friendly text became a sales channel. Three billion inboxes became, very quietly, a marketplace. There is a small, capital-efficient, Alibaba-backed company in San Francisco that has spent five years insisting this would happen. It has been a strange thing to watch them be right.