Eli Chait

Spark Woodfire Grill in Los Angeles. A twelve-year-old at the back office, punching paper invoices into an accounting system. His father's restaurant. That's where Eli Chait's career actually started - not at Berkeley, not at the venture fund, not at OpenTable. In a kitchen office, surrounded by the paper chaos that defines how food businesses settle their debts.

Twenty-plus years later, Chait is still working on that same problem. Only now, the scale is different. Wholesail, the San Francisco-based B2B payment platform he co-founded in 2018, processes payments and automates accounts receivable for food and beverage distributors who move goods through the fractured, cash-hungry $1+ trillion US food distribution network.

The linearity of it is almost too clean. But it's real.

Wholesail is not an invoicing tool dressed up as a platform. It's a payment risk management company that combines credit management, automated AR communications, customer onboarding, a self-service payment portal, and ERP integration into a single system for distributors.

The problem it solves is specific and expensive: food distributors extend credit to restaurants and retailers on terms that are difficult to enforce, painful to track, and reliant on relationship calls and paper checks. Invoices get lost. Communications break down. Payments arrive late, or not at all.

Wholesail's answer is infrastructure: plug into a distributor's existing ERP system, automate the entire AR workflow - from credit applications to payment reminders to reconciliation - and give buyers a self-service portal to view and pay invoices online. Distributors using the platform report collecting payments 35% faster without changing their underlying systems or processes.

The most interesting thing Wholesail has built isn't the payment portal. It's Lighthouse - a real-time credit exchange where distributors who opt in share buyer payment behavior data, creating a cross-vendor intelligence layer that no single distributor could build alone.

In early 2026, Wholesail launched Risk of Default Scores on top of Lighthouse: a machine learning model trained on millions of invoices and a decade of payment history that predicts the probability a specific buyer will default. The model was developed with Dan Massoni, who spent 30 years at American Express as Chief Commercial Credit Officer.

The logic is elegant. A seafood distributor and a produce distributor selling to the same restaurant chain have both been burned by the same late payer. With Lighthouse, that information doesn't stay siloed. The network learns. Credit decisions get sharper.

That's not accounts receivable software. That's a data business with network effects wearing an AR platform's jacket.

Berkeley Business Administration. Then Alsop Louie Partners, a San Francisco venture firm, where Chait spent three years as a Venture Associate learning how money flows into startups rather than through them. That period planted something.

In 2011, he co-founded Copilot with Dave Amusin - a restaurant revenue management company that used POS data and local market comparisons to let restaurants benchmark their performance against competitors. It was early, it was clever, and OpenTable acquired it in 2014.

The acquisition wasn't an exit in the traditional sense. Chait walked into OpenTable and ran product - leading a team of six product managers covering analytics, restaurant growth, legacy systems, and the GuestCenter flagship product. He orchestrated the migration of 20,000 restaurants from OpenTable's legacy Electronic Reservation Book to the cloud. At scale. With real operational consequence.

That experience matters. Wholesail isn't a two-person idea company. It's a machine built by people who have shipped products to hundreds of thousands of restaurants and understand what it takes to change behavior at industry scale.

Chait didn't start Wholesail alone. He brought a founding team forged over two prior acquisitions: product managers, engineers, and designers who built Ness Computing (a restaurant recommendation engine), Copilot, and then worked together again at OpenTable. By the time Wholesail launched in July 2018, most of the founding team had already worked together across three companies.

Co-founders Corey Reese (COO), Clarence Yung (Head of Design), Chris Pennello (Technical Co-Founder), and Adam Wagner (Product) form a unit that had already shipped together under pressure. That kind of institutional trust doesn't show up in pitch decks, but it shows up in execution.

In January 2022, Wholesail closed a $22.6M Series A backed by Fin Capital, Foundry, 8VC, Thomvest Ventures, and Ulu Ventures. The round validated a specific thesis: that the food distribution market - historically served by decades-old ERP systems and relationship-based credit decisions - was ready for a purpose-built payments network.

The investor mix is telling. 8VC brings deep operations and logistics expertise. Fin Capital is specifically focused on fintech infrastructure. Thomvest and Ulu round out a portfolio that understands both B2B software and financial services. This wasn't a consumer bet dressed up as enterprise. It was a conviction play on vertical fintech in a market most investors had never looked at twice.

Before launching Wholesail, Chait spent six months researching marketplace economics. He analyzed the 100 largest marketplaces in the world and published a three-part essay series on Medium in 2018 exploring how they solved the chicken-and-egg problem, why sharing economy platforms raised over $50 billion, and why buyer fragmentation is the defining variable in marketplace success.

The third essay's thesis - that billion-dollar marketplaces need at least one million buyers - maps directly to what Wholesail is building. Food distribution has millions of restaurants, bars, and retailers buying from thousands of distributors. The buyer fragmentation is extreme. The network value is enormous. And no one had built the payment rails to capture it.

Most CEOs talk about research as a precursor. For Chait, it was a design brief.