BREAKING  Wholesail digitizes the paper invoice of a $1T food supply chain Payments accelerated ~8 days on average 400+ distributors · 100,000+ buyers connected 55% of customers run on autopay $22.6M Series A · 8VC, Foundry, Fin Capital 82% of payments move via ACH BREAKING  Wholesail digitizes the paper invoice of a $1T food supply chain Payments accelerated ~8 days on average 400+ distributors · 100,000+ buyers connected 55% of customers run on autopay $22.6M Series A · 8VC, Foundry, Fin Capital 82% of payments move via ACH
San Francisco · Founded 2018 · Fintech

Wholesail

The accounts receivable platform that keeps food & beverage distributors getting paid - faster, and without the awkward phone call.

AR Automation B2B Payments Credit Risk ACH & Autopay
Wholesail brand graphic
WHOLESAIL. The unglamorous middle of the food chain - invoices, terms, and trust - rebuilt as software.
$22.6M
Series A raised
400+
Distributors
100K+
Buyers connected
~8 days
Faster payment
The Dispatch

The least glamorous problem in food, solved on purpose

Somewhere right now a produce distributor is loading a truck before dawn, and somewhere else a stack of paper invoices is waiting to be chased by phone. That gap - between delivering the goods and actually getting paid - is the quiet drama of the food trade. Wholesail decided that gap was worth a company.

Most fintech chases the swipe at the checkout. Wholesail went the other direction, into the back office of the $1+ trillion US food and beverage distribution market, where invoicing and payment are still nearly entirely manual and paper-driven. It is not the part of the supply chain anyone writes songs about. It is the part where margins live or die.

"Reduce payment risk to grow sales with confidence."- Wholesail, company tagline

The pitch is plain: onboard customers with confidence, let them pay on time, help accounts receivable collect, drive payments to ACH instead of expensive cards, and put a real-time credit score on every buyer. No fax machine required.

The Product

One platform for the whole awkward conversation

Wholesail bundles the things a distributor used to do across spreadsheets, banks, and a lot of follow-up calls into a single accounts receivable platform.

01

Autopay

Payments run automatically - on delivery, weekly, monthly, or when invoices come due. Customers on autopay stay in good standing. More than 55% use it.

02

Lighthouse

A cross-vendor credit engine powering real-time decisions, cut-offs, collections, and Risk of Default Scores on every customer.

03

Payment Portal

A self-service portal where buyers view and pay invoices via ACH or card. Around 78% of customers use it - so AR teams stop chasing.

04

Sales & Risk Monitoring

Reps see past-due accounts, send reminders, and take payments from anywhere, with real-time data at their side.

05

Fee Reduction

Nudges buyers off credit cards toward ACH - 82% of payments now move via ACH, trimming processing costs.

06

AP for Buyers

The other side of the network: buyers automate accounts payable to save time and money paying their vendors.

By The Numbers

What adoption actually looks like

Network effects are easy to claim and hard to prove. Wholesail's own platform metrics give the texture: once buyers are on, they tend to stay self-service and on autopay.

Set up ACH or card
80%
Use the payment portal
78%
Payments via ACH
82%
Payments on autopay
55%

Source: paywholesail.com platform statistics. Figures approximate and self-reported.

The Origin

It started with a 12-year-old and a stack of invoices

CEO Eli Chait grew up in the restaurant business. His first job, at age 12, was entering invoices into the accounting system at his father's restaurant, Spark Woodfire Grill in Los Angeles. He saw early how much friction lived between vendors and the people who owed them money.

Years later he was Director of Product Management at OpenTable. He co-founded Wholesail in 2018 with Christopher Pennello and Corey Reese - a team of repeat entrepreneurs who had built products together at OpenTable and at two startups it acquired, Ness Computing and Copilot. Between them, experience serving more than 40,000 small and medium businesses.

EC

Eli Chait

Co-Founder & CEO
CP

Christopher Pennello

Co-Founder
CR

Corey Reese

Co-Founder
In The Field

Who uses it, and what changes

Produce distributors, seafood and dairy suppliers, bakeries, breweries, specialty food providers - the businesses that keep restaurants stocked and rarely get the spotlight. They are the ones for whom a few days of faster cash is the difference between comfortable and tight.

$163K collected in 30 days

One distributor pulled in more than $163,000 in past-due sales within the first month of using Wholesail.

57% → 78% current

Within months, one company's share of customers with current balances jumped from 57% to 78%.

20 hours a week back

A customer reports saving roughly 20 hours weekly that used to go to chasing and processing payments.

14+ ERP integrations

Out-of-the-box connections to QuickBooks, NetSuite, Xero, Sage, Entree and more - so the back office stays in sync.

"I cannot speak highly enough of Wholesail - they have a great product which is backed by great people, providing for a great experience."- Wholesail customer testimonial
Money & Milestones

$22.6M to bet on automated trade

In January 2022, Wholesail closed a $22.6M Series A. The backers read like a roster of B2B fintech believers, and the company's earliest checks came from operators who had built at Stripe, Square, Dropbox, Yelp, OpenTable and Everlane.

8VCFoundryFin CapitalThomvest VenturesUlu Ventures
The Network

Plumbing built with the right partners

Modern Treasury

Payment operations infrastructure powering Wholesail's B2B payments platform.

Plaid

Instant bank data and account verification for onboarding and payments.

Stripe

Card payment processing inside the Wholesail platform.

NECS · entree

ERP partnership streamlining AR for food distributors.

CAI Software

Integration enhancing AR automation and credit management for manufacturers.

QuickBooks / NetSuite / Xero

Among 14+ pre-built accounting and ERP integrations.

Marginalia

Four things worth knowing

The CEO's first job at 12 was data-entering invoices at his dad's restaurant. The problem found him early.

The credit engine is named Lighthouse - built to spot trouble before you run aground.

The founding crew reunited from OpenTable and two of its acquisitions - Ness Computing and Copilot.

The market it's after - US food & beverage distribution - is worth over $1 trillion and still runs on paper.

The Close

Back at the loading dock

The truck still leaves before dawn. The produce still has to be delivered, the seafood still has to be fresh, and the bakery still wants its flour on time. None of that changed. What changed is the stack of paper invoices waiting to be chased - because for 400-plus distributors, it isn't a stack anymore. It's a portal, a score, and an autopay that already ran.

Wholesail didn't make food distribution exciting. It made getting paid for it boring, in the best way - predictable, automated, and roughly eight days sooner. In an industry of thin margins and early mornings, that is the kind of quiet that operators will gladly pay for.

Connect & Share

Find Wholesail

Sources: paywholesail.com, LinkedIn, Crunchbase, Wellfound, PitchBook, CB Insights, Modern Treasury, CAI Software. Some figures are self-reported and approximate.