Welcome Squire to the Trinity Family

Schwark Satyavolu
Trinity Ventures
Published in
4 min readJun 25, 2019


We’re excited to back the team whose technology is changing the game for appointment-based small businesses

“How much do I owe you?” — That is how most interactions between consumers and businesses or service providers end. But that ending is slowly starting to disappear to the point where, in a decade, we may not even have to utter that phrase very much anymore.

Most people think of the word “transaction” as payment for goods and services. In reality, real-world transactions between consumers and service providers are actually multi-faceted experiences with typically three essential steps:

STEP 1: Access — hail a cab, walk into a store, book an appointment

STEP 2: Experience — take a ride, choose a product off the shelf, get a manicure

STEP 3: Pay — hand over cash, swipe a credit card

Payment has always been a distinct and separate piece of the transaction puzzle. But thanks to technology, there is an evolution happening that blurs the lines between these steps and even eliminates them altogether. Uber was able to eliminate the payment step for transportation, but not without reimagining everything about the driver and passenger experience. AmazonGo is starting to do the same for retail, but not without changing the entire layout and infrastructure of the traditional bricks-and-mortar store.

In order to deliver a new generation of delightful and seamless consumer experiences like these, you have to replace the entire “operating system” of the business at a fundamental level. This kind of disruption requires a whole stack of services that can be adopted by both sides of the transaction: the consumer as well as the service provider. At Trinity, we have been looking for companies that are taking this hyper-vertical approach to creating what is, in effect, a vertical-specific small business ERP that makes consumer interaction easy and friction-free — and makes the payment step disappear.

Appointment-based businesses are particularly complex for service providers and their customers. The solutions for this particular SMB market out there today are a patchwork of disparate and ineffective solutions that solve one small part of a complex puzzle of problems. This market desperately needs the kind of re-imagination that we’ve seen in transportation and retail.

That’s why I’m excited to announce our investment in Squire, a full-stack business management platform that is changing the game for appointment-based service providers — starting with barbershops.

Founders Dave Salvant and Songe LaRon have cracked the code on delivering a delightful experience for both shop owners and their customers by effectively redefining how these businesses operate. Before founding Squire, Songe and Dave left successful careers in law and finance to open their own barber shop in Manhattan. They had an idea and wanted to learn the intricacies of the business firsthand before entering Y Combinator to develop the technology that solved for every point of friction. They have figured out exactly what this vertical of SMBs need, they have delivered it effectively, and they’re seeing massive adoption as a result.

Squire’s Commander platform for Barbershop POS

Squire has managed to create a solution that drastically improves the barbershop client experience while also completely streamlining the operations of the barbershop itself — all the way from appointments and point of sale to payroll to inventory management — in one seamless, integrated platform. The beauty of this platform is reflected in the amazing sales efficiency of this company which has industry-leading metrics for any SMB-focused business.

I’m truly thrilled to be backing Songe and Dave on this journey, and proud to join existing investors 43North, Y Combinator CEO Michael Seibel, serial entrepreneur Paul Judge, Ph.D., Gmail creator Paul Bucheit, and former Facebook executive and Global VP of TikTok, Blake Chandlee. The team is growing fast (current job openings here) and I can’t wait to see where this fresh round of funding takes us.

To the entire team at Squire, hearty congratulations and welcome to the Trinity Family!

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Schwark Satyavolu
Trinity Ventures

professional rollercoaster pilot turned investor @TrinityVentures