Participated · Equity · Mar 2026

Founded in 2016, Chowbus offers a full-stack restaurant operating system that combines cloud-based POS, analytics, and AI-driven marketing solutions tailored to independent, culturally focused eateries. Its first AI product, AI Digital Ads, helps restaurants run targeted campaigns, and the company is now adding AI modules for automated accounting, supply ordering, insurance, and other back-office functions. Chowbus supports thousands of restaurants across all 50 U.S. states and Canada, processing roughly $4 billion in annualized transaction volume. The business currently generates more than $120 million in Annual Recurring Revenue—representing 9× growth over the past four years—and positions itself as a mission-critical partner rather than just a software vendor. Management plans to deepen its service integration, reduce operator overhead, and expand further into Canada. By leveraging AI to deliver 10× efficiency gains versus traditional solutions, Chowbus aims to help independent restaurants compete with large chains. The company’s strategy centers on becoming the comprehensive operating system for the $240 billion Asian restaurant segment and adjacent culturally rooted markets.

Participated · Series A · Apr 2023

Summer provides an end-to-end workplace student loan solution that partners with employers to deliver benefits for saving for education, managing student loans, finding forgiveness options, and lowering monthly payments. The company is led by CEO Will Sealy and is a Certified B Corporation. Summer has partnered with over 800 employers, financial institutions, unions, and government leaders and reports generating over $1.6 billion in savings for borrowers. The company intends to use the new funding to expand its leadership team, grow its Advisory Board, and further enhance its tech-based solution. Summer focuses on making it simple for employers to implement a range of student loan and education assistance benefits. The company is based in New York City. Summer provides a digital, employer- and institution-facing platform that helps individuals plan for college costs, reduce student loan burdens, and optimize retirement savings through products like Summer Secure for SECURE 2.0 retirement matching. The company offers an API suite and operational expertise to turn complex student loan policies into high-adoption workplace solutions, and it combines technology with human support. Summer has expanded partnerships with retirement recordkeepers, payroll providers, Fidelity Investments (2022), Credit Karma, and the American Federation of Teachers to reach large populations (the AFT partnership supports 1.7 million teachers, government employees, and healthcare workers). The firm has hired Leigh Gross as Chief Revenue Officer to lead partnerships with recordkeepers and financial institutions. Summer says it has delivered and surpassed $1 billion in total projected savings for borrowers. Founded in 2017 and operating as a certified B Corporation, the company plans to use new funding to expand its platform and accelerate growth of its student debt and education assistance offering. Summer offers a 360-degree software platform that helps borrowers understand their student loans and identify repayment paths, including eligibility for loan forgiveness. The company builds support for 120 loan forgiveness programs and tracks more than a hundred state-level proposals. Summer does not charge end users; it sells its product through employers and associations as an employee benefit. Launched in 2017 by founders who started the company at Yale, the team later migrated to New York City and has grown to about 13 employees. CEO Will Sealy previously worked at the Consumer Financial Protection Bureau in the Office of Students. To date Summer has helped 10,000 borrowers and saved users roughly $8 million this year.

Participated · Debt Financing · Dec 2021

FileCloud's platform delivers end-to-end secure content collaboration and data governance capabilities, enabling enterprises to manage sensitive data while meeting regulatory frameworks such as GDPR, HIPAA and ITAR. The company serves customers across 90+ countries, including Fortune 500 firms and organizations in healthcare, finance, education, public sector and defense, and its platform powers over 3 million users. FileCloud also sells its technology in OEM form through Managed and Cloud Service Providers and added Signority (an e‑signature and document workflow platform) to its portfolio in May 2024. The company is investing in AI-powered data governance and secure collaboration features and plans to accelerate platform innovation. FileCloud intends to expand its partner ecosystem and strengthen its footprint in North America, the Middle East, Europe and Asia. FileCloud is a hyper-secure content collaboration platform (CCP) that provides compliance, data governance, data leak protection, data retention, and digital rights management capabilities. Its platform integrates workflow automation and granular control of content sharing, with file sharing, sync, and mobile access across public, private, and hybrid clouds. FileCloud serves millions of users worldwide, including Global 1000 enterprises, educational institutions, government organizations, and managed service providers. The company has grown organically and was bootstrapped prior to taking institutional capital. Headquarters are in Austin, Texas. Management plans to use new investment to continue product innovation and accelerate domestic and international market expansion.

Participated · Seed · May 2021

Roofr is a software company that builds an end-to-end operating platform and CRM tailored to roofing businesses, offering tools such as measurement reports, lead capture, proposals, payments, invoicing, material ordering, workflow automation, event tracking, job boards, and customer communications. Since its 2016 inception the company has grown its remote team from about 10 to 150+ employees and says over 12,000 roofing companies rely on its platform. Roofr emphasizes a customer-first, people-first product approach and prices its software to be affordable for roofing businesses; the company notes many customers have scaled, with some grossing millions after adopting the platform. The product roadmap includes new features like canvassing, marketing, a document builder, job costing, and work orders. Roofr plans to use new funding to accelerate hiring across product, engineering, sales, support, customer success, G&A, and marketing to speed product delivery and scale operations. The company is headquartered in San Francisco and was founded in 2016. Roofr provides roof measurement reports, instant estimators, custom proposals and a recently launched CRM aimed at helping roofers streamline job management. The company plans to expand its product suite with payment processing, integrated financing, material purchasing and customer communications. Roofr intends to use new funding to accelerate development and launch of those roofing solutions and to improve existing tools. Its CRM includes job management features such as workflows, tasks, job boards and an analytics dashboard. The company emphasizes building features based on roofers' feedback and pain points to help contractors win more jobs. No operating metrics (revenue/users) were disclosed in the article. Roofr provides a SaaS roofing software platform that lets contractors generate instant estimates, measure roofs via aerial imagery, and create visual proposals. The platform functions as a sales toolbox for roofing contractors. Roofr recently partnered with CompanyCam to let roofers connect images and notes from in-person site visits with its digital sales solutions. The company intends to use proceeds to add new features including payments and lead acquisition, increase support and grow the team. Roofr is also focusing on strategic partnerships and integrations that benefit its users. The company raised $12m in Series A funding, bringing total funding to $19m. Roofr is a sales platform for roofing contractors that enables remote roof measurement and streamlined initial sales. It ingests high-definition imagery from partners like Nearmap and lets contractors draw measurement reports or pay Roofr $10 per report for measurements. The company also sells to independent insurance adjusters and counts some of North America’s largest roofing contractors among its customers while targeting small, fragmented roofing businesses (more than 100,000 registered in the U.S., most with five employees or fewer). New features include a subscription that auto-populates estimates based on materials lists and desired profit margins and a digital contracts capability. COVID-19 accelerated adoption by allowing contractors to send quotes without visiting job sites. Roofr is a five-year-old, 31-person company that has raised $8.25 million in total funding. Roofr uses aerial and satellite imagery to measure roofs and provide customers with an instant, free online roofing estimate, then connects them with a vetted roofing contractor for an in-person inspection and final proposal. The company assigns a dedicated project consultant to manage each job from start to finish. Roofr’s long-term goal is to offer roofers a suite of free tools to streamline operations and boost profitability. It plans to launch a free satellite measurement application so contractors can measure and estimate roofs from their desks. The company currently serves the Bay Area, the entire state of Florida, and Ontario, Canada. Roofr says it will use new funding to expand into additional marketplaces, including Texas, and to grow its engineering, sales, and marketing teams.

Participated · Debt Financing · Dec 2020

Trilio provides cloud-native data protection and management, with its TrilioVault technology used for backup and recovery, migration, ransomware protection and application mobility. The product targets cloud architects and DevOps engineers supporting applications on Kubernetes and OpenStack. Customers span telecom, defense, automotive and financial services and use TrilioVault for migration, rapid ransomware recovery and disaster recovery compliance. The company said it will use new funding to increase focus on product development, engineering and customer operations. Leadership includes CEO Massood Zarrabian; David Safaii has transitioned to Executive Chairman and Christina Lattuca joined as CFO and VP of Operations. The company is based in Framingham, MA and has raised a total of $36M to date. Trilio's core product is TrilioVault, a cloud-native data protection platform for Kubernetes, OpenStack and Red Hat Virtualization that supports backup and recovery, migration, DR and application mobility. The company recently released TrilioVault for Kubernetes v2.0, including a multi-cloud management console, and achieved Red Hat OpenShift Operator certification. Trilio serves customers in telecom, defense, automotive and financial services and reported 300%+ growth in 1H 2020. The company plans to use new funding to expand go-to-market capabilities and accelerate adoption across hybrid- and multi-cloud markets. Trilio will further invest in product development, sales, marketing and customer success to bring TrilioVault to markets across the globe. Leadership highlighted the platform's fit for Kubernetes-era data management challenges and the company has received recognition from GigaOm and Gartner. Trilio Data, founded in 2013 and based in Boston, provides a business assurance platform for IT organizations and cloud service providers deploying application workloads in public, private and hybrid clouds. Its flagship product, TrilioVault, is a data backup and recovery solution for OpenStack adopters that supports data protection, migration, resource management, configuration, change management, and sandbox-as-a-service. The company is led by CEO David Safaii. Trilio intends to use the funds to grow its engineering, sales and marketing teams and to increase channel enablement support for its global customer base. The company’s core focus is protecting and managing application workloads across cloud environments.