The Venture Codex

Participated · Series A · Dec 2025

Founded in 2022 by Davis Gilbert and Josh Pillsbury, Summit Commercial Solutions operates as a technology-driven commercial insurance brokerage serving thousands of Canadian businesses. Its core offering combines traditional brokerage services with proprietary software, data infrastructure, workflow automation, and an AI-powered compliance tool called Summit Sherpa, which modernises risk verification and policy management for property managers and corporate clients. The company positions itself as a platform for entrepreneurial brokers, aiming to increase producer productivity rather than replace them with automation. Since IA Capital’s initial investment, Summit has more than doubled its top-line revenue and expanded into group benefits while building internal wholesale capabilities. With the latest funding, Summit plans to open new offices across Canada, deepen its talent-acquisition vertical, and enhance its data and AI capabilities. The capital will also support the launch of new divisions in Group Benefits, Private Client, and a delegated underwriting authority ecosystem to offer comprehensive commercial, personal, and embedded insurance solutions.

Led · Series A · Apr 2025

Vivere Partners is a specialty insurance organization focused on niche lines, combining underwriting depth with engineering and AI to improve transparency and alignment across the insurance value chain. The company emphasizes an "Underwriting Driven, Tech Enabled" approach, using data and analytics to accelerate underwriting decisions and collaboration between human experts and AI. Leadership includes founder and CEO Chris McKechnie and CTO Sachith Gullapalli, who together bring insurance and engineering experience. Vivere is recruiting top-tier underwriting leaders and pursuing acquisitions of insurance businesses such as program administrators, program managers, MGAs, and MGUs to scale capabilities and distribution. The company plans to build a cutting-edge technology infrastructure to power its underwriting platform and to drive operational efficiency and profitability in niche markets. Vivere positions itself to address persistent MGA challenges—misalignment and lack of transparency—through a combination of underwriting discipline and technology innovation.

Participated · Seed · Feb 2024

Armilla AI benchmarks and assesses third‑party AI models and then underwrites warranties that reimburse customers for model fees if the model fails to meet agreed standards. The company tests models for hallucinations, racial and gender bias, robustness, security and compliance with emerging regulations such as the EU AI Act and NYC Local Law 144. Armilla launched warranty coverage in late 2023 backed by insurance carriers and serves enterprises and third‑party AI vendors seeking a trust signal to shorten sales cycles. The firm reports roughly 10 customers (including a healthcare client using GenAI on medical records) and says customer traction has been growing ~2x month‑over‑month since Q4 2023. Armilla is based in Toronto and has 13 employees. Proceeds from its recent fundraise will be used to expand its warranty offering and introduce new products. Armilla AI is an all-in-one AI governance platform that automates model testing, validation, and monitoring across the model development lifecycle. The platform continuously runs more than 50 tests to assess robustness, accuracy, fairness, data drift, bias and other faults, and includes Armilla FingerPrint™, a validation framework that learns system sensitivities and riskiest components. Armilla centralizes transparency, auditability, and traceability, enabling executives, managers, risk and compliance teams, and data scientists to collaborate on test results in real time. Customers cited range from financial services to other businesses leveraging machine learning, using the platform to catch issues such as discriminatory credit decisions or faulty insurance pricing. The company announced its launch and $1.5M in funding to support its go-to-market and product activities. Armilla positions itself to help organizations responsibly deploy robust, trustworthy AI models and meet growing regulatory machine-learning compliance requirements through continuous stress-testing and auditable logs.

Participated · Series A · Feb 2024

Shepherd combines proprietary AI underwriting, real-time construction data integrations (partners include Procore, Autodesk, OpenSpace, DroneDeploy and Samsara), and industry expertise to price commercial property and casualty coverages for construction and infrastructure projects. The platform functions as a managing general underwriter (MGU), retaining underwriting authority while partnering with large carriers to deliver capacity. Shepherd offers products including general liability, commercial auto, and builder's risk, and has expanded into renewable energy and power verticals. The company has grown revenue more than 7x in the past 24 months, serves over 600 customers, has issued 1,500+ policies, and insures more than $400 billion in project value. Shepherd is pursuing a roadmap toward fully autonomous underwriting, aiming to shift underwriters from processors to portfolio orchestrators while scaling capacity and pricing precision.

Participated · Seed · Feb 2024

MIC Global builds and underwrites embedded microinsurance and digital reinsurance solutions that pay out for loss of income, everyday risks, and identity theft. The company embeds simple, point-of-sale insurance products through banking, mobile, digital/technology, insurance, and insurtech partners. MIC operates in over 17 countries and plans rapid geographic expansion in 2024 via existing and new platform, insurer, and operating partnerships. It performs in-house underwriting through Lloyd’s Syndicate 5183 and MIC Re, supporting long-term sustainable premiums. Those underwriting arrangements are backed by Lloyd’s AA- ratings from Fitch Ratings, Kroll Bond Rating Agency, and Standard & Poor’s. The company intends to use new capital to invest in infrastructure, talent, and market expansion to scale its technology-enabled insurance platform.