Summit Commercial Solutions Launches Sherpa — A Compliance-First Insurance Platform Built for Property Managers, Asset Managers and Portfolio Operators
Kelowna, BC - February 4th - Summit Commercial Solutions, a national insurance brokerage reimagining how risk and compliance are managed for Canadian businesses, today announced the public launch of Sherpa — its new insurance compliance platform designed to help property managers and portfolio operators maintain continuous, verifiable tenant insurance coverage without manual chasing, spreadsheets, or administrative burden.
In an industry where tenant compliance is typically checked once at leasing and then left to chance, Sherpa introduces a systematic, automated approach that tracks coverage, documents expiries, verifies against contractual requirements, and applies an insurance back-stop across entire portfolios to eliminate cancellation gaps. By modernizing what has historically been a reactive process, Sherpa enables operators to surface risk early and act with certainty, rather than discover gaps after they become costly problems.
“Most property management teams don’t fail compliance because they’re careless.” said Joshua Pillsbury, Co-Founder of Summit Commercial Solutions. “They fail because there hasn’t been a system designed for the real-world problem of maintaining insurance compliance. Site teams rely on inboxes and spreadsheets — and that inevitably breaks when policies are cancelled after move-in, completely undetected. Sherpa was built to solve that precisely. By automating compliance and embedding coverage, we can guarantee 100% compliance across portfolios.”
The platform is an extension of Summit’s broader mission to modernize insurance through better technology, clearer workflows, and proactive risk management — a vision recently accelerated by Summit’s $7.5 million Series A investment, which specifically highlighted the importance of Sherpa’s development in enhancing verification and policy management tools for businesses and risk teams alike.
Sherpa is available now for property managers and portfolio owners interested in gaining both clarity and control over their residential and commercial insurance compliance processes. To support early adopters, Summit is offering a structured Sherpa Audit, a 30 to 45-minute diagnostic that assesses current compliance health, identifies risks and inefficiencies, and outlines a practical implementation strategy.
“Insurance compliance shouldn’t depend on reminders and manual tracking. It should be a transparent, simple, and continuous part of portfolio operations,” added Pillsbury. “Sherpa brings that visibility to life.”
About Summit Commercial Solutions
Founded in 2022, Summit Commercial Solutions is reshaping commercial insurance in Canada by combining deep industry expertise with technology-driven risk management and client experience. Summit serves thousands of Canadian businesses with tailored insurance solutions and modernized compliance workflows.
About Sherpa
Sherpa is an insurance compliance platform built by Summit Commercial Solutions to help property managers, portfolio operators, and organizations maintain continuous, verifiable insurance compliance without manual tracking or administrative overhead. Sherpa automates the collection, verification, and monitoring of insurance documents, ensuring coverage remains aligned with contractual requirements over time—not just at onboarding. Sherpa replaces reactive, spreadsheet-driven processes with real-time visibility and structured workflows that surface risk early and support better operational decision-making.
Media Contact
Davis Gilbert
Summit Commercial Solutions
Email: media@summitcover.ca
Website: www.summitcover.ca
