Small team, diverse tech Willow Insurance Services operates with a small team (2-10 employees) but relies on a broad tech stack including DNN, Microsoft 365, Office 365, Windows Server, ASP.NET, and IIS. Sales opportunities include offering scalable cloud and security services, SMB-focused IT consulting, and cost-effective SaaS solutions that fit a lean operation.

Regional presence Based in La Grange, Illinois, Willow serves a local market footprint. There is potential to pursue regional insurance technology and compliance solutions, local cybersecurity offerings, and partnerships with nearby brokers or carriers to expand geographic reach.

Technology modernization The use of legacy-oriented tech like DNN and Microsoft IIS suggests opportunities for modernization services, migration to contemporary web stacks, and managed cloud hosting to improve reliability, security, and scalability for insurance workflows.

Security and compliance Given a typical insurance operation, there is likely emphasis on data protection, regulatory compliance, and secure document handling. Offer security assessments, IAM enhancements, and SOC 2/ISO-aligned controls as a path to trust and competitive differentiation.

Vendor and support needs With a small internal team, Willow may benefit from outsourced MSP services, help desk support, and managed infrastructure. Propose bundled IT support, disaster recovery planning, and ongoing system monitoring to reduce operational overhead.