Acquisition Opportunity Recently acquired by Smith Brothers Insurance LLC as of July 1, 2025, Charter Oak Agency may benefit from cross-sell opportunities, integration support, and expanded service capabilities through the acquiring group.

Mid‑Market Focus With revenue in the 10M–25M range and an insurance focus, Charter Oak Agency sits in a mid-market segment where tailored coverage, risk management, and digital quoting enhancements could drive growth and retention.

Technology Leveraging Current tech stack includes WordPress, HubSpot, Google Tag Manager, and Cloudflare, suggesting sales opportunities around digital marketing optimization, CRM-driven lifecycle campaigns, and website conversion improvements.

Regional Presence Located in Old Greenwich, CT with proximity to Glastonbury, CT via the acquisition, there is potential to expand regional partnerships, carrier relationships, and local market programs in the Northeast.

Competitive Benchmark Revenue scale and employee benchmarks align Charter Oak with major national insurers; there is room to position value-add services such as cyber, small business packages, and workflow automation to differentiate post‑acquisition.