How this $1M bootstrapped SaaS can expand into a new market. | Smart Bear Live 002
Aug 16, 2026 · 2:14:17
Jesse Schoberg's DropInBlog has 2,000 customers, 2% monthly churn, and a plateaued growth curve; hosts Jason Cohen and Rob Walling argue DropInBlog should deliberately push into BigCommerce businesses and agencies serving them. Schoberg says enterprise visitors were 5% of traffic but converting zero; after adding invoicing, audit logs, and white-glove migrations, $399/$499 plans began selling. They tell him to market engineers and marketers separately, pitch marketers on AI/LLM visibility as job security, use ads to learn messaging not just ROI, and build an agency channel because one agency can bring multiple clients. They also challenge his Laravel focus, argue BigCommerce is where the fish are, and advise giving each initiative an owner, separate metrics, and company-wide alignment.
