A very common journey for B2B software companies is to build a product for the low-end (in terms of deal size / market segment), achieve product-market fit (PMF), then scale the business by taking that solution “upmarket” to larger accounts (i.e. enterprises). A lot of ink has been spilled on how to pull of this go-to-market (GTM) motion shift quickly, cleanly, and cost effectively. It usually involves hiring a field sales team, managing accounts in a more hands-on manner, being more targeted in your outbound, relying on intermediaries and proxies that cover the domain/industry for pipeline, and priming accounts for regular up-sells and cross-sells. The industry is full of companies that successfully pulled off this maneuver, to that degree that attempting it is not even seen as risky strategy, but rather a scaling milestone.