Selling Upmarket Takes More Than a New GTM Hire

It’s a familiar pattern we see across our GTM search work: a portfolio company finds success with mid-market/SMB (small and medium-sized business) customers, growth catches the board’s attention, and the conversation quickly turns to enterprise. The assumption is that since the product works for one segment, an experienced GTM leader should be able to tailor the approach for enterprise customers. 

That sounds simple in theory, but success with a smaller customer segment does not guarantee success at a higher level. Enterprise customers bring a far more demanding set of expectations than the customers a company may be used to serving; even the most versatile GTM leader won’t be able to make progress if the product or operating model fails to align with what those customers need. 

Before hiring an enterprise GTM leader, companies need to ask themselves a basic question: what problem are we really trying to solve? If the goal is to secure enterprise customers, the company may need to address its own readiness before beginning the search. 

Product Readiness Is Not the Same as Product Strength

A company may have a product that’s intuitive, easy to implement, and valuable to mid-market customers, but it may still be years away from being enterprise-ready. 

When that company begins pursuing enterprise customers, the sales process can change quickly. Questions surrounding pricing, product capabilities, security controls, access management, customer support, and implementation become much more nuanced and detailed. If the team cannot answer those questions, or the product cannot meet those requirements, promising conversations can stall. In that scenario, the company is not selling a bad product, but one that’s not suited for enterprise customers. 

Larger accounts often have longer buying processes and more internal stakeholders involved in the decision. If the product, support model, or implementation process does not keep pace with those demands, the company may struggle to close the deal, even when prospective customers see value in the product. Before pursuing a new customer segment, companies need to make sure the product aligns with the sales motion they want to pursue. 

Can the Company Support What Sales Is Promising?

For enterprise customers, product fit is only part of the equation. What happens after the purchase matters just as much. Larger accounts often require more structured onboarding, technical assistance, training, administrative controls, and ongoing customer success. 

That level of service can be difficult for a company that is used to working with smaller customers or a single point of contact. A single enterprise account may require coordination across sales, implementation, product, engineering, customer success, and executive leadership. If the company does not have that support structure in place, teams can quickly become stretched too thin, creating friction across departments and risking a weaker customer experience. 

GTM Strategy Requires Company-Wide Alignment

Companies that ask sales teams to pursue enterprise customers before the broader organization is aligned can create unnecessary tension across the business. Product teams may not be ready to deliver the features those customers expect. Implementation teams may not be prepared to support more complex deployments. Customer success teams may not have the bandwidth or structure to manage larger accounts. Over time, those gaps can affect customer confidence and make the GTM motion harder to sustain. 

Some boards and investors may assume that hiring a senior GTM executive will solve that problem. But this work extends beyond the commercial function. Product, engineering, finance, operations, implementation, and customer support all need to understand what the company is trying to sell, who it is trying to serve, and what will be required to support those customers. 

A GTM leader can help translate that strategy into a commercial plan, but they should not be expected to create a company-wide plan on their own. Before hiring, stakeholders need to be clear on whether the business is prepared for the market it wants the leader to pursue. 

Moving upmarket successfully starts with the company, not the hire. Boards and stakeholders need a clear view of what they are asking a future GTM leader to sell, and whether the business is positioned to back it up across product, support, and delivery.