How do you take the leap to enterprise from PLG?

At SurveyMonkey, we had several false starts when first introducing our Enterprise sales motion (thinking back to my earlier years at the company in 2015-16). The main challenges we ran into were around (1) feature differentiation between our self-serve and enterprise offering, and (2) ensuring the profitability of our sales business given we were introducing the new cost of a sales and customer success teams + all of the supporting cross-functional teams and software/tools needed to run that arm of our business.

Here are several things that would indicate you may be ready to introduce an Enterprise sales motion:

• A significant portion of your existing customer base works at medium to large size companies (indicator that there would be larger budgets)

• There's a high prevalence of having multiple users at the same company (either used by an entire team or multiple departments). Or you notice there is a high prevalence of account sharing (which was the case at SurveyMonkey).

• Self-service checkout is no longer sufficient for customers -- you're being asked for invoicing. Some companies have policies & limits for what employees can expense vs what requires going though a procurement process.

• You're starting to notice that there is a difference between buyers and users of your product.

A successful leap to enterprise requires a significant investment in the following:

• Product: Building product differentiation between your enterprise and self-serve product. This could fall into several buckets including:

  • Organizational differentiation to meet the demands of larger organizations, like user administration or enhanced data privacy/security

  • Consumption-based differentiation to align value with high customer usage, like unlimited API calls or AI prompts

  • User-level differentiation that reserves advanced features/functionality typically needed at larger companies, like premium integrations

• Go-to-market team headcount across sales, customer success, product marketing, and later introducing more operations & enablement teams as you scale

• Tools & technology like your CRM & contracting tools

• Data & research to inform your GTM strategy

Things to consider when making the leap:

• Start by mining your existing customer base vs trying to drive pipeline

• Start with a narrow ideal customer profile (ICP), do a test pilot, learn/iterate, and only expand once you see success