Going Enterprise?

The word of the day seems to be enterprise.

It may be the most over-used word in SaaS right now. It’s abused in press releases, funding announcements, internal company meetings, marketing messaging, and sales conversations.

What does it even mean?

It sounds cool, it sounds BIG, and it sounds like it’s going to make everyone rich. But like most nebulous business jargon (e.g. leverage, move the needle, tiger team, ecosystem), companies that adopt the buzzword need internal alignment on what it means beneath the surface.

If you’re in SaaS, think about all the times you’ve heard these phrases: We’re going enterprise. We’re building enterprise solutions. We’re setting up an enterprise team. We’re focused on enterprise accounts. We’re doing enterprise deals. Our systems are enterprise-grade. We’re enterprise ready.

When we say enterprise are we talking about product, sales model, accounts, deal size, or all of the above? And where do you draw the line between what’s enterprise and what’s not? That’s why enterprise is a dangerous word. Without clear cut definitions, you confuse your organization, your customers, and your investors.

Precision matters in defining and executing an enterprise strategy. Going enterprise often means chasing bigger deals, going deeper in existing accounts, or focusing on larger customer accounts. Depending on your definition, it can require changes to product, sales models, marketing messaging, and account deployment.


Some of the shifts that may be required include:

Shifting From Product to Platform
You may be required to add functionality that meets the more complex needs of larger clients. This can be the hardest change to credibly make, especially if you’ve been known as a freemium offering. Too many SaaS companies try to go enterprise without changing anything about their product.

Standing Up a Field Sales Team
You may need to add a field channel to your online or inside sales model. This will require you to have better internal communication tools, an updated and accurate directory of internal contacts with clear responsibilities, and better training to enable those remote salespeople. Too many SaaS companies expect immediate results from their new enterprise field reps, without enabling them with the internal resources and relationships that they need to succeed.

Adding Supporting Sales Resources
Bigger deals - enterprise deals - are more complex and usually require more technical expertise and support to win and implement. Hiring expensive enterprise reps without adequate technical staff to support them is like putting a hitter in the batter’s box without a bat.

Shifting from Feature-Selling to Value-Messaging
Larger enterprise customers expect you to prove the ROI before they commit big funds. While your simple and elegant feature messaging may have worked for small transactional customers, enterprise buyers will require you to instill confidence that your product or service will transform their business. That means new content, messaging, and training. These enterprise buyers are putting their reputation on the line by investing so much in your offering. Your old feature-based messaging won’t work.

Selling Higher in the Organization
In some cases, going enterprise can mean selling into the same accounts but to different people. As a result of selling higher, scope and deal sizes expand. Selling higher in an organization will require a more sophisticated sales motion and a team selling approach (versus an individual do-it-all rep). Make sure that you design your go-to-market model around this new buyer (and make sure this buyer exists or your strategy is DOA).


Before you embark on your enterprise journey, be precise in how your sales model, supporting resources, product, marketing, and most importantly, target buyers will change.

Here are a few final tips for those of you who are looking to go enterprise:

  • Be precise (and aligned cross-functionally) about what exactly needs to change across your business.
  • Take adjacent steps, be careful to not over-rotate and abandon your core business.
  • Be prepared for tension. The move to enterprise will create tension as resources are diverted towards the enterprise and the payoff doesn’t come immediately.
  • A strong sales culture is crucial. You are going to have to test your faith in your ability to chase, win, and deliver deals outside of your comfort zone.
  • Attribution gets hairy as deal cycles increase and resources are added to the mix. Don’t waste too much time on a never-ending math problem.
  • Monitor your progress using win-loss interviews with your initial enterprise opportunities - both won and lost. Third-party interviews with those buyers will enable you to adapt fast.
  • Be prepared to invest across your go-to-market model and product simultaneously. Many “enterprise” strategies fail because companies fail to identify the new buyer and adapt their product and go-to-market accordingly.

Good luck!