Want to Sell to Enterprises? 3 Things to Know Before Going Upmarket

For entrepreneurs, there aren’t many things more exciting than killing it in sales. It’s a rush knowing that good sales are a result of your product or service meeting a need in the market and delivering on its promises to customers. Many SaaS companies and those that sell services to them, often start their go-to market strategies selling into small and medium-sized businesses (SMB) — and it’s a good place to be. Most often, selling into SMBs means shorter sales cycles, closer relationships with customers and a predictable path through the buyer’s journey. Things are good, so it makes sense to take the next leap and start targeting enterprise customers, right?


Enterprise is a different type of animal that requires a different set of skills and expectations. Here are three things to know before taking the leap.

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You can’t serve two masters

While your product or services may, for a short time, be able to work for both the SMB market and enterprise, the real truth is that they are very different and require different leadership and execution teams. The only way to grow and truly succeed in the enterprise market is to be ready, and comfortable, saying no to once good opportunities so you can become the best option for your best opportunities. 

We see this in the SaaS world often. A product starts with one particular set of features that serve SMB well, but as a company goes upstream, the newest features and product releases serve the enterprise’s demand, not the needs of the SMB. The same goes for service-based businesses and consultancies. When I started my company, it didn’t matter if you were a Hookah shop or plumber. We were going to help you succeed! Now, as we’ve transitioned into selling into the enterprise market, the services, products and, yes, pricing, don’t fit for SMBs. The hard truth is that it requires loss to gain. You’ll lose customers, clients and partners. But if you’re actually ready to sell into the enterprise, it will be worth the pain.

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Mastering the procurement process is a must

The procurement process is long. Like, really long. It is also hard. The enterprise buying committee is a complex one, filled with many individuals with many different goals. However, in order to get the budget you desire, you’ll need to understand the goal of the procurement person/team. When you’re far enough into the journey to work with procurement, think of them as the buyer all by themselves. What are their goals and pain points and how is approving your budget going to get them to their goals quickly and make them the hero? That, my friends, is the golden ticket.

Another key to procurement is knowing, and playing by, their rules. They often have set budgets and rigorous hoops to jump through. Be clear with the ROI of your engagement and services and be armed and ready to present business use cases. Lastly, selling into procurement means being ready to be agile with contracts and terms to seal the deal. In the beginning, you’ll likely settle for less to get those first big wins. But trust me, the lessons you’ll learn along the way are just as valuable.

Measure, fix, measure, repeat

While this is good practice regardless of who you are selling to, it’s especially important when starting the process of going upmarket that your entire team is measuring and pivoting quickly. No team is immune to it and you learn as you go. The key to success in anything is to clearly articulate the outcome you are trying to accomplish from an initiative and then adjust as you measure your success to that goal. Setting specific benchmarks early on will help ensure that each tactic and strategy approach is fine tuning and becoming even more targeted in reaching your goal of enterprise acquisition. 

No one said it was easy, because it isn’t. However, enterprise accounts are a surefire way to ensure growth of an organization. Get your sales teams to a mature place, understand who your target accounts are, how to seal the deal through procurement and measure as much as you can to perfect the process. Or die trying. 

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