Enterprise Sales: How to navigate and win $50K+ Deals

Veronika Traublinger
September 14, 2021

Navigating several stakeholders and complex organizational structures can be tough. With our winning 5 step plan, it gets easy as pie.

As the name implies, enterprise sales - or complex sales - is all about selling to large organizations. And this isn’t typically linear. In the past, salespeople have been able to sway a single person to close the deal, but now they have to create consensus among a group of decision-makers with buying power from different departments.


So, how can you effectively navigate an enterprise deal without losing track or missing any important details? Based on our own experience and insights from our customers and partners, we compiled all you need to know about enterprise sales - including our winning 5 step plan to close more deals.


Let’s start with the basics:


Enterprise sales: the characteristics


Enterprise sales refers to a type of selling environment with the following key characteristics:


  • Target customers are large organizations
  • There are multiple decision-makers involved on the buyer’s side with different priorities and goals
  • Sales cycles can take several months
  • The average deal size is large; 6-digit contracts are common
  • The buyers are well-informed and often talk with several competing vendors at the same time



5 steps to win enterprise deals


Ok, now that we’re on the same page on what enterprise sales is, let’s take a look at our 5 step plan to help you win more enterprise deals.


1. Have a plan

Although enterprise sales isn’t linear and not every prospective customer is like the other, there is a list of things you need to uncover in EVERY deal if you want to be successful. This includes common qualification criteria like pain points, goals, and budget and topics that related to your product or service specifically. 


A Deal Map lets you sketch out all relevant topics that you need to address during your sales process. With each nugget of information you collect during interactions with your prospect, you further fill your template with key information to help you move your deal forward. The Ciara assistant even captures relevant information live in your online customer meetings and automatically fills in the canvas. This helps you stay on track with your deal. 




2. Create a dialogue

The goal of every conversation with your prospect is to build rapport and understand their needs on a deeper level. This can only be done by asking the right questions and listening carefully. This way, you can fully understand their concerns, provide meaningful solutions and build a long-lasting relationship.



3. Know the stakeholders and their needs

The average enterprise deal has 5+ stakeholders involved. Understand who all those stakeholders are and uncover their priorities and goals. Only if you can convince all of them of your product’s value, you can be successful.



4. Document findings

When talking with prospective buyers and learning more about their challenges and needs, make sure to document all the insights you get. That information will help you along the way to create a well-targeted buying experience. And who can say they can remember everything that’s been said across several conversations in a multi-month long deal process?


As a sales rep, you’re not the only one benefiting from this information. Other departments in your organization, from marketing to customer success, can use it for their work.


Ciara lets you easily take notes in a structured way and tracks what topics you’ve discussed with your prospect. This way you always stay on top of your opportunity and can easily plan next steps.



5. Record and transcribe meetings

Recording and transcribing customer meetings comes with several benefits for building better customer relationships.


  1. You can better focus on your customer and think less about taking precise notes during the conversation.
  2. You can refer to the recording and transcript when writing follow-up emails or creating other sales collateral.
  3. You ensure all insights are documented.
  4. You can use the recording for effective, deal-based training with your manager or sales trainer.


Ciara records and transcribes your meetings in real-time. The transcript and recording are searchable, enriched with valuable conversation statistics, and can be shared with colleagues, managers, and trainers.  




Enterprise sales is complex, and moving a deal forward can get challenging. These 5 steps help you to better navigate complex deals, always stay on track, and quickly identify next steps.


Want to learn how Ciara can help you navigate and win more deals? Chat with us!