How to Do Enterprise Sales

Sophia Obrecht
August 22, 2021

Want to learn how to succeed in enterprise sales? We've covered the basics of complex sales plus the latest enterprise sales software.

There is money to be made in sales, especially in complex enterprise sales. Defined by big digit contracts, large target companies, and long sales cycles, mastering enterprise sales can be a challenge, but the rewards are even better. So how do you do enterprise sales? What do sales reps and their leaders need to know in order to succeed in enterprise sales? How can enterprise sale technology give you the competitive edge? We’ve got the answers! Here’s what you can expect to learn in this article. 

  • What is enterprise sales? 
  • What does a typical enterprise sales process look like? 
  • How to navigate an enterprise sales deal.
  • How to onboard for complex sales.
  • What does the future of enterprise sales look like? 
  • What kind of enterprise sales software is available? 
  • What do I need in my enterprise sales tech stack? 

What is enterprise sales? 

Enterprise sales - or complex sales as it is also known - is all about selling to large organizations or enterprises. And this isn’t typically linear. Key characteristics of enterprise sales include selling to large organizations, working with multiple decision makers and departments on the buyer’s side each with different priorities and goals. As a result, enterprise sales cycles tend to be long and complex, taking several months. The average deal size in enterprise sales is large with 6-digit contracts. Another key feature of complex sales is that buyers are well-informed and well aware of competitors, who they may already be in communication with. 

The challenge for sales professionals working in enterprise sales is creating a strong consensus among a larger group of decision-makers across multiple departments, sales reps must also navigate a much more complex sales cycle in order to close a deal. 

What does a typical enterprise sales process look like? 

A typical enterprise sales process is more complex than the average sales cycle, hence why enterprise sales is also known as complex sales. Unlike your usual sales process enterprise sales involves much more consultation and longer trial periods. The reason for this is that many more departments are involved in the decision-making process, while IT systems in larger companies require greater integration and consultation. 

Here’s what a typical enterprise sales cycle might look like...


As with any sales cycle, complex sales begins with prospecting, in other words researching and reaching out to potential leads. The key to prospecting in enterprise sales is a good understanding of your buying personas and potential stakeholders. When reaching out to potential customers, be sure to contact someone with enough authority to drive your deal forward. But remember in enterprise sales there are a number of individuals with buying power, your challenge is finding one who will champion your product within the target company. 


The discovery stage of your complex sales process should be all about getting to know your prospect better. And this is exactly how you should position your outreach when you contact your leads to set up a meeting. As a sales rep working in enterprise sales you should always focus your sales calls around your prospect’s needs and challenges and present yourself as a product consultant working to get the results for your client. This way you build rapport and trust with your clients

The discovery stage of your enterprise sales process also helps you to discover if the client is a good fit for you and worth pursuing. After all, you will likely spend the next several months working to close this deal given the complex nature of enterprise sales, it is essential you are working with a quality lead who has the potential to close. 

Download our free guide to qualification calls to get up to speed on sales discovery.


Giving a product demonstration is an important part of any sales process. Of course, during an enterprise sales process, you may have to give a number of different product demonstrations to a number of different stakeholders across a number of different departments. The key is to be consistent in your demo storytelling but make sure you tailor each demo to the different stakeholders being sure to highlight your value proposition as it relates to their interests. 

If you’re fortunate or skilled enough to get all your decision-makers into the same meeting why not bring in other members of your team into the room to get the ball rolling and boost your product expertise. Inviting your tech engineers and customer success managers into this kind of meeting can speed up your enterprise sales process up as buyers have more opportunities to ask key questions and get expert answers during your product pitch.

Read this article to get tips on preparing your sales demo, or download our Ultimate Guide to Demos That Win Deals.



Product consultation after your demo call is another great opportunity for you to bring tech experts and customer success managers onboard to showcase everything your product has to offer, but also the quality of your customer services. After all, the key to enterprise sales is a smooth buyers journey that prioritizes customer experience for the hyper-informed customer of today’s sales world. 

During this stage of your enterprise sales process, your contact might need to open discussions with other stakeholders in their organization. So be patient, offer support where needed but be aware that these decisions can take time. A great way to help your sales contact is to pre-record your demo so that they can easily share this with other decision-makers who are not yet fully up to speed with what your product can do. 

Trial period

Given the large figures involved in complex sales contracts, it is very common for an enterprise sales process to include a test or trial period to allow customers to assess how well a product fits into their workflow, and whether their users will really benefit from your solution. 

Be sure to set a clear timeline for your trial period, long enough that your client can see the full benefits of your product but short enough that you lose out on revenue. Bring your customer success team on board and put your best foot forward in order to win over a client and show them the benefits of your product. Remember, don’t give absolutely all your features away for free, save some for after the sales to keep your clients interested and incentivized to sign on the dotted line. 

When setting up your trial period be sure to define clear success criteria so you and your customer success team know what they should be focusing on and which features need to be front and center. This will also help you measure how well your trial period is progressing and whether or not a deal could be at risk. 

Onboarding & Customer success 

During your trial period, it is essential that you personally introduce your client to your customer success team. It will be the customer success team that handles onboarding and ensures a customer is happy with the product. 

But just because you’ve handed a customer to the customer success team that does not mean that your touchpoints with this client ends. Be sure to check in regularly to make sure everything is running smoothly and to tackle any concerns.  


The time has come to close your deal after what may have been a lengthy and complex enterprise sales process. If you feel your sales process is taking longer than it should and a prospect is taking longer than expected to move through their trial or onboarding stages, simply ask what their timeline is for signing a deal. Once you have completed this step, be sure to make signing your sales contract as simple as possible for your client, you can use digital signature tools for example. 

How to navigate an enterprise sales deal.

Navigating an enterprise sales deal can a be complex and drawn-out process. There are a few things you can do to improve your chances of closing an enterprise sales deal. 

  1. Plan and research 
  2. Build a partnership 
  3. Understand different stakeholders
  4. Document meetings 

The first step is to create a clear plan for the deal. This should be a plan that all of your sales reps have access to, and it should be based on your existing broader sales process. Once you have created a Deal Map encourage your sales reps to conduct in-depth research into potential clients, be sure to learn more about industry trends and challenges. 

The next step in navigating your complex sales deal is to work on building a strong partnership with your prospect. Invest time in qualification and discovery calls, and position yourself as a product consultant whom your prospect can trust and rely on.

As part of this stage of your enterprise sales deal be sure that you are informed about the different stakeholders involved in your deal. You need to be able to build a relationship with each one, but it doesn’t hurt to spend extra time building a connection with a chosen “champion”, a.k.a a stakeholder or decision-maker who is invested in your product from the beginning and who will champion your product to decision-makers within their organization.

Be sure to document and record your calls this will help you with the complexity of enterprise sales deals. Not only with documenting your calls allow you to understand and reference what happened during your last calls, but it also lets other departments or sales reps know where your deal stands. 

Learn more about how Ciara can help you automate your sales documentation and bring unique insights into your enterprise sales pipeline

To learn how to navigate a $50k plus enterprise sale deal read this article.

How to onboard for complex sales. 

Training and onboarding are an important part of being successful in enterprise sales. To effectively train a sales team for enterprise sales, it is important to standardize onboarding, implement real-time coaching, and peruse a program of sales training reinforcement. 

Standardize onboarding. 

According to a survey by the Society for Human Resource Management companies with a standardized onboarding process see 50% greater productivity in new hires. Sales leaders must create a clear onboarding structure that all new hires must complete. This might include an initial training kickoff, classroom or remote lessons, and onboarding materials like scripts, example videos, or pdf guides. 

Download our free guide to enterprise sales training and onboarding here.

Implement real-time coaching.

Alongside a standardized initial onboarding, it is important to implement real-time contextual sales training that both new and experienced sales reps receive during their daily sales activities. Not only does this provide more accurate sale coaching because sales reps get tips during and immediately after their enterprise sales deals, training your reps during their calls means they have more time selling vs time spent in training workshops. 

Pursue a program of sales training reinforcement.

According to the forgetting curve, we lose over 70% of learning if it is not reinforced after 6 days, which means when onboarding and training your enterprise sales reps, you must also pursue a program of sales training reinforcement. Sales training reinforcement for enterprise sales means repeating learnings from initial training throughout sales activities. You can do this by focusing on micro training, or by using context-driven sales training approaches, such as call feedback or real-time sales coaching. 

Learn more about sales training reinforcement in our free guide.

One way to integrate sales training and sales training reinforcement into your enterprise sales organization is to invest in products like Ciara, an enterprise sales software designed to work in real-time during sales meetings to provide call and deal guidance, but also real-time coaching and sales feedback. With Ciara’s call summaries and insights sales, reps get constant feedback on how they performed in each meeting, plus Deal Maps give sales reps support during their call highlighting key questions and missed topics. 

Find out more about Ciara for enterprise sales training here

What does the future of enterprise sales look like? 

Today’s customers are more informed than ever. Enterprise Sales may be associated with dealing with complex software, intricate set-ups, and specific client requirements, but customers have evolved to understand their challenges and needs like never before. The future of enterprise sales will be about pursuing seamless digital buyer’s journeys for the connected customer. The connected customer is informed about technologies available, competitor options, and deeply engaged with the challenges they need to solve, the connected customer has high expectations and requires product information at their fingertips before they begin engaging with sales reps. 

Put most simply, to succeed in Enterprise Sales tomorrow, sales leaders and their teams must invest time and money in understanding individual customers, while embracing new forms of sales technology to better analyze and customize customer experience (CX). Part of this process will involve building closer relationships across marketing, sales, and customer success teams as Enterprise Sales swings towards more digital and product-led touchpoints.

But tech will also play a big part in the future of enterprise sales. New conversation intelligence software centers on memory and a decision-making “mind” which can help users make the right decision or next steps and which works in parallel with users at human speed. According to KPMG 62% of high-performing salespeople foresee a significant role for guided selling tools which then rank potential opportunity value and suggest next steps.

Get more insights on the future of enterprise sales with our complete guide.

What kind of enterprise sales software is available? 

So given that enterprise sales software will play an important role in the future of enterprise sales what kind of enterprise sales software is available to boost your sales approaches. 

A key technology in enterprise sales is Conversation Intelligence Software

Conversation intelligence software (CI) is a relatively new type of enterprise sales software. CI records, transcribes, and analyzes sales conversations giving insights into weaknesses and opportunities in customer communications. More advanced conversation intelligence tools, like Ciara, combine the recording and analysis functionalities with real-time conversation guidance and productivity features such as automated conversation summaries and CRM updates, which means additional support for your training efforts and a productivity boost for your reps. You can learn everything about Conversation Intelligence here.


Conversation Intelligence - Everything you need to know


What do I need in my enterprise sales tech stack?

By now, there is a variety of enterprise sales software on the market. Here are the four must-have sales tools for your enterprise sales stack. 

1. Ciara for conversation intelligence to simplify complex enterprise sales.‍

Ciara Conversation Intelligence Software

Ciara is an advanced conversation intelligence tool that provides not only transcription, recording, and detailed conversation analytics functionalities but also real-time coaching.  

By understanding the context of the conversation, Ciara reminds your reps about essential topics to discuss and provides them with the best questions to ask or guides them through an objection.

Ciara comes with the unique functionality of Deal Maps. For every sales opportunity, Ciara collects all insights from customer conversations in a deal map, allowing reps to have an always up-to-date pipeline overview and quickly identify the best next steps and deal risks. 

Ciara includes a built-in meeting platform, allowing you to reduce your sales tech stack. The instant CRM integration lets you smoothly integrate Ciara into your workflow, ensures that no insights get lost, and prevents double-documentation. 

Ciara offers a 14-day free trial - no credit card required. 


2. Discord / Slack for people management and team communication.

Remote work is nothing without communication. In a time when your team isn’t together in the office to ask each other questions, it’s said that over-communication is better. Using a messaging platform such as Slack or Discord is a staple for remote work. One tip from the Ciara team is to really drill down and organize your channels into as few as possible. Combine similar channels into one, create channels specifically for random, casual conversation, etc. Organizing your communication channels is key to keeping information flowing and helps stop miscommunication.

3. Intercom for prospect communication. 

Using Intercom is a key way to get your website visitors, prospects, loyal customers, and more answers to their questions right away. Talk about immediate gratification! Intercom keeps the personal touch in your automated business messaging and allows you to stay connected to your audience. We use Intercom to help us specifically maintain customer relationships by having an alternative method to communication than strictly emailing or Linkedin, which tend to be asynchronous.

4. SalesLoft for sequences and sales engagement. 

With SalesLoft, you can build multi-channel sales cadences that guide your sales team through the sales and renewal process. Align your outreach efforts and make sure no prospect is left behind.

You’re ready to succeed in enterprise sales!

We hope you picked up some important learnings about the world of enterprise sales! To learn more about enterprise sales download our free guide or visit our Ciara sales blog for more insights.

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