Enterprise SaaS Sales: 7 tips for closing complex deals

There's a clear case for moving upmarket: 

• Bigger average contract value
• Higher ROI on sales time
• Lower churn rates — because once you're in, you're in. 

But, if you're used to selling your SaaS products to SMBs, it's a mistake to underestimate how different the enterprise sales process will be. To quote venture capitalist Tomasz Tunguz:

"Moving upmarket is an experiment. It's a new sales motion. Very few businesses have clear demonstration of success in enterprise sales cycles without effort."

Enterprise deals are bigger, slower, more complex, and way more demanding on the whole GTM organization. It’s like building a new company within a company.

In this article, we'll break down: 

• The biggest challenges of enterprise SaaS sales 
• How the enterprise sales process differs — and how to adapt 
• Best practice tips from experts on selling SaaS to enterprises 

What is enterprise SaaS sales?

Enterprise SaaS sales is the process of selling software subscription products to large organizations—typically with $1 billion in annual revenue and over 1,000 employees.

Most enterprise SaaS deals involve six- or seven-figure price tags, dozens of stakeholders, at least a six-month sales cycle, complex security and compliance requirements, and long post-sale implementations. 

Enterprise SaaS Sales Challenges 

SaaS companies moving upmarket into the enterprise will need to overhaul their sales processes to account for:  

(Much) Longer sales cycles 

SaaStr Founder Jason M. Lemkin estimates deals over $100K typically take 6 months. Larger deals ($500K - $1M) will probably take over a year or more.

By contrast, a typical B2B SaaS deal with an SMB or startup — say $499 for a monthly subscription — can close in the same day or, at worst, a month or two.  

More stakeholders

If you're used to SMB sales, you're probably used to talking to the decision-maker and maybe one other stakeholder — and you have the systems and scripts for that scenario.

With enterprise deals, you'll be talking to a buying committee of 11 to 20 people, often with competing priorities and budgets. And you'll need sign-offs from multiple decision-makers, including IT, finance, legal, executives, and so on. 

Basically, you're going to need a bigger boat. 

More hoops to jump through 

You aren't just dealing with more people in enterprise deals. You also have to meet more requirements: 

• Formal procurement processes, including submitting a detailed proposal 
• Documented buying criteria 
• Security and compliance checks
• Product customization 

More demands on the Sales team (and everyone else)

Enterprise buyers expect a white-glove experience and expect you to work within their standard procurement processes rather than adjusting to yours.

Plus, your sales team will need to ask more of all the other teams involved in GTM. 

They'll field customized development requests to the product team, ask marketing for personalized collateral, and pull in customer success to showcase the quality of service. 

In short, enterprise SaaS sales are much more complicated and demanding, and not every organization is ready to handle them. 

Enterprise SaaS sales best practices

If you decide to make the move upmarket, here are six pointers to help you make the process of enterprise sales a bit easier on your salespeople: 

1. Make sure your AEs have the right skillset

The qualities that make someone a great SMB sales representative are different from those that make for an enterprise account executive says Rich Liu, CRO of Everlaw. 

On Grow & Tell, he explained that when he led sales at Mulesoft, they drilled deep into the exact traits that they needed for each sales motion:

"For every single role, we basically said, 'What are the jobs we need to deliver well against? For an enterprise AE it's linear execution: Can they drive a sales process, and orchestrate across a lot of orgs? Are they compelling in the room? Can they lead an effective meeting, and effectively follow through on an executive meeting?'

In an SDR role, it might be coachability, a high-growth mindset, and a passion for sales."

2. Embrace "land and expand"

The hardest part of enterprise sales is often just getting in the door. Instead of targeting max ACV right from the off, consider the "land and expand" approach — deliberately pitching a lower ACV deal to close the client and growing the account over time.

"Land and expand" is highly effective for moving upmarket because: 

• You start with what you know. Instead of suddenly pitching a six-figure solution, you can sell a smaller package that you've already pitched successfully in the SMB market. You're solving a single, obvious pain point, so it's easier for your new enterprise prospects to say yes. 
• You reduce the risk for the buyer. Enterprise buyers are notoriously risk-averse. By selling and delivering a useful solution, you've proven that you do what you say. They're more likely to trust you when you approach them with a larger deal. 
• You're already in. Once you've passed their security reviews and procurement process, you're in the system. It's now much easier for them to buy other solutions from you than from a new vendor. 

📖 For a full guide to the "land and expand" approach, check out our article, The Land & Expand Sales Strategy: Close now, win later

3. Enable your buyer champion

You can't close enterprise deals unless you know how to partner with your buyer champion (the person advocating for your solution in your prospect's organization).

Buyers spend only 5-6% of their buying time talking to your sales rep. The vast majority of their decision-making process happens behind closed doors. Your buyer champion is the person in those rooms, supporting your solution as the best option.

Focus on building a strong partnership by providing them with the right resources and positioning your product as the most convenient and straightforward option.

For example: 

• Co-write the business case for your product together. Map their problems and goals to your solution, to show how you'll help them reach those goals.  
• Understand the buyer champion's individual needs and motivations. For enterprise deals, you need to keep your champion engaged for months (or even years). In addition to figuring out the needs of the wider organization, make sure you get a good sense of what makes your champion tick and what's in it for them.  
• Give them the right resources to make their lives easier. Think concise messaging about "why us" and "why now," ROI studies, competitor side-by-side comparisons, and product feature demos for their specific use cases.  
• Be upfront about pricing. Once you've got a certain amount of buy-in from your champion, give a ballpark estimate they can use in internal meetings.
• Help prepare them for objections. Give them the content they need to overcome internal roadblocks, such as alternative pricing options, case studies from similar organizations, and security information. 

📖 For more tips on supporting your buyer champion, check out our Buyer Enablement Guide.

4. Multithread relationships 

When you sell SaaS to enterprises, you'll be dealing with a buying committee, which means a single solid relationship is no longer enough. 

You need to connect with all stakeholders to ensure you fully understand the organization and can evolve your messaging effectively as the deal progresses.

To build those multithreaded relationships across your prospect accounts:

Verify who you need to connect with. Work with your buyer champion to make sure that you've correctly identified all the key decision-makers involved: 

• Additional potential buyer champions
• The economic buyer 
• The technical decision-maker 
• Key end users (if not the same as the buyer champion) 
• Executive stakeholders 

💡 Don't hide this information away in an internal sales tool, by the way. Instead, share it with your potential customers so they can verify you're talking to the right people. Check out our guide to collaborative account mapping to learn how. 

Take a many-to-many approach. Instead of tasking a single AE with building multiple relationships, connect the people on your team with their counterparts on the buyer's side. 

Your CFO should meet their CFO. Your VP of Sales should meet their VP of Sales. Your marketing leads should connect too. They'll speak the same language, so they're more likely to build strong relationships.

Check if your multithreading is working. For instance, if you're using Dock as your digital sales room, you can check who is looking at your sales collateral, what they're looking at, and how often. If you notice that your buyer champion is the only one accessing the workspace, you'll know you still have work to do. 

5. Focus messaging on outcomes, not features 

The features/benefits messaging you've been using for SMB customers is less likely to resonate with enterprise buyers. You're talking to a buying committee, not just an excited potential end user. 

Provide your sales team with enablement messaging that focuses on the business problems you solve, not the key features of your product (i.e. value-based or solution-based selling).

To quote Robby Allen, ex-Zenefits, now CRO of AgentSync:

"We're not selling to executives in the sense that executives don't log in and use our product. It's typically two or three departments below them or levels below them. But we still need to get executive alignment. So how do we attach our value to executive priorities?"

On Grow & Tell, Allen explains how his 250-person sales team at Zenefits revamped their messaging for enterprise buyers: 

"As we moved upmarket and the pain became more and more sharp, we actually found that there was a big value correlation with our product upmarket that was less correlated down market — in the sense that people were already spending more upmarket to solve this problem and were willing to actually spend even more than they already were spending to solve it..."

6. Address risk mitigation

Enterprise buyers are uniquely risk-averse — so helping address and overcome risk-related objections needs to be your top priority. Here are a few suggestions: 

• Start with small proof-of-concept projects (POCs). Instead of going straight for the big deal, put together a smaller pilot project with a single team. This lowers the risk for the buyer and gets you on their approved providers list. 
• Present security and compliance information early in the deal. Enterprise buyers will likely have additional security requirements, like GDPR or SOC2 compliance, or compliance with local data regulations. Anticipate these needs and share your compliance and provisioning documentation with the buyer's IT team as early as possible. 
• Provide case studies and proof of ROI. Enterprise buyers want to see that you've worked successfully with large organizations in the past. Include case studies in your demos, sales decks, and digital sales room. ROI reports from third parties like Gartner, Forrester, or G2 are also helpful.

7. Tighten up Sales and Customer Success collaboration 

Remember, it’s software-as-a-service. 

When closing larger deals, you have to highlight the "service" element in particular. Enterprise buyers aren't just buying software. They're also investing in the group of people behind the software.

So, your sales process isn't just about showcasing your products — you're also demonstrating the quality of attention the customer can expect once they buy.

To demonstrate that you have an enterprise-grade quality of service, we recommend that you:  

• Use a mutual action plan to create a structured sales process. The professionalism of your deal process tells your buyers how you'll be to work with. A mutual action plan lays out all the steps involved in the deal, providing a well-organized and reassuring roadmap. 
• Address change management as part of the sales process. Managing the process of change during software implementation is a major challenge for enterprises. Hundreds, or even thousands, of employees will need to adapt to a new product. As the vendor, it's your job to reassure your enterprise buyers that you'll help them throughout this process.
  
  Show them that you have plans in place for addressing implementation and onboarding. For instance, include done-for-them training documentation, tutorials, and slide decks in the deal room. 
• Tighten the Sales-to-Customer Success handoff. Bring your CSMs into the deal early, so they can start building a relationship with the buyer and begin the implementation conversation. 

📖 Learn more in our deep-dive guide: The Enterprise Sales Guide: How to move upmarket

The enterprise software sales process

Moving into enterprise SaaS sales will mean overhauling the entire sales motion, at each stage of the process: 

Discovery

Enterprise SaaS sales isn't so much about transactional sales, as making sure that you've got a solid match between what you're selling and what the buyer needs. You'll need to take a consultative approach, while also: 

• Over-indexing on qualifying ideal customers. With the higher customer acquisition costs involved in enterprise deals, qualification becomes even more important. You don't just need to capture buyer pain points; you also need to make sure you've mapped the account effectively, identified all the relevant stakeholders, verified that you've found an effective champion, and assessed technical fit. 
• Using a standardized sales methodology. A qualification method like Sandler Sales or MEDDIC will make sure that your AEs consistently ask the right questions. 

Demos

Unlike the one-and-done demo (or even self-service demos) you might have for SMB deals, with enterprise buyers you're signing up for a multi-stage demo process. 

• Prepare for technical demos. You may need to build a staging environment or at least a self-serve sandbox.
• Embrace async demos. You’re meeting with more people, and getting them all in a room - or even just online at the same time - may not be feasible. If you record your demos and share them in your Dock sales room, you can track which stakeholders have viewed them.  
• Partner your AEs with a sales engineer. Once you're confident you've got a qualified prospect, bring in the SE to scope out a high-level solution, prepare a demo, and manage the POC. 

📖 Check out our sales engineering guide for more details on how and when to add sales engineers to your team. 

Follow-up 

If you've been handling post-demo follow-up with long email chains, now is the time to stop. Enterprise deals require a far more comprehensive follow-up process: 

• Swap the email thread for a digital sales room. You need to get your content in front of multiple stakeholders, which means you need to make it as easy as possible for them to access. Relying on a single point of contact to forward on emailed links and attachments is not the way to close enterprise deals. Instead, use a digital sales room with a single link. That way, it's easy for everyone to find — if you use Dock, you can check to ensure they're all accessing it.
• Share content to create consensus and handle objections. Use your deal room to upload content that will directly address objections, such as ROI calculators, competitor comparisons, comprehensive product specs, security information, and relevant case studies. 

Proposal

It's easier to standardize pricing for SMBs than for enterprises. Instead of offering flat fees: 

• Build a sales business case. This is a framework for presenting your pricing within the context of the value and ROI that your product can bring. Think of it as a pitch directly aimed at the CFO. Here's a handy business case template if you need one. 
• Provide a dynamic pricing proposal. That way the customer will always have the most up-to-date quote, instead of having multiple versions of a PDF scattered across the account. 

Sales proof of concept

Enterprise buyers typically expect more hand-holding during the evaluation process — such as running a proof of concept (POC) rather than a self-serve/sandbox testing process. To get this right: 

• Pitch the POC as a mutual success plan. Instead of positioning the process as an extended sales pitch, work towards your prospect's most relevant success metrics. 
• Keep the momentum going. Partner with the prospect to define a successful POC, what will happen if you nail the POC, and how you'll address any potential roadblocks. Keep the POC under three months to avoid overextending the whole sales process.
• Involve a sales engineer. Enterprise buyers need to know that your solution will work with their existing tech stack. A sales engineer can reassure them by partnering with their technical team, building a detailed implementation plan, and offering specific guidance on necessary customizations. 

📖 For more on sales POCs, check out our guide, "The Sales POC Playbook: How to run a sales pilot." 

Close

Prepare for a slow close. Enterprise deals typically require extensive negotiations with procurement and legal and can hinge on factors like security, compliance, risk, and scalability. A few tips at this stage: 

• Use your mutual action plan to make the final steps involved in closing the deal seem easy and obvious. 
• Anchor your close date to the customer’s timeline. For instance, “If you want to launch this by January 1st, we’ll need to close by November 30th.” This gives them a real reason to sign by the deadline — instead of just feeling like you’re pushing them to close so you get the deal. 
• Monitor stakeholder engagement in your deal room, to spot if a deal is stalling out at the final hurdle. 
• Make it easier to buy. For instance, you can use Dock to transition your proposal into a sign-able order form in the same deal room you've used throughout the process.

Onboarding & implementation

As our Customer Success Lead, Madison Kochenderfer, explains, onboarding enterprise customers is a "unique pressure you don't see with smaller accounts."

Here are some quick tips to level up your onboarding and implementation game for your new customers in the enterprise space: 

• Consider adding a separate onboarding team to your existing customer success structure, to handle the greater demand. 
• Build in processes and guidelines for feedback. Enterprise customers will expect you to accommodate their requests in your product roadmap. You need to know in advance how you'll handle these requests, and what you can and can't promise. 
• Keep the transition seamless. For instance, if you use Dock, you can repurpose your existing deal room into a customer onboarding portal. 
• Set up a regular engagement schedule for each buyer persona. To keep those multi-threaded relationships going, you'll need a plan in place to engage with each stakeholder. 

📖  For more tips, check out Enterprise Customer Onboarding: A guide for scale-ups

Executive Business Reviews (EBRs)  

You're going to need a regular cadence of follow-ups with your enterprise clients. Unlike the less formal “just checking in” processes you've probably got in place for your SMB clients, these EBRs should be strategic, covering business outcomes, usage analytics, and the future roadmap.

A few quick pointers here: 

• Use your client portal to present the information. That way, everything stays in the same place and your customers can easily keep track of progress. 
• Back up key points with data. Detailed performance data shows the decision-makers exactly how your product fits into their business. 

Renewals 

SMB renewals are usually fairly straightforward and often automated. By contrast, enterprise renewal cycles are longer. Here are a few pointers: 

• Find out their annual renewal cycle during discovery. Retaining enterprise clients means getting on their annual budget when making budgeting decisions, not when their license runs out. So make sure you know when they'll be reviewing budgets and start the renewal conversation on their timeline, not yours.
• Involve both Sales and Success in renewal conversations. While the Sales-Success relationship looks different in every organization, they have to work in close partnership for effective enterprise account management.

Sales should engage with customers before, during, and after the deal closes. Success should partner with them to flag potential expansions, upsell opportunities, and at-risk accounts. 

📖 For more tips on renewals, have a look at our Customer Renewals Guide. 

Enterprise Sales Software

You may also need to level up your tech stack to handle the longer sales cycles involved in high-value enterprise deals. Here are a few platforms to consider: 

CRM

If you've been using a home-made CRM solution like Airbase or Notion, now's the time to consider purchasing a full product suite to handle the more comprehensive customer info involved in big enterprise deals. Options include: 

• Salesforce
• Hubspot
• Zoho CRM
• monday.com 

Sales rooms & client portals

A digital sales room solution is a must-have for enterprise sales. Sales rooms are collaborative workspaces where you can share key information with your enterprise buyers, such as sales enablement assets, mutual action plans, proposals, security information, and so on. 

The best tools, like Dock, also let you track buyer engagement and ensure that your deals are progressing. 

Some options include: 

• Dock
• GetAccept
• Accord
• Allego
• Aligned
• DealHub
• Trumpet
• Seismic
• Vidyard

📖 Learn more about your options for digital sales rooms in our guide to the best digital sales room software platforms. 

Presales software

You should also add some tooling for your more comprehensive enterprise sales demos and create virtual environments for technical demos and POCs. Here are a few examples:

• Walnut, Navattic, or Storylane for interactive product demos 
• TestBox, Reprise, Demostack, or Demoboost for live POCs and sandbox environments 

CPQ software 

Configure, Price, Quote (CPQ) tools are useful for building quotes for complex enterprise deals. They can be part of your CRM (Salesforce has CPQ functionality, for instance) or a standalone solution.

Options in this category include: 

• Dock’s sales order forms
• Salesforce Revenue Cloud
• HubSpot Sales Hub
• DealHub CPQ
• Oracle CPQ
• PandaDoc
• RevOps

Proposal & contract management software

You'll need a tool to create, track, and store customized proposals for your enterprise deals that can be signed electronically. Again, your CRM or CPQ tool may be enough for this, or you may decide you need a standalone proposal platform.

Here are a few choices: 

• Dock
• PandaDoc
• Qwilr
• Proposify

Close more enterprise SaaS deals with Dock

If you're ready to start selling SaaS products to enterprise clients, Dock is a great place to begin. Dock's collaborative workspaces make it easy for you to: 

• Keep long deals moving forward with mutual action plans
• Get compelling sales content in the hands of your buyer champions
• Build multi-threaded relationships and track buyer engagement with deal content 
• Create a white-glove experience at scale with customizable deal rooms
• Accurately forecast enterprise sales and increase deal close rates 
• Consolidate the long sales cycle in a single shared workspace 

Curious? Book a demo with our team for a personalized walkthrough of Dock.