The Enterprise Sales Guide: How to move upmarket

The Dock Team
February 25, 2022
April 30, 2024

Congratulations! Your SaaS startup has found product-market fit and you’ve decided to move up-market.

The decision to move up-market is a big one for any SaaS company: you’ll rely more on sales and you’ll need to modify your product. But the payoff is potentially huge: big-dollar contracts and fewer customers to service.

But even if you are ready to hunt your first big six-figure whale and brave the stormy seas of enterprise sales, here’s the bad news:

The sales tactics that earned you success with small B2B buyers won’t work with enterprise-sized clients. 

Enterprise buyers expect a more formal sales process, have more stakeholders to convince, and they hate the risk of buying from unknown entities.

To sell to enterprise clients, you have to do everything in your power to prove your value.

In this article, we’ll explain the key differences between traditional vs. enterprise sales, and steps you can take to close more enterprise accounts.

Enterprise vs. SMB sales: Challenges and Key Differences

Enterprise sales, also known as complex sales, involve high-price-tag deals, large organizations with multiple stakeholders, longer sales cycles, and complex procurement processes.

In contrast to transactional B2B sales with SMBs (small- and medium-sized businesses), enterprise sales have:

Larger customers - Target buyers are large organizations—often Fortune 500s.

Bigger contract values - Most enterprise deals are north of $50,000.

Longer sales cycles - From initial contact to contract signing, enterprise deals have long sales cycles that last from six weeks to several years. Contrast this with SMB sales where deals can happen within days.

Different buying signals - Enterprise buyers show true buying intent in the form of deal progress (e.g. RFPs get sent out, meetings get scheduled, stakeholders get pulled in, etc.). SMB buyers typically show intent with flairs in communication or consumption of marketing materials (e.g. landing page visits and email opens).

More stakeholders - Enterprise deals involve several stakeholders, teams, and decision-makers with competing priorities, budgets, and timelines—so it’s more challenging to identify and win over the key influencers. SMB sales normally have one or two stakeholders on the buyer team.

More established buying and vendor approval processes - Enterprise buyers have formal procurement processes, including RFPs (request for proposals), security and compliance review, and documented buying criteria—both for your sales team and your finance and IT teams. Therefore, enterprise salespeople have to work within the buyer’s parameters. SMB sales are often a Zoom call and a handshake.

More mature buyers - Enterprise customers are more experienced and know what to look out for. 

More rigid product requirements - Enterprise deals require that you customize your implementation to the customer’s needs. SMBs are more often looking for a plug-and-play solution. That’s why moving up-market is more of a business decision than a sales decision.

A higher sales touch - Because of all of the above, there’s far more of a burden placed on an enterprise salesperson. Enterprise sales require a more hands-on sales approach, more personalization, and less reliance on automation and self-serve sales.

In summary, everything is bigger, higher-stakes, and more complicated with enterprise deals.

How enterprise prospects buy

Traditionally, enterprise deals were top-down deals driven by company management. 

But thanks to the consumerization of the enterprise, we’ve seen many SaaS companies shift to a bottoms-up, product-led growth (PLG) model.

Let’s quickly explore both sales motions.

The traditional enterprise sales motion

The traditional enterprise sales motion is waning in popularity, but still applies to massive company-wide purchases, such as cloud services or CRMs like Salesforce.

From the buyer’s side, the traditional enterprise buying process has followed a path like this:

  1. A senior member in the organization identifies a problem or opportunity (e.g. someone in the C-suite wants to increase efficiency).
  2. They ask a director or manager to evaluate solutions that may solve their problem. 
  3. A small buying team is formed to make a few recommendations. In large enterprises, there are procurement teams that do nothing but evaluate and purchase software solutions.
  4. The buying team has to convince stakeholders by proving ROI.
  5. A preliminary decision is made on a tool.
  6. Each stakeholder’s team or operations group evaluates the tool relative to its own bureaucratic processes and requirements (e.g. security and legal review).
  7. A decision is reached.

The complexity of this process changes the nature of how you’ll sell.

The product-led-growth sales motion

Companies like Dropbox pioneered the PLG model. They take a bottoms-up sales approach by offering a free version of the product to individuals. Once enough individuals are using the product, a company has no choice but to adopt the platform company-wide.

These days, the PLG model is the default—and has been adopted by collaboration apps like Invision, Slack, Asana, and many others.

Here’s a typical PLG sales motion (for cases where it’s not totally self-serve):

  1. A trendsetting user adopts the product.
  2. Other end users see the product and want to start using it too.
  3. A sales rep at the product's company sees the product spreading virally through the user’s company.
  4. The sales rep builds a case for management and IT by showing the product’s usage and the different features that management/IT can get access to if they upgrade to an enterprise plan. 
  5. Management/IT agree on the product and then it goes through a more traditional procurement process.

This can also happen in reverse, where management and IT reach out to a sales rep because they need to "get control" of the product that's spreading through their organization. Read more about product-led sales here.

Enterprise sales phases

From the business development side of the deal, the account executive’s selling process breaks down into roughly three phases:

Phase 1: Convince the champion - Convince at least one influential member of the buyer’s team that your solution will solve their problems. This is achieved through the product itself, marketing materials, discovery calls, qualification questions, and demos.

Phase 2: Help the champion convince others - Give your champion the information and tools they need to convince the key stakeholders. This may include training materials, executive presentations, case studies, walkthroughs with sales engineers, and proof-of-concept trials.

Phase 3: Procurement - Go through the buyer’s process for the nuts and bolts of the deal. This includes pricing, change management plans, security, legal, and other compliance reviews. 

SMB sales usually end at phase 1, so it takes a different set of skills to be a great enterprise seller.

What makes a great enterprise salesperson?

The most successful SMB sales reps aren’t guaranteed to make great enterprise sales reps.

You can succeed in SMB sales with a hustle-hard, numbers-game, transactional approach—sending hundreds of outreach messages and logging dozens of calls per day in your CRM. But these brute force strategies don’t mesh with the complexities of enterprise sales.

Enterprise sales reps are typically more mature in their ability to build relationships and follow sales methodologies.

The ideal enterprise salesperson has these four qualities:

1. Charisma - They need to be able to build relationships with people. They’re someone you want to talk to. They’re texting back-and-forth with their champion. And they’re charismatic enough to win over the CEO.

2. Patience - Enterprise sales take a ridiculous amount of patience and optimism. Deals take a long time, so they need to have the belief that things will work out if they do the right things.

3. Process mindset - Optimism isn’t enough to close a deal. They also need to be organized, forward-thinking and process-driven enough to navigate the complexities of selling over a months-long endeavor. They foresee issues before they happen and have a plan to overcome them.

4. Creativity - Your core sales playbook will work to an extent, but the best enterprise reps will recognize when and how to go above and beyond for a deal. For example, maybe a billboard outside the buyer’s office will be enough to tip the deal in your favor.

5. Trustworthiness - You have to be able to speak very directly and specifically to the problems your prospects have. Your prospect needs to see you know your stuff and that you have the experience they need. This will automatically build trust and help you close more deals.

Don’t worry if you aren’t a superstar in all five categories right off the bat. These are all muscles that can be developed with practice.

Tips for closing more enterprise deals

Here are ten actionable strategies that will improve your close rates for enterprise sales that will look significantly different than your SMB sales processes.

1. Standardize your sales processes

You can’t force enterprise deals. There has to be an airtight match between your solutions and your buyer’s needs.

Therefore, enterprise selling is less about “selling” and more about identifying the right buyers and then being structured in your sales process—with room for flexibility.

It's like being the captain of a cruise ship. You have to get from point A to point B while serving a buffet and stopping drunk people from falling off the boat

Qualification is everything. The best enterprise salespeople ask the right questions to qualify their buyer, hold up a mirror to the buyer’s pain points, and then show how the solution can make their life easier.

But the key to qualification is standardization.

Sandler sales and MEDDIC are two great sales methodologies to consider for approaching mature enterprise buyers as they both put emphasis on qualification.

These methodologies will help you standardize your sales processes for each customer segment—helping you identify potential blockers and better predict your pipeline.

You’ll quickly learn the right qualifications questions to ask for each segment. For example, if your product doesn’t offer localized language support and it’s a must-have requirement for your client, it’s best to find that out in the discovery call.

Your qualification questions will be different for each segment, but your methodology will be the same.

2. Understand stakeholders through account mapping

In a short sales cycle, you only need to get buy-in from one point of contact. Easy enough.

But for enterprise deals, it may be more complicated.

For most PLG companies, convincing one end user, who will convince their team is enough to tip the scales in your favor. From there, you can move through the organization, gobbling up one team at a time. 

The best enterprise sales reps are able to see this usage and then go to a senior leader at the director or VP level to implement the enterprise solution across the organization.

For heavily IT-focused solutions (e.g. AWS), you may only be fighting for the buy-in from one person (e.g. the CTO or the Director of IT).

But for the traditional enterprise sales motion, you may need to convince an entire organization. Your main point of contact may be a boots-on-the-ground manager, but you’re ultimately going to need buy-in from the COO, CFO, IT team, and other groups to close the deal.

There’s a major challenge here: your buyer might not always make these stakeholders obvious (or readily available).

Regardless of your sales model, to better understand your enterprise buyer, get to know their organizational chart. The best sales reps will literally print out or draw the org chart of the company they’re trying to sell to.

You can then use the org chart for account mapping. This means identifying all potential influencers, blockers, and champions, and then building a strategic plan for how you’re going to go after each key member.

3. Build multi-threaded relationships

Building multiple relationships across your buyer’s organization is known as multi-threading.

Not only does multi-threading avoid having the deal hinge on any particular person, but it also creates strategic alignment between your organizations.

For SMB sales, you’re selling a tactical, out-of-the-box solution. The relationship between seller and buyer is purely transactional.

For enterprise sales, you’re making a multi-year strategic commitment to each other. You’ll be developing and evolving together. It’s not just about whether your solution can get the job done, it’s also whether you’re the right partner and whether your roadmaps align.

So how can you go about multi-threading in practice?

To start, you should work with your champion to get introductions to all the key stakeholders. If that’s not possible, you can try the cold outreach approach on LinkedIn. 

But you shouldn’t work alone in this. You should also link up like-minded people from across both organizations—not to discuss the nuts and bolts of the deal, but to create personal connections. 

Your CEOs can meet over coffee. Your VPs of Sales can swap stories. Your Marketing Managers can share best practices. 

These many-to-many relationships will help build mutual understanding and rapport.

4. Get your foot in the door with proof-of-concept projects

With enterprise selling, the best way to make inroads within an organization is by starting with small proof-of-concept projects (POC).

This normally involves running a pilot project with a single team or division, or starting with one of your product lines (instead of your entire suite).

While it’s tempting to go straight for the big deals, proving your solution’s value on a smaller scale acts as tangible proof of your value.

Getting into the company’s procurement system and onto their approved buyers list can open the floodgates for more sales in the future.

That said, 78% of the 2,000 IT executives surveyed as part of a 2020 Sapphire Ventures survey said that at least 50% of their POCs failed.

How can you make sure your POC succeeds?

  • Set clear goals: Define clear success metrics for the project with the client.
  • Keep it small: Keep the POC under three months to avoid dragging out the sales process.
  • Ask for payment: Avoid running the POC as a free trial. Paying for the test project shows genuine buying intent from your prospect.

5. Create flexibility with sales engineering

Part of running a POC is about being flexible with your product offering. You can achieve this through sales engineering.

Smaller buyers want to be told how to use your software. They adapt to you.

But bigger companies can’t change their systems as easily. They need your solution to fit with their processes. You have to adapt to them or they’ll never buy from you.

This makes the enterprise sales process very different—mainly because it introduces a sales engineer or solutions architect to the process. 

A sales engineer is part salesperson, part technical expert. They create a bridge between your sales and product development teams. They gather requirements from the client in order to understand their specific challenges, and then propose solutions that best fit their needs.

Your sales engineer will provide recommendations for customizations, build implementation plans, and provide detailed estimates for your client.

6. Personalization creates a better buying experience

This level of personalization and customization has to extend throughout your entire sales process. Your buyer has to feel taken care of. Buying from you should feel like a VIP, white-glove experience.

Make custom content and sales decks tailored to your client’s unique needs, pain points, and decision-making process. This will differentiate you from competitors.

The challenge, of course, is being able to consistently achieve this level of personalization at scale—but Dock makes this possible.

With Dock, you can create a customized shared space for each of your prospects. This shared space aligns buyers and hosts all the key information about the sale in one place.

Our enterprise sales template, for example, contains:

  • A project overview
  • Your contact information
  • A mutual action plan
  • Procurement steps
  • Demo recordings and links to meeting notes
  • Your pitch deck and other relevant documents
  • Customer service specifications
  • Case studies
  • Security and privacy information
  • ROI analysis
  • Links to onboarding documentation
  • And more

If this feels like a lot, it is.

But most companies share these assets one by one over email, sharing ad hoc spreadsheets, Google Docs, and Dropbox folders.

This gets out of hand quickly when you’re dealing with a months-long sales process.

Having all of this information neatly organized in one sharply designed place creates a personalized, premium-feeling buying experience for your prospect and helps both sides stay organized.

7. Mutual action plans push deals forward

Mutual action plans (MAPs) are the catalyst for closing enterprise deals.

MAPs are customer-facing sales roadmaps that document all the steps needed to achieve mutual success on the project (up to and beyond signing the contract).

They identify who’s responsible for what, what actions need to be taken by the buyer and the seller, key dates and timelines, and measures of success.

MAPs typically split high-level tasks into four stages:

  1. Discovery: Introduction calls and defining success criteria
  2. Validation: Demos and project roadmaps
  3. Final agreements: Compliance review, references, and contracts
  4. Implementation: Project kickoff and onboarding

Keeping track of these steps in a Dock space consistently proves value to different stakeholders and keeps everyone aligned—reducing risk for both parties and keeping sales on track.

MAPs are especially helpful when you’re dealing with an inexperienced buyer or champion who may not realize all the steps needed to launch the project.

For more, check out our guide to mutual action plans.

8. Security and compliance are serious business

One of the biggest differences between SMB and enterprise selling is the strict security and compliance demands. 

Enterprise buyers don’t want to take on any risks, so they will do lots of due diligence to make sure you won’t cause them any issues down the line.

For example, your buyer may need proof of GDPR or SOC2 compliance, or compliance with their local laws. 

Of course, you have to meet these requirements—so keep your product team in the loop to anticipate your buyer’s security needs.

These shouldn’t be seen as obstacles, though. If you get it right, these are hooks to get buy-in from the company’s IT team. 

For example, IT might care a lot about provisioning and deprovisioning software. Things like  Single Sign-On (SSO), SAML 2.0 (i.e. Okta integration), SCIM Support are important to them.

You as the salesperson can instill lots of confidence in the buyer’s IT team by presenting your compliance and provisioning documentation as professionally as possible.

Using Dock, you can create a resource hub with all of your security and compliance information neatly organized in one portal. Getting ahead of the buyer’s security questions gives them the confidence that you have your ducks in a row.

9. Lead the change management

Software implementation is really hard for enterprise companies.

For example, Workday is the biggest enterprise HR software. Companies may spend $1 million to buy the software and another $1 million just to have Deloitte consultants implement it.

Whereas SMB buyers only need to know your product does the things they need it to do, enterprise buyers also need to see how you’re going to implement your solution within their organization.

Implementing your product will impact the workflows of potentially thousands of employees, so you have to show you can provide training and education for their teams to get from point A to B.

This is known as change management, which can happen at several levels:

  • At the senior leadership or management level
  • At the operations and systems level
  • At the end-user level

As part of your sales process, show your post-sale plan for addressing implementation, customer success, and onboarding for each segment.

Practically, this may mean creating a change management hub in Dock with customized slide decks that the company can use to explain the change management plan to the different types of stakeholders in the company.

These would show what the person’s world looks like now, how it would change with your solution, and all the necessary steps to get there.

90% of the content will be the same for each group, but you can personalize each deck slightly to appeal to that persona’s biggest questions and potential pain points.

Management, for example, cares most about dashboard views. They want to understand what's happening across their organization—holistically and on an individual basis. They also care about user adoption, so it’s important to highlight what training will take place and how they can monitor performance.

10. Case studies are fundamental

Case studies and success stories are fundamental to reducing your buyer’s anxiety during the sales process.

The saying “Nobody ever got fired for buying IBM” has been around since the 1970s because enterprises don’t like betting on unproven commodities. 

Your prospect has to see that your solution has worked for companies with them in the past.

Case studies will become your most important piece of sales content during the sales process and should be included in your demos, sales decks, and Dock space.

If you can, you should also show proof of ROI from analyst reports such as Gartner, Forrester, and G2. The bigger the company, the more they’ll want these. 

Move up-market with Dock

Dock is the first tool built for enterprise sales teams to prove their value to their prospect.

Dock gives you all the tools you need to move your sales process up-market:

  • Dock makes it easy to manage multiple stakeholders via mutual action plans
  • Dock helps champions make the case to internal stakeholders
  • Dock allows sales reps to provide a personalized experience at scale
  • Dock helps with forecasting enterprise sales deals

To start closing more enterprise deals, check out our enterprise sales template or book a demo with our team for a personalized walkthrough of Dock.

The Dock Team