How to Generate Leads and Land Deals for Your Enterprise SaaS Product

Landing an enterprise account can mean hitting your revenue quota in one fell swoop. But are you prepared to handle the multiple complexities of an enterprise SaaS deal? Here’s a look at the mechanics of a complex sales process from lead to close.

how to generation leads and lead deals for your enterprise saas product

11 min. read

If you’re used to selling to small and medium size companies, navigating an enterprise deal is a rapid transition to the big leagues.

Navigating and finalizing enterprise SaaS deals is a long and demanding process, one that can involve months of back-and-forth between the multiple stakeholders who need to sign off on the deal.

But closing an enterprise account can result in a big pay day and smashed quotas. Not to mention the multiple auxiliary benefits that go along with having a well-known company as a client.

Let’s take a look at the mechanics of an enterprise SaaS deal from generating initial awareness of your product or service, to navigating the multi-tiered consideration stage, closing the deal like a pro, and retaining that account post-sale.

Generating awareness: getting on the enterprise radar

No matter what you’re selling or who you’re selling it to, drumming up awareness for your company and your product or service is the jumping-off point for all sales.

When it comes to generating enterprise leads, there are certain strategies and pieces of content an enterprise prospect will look for and will need to see before moving forward with your company.

Like all campaigns designed to create brand or business awareness, success relies on the extent to which you understand the motivations of your audience. The reasons an enterprise prospect buys from your company differ from those of smaller buyers, and an understanding of these motivations must permeate the strategies you employ to generate awareness for your product among an enterprise audience.

Selling small—in this context I’m talking transactional SMB sales—is all about emphasizing the upsides to your product or service. The SMB sale revolves around how effectively your solution addresses your prospect’s problem and saves them time and money.

Selling to enterprise, on the other hand, is less about promoting the benefits as about suppressing and mitigating potential downsides.

Once you’re on the enterprise radar, make sure you have the kind of sales and marketing collateral available that illustrates exactly how your solution will work with the established processes of the company.

Here are some examples of material and strategies designed to get your foot in the door with enterprise:

Contribute to industry publications

Getting your name out there via the byline of an informative, industry-specific article published in a reputable publication is a great way to build your profile as an authority in the space.

In the early days of your business, when your company blog has yet to gain much traction, contributing an article in a widely-read publication specific to your industry is a great way to get your ideas, name, and product in front of a relevant audience.

Get familiar with the publications your prospects read, review their contributor requirements, and pitch an idea for an article. Getting published in a reputable magazine or blog gets your name in front of an audience with more than a few potential customers.


Enterprise prospects want proof that implementing your product or service is going to be good for business. Whitepapers are a chance to show prospective buyers you’ve done your homework.

A whitepaper is the academic article of the business world. It’s a detailed, thoroughly researched report into a specific topic. Much like a scientific paper, a whitepaper is a formal document which presents a logical solution based on evidence.

It’s true; they’re not the most exciting pieces of content to read. But they’re not designed to be riveting or persuasive reading. Their fundamental purpose is to build credibility and trust with your readers and position you as an expert on the matter.

Plus, the simple fact that a prospect is willing to dive into a whitepaper is indication that they are progressing further down the sales funnel.

Attend industry events

If you play your cards right, there’s a whole lot more ROI on offer at tradeshows and conferences than lanyards and stress balls.

Industry events are a great way to generate high-quality leads, if you have a plan.

First, choose your conference carefully. They’re expensive to attend, especially if you’re exhibiting and require a custom booth. Do your research; make sure the types of people attending are the kind of leads you want to attract.

You also need to determine specific goals. Why is it important to attend this conference? Is it to generate leads? Increase brand awareness? Get some product feedback? Select a metric by which to track the ‘success’ of attending that show. Afterwards, determine whether it was worth your investment.

Try and land a speaking engagement. There are few better ways to get your company and your product in front of an audience of potential customers. Whether you demo your product or speak to an industry-specific topic, offer something of value; give your audience a reason to keep you in the back of their minds.

At any given trade show, convention, or conference, 81% of attendees have buying authority. That means four out of every five people to walk by your booth, listen to you speak, or introduce themselves are potential customers.

Consideration stage

It’s at this stage where enterprise deals really start to differ from selling to SMB. Even if your lead generation strategies have paid off, and there’s a significant buzz around your business, you still need to navigate the complex web of decision-makers and bureaucracy that defines an enterprise deal.

The team behind the breakout sales book Challenger Sale put the number of decision makers in a complex B2B deal at between 6 and 10.

That’s 6 to 10 individuals bringing their own objections, questions, and agendas to the table every single time.

Too often, deals fall apart because reps fail to bring all the stakeholders together into one meeting where they can collectively agree on the exact problem to be fixed and the most appropriate solution.

You may understand the various motivations of individual decision-makers, but the key to a successful enterprise deal hinges on whether you understand the collective motivation of the group. Fail to do that, and you’ll have an extremely hard time selling to enterprise.

Part of the strategy at this stage of the deal comes from successfully identifying individuals inside the organization who will help you move the deal along, and those decision-makers who have the tendency to squash a deal as soon as something feels off.

To succeed, you need to identify the champions and the gatekeepers.

Develop an internal champion

The champion—or influencer—most likely does not have the final say on whether to sign on the dotted line. But chances are they have significant sway over the person who does.

They can be a valuable asset within an enterprise company with whom you’re trying to close a deal. Staying in their good books and presenting them with the appropriate material is a great way to have someone selling your business on the inside.

It helps to have someone promote your solution when they inevitably report on their research and contact with companies competing for the contract to their superiors.

Identify the gatekeeper

Just as there are those who will act as advocates, there are key stakeholders who will kill the deal the minute a red flag goes up.

These gatekeepers are the ones who need to be shown beyond doubt that doing business with your company is a safe bet. They won’t hesitate to shut you down if it means protecting the company.

In my experience, security and legal concerns tend to be the biggest hurdles blocking closed enterprise deals.

For instance, an IT executive who’s in charge of the integrity of their company’s systems doesn’t care one iota that your software is invaluable to the sales team. If it isn’t up to scratch with their data-encryption standards, consider the deal dead in the water.

Make sure those white papers, legal disclaimers, and security pages are in place to show that you’re serious about these issues. Appeasing these key players in the enterprise deal process is critical to keeping the deal moving forward.

Be patient and prepared

Enterprise sales are characterized by extremely long sales cycles, sometimes deals going as long as 18 months before they either close or fold (and they do fold, by the way, and you need to be ready for that, too).

You need to be prepared to settle in for the long haul. Be realistic about the resources required to make this deal happen. That might mean an AE dedicated to a single prospect for a year. It certainly requires a comprehensive customer success strategy after the deal is done.

Catching the big fish is amazing for all the obvious reasons; huge revenue potential, higher MRR, and even the brand equity and bragging rights that come along with having a big enterprise company as a customer.

But you need to be willing to put in the hard work to make it happen.

The final stages

As the deal starts to solidify, make sure you’re ready for the big questions that will inevitably arise.

Enterprise selling and buying is a different beast, and the rules are fundamentally different from regular transactional sales. Enterprise customers don’t buy off the shelf; they expect your product or service to be adapted to meet the needs of their organization.

Requests for volume discounts, dedicated training and onboarding, additional features, and product customization to meet the needs of the enterprise are commonplace as you start to hammer down the specifics of the deal.

I’ve spoken before about whether you should charge enterprise clients more that regular SMB buyers. The short answer is yes, you should. The long sales cycles, extra attention required from enterprise customers, and the fact that they have the budget (and they expect a larger price tag) for a comprehensive solution to a complex problem are good reasons why you should bump up the price for an enterprise deal.

These are often decisions that you as the founder or sales leader can’t make alone. Engineering, product, and customer success all need to be roped in at some point to make sure what your customer needs is realistic. Anticipating these conversations and proactively addressing these concerns make a difference in shortening the sales cycle of an enterprise deal.

Closing the deal

When your prospects are finally ready to buy, you can expect them to release a request-for-proposal, or an RFP.

When that moment comes, dragging your feet and wasting time scrambling to get all of your documentation together into one proposal is simply not an option.

If you’ve spent months making this deal happen, now’s the time to get in there and close with finality and confidence.

The close is the most important—and the most rewarding—stage of the sales cycle. It’s one last chance to remind your soon-to-be customer why the months of working with you to get to this stage was all worth it.

Shameless plug alert: Proposal software, like Proposify, simplifies the process of closing high-touch deals. Enterprise deals are extremely complex to navigate. It pays to leverage tools and processes designed to give you a leg-up when it counts.

Regardless of how you close, don’t blow it at this critical stage of the sale with an amateurish approach.

Are you giving your junior sellers the hardest job?

SaaS is facing a conundrum when it comes to enterprise sales best practices.

The nature of enterprise sales means the prospects who ultimately approve or reject your advances are seasoned professionals; high-level managers, directors, and executives with decades of experience.

The way the B2B SaaS sales model has shifted in the last ten years means that opening doors with these prospects is often left to junior sales reps at the start of their career.

Opening doors and getting enterprise buyers interested in your company/product/service all comes down to how well that salesperson can understand their prospects pain points and communicate that understanding through the ideal positioning of your solution.

When you have a junior salesperson fresh out of college pitching to a CTO of an enterprise company, no matter how keen, hungry, and well intentioned the rep may be, it’s still a massively unbalanced dynamic.

We go into far more detail on the validity of this model in the podcast—check it out to hear Proposify’s Director of Sales Daniel Hebert discusses in depth why he thinks the outbound BDR process is fundamentally broken.


Closing enterprise deals is a long, arduous process, one that continues long after the final sale. But a handful of happy enterprise clients can very well add enormous amounts of steady revenue to your business.

Success in SaaS sales on an enterprise level centres around a fundamental idea: you’re ultimately selling more than just software, you’re selling a solution to a complicated and expensive problem.

No matter how experienced the buyer, a sales rep who can empathize with their prospect’s pain points and deliver the right message at the right time has a chance at moving a high-stakes deal in the right direction.

What’s your sure-fire way to close enterprise deals? I’d love to discuss your methods in the comments.

How to Generate Leads and Land Deals for Your Enterprise SaaS Product

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