Enterprise SaaS Sales: What it is and How to Build a Successful Strategy in 2025

Enterprise SaaS sales is a beast of its own. The sales cycles are long (often a slog), often involving endless meetings and an ever-growing list of stakeholders and decision makers. 

If you’re used to transactional sales or small-to-mid-sized deals, enterprise sales can present a steep learning curve. So in this article, we’ll lay out what to expect and how to six-, seven-, and eight-figure deals. 

Key takeaways

• Enterprise vs. traditional SaaS sales are completely different beasts. Enterprise deals involve longer sales cycles, more decision makers, and a lower volume of potential customers to pull from. 
• Key to success with enterprise sales is a deep understanding of your ICP, so you can personalize your marketing and sales content directly to their needs
• Three critical components of enterprise SaaS sales include building out your team, playbooks, and tech stack
• There are a range of KPIs to help gauge your success with enterprise sales, including weighted pipeline value, LTV:CAC ratio, sales velocity, and more

What is enterprise SaaS sales?

Enterprise SaaS sales is the process of selling high-value products to large and mature organizations with complex use cases. These are large contracts often in the six- or seven-figure range.

Because of the price tag at stake, enterprise SaaS sales aren’t transactional. Sales reps work proactively, sometimes for months or even years, to develop a strategic, consultative sales process to ensure the product actively contributes to the target account’s bottom line. 

What’s more, the enterprise sales model focuses not only on acquiring large customers, but also working to retain that business when the contract comes up for renewal. This often includes having a thorough onboarding process, continual user training, and even monitoring ongoing use and adoption to make sure the customer is maximizing your platform’s benefits. 

How does enterprise SaaS sales differ from other types of selling?

If you’re used to selling high-five and low-six figure SaaS deals, you’ve been playing in a completely different league from enterprise SaaS sales. Not that those smaller deals aren’t important. However, the methodology behind these sales approaches are different. 

The major differences between enterprise SaaS sales and other types of selling include:

• Consultative, strategic sales approach—emphasis on building trust and enthusiasm in proactively solving a large business problem
• Relationship building is a key part of enterprise sales—namely because the average enterprise sale has 6-10 decision makers involved
• Longer B2B sales cycle lengths due to high degrees of trust, proof, and buy-in necessary to successfully close
• Low volume of marketing and sales qualified leads, as enterprise audiences have fewer members
• Typically reliant on custom marketing and sales outreach through an expansive, diverse range of inbound and outbound channels

Enterprise SaaS sales cycle vs. typical sales cycles

In the section above, we mentioned the difference between enterprise vs. typical sales cycle lengths. According to Databox, the typical B2B sales cycle is 2.1 months. Compare this with the typical enterprise sales cycle, where you’re looking at a six month minimum sales cycle. 

According to digital marketing expert Pat Ahern, “B2B sales cycles should increase in length as the size of the deal increases. A $1,000 purchase may only take a few weeks to close, whereas a $50,000 purchase might take 3 months.”

Selling SaaS products to enterprises is a long-term play. For that reason, regular communication, nurture, and engagement is key. For most sales organizations, this requires some kind of automated sales workflow software. 

3 types of SaaS selling models

Most SaaS companies use one of three sales models. Often these models will overlap and apply to various customer segments and stages of maturity in the business. 

1. Self-service sales

Self-service sales works well for small sales teams with low price points. Users simply visit your website and sign up for an account with a Stripe credit card link. Often you can use free trials to incentivize new user acquisition, convert those users into paying customers, and potentially drive them to add more seats to the account. 

Self-service sales is particularly common among organizations adopting product-led growth (PLG) sales strategies. Enterprise SaaS sellers can also use self-service to identify users within companies that have high growth potential, then deploy both sales and marketing teams to expand product usage across the broader organization. 

2. Transactional sales

Under the transactional sales model, there are set pricing tiers that increase in available functionality. A standard example of this is the HubSpot model, which includes Starter, Pro, and Enterprise tiers for users with different needs and budget: 

Image source: Red Pandas

While many SaaS products do include available add-ons to their pre-determined pricing tiers, on the whole there is limited customization within these tiers. Under a transactional model, a key part of inbound lead qualification is figuring out whether a lead fits into one of these pricing tiers and which one is best. 

3. Enterprise SaaS sales

The third and final tier listed here is enterprise sales, which overlaps significantly with Account-Based Selling (ABS). Although it requires the most investment in time and money, it promises outsized returns in terms of larger contracts with bigger brands. 

While you’ll occasionally get inbound leads that belong to enterprise accounts, nine times out of 10 you’ll end up approaching them through outbound sales. However, if you do get an enterprise inbound lead, it’s a good idea to identify that account’s potential sooner rather than later. That way your sales reps can move accordingly. 

How do you build an enterprise SaaS sales strategy?

Let’s take a look at the process of building out an enterprise SaaS sales strategy. In general, it’s a bad idea to rush this process. The more time you spend building out your strategy, the better prepared you’ll be when you start engaging with enterprise prospects, whether through inbound or outbound. 

1. Define your ideal customer profiles (ICPs) and unique selling propositions (USPs)

The first step in any sales strategy is to figure out what you’re selling, who you’re selling it to, and why they should buy it. However, enterprise deals have multiple stakeholders and decision makers, layers of compliance, limited budget flexibility, and key strategic initiatives any new investments must support. Success in these conversations requires a more rigorous, detailed approach to your sales strategy and defining your target market.

Part of this process is defining your ideal customer profiles (ICPs) and unique selling propositions (USPs). You should develop these two in tandem, as the customers you attract will define the value of the product. And vice versa: the value of the product defines which customers you should target. 

For enterprise SaaS sales, the first and perhaps most important aspects of defining your ICP are annual revenue and number of employees. These are quick ways to filter out those prospects that actually have a high likelihood of buying. You can then flesh these out in detail based on your specific product. 

In terms of USP, you’ll start with your competitive differentiators. However, in enterprise sales, often you won’t know how to position your SaaS product until you have several conversations with your internal contacts. The more specific your USP is to that particular prospect’s strategic objectives, the better. 

2. Build out your enterprise sales playbooks, tools, and team

Once you’ve defined who you’re selling to and why they should buy, the next step is to build your game plan: the people, sales techniques, tools, and tactics necessary to move enterprise deals through the sales funnel. 

Playbooks

For smaller or mid-sized deals, you can typically get away with an ad hoc approach to selling. Not so with enterprise sales. There are simply too many dollars on the line, and the value of large clients make these deals highly competitive. 

Enterprise sales playbooks are generally divided into four parts:

1. Discovery plays. These are the key questions to help sales reps qualify prospects and identify the key reasons they would benefit from your SaaS product. This will enable you to tailor your USP to the enterprise client. 
2. Sales presentation plays. Once you’ve qualified the prospect, your sales team will develop a tailored sales presentation for that client. It’s important to cover strategic objectives, potential pitfalls, benefits, features, and objections raised earlier in the process. 
3. Follow-up plays. Given the long-term nature of these deals, sales representatives should have clear instructions for how to follow-up in case a deal stagnates. It’s important to specify your follow-up plays so you don’t cross your wires and put the deal at risk. 
4. Close plays. Too many sales deals are lost in the final stages. This section of the playbook includes language for annual contracts, onboarding plans, thank-you templates, and other post-close actions. 

Team

Enterprise SaaS sales never fall into the lap of a single rep. It takes a concerted effort to plan and execute enterprise sales playbooks. Some of the key members of your team will include sales managers, SDRs, and AEs. However, you could require additional support from sales operations managers, sales admins, and even marketing and customer success teams. Depending on the size of your organization, your executives or founders may even get involved. 

The larger your team, the more important it is to have well-defined playbooks that make everyone’s role in the sales process clear. That way, the organization works in tandem and people don’t counter or duplicate each other’s efforts. 

Plus, the more smoothly your team runs, the more confidence your prospect will have that you can handle large-scale projects and deployments—which is what you’re selling in the first place. 

Technology & tools

It’s also important to ensure everyone on the team has the resources and technologies necessary to execute key plays in the enterprise sales process. Mission-critical components of your stack are:

• Lead enrichment software to give you as much information about the lead as possible
• Automated scheduling and lead routing software so leads stay informed of every action a contact with a target account takes
• Lead-to-account matching so new inbound leads are automatically included in the enterprise deal 
• Trigger-based workflows and automations based on your playbooks, so there’s no delay as prospects move from one stage of the process to the next

Relying on enterprise sales technology that’s slow, unwieldy, and relies on extensive integrations is often more trouble than it’s worth. See how Default’s all-in-one enterprise RevOps software offers the features and orchestration capabilities you need to close more enterprise deals.  

3. Build your enterprise sales pipeline

Now that you’ve done your prep work, the next step is to start building out your enterprise sales pipelines. These pipelines will be smaller and slower than typical B2B SaaS pipelines. Enterprise opportunities are few and far between, and that’s before you disqualify those enterprises that aren’t a good fit. 

One of the challenges of building and managing an enterprise SaaS sales pipeline is that often prospects are locked into contracts with a competitor. Understanding those expiration dates can help inform a realistic picture of when those deals will close. 

Additionally, predicting enterprise pipeline close rates—and, thus, your weighted pipeline value—can be a challenge when your sample size is so small and deal sizes can vary widely. With enterprise sales, there’s a bit more subjectivity that needs to be taken into account when deciding when and where to spend your time. 

4. Engage decision-makers within target accounts

The average number of decision-makers in a B2B SaaS deal is 6-10 people. So once you engage a contact within a target account, you’re just getting started. The next step is to expand your contact base within that account.

SaaS acquisition and implementation often touches a number of functions. This starts with the core user base, but also finance, procurement, IT, legal, and more. So while, yes, you want to expand your contact base vertically to reach the highest levels of the organization, you should also expand horizontally to ensure you get buy-in from all these stakeholders.

Generally, these stakeholders’ concerns fall into three categories:

• Return on investment—will this help save or make the organization more money?
• Time to implement vs. time saved—will using this technology prove to be a time and cost sink? 
• Internal adoption—how much training and coaching will be required to onboard the team and enforce their use of the technology? 
• External risks—does this technology compromise existing infrastructure, and will it require additional effort to mitigate those risks? 

Although most enterprises have roughly the same formal organizational structure (e.g. CEO, CFO, VP Sales, IT Director), every team has different internal dynamics. You never know which person has heavy influence or veto power over the process. 

According to Gartner’s 5 Ways the Future of B2B Buying Will Rewrite the Rules of Effective Selling report, “Successful B2B purchase decisions are effectively contingent on customers’ ability to successfully navigate complex institutional change. Over 80% of customers voiced uncertainty in their own ability to manage such change, and their suppliers must share in that concern.”

Remember: the average sales cycle for enterprise SaaS is often 12+ months. In that time, your point of contact could resign, switch departments, or be promoted. Any of these changes can affect your standing within the organization and impact your sales effectiveness, for good or bad. As such, it’s important to build as many relationships as possible and proactively work to maintain them. 

5. Create custom collateral & content

As you build relationships with your target enterprise accounts, you’ll quickly discover concerns, needs, and roadblocks that are unique to that client. To overcome these and increase your odds of closing the business, you’ll need to create custom collateral and content which speak to those needs.

For most sales processes, custom content for each prospect isn’t economically feasible. For enterprise deals, however, it’s a comparatively small investment when you consider the financial upside. 

Which enterprise SaaS sales metrics & KPIs should you track?

Executing the sales plan laid out above is a heavy investment. Justifying that ongoing investment requires you to continually track and measure your progress toward those goals. Here are some of the core metrics and KPIs for enterprise sales success. 

Weighted Pipeline Value 

One of the most important leading indicators of enterprise sales success is your Weighted Pipeline Value. You can calculate this metric using the following formula:‍

(Number of Deals in Pipeline) X (Average Contract Value) X (Win Rate) = Pipeline Value

‍So, for example, 10 deals, at $500,000 Average Contract Value, and a 30% Win Rate, gives you a Weighted Pipeline Value of $1,500,000. 

As mentioned above, this compound metric is difficult to track because of the low number of deals, variable contract values, and widely different factors that impact the likelihood to close. So while you’ll want to measure this KPI, make sure you include qualitative insights from your reps to get the full picture of each individual in the pipeline. 

Sales Velocity

Another helpful metric to track is Sales Velocity. Simply divide your Weighted Pipeline Value by Average Sales Cycle Length. So if you have a sales cycle of 180 days, your Sales Velocity is roughly $8,300 per day. 

Given that enterprise SaaS sales have a long cycle with a high return at the end, Sales Velocity can help clarify whether the sales organization is in a healthy place or whether you need to increase your sales game. 

Lifetime Value to Customer Acquisition Cost Ratio (LTV:CAC)

Enterprise SaaS deals have high Customer Acquisition Cost (CAC). The only way to justify this investment is if the deal has a much higher Lifetime Value (LTV). So you should constantly keep your LTV:CAC ratio top of mind. 

Sales Cycle Length to Average Deal Size Ratio

Not only do enterprise SaaS deals have a high acquisition cost, they also have a high opportunity cost. If reps are spending significant time on average-sized deals, you’re not only deploying your sales resources inefficiently, but you’re probably missing out on other opportunities. 

It’s important, then, to track the ratio of Sales Cycle Length to Average Deal Size. If the latter is a function of the former, then your organization is healthy. If not, you’ll need to make some changes. 

Enterprise SaaS sales FAQs

What is the difference between SaaS and Enterprise SaaS?

SaaS sales is a broad category that includes self-service or product-led growth, transactional selling, and enterprise SaaS. Enterprise SaaS sales targets high-value customers with personalized messages and product offerings to close larger deals. 

What is the typical sales commission for Enterprise SaaS?

The average enterprise SaaS sales rep receives a commission of 8-15%. The upside for enterprise sales isn’t a higher commission, but a larger deal size. 

How to speed up the enterprise SaaS sales cycle?

The best way to speed up the enterprise SaaS sales cycle is through use of automations that accelerate enrichment, qualification, scheduling, and follow-up. These are the areas where reps spend the most time on manual tasks and, thus, slow down the sales process. 

Add enterprise SaaS sales tools to your tech stack and make selling easier

Enterprise SaaS sales require more effort and investment than transactional and self-service models. With the right automation tools, however, you can reduce the amount of manual effort necessary to nurture these accounts over the long haul. 

Default’s full-stack enterprise SaaS sales software automates:

• Lead enrichment, pulling in hundreds of demographics and signals to help personalize your outreach and nurture efforts
• Qualification, to identify when contacts within target accounts are increasing their engagement
• Nurture & outreach, to help maintain constant communication with enterprise contacts over the long haul

What’s more, Default does this while mapping onto your current processes. Whatever enterprise sales motions or workflows you have in place, we can automate them.

See for yourself. Schedule a Default demo today.

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