10 Strategies to Shorten a Long Sales Cycle

When long sales cycles get even longer, and deals start slipping into the next quarter a little too often, most sales leaders look inward at their sales team.

They ask: How can we get more efficient? Do we need to offer more time-limited discounts? What new processes can we implement? What are our best reps doing that others aren’t? 

But most sales leaders should be looking outward, at their buyers.

Because most of what slows down an enterprise SaaS deal happens on the buyer side: too many stakeholders get pulled in, new technical requirements emerge, your champion leaves the company, and unexpected security reviews pop up. 

The best way to shorten a long sales cycle is to make life easier for your buyer. That means reducing complexity, adding structure to the buying process, and helping your champion sell internally.

In this post, we’ll explore practical tips and techniques for shortening a long sales cycle and closing the right deals faster without undercutting yourself.  

How long is a long sales cycle?

In B2B sales, a long sales cycle is considered anything between 6 months to 2+ years.

If you’re selling into a highly regulated industry, Fortune 500s, or governments, the sales process can drag on for years.

What makes a long vs. short sales cycle? 

According to a Databox survey of 300 companies, the median B2B sales cycle lasts 2.1 months. 

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When people talk about a short sales cycle, they normally mean anything up to 3 months. Most sales take a quarter or less to close. This usually involves simpler, lower average contract values (ACV) where the decision-making process is much quicker and the sales process is more transactional.

When people talk about a long sales cycle, they’re normally talking 6 months to 2+ years. This typically involves complex solutions that require a thorough evaluation process from multiple decision-makers in a buying committee. Each stakeholder in the buying committee needs to be convinced of the product’s value, which often requires in-depth consultations, detailed demos, and working through objections.

What causes a long sales cycle? 

The biggest differences between long and short sales cycles boil down to deal complexity and the number of decision-makers. 

However, the product you are selling, associated switching and onboarding costs, who you are selling to, and even the experience level of your sales team can all play big roles in managing expectations. These all factor into whether you are able to close deals in a couple of weeks or whether you are looking at one-year (or longer) sales cycle. 

The most common reasons for sales cycles dragging on for several quarters are:

• Multiple stakeholder approvals: Enterprise deals often involve large purchases that require sign-off from various decision makers (IT, finance, legal, executives, etc.)
• Extensive evaluation and vetting process: Organizations thoroughly vet and test products/services to ensure they meet requirements and integrate well with existing systems
• Complex, longer contract negotiations: Large deals involve intricate contract terms that get scrutinized and negotiated line-by-line by legal teams 
• Procurement processes: Enterprises have structured budgeting cycles and procurement policies that can extend timelines
• More bureaucracy and red tape: Large organizations tend to have more bureaucratic layers and approval chains to navigate
• Change management concerns: Adopting new enterprise solutions requires change management planning across the organization 
• High costs and high stakes: The high costs and business impacts of enterprise deals raise the stakes and due diligence required. 
• Existing vendor relationships: Evaluating new vendors against incumbents means more time requesting and evaluating RFPs. 
• Security reviews: Data security, compliance, and regulatory requirements get scrutinized. 

Tips for shortening a long sales cycle

It's unrealistic to transform a nine-month sales cycle into a nine-week sprint without risking the deal or leaving significant money on the table. Here are several tactics that can help you increase sales velocity in the most practical timeframe. 

1. Spend a lot of time with your ICP 

Many companies and salespeople believe they know their ideal customer profile (ICP), but the reality is often different. According to Trinity Nguyen, VP of Marketing at UserGems, only 20-30% are capturing it accurately. 

This disconnect usually comes from relying on assumptions, outdated data, and not spending enough time around your ICP. 

If you want to close this gap, you need to continuously monitor and refine your ICP mix. This will help you close deals faster and more effectively.

2. Build a strong brand

Trust is everything in high-ACV deals. The best time to build trust is before the sales cycle even starts. That means building a strong company brand.

Most sales leaders think Marketing’s job is to fill the top of the funnel, but a strong brand can be a huge sales accelerant. 

Alina Vandenberghe, co-founder of Chili Piper, excels at this. In a crowded market that’s notorious for long sales cycles, her company’s differentiator is creating a human brand and fostering authentic relationships at scale. They engage in joint marketing campaigns, share sales playbooks, and host office hours to build robust partnerships. 

This trickles down to customers by not only sharing tactics that will help them use their product better but also at a human level by sending soup when they're sick. These genuine connections help Chili Piper achieve organic, word-of-mouth marketing that reaches far and wide. The more people you help, the more your reach compounds.

At Dock, we’ve aimed to build trust with our ICP by hosting our Grow & Tell podcast, overinvesting in website design, showing up on LinkedIn, sponsoring Sales and Sales Enablement communities, writing blogs like this one, and tons of other initiatives.

But if you’re a sales leader or rep with relatively little impact on your company’s marketing strategy, you can also take to building your personal brand on LinkedIn or wherever your ICP lives.

Brand building is a long-term effort that requires a ton of patience, but it pays off down the road.

3. Hire process-minded salespeople

Long, enterprise sales cycles require a completely different skill set than smaller SMB deals.

Compared to SMB sales, enterprise deals require more relationship-building, proactive selling, and project management. 

Bringing in experienced sellers who already have enterprise sales experience can drastically shorten your sales cycle. They likely already excel at anticipating and addressing potential objections early, preventing delays, and minimizing the risk of deals falling through at the last second.

Ben Braverman, former CRO of Flexport, advocated for this on Grow & Tell:

"Flexport really was three businesses in one: it's an SMB business, a mid-market business, and a key account business or Enterprise business,” says Ben. “Each of those sales is a totally different profile. The SMB motion was purely a function of positivity, energy, and project management. The profile for SMB generally does not translate that well into key accounts."

On Grow & Tell, Rich Liu shared how Mulesoft thought about hiring enterprise sellers:

“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, high-growth mindset, and a passion for sales.”

4. Implement a discovery-focused sales methodology 

A great way to shorten the sales cycle is to quickly close out unqualified deals.

Using a structured sales methodology system like Sandler or MEDDIC can systematize discovery and follow-up so that every rep follows the same qualification process. 
Not only do these methodologies emphasize qualifying buyers early on — you’ll also uncover key stakeholders and establish trust early on in the sales process, which ultimately shortens the sales process.  

5. Practice value selling 

Another way to accelerate a deal is to create more urgency on the buyer’s side. 

But you can’t create fake urgency. The buyer needs to feel your product is a solution to an urgent problem.

Value-based selling, or value selling, is a sales methodology that prioritizes aligning your product or service with the measurable value a prospect needs and wants rather than simply pushing for a sale. 

This approach focuses on delivering a value pitch instead of a sales pitch, addressing the entire sales process through the lens of needs, pain points, and tangible outcomes.

So, your sales reps transform into trusted product advisors who deeply understand the return on investment (ROI) that prospects seek. This involves quantifying the value in terms prospects care about in one or more of these ways: 

• Money saved. Demonstrate how your solution reduces costs.
• Money earned. Highlight opportunities for increased revenue.
• Risk avoided. Explain how your solution mitigates potential risks.
• Efficiency/Productivity gained. Show how your product enhances productivity and efficiency.

Try shifting the focus from simply selling a product to sharing a measurable value proposition and demonstrating it with relevant metrics and social proof. Testimonials on LinkedIn and case studies focus on specific outcomes so you not only meet your prospects' needs more effectively but also build trust and stronger relationships.

This approach ultimately leads to shorter sales cycles because you connect yourself to urgent value.

For instance, this is what Robby Allen did at Zenefits, where he was able to help his 250-person sales team better attach the product to specific executive priorities. 

“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...”

“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?”

6. Create digital sales rooms for each deal  

According to Allyson Havener, VP of Marketing at TrustRadius, 100% of buyers want to self-serve most of the information in the buying process. 

That’s why buyer enablement is so important. When you equip your buying team with all the collateral and information they need to make a decision on their own — you’re far more likely to close deals.

Dock’s digital sales rooms can bridge this gap effectively because: 

• Your champion will be doing most of the selling for you. The better organized/well-prepared they are, the shorter the sales cycle. 
• It makes tracking buyer engagement easier. See when buyers are/aren't taking action. See who's accessing the deal room. This helps with more timely follow-up and gives insight into what's happening on the buyer side.

For instance, Helen Ralowicz-Chapman, formerly part of Marqii’s mid-market sales team and now a Strategic Growth Partner, has successfully used Dock to keep multiple buyer stakeholders educated and aligned throughout a long sales cycle.

“When I'm like, ‘Hey, did you look at the links I sent over?’ Well, if you didn't open the Dock, I know that you didn't. I know that you maybe aren't as engaged,” said Helen. “So I need to do something else to either make [the Dock workspace] more relevant to you or make it easier for you to access.”

“On the flip side, when someone is really clicking around, when I can see the CMO has forwarded it to the COO and there's some new person clicking around in there too, that is a signal to me that that person's actually really engaged. They care about what's online. And they want to fix it. And so then if they want to fix it, I am all here for that.”

“It’s really helpful to see that type of activity, and also gauge: are they interested? Are they not? It answers that question for me, too.”

By creating digital sales rooms for each deal, you can provide all necessary information in one accessible place. This approach not only meets the expectations of modern buyers but also streamlines the sales process, making it easier to manage and faster to close deals.

7. Create your mutual action plans around the buyer’s timeline 

Implementing mutual action plans is a powerful buyer enablement tactic, particularly when used alongside a digital sales room. 

That’s because a mutual action plan allows you to clearly define the goals and anticipate roadblocks that the buyer might encounter (e.g., budget approval, security reviews) at every stage of the buying process. 

Then, you can create personalized mutual action plans that outline the steps both you and each stakeholder in your buying committee need to take to move the deal forward. 

We recommend anchoring the deal timeline and task deadlines to the buyer's timeline. 

For example, "If you want to launch this by your Q3 kickoff, we'll need to do step 5 by June 30, step 4 by June 21," etc., moving backward. 

This will give the buyer a sense of urgency about why they need to take certain steps so far in advance and reduce the need to use an end-of-the-month discount as a crutch.   

📖 Further reading: Check out our complete guide to using mutual action plans in the sales process.

8. Multithreading

Multithreading means engaging multiple stakeholders within a target company simultaneously, ensuring that you're not reliant on just one point of contact. 

Put another way, it is all about creating a cohesive, omnipresent strategy that increases your chances of closing deals more efficiently.

For instance, Champify uses Dock as a sales artifact to multithread within an organization. 

“If we realize we’re not talking to the right person and need to thread out to a leader in an adjacent department, Dock gives us a great way to do that,” said Stephen Ruff.

Rather than making another hard ask for a leader’s time, Stephen uses their Dock workspace as a jump-off point for a conversation. “Instead, we say, ‘Hey, check out this Dock. Here's what we've been working on, and how we're thinking about things. Let me know if you think this is interesting.” 

This is far from the only way to incorporate multithreading. Multithreading can also be effective through ads, especially as part of an account-based sales strategy.

For instance, Trinity from UserGems found that involving at least two personas in the buying process increased their win rate by five times. Armed with this knowledge, they adjusted their approach to continue targeting and advertising to the other relevant personas within the same company. 

They used multithreading to target potential blockers, usually the CFO, at the end of the deal. The goal is to use multithreading ads to familiarize them with your brand and what you offer and address any objections before they become issues. 

9. Don’t fear paid pilots 

While it's true that paid pilots can mean double the work and perceived risk for sales reps—potentially affecting their commissions—pilots and proof of concept projects offer significant advantages for prospects that can outweigh these concerns.

For the prospect, a paid pilot reduces the risk of committing to a full-scale implementation without first seeing tangible results. This approach provides a low-risk entry point for your solution.

Even if your company is doing $10 million in Annual Recurring Revenue (ARR), if you are selling to a Fortune 100 corporation, you’ll be viewed as tiny and a potential liability. That’s why offering a paid pilot can be an effective land-and-expand strategy to build trust, get your foot in the door, and demonstrate value. 

Here's why embracing paid pilots can benefit your sales strategy.

• Reduce risk. A paid pilot allows prospects to evaluate your solution's effectiveness without a full commitment, making them more comfortable moving forward.
  
• Demonstrate proof of value. Showing the real-world impact of your solution through a pilot can help overcome objections and build a strong case for a full deployment.
  
• Get a foot in the door. Successfully completing a paid pilot can pave the way for larger deals and long-term relationships with big companies. Once you are with a big company, they tend to stick around for a long time. So, it becomes about landing and expanding.
  
• Solicit feedback. Pilots provide valuable feedback that can be used to refine your offering and address any issues before a full rollout.

10. Get ahead of security reviews and other deal blockers

Security assessments are a critical step in any sales process, but they often become significant roadblocks that delay closing deals. 

When a buyer requests a vendor to complete a security assessment, the sales team normally passes the security questionnaire to another internal team.

This typically results in constant back-and-forth with the security team, asking about the location of security documents, how to answer specific technical questions or worse: the sales team guessing their way through the buyer’s questionnaire. 

This can lead to providing incorrect information, eroding trust with the buyer, and potentially jeopardizing the deal.

This familiar scenario not only slows down the sales cycle but also creates compliance issues for the security teams and can lead to lost revenue. Anticipating this common ask and objection by getting ahead of security reviews is essential.

Dock’s Security Profiles can streamline this process by giving your sales team a readily accessible security profile. This gets ahead of your buyer’s security questions, builds trust proactively, and ultimately speeds up deal cycles while still maintaining compliance. 

How Dock can help you manage long sales cycles

Accelerating your sales velocity hinges on empowering your sales team with excellent content and the right technology. When you combine this with a buyer enablement mindset and a toolkit that simplifies and speeds up your prospects' purchasing process, you'll see significant sales acceleration over time.

Dock is the first tool built specifically for mid-market and enterprise sales teams to demonstrate their value to prospects.

Here’s how Dock can help you manage long sales cycles effectively:

• Manage multiple stakeholders. Dock makes it easy to coordinate and engage multiple stakeholders through mutual action plans.
• Empower champions. Dock provides tools that help your champions within the prospect’s organization make a compelling case to internal stakeholders.
• Provide a personalized experience at scale. Dock allows sales reps to deliver a tailored experience to each prospect, even at scale.
• Forecast enterprise deals. Dock aids in accurately forecasting and managing complex enterprise sales deals.

By leveraging Dock, you can equip your sales team with the tools they need to close deals faster and more efficiently, even in the most challenging enterprise environments.

‍Try Dock for free here.