Back in the day, selling was about going out there and meeting clients to stay top of mind. Things are a lot different today. Buyers in 2023 have been asking for more flexibility, transparency, and autonomy. 

And sales professionals are adapting their strategies and adjusting the buying process to cater to those new customer needs (which made buyer enablement one of the key trends of the past year).

Yet, sales processes are also getting more complex and require more touchpoints, stakeholders, and handholding than ever. Enterprise selling has its own rules, best practices, and trends.

Let’s take a look at the major trends in complex selling and best practices to make it work in 2024, based on the insights from the top sales voices on LinkedIn. 

What does a complex sales cycle look like in 2024?

Typically, it’s considered that there are 4 stages of a buying cycle: 

• Awareness
• Consideration
• Decision
• Retention and Advocacy

And it can be true for simple, transactional sales processes. In reality, especially in large companies or enterprise businesses, the situation is very different now. A buying/selling cycle can get a lot more complicated with a lot more steps involved, like a few demos, internal discussions, price negotiations, battles with legal and IT teams, delays, follow-ups, etc. 

“If your sales cycle looks like this, it doesn’t make you a bad sales person. Sales is complex. Buying decisions are complex. People are complex. Keep on keeping on.” — Richard Smith

And the bigger the ticket — the longer it takes to close, especially in tech sales with more complex products where deals over $200k in ARR might take over 200 days to sign.

This is something sales teams, especially in enterprise selling, should try to get used to and learn to navigate. 

“In sales momentum is a major factor. As a sales rep you need to be able to get to a "yes" or "no" as quickly as possible. As sales cycles increase, momentum can be lost and a lot of reps leave deals in their pipeline for way longer than needed. Insane amounts of unproductive time gets spent here.” — Florin Tatulea

For a longer, complex sales cycle, it’s crucial to keep the prospect engaged and build trust along the way. You can do this by constantly adding value — sharing resources and acting like a trusted advisor to help potential customers discover more ways to solve their problems.

Dealing with multiple stakeholders in complex sales

Another key trend for complex or enterprise selling is that they don’t just take more time, but involve multiple stakeholders — influencers, evaluators, decision-makers. Armand Farrokh suggests that shouldn’t stop once you book a meeting, but keep building connections across different departments, both vertically and laterally (even if this means prospecting 10+ people on an account). 

The main challenge in talking to multiple people at a single company is that each person will have their own pain points, care about different things, and view your product differently, depending on their role and responsibilities. For example, a CFO will obviously be keen to discuss pricing and ROI, the legal team will care more about the contract terms and compliance, while the end user will focus on product features and how they can actually make their life easier.

Your main task here is to build champions so they can advocate for your solution internally and keep “selling” your product and influence the purchase decision, even when you’re not in the room.

As a result, multithreading becomes more important than ever. When done right, it can help you create cohesion in the buying committee or point out gaps you need to fill.

For example, here’s a multithreading tip for complex sales cycles from Jacob Karp:

“You should be socializing the conversations you’re having with your prospects to other target personas in their org early and often.

Think of it as an information share and a courtesy to them. 

Here’s how it works:

1) conduct initial call or meeting 

2) create summary follow-up email

3) take summary email and pass on to 3-5 additional target personas.”

Yet, as you navigate your way through the buying group, don’t forget to build personal customer relationships with each champion. Brian LaManna shares his approach to building an army of champions.

How to speed up a complex sales process?

While offering a discount to speed up a deal might be a good idea in B2C selling, enterprise sales require a more strategic approach. For example, if a deal is forecasted to close next month after you finalize the paperwork, giving 50% off if they sign this month just to reach your quota will only mean you will need to find that 50% of revenue elsewhere.

So, instead of trying to move the deal forward by dropping the price, be consistent in your communication with the prospect and always book the next steps as soon as possible to keep the momentum going. 

Having a mutual action plan can help streamline communication and ensure that everyone is on the same page, reducing misunderstandings and delays in the most complex sales process. By outlining specific steps, responsibilities, and timelines, the plan creates transparency, builds trust, and facilitates a more efficient sales process as both parties actively work towards a common goal.

Recollecting a 208k deal he closed last year, Troy Munson perfectly sums up the main challenges of complex selling as well as one step to fix a stalled deal:

“It takes a lot of steps. Tons of trust has to be built. Value needs to be delivered consistently. If your deal is stalling, ask what's preventing them from moving forward.”

There are many things that can impact your deal and define its outcomes. But it all starts with proper discovery. 

Here’s what you should be doing during the discovery to shorten your sales cycle, according to Matthew Codd:

• Make sure your solution can deliver genuine value to your customers (and set realistic expectations about what you can do for them).
• Be clear on the sign-off process and ROI of your product.
• Draw on previous sales processes to coordinate the sign-off process.
• Train your champion to communicate with key stakeholders internally, when you’re not there.
• Simplify contracts and pricing to make it easy for everyone involved in the process to understand.
• Identify the economic decision-maker early on.

Sometimes, offering personal guidance or a more tailored, personalized buyer experience might be a good idea. This can be a hands-on demo or a proof of concept project — anything that will help you get everyone on the same page and show clear ROI to the buyer.

For example, Patrick Trümpi shares the game-changer tactic their company implemented after going 100% enterprise — “the value workshop.”

After all, it's the buyer experience in general that will define the outcomes of the deal. As Megan Bowen put it:

“The buyer experience can be the difference between winning or losing deals. B2B buyers today want relevance, simplicity, information and control. Designing the right experience should be given the same focus as designing the actual product / service you are offering.”

Complex B2B sales trends for 2024

With all the challenges and struggles sales teams faced in 2023, there’s an opinion that B2B sales is dead. And it’s true to some extent — the old, traditional sales is dead. It now takes more time, more relationship building, more multi-threading, more value to be delivered to multiple decision-makers. And it takes even more effort when getting started from scratch.

David Blinov perfectly outlines what it’s like to work in enterprise sales:

• Slow processes
• Budget approvals 
• Thousands of touchpoints
• Long sales cycles (6+ months avg)
• F2F sales still plays an important role
• Procurement and legal
• Large buying committees with influencers and budget holders
• Most of your audience is not ready to buy. Not now, and maybe not in a year.

And salespeople should embrace this new reality and adjust their strategies to cater to the modern buyer considering all the intricacies of B2B sales. 

Yet, regardless of your overall process, tactics, or tools, the basics remain the same:

1. Understand your ICP, including each one of the multiple decision-makers.
2. Determine specific qualification criteria (e.g., based on your existing customer data).
3. Adopt a bottom-up approach when prospecting new customers.
4. Multi-thread to build champions internally.

In other words, mastering enterprise sales requires a down-to-earth approach. It's not about mastering complicated techniques but having meaningful conversations and building business cases that simply make sense. So don’t just follow protocols, be ready to adapt to the twists and turns of the sales trends.