The AE Playbook for Driving Deals from Demo to Close

You wouldn’t buy a car without taking it for a test drive. You need to feel how it handles. How’s the acceleration when you pull onto the highway? What’s the stereo sound like? Is the air-con an arctic blast or a feeble cough? 

Just as consumers want to see a product in action, so do B2B buyers. 

That’s why we have sales demos.

They’re an opportunity to build confidence, assuage doubts, and pique interest. But they’re not always a home run. Much like a chainsaw, sales demos can be a useful tool in the right hands and disastrous in the wrong ones. 

So how do you stay on the right side of demo delivery, keep your stakeholders hooked, and entice buyers to take your next meeting? 

Let’s find out.

Qualification-led demo framework

Sales demos are not informal walkthroughs of a product. The best demos are tightly orchestrated and carefully crafted. They’re unique to each buyer, pulling on their pain points and solving their challenges.

One of the best frameworks we’ve come across is Gong’s five-act demo structure:

Here’s how it works.

Act I: The contextual overview

Start by recapping and reinforcing your prospect’s business problems, narratives, and insights.

This opening has three advantages.

1. You’re placing the status quo at the front of your buyer’s mind. If your prospect is struggling with hiring, remind them of the hours they spend on LinkedIn, trawling for potential applicants. If their pipeline is empty, highlight their looming end of quarter. Make them feel the pain of the status quo.

2. You’re spelling out the stakes and opportunities. Sticking with the status quo means inefficiencies, frustrations, and losses. Moving forward means productivity, revenue, and efficiency gains.

3. It resonates. You’re proving you understand their position. With that understanding, your rapport, relationship, and trust are all growing.

With the foundation set, it’s time to jump into the demo proper.

Act 2: The upside-down demo 

Most demos build to a crescendo. They tease out some minor functionality and showcase peripheral use cases. Then, when everyone is bored, they dive into the juicy stuff. 

This is the wrong way to do things, especially for remote demos. You have to grab your prospect’s attention from the first minute. 

Rep: During our first call you told me you were struggling with [Problem #1]. Is that right?

Prospect: Yes, that's right.

Rep: Got it! Let me show you how our solution can help.

By flipping the demo, leading with your most impactful use cases, and cutting the rest, your demo can be short. Like, really short. 

“If you have done your job correctly, your demo can be 30 seconds,” says Cameron McCormick, Sales Manager at Clearbit. “And it can be as effective as a 30-minute demo.” 

McCormick recommends sellers double down on the potential future state. Don’t show features and functionality. Instead, show what your product could achieve for your prospect’s business. 

Don’t bother with the stuff that might interest them. Deliver a crystal clear end state of the outcomes that do.

Act 3: Social proof 

You’re not going to like hearing this, but prospects aren’t impressed by your logo slide. Sure, it’s nice to know you’ve worked with Walmart, Amazon, and Apple, but name-dropping can potentially alienate your prospects and harm your close rate. 

According to Gong, sellers who misuse social proof tactics have a 22% lower close rate. When deployed in early meetings, the effect is even worse. Dropping names in your first meeting with a new, qualified buyer reduces your close rates by an eye-watering 47%. 

Instead, you’ve got to make prospects feel a kinship with your existing customers. They’ve got to feel like they’re part of the same demographic or market. In Gong’s demo framework, you do that with short before-and-after stories. 

"Katalon (customer) needed to streamline meeting scheduling and accelerate their sales cycle (objective). They empowered their prospects to schedule calls instantly with Calendly (solution), allowing them to reduce their response time by 24-28 hours (benefit). Currently, Calendly-sourced leads are two-to-three times more likely to convert (benefit) and no-shows have fallen by half (benefit)."

Your goal isn’t to blow buyers away with big brand names. It’s to align their starting positions and provide yet more examples of potential outcomes. 

Act 4: Solve exactly 

The penultimate act comes back to McCormick’s earlier advice: be brief, be personalized, be impactful. More is not always better. Instead of focusing on a disparate group of use cases, select the one or two that mean most to your prospect and make them the centerpiece of your call. 

When you’re not racing through a dozen different applications of your product, you’ll suddenly have time and space to breathe. Instead of talking at your prospect, you can solicit questions and turn the demo into a conversation. 

Ask simple, open-ended questions: 

“I’ll pause here if you have any questions. What are you thinking so far?” Or prompt them to respond to specific features or use cases: 

“How do you see your team using this product? Why do you need this solution now?” 

And don’t forget to bring them back to outcomes and results: 

“How would this solution help you overcome [current problem]? How much money would your company save by implementing our product?” 

Don’t be afraid to ask follow-ups. If someone tells you about a hard deadline, dig down until you discover why. 

“You need to implement a solution by the end of the quarter? Why is that? Is it a budget consideration?” 

Likewise, if someone is drifting away and says they probably don’t need your services, find out why. 

“Your team doesn’t need this product now? Huh, why do you think that?”

When prospects give you a positive response, that demands a follow-up too. Say a prospect starts talking about potential savings. 

“You could save $500,000 a year with our product? Amazing! Where would you invest that cash?” 

Follow-ups turn generic demos into highly personalized experiences. That’s what earns trust and drives deals forward.

Act 5: Next steps 

The best AEs keep their deals moving. 

Want to know how they do it? 

Booking next steps. 

When you’ve wrapped your demo, don’t just hang up. Suggest the next step — sending a proposal, setting up an executive alignment session, technical discovery meeting, whatever. 

If your next step is another meeting, share your Calendly link and ask your buyer to book a slot that suits them. How you present your Calendly link matters. Work on a few phrases to soften up the ask and make it clear that it’s for your buyer’s benefit. 

“I’ll drop my calendar in the chat for your convenience.” 

“If you have a calendar link, please send it my way. If not, here’s mine for your convenience.” 

“I know you’re busy. To avoid a lot of scheduling back and forth, I’ll post my Calendly link in the chat.”

Finally, stay on the line until you see a calendar confirmation arrive. 

When your prospect gets back to their day-to-day work, it’s easy to forget something as simple as booking a follow-up. If you have their undivided attention, capitalize on it. Hold out, secure your next step, and keep your deal momentum high. 

Product-led demo strategy 

With the rise of self-service, self-directed buyers, and product-led growth strategies, buyer expectations of product demos are changing. They no longer expect a simple walkthrough from their sales rep. They want access. They want to experiment. They want proof of concept. 

While some sellers disregard these sorts of trials as a distraction, others are embracing them as a new sales tactic. 

Ranjay Matharu is one of those people. 

As a founding partner at Rattle, he’s been instrumental in designing the startup’s sales strategy. From the company’s early days, he included demos and trials in his sales motion. Specifically, he offers prospects a 45-minute demo followed by a week-long unlimited trial of Rattle’s product, a Slack integration for Salesforce. He says the trial allows prospects to enjoy benefits and value that just aren’t possible in the demo’s instances. But the trial plays a far more important role than just letting people loose on the product.

During the week, Matharu closely monitors product usage and highlights opportunities and risks based on product engagement and utilization.

High usage: Users engaging above the baseline are classed as heavy users. They make great stakeholder champions. High usage among executives and economic buyers suggests buy-in at the top.

Low usage: Stakeholders with below-average activity are highlighted as a risk. Triage the problem: Do they understand the value proposition? Were they onboarded correctly? Are they using a competing product? Depending on the issue, rectify the problem immediately. Offer coaching in the product, if you can. Set up additional training sessions. Assign them a buddy.

Extended demos and trials aren’t just helpful for strengthening existing relationships, though. As usage spreads throughout an account, sellers like Matharu watch for new names appearing. Each new user is an opportunity to add another thread to the deal.

"We look at who’s trailing and testing the product. Those people become contacts. We set up shared Slack channels with them. We’ll ping them and offer help and support."

Admittedly, this strategy isn’t universally applicable. Products with long or disruptive implementation phases are likely unsuitable. Another no-go are companies with copyable IP, such as data providers, where trials amount to permanently giving your product away for free.

Premature Presentation Syndrome 

“If you’re just aimlessly walking through features of your product and hoping that they resonate, you’re done.”

That’s Cameron McCormick again. If he has one pet peeve with sales demos, it’s reps launching into walkthroughs without any prior qualification. He calls it Premature Presentation Syndrome. It comes from a place of insecurity or inexperience.

New AEs often feel uncomfortable in less structured conversations. They don’t know how to dig down into a buyer’s underlying pain points or explore strategic consequences. So they jump to what they do know: their product.

"If you’re jumping into a demo after asking three questions, you’ve reduced your chances of winning this deal by at least half. If you’re still gonna win that deal, you’ve extended your sales cycle and probably lowered your sale price."

So when should AEs segue into a demo or push for a dedicated demo meeting? That’s simple: When you know why a prospect agreed to meet.

That insight always comes from good discovery. Identifying the foundational challenge or need is present in every common qualification framework. Take a look at these four leading qualification frameworks:

Budget, Authority, Need, Timeline

Challenges, Authority, Money, Prioritization

Funds, Authority, Interest, Need, Timing

Metrics, Economic Buyer, Decision Criteria, Decision Process, Identify Pain, Champion

“If you do the right kind of discovery, you can uncover the reason that a prospect agreed to meet with you,” says McCormick. “It’s usually very specific and tied to a high-level of business priority.”

He recalls a recent deal for Clearbit Advertising. His buyer had just raised a Series C round of funding and their board set an aggressive revenue target. They had backed into an MQL quota to hit that target and it was 250% of what they achieved last quarter.

That’s why they were meeting with McCormick’s team.

They wanted to learn how Clearbit Advertising could help increase their MQL generation by 250%.

Only when he knew that could McCormick advance to a demo.

Turn features into narratives

People don’t buy features. They buy outcomes.

Think about a sales engagement platform. It probably has lots of features like campaign automation, deal forecasting, performance analytics, and so on. A mediocre sales demo will walk through each feature, explaining how it works. But no one is buying an expensive hiring tool because of its feature list.

What if you turn those features into outcomes?

• Campaign automation: Automate repetitive and low-value work, freeing your reps to focus on high-impact touches.

• Deal forecasting: Crunch pipeline, communication, and market data for pinpoint accurate forecasting.

• Performance analytics: Uncover hidden friction points in your sales process and highlight successful experiments.

That’s a lot better. Suddenly, every feature means something — a stronger customer experience, frictionless working environment, or more productive workforce. But we can do even better than abstract benefits

“What makes a good demo is engagement. You make demos engaging through storytelling.”

Instead of trudging from one feature to another, Adair has a battery of go-to stories (both customer stories and fictional examples) to engage her buyer. She sets the scene, explains the pain point, and demonstrates how Ironclad can solve the challenge. 

To avoid sounding too formulaic, sales reps can borrow from a wide library of copywriting formulas. 

Here’s an example of one of the simplest (Problem, Agitate, Solve) used for a recruiting platform:

“Look, the market is brutal right now. Most sales leaders I talk to are struggling to hit their numbers these days.”

“There was this one manufacturing company I worked with that built its business on field sales. Every year, they were hitting hundreds of roadshows, exhibitions, and conventions. Well, the pandemic put an end to that. Overnight, they had to pivot their long-term field reps to inside sales. I’ll be honest with you, it was complete chaos.”

“We got them set up on our sales engagement platform and our solution engineers helped turn their field strategy into an inside sales playbook. A lot of it worked, but some didn’t. Because we were tracking not just reply rates, but the sentiment of those replies, we could cut underperforming tactics and campaigns, leaving just the good stuff.

Within six months, we’d gotten their pipeline back to pre-pandemic levels. I checked in yesterday and they’ve smashed their Q4 quota with three weeks to go — and that’s on top of all the travel and event savings!”

There are dozens of different storytelling formulas. Test them out, add variation to your demo scripts, and see which ones land best.

Sales blogs almost always focus on the early stages of the sales cycle: prospecting, discovery, and demo.

But what comes next is equally important: negotiation.

It’s the difference between signing a long-term contract for list price and closing a one-year deal with a hefty discount.

It’s the difference between healthy margins and unprofitable deals.

The best account executives treat negotiation as a distinct stage in the sales process. They call on different skills and deploy unique strategies. They slip out of a sales mentality and into a negotiator’s mindset.

“Shifting into a negotiator mindset is thinking you already have a deal,” explained Kwame Christian, founder and managing director of the American Negotiation Institute, in an article for Forbes. “It’s just a question of what product and in what terms.”

Competent negotiators rebalance the power dynamic between buyer and seller so neither is on top. While negotiation skills take a lifetime to master, there are some simple tactics you can implement today to drive deals toward the finish line.

A proven process for negotiations

Two-thirds of your net income.

That’s how much cash you’re putting at risk by not having a formal negotiation process, according to a two-year study from Huthwaite International. But it isn’t just about limiting losses. Huthwaite’s study suggests even mediocre negotiation strategies can improve financial performance.

But what does a negotiation process actually look like?

Steve Bookbinder, long-term sales executive turned sales coach, suggests organizations tackle negotiations across five steps:

Take all the information gathered through your sales process and systematically apply it to your negotiation. Refer back to your qualification framework and ensure you have all the information you need and it’s all up-to-date. Bookbinder also suggests some additional non-qualification-specific questions: What are your objectives for the negotiation? And what is your BATNA (Best Alternative to a Negotiated Agreement)?

Just as unstructured meetings ramble and roam, so too do negotiations. Set your ground rules early and communicate them to all parties. Where will the meeting take place? How much time are you allowing? What’s the agenda? Are there any off-limit issues? What contingencies are in place if no agreement is made?

This is the meat of the conversation. The sales rep presents their business case along with the price (more on this later) and the buyer presents any issues, objections, or requests. Give ample time for all parties to give their two cents and for everyone to ask questions.

If you experience objections or resistance, don’t try and steamroll them. Dig deeper and unearth what’s really going on. Bookbinder recommends phrases like:

• “Can you help me understand…”

• “Talk to me about…”

• “Walk me through…”

In the third step, you should have surfaced any disagreements or tensions. In sales, this tends to be around topics like price, contract length, seats, competitors, and so on. The fourth stage is all about defusing those concerns and pushing the deal closer to the finish line.

There are two strategies to call on here: bargaining and problem-solving.

We’ll touch on effective bargaining a little later, but the short version is this: Don’t discount unless asked, and don’t discount without a trade.

Problem-solving is an alternative (and often preferable) option. It involves finding a mutually beneficial solution that satisfies everyone.

Agreements, handshakes, and high-fives signal the end of a negotiation — but not necessarily the end of the deal. Agree on your next steps and assign responsibility for who is doing what. There’s a lot of nuance to post-negotiation work so we’ll explore this more in the final chapter of this book.

Bookbinder’s five-step process is a great starting point. It’ll catapult you out of the poor performer category straight into the middle of the pack. But climbing into the upper echelons of negotiators requires skill and craft, alongside process.

Let’s look at three skills that separate good from great negotiators. 

Build to your price and wrap in benefits

“Hey James, thanks for joining the call today. We’ve crunched the numbers and we can offer you a deal at $12,500 per year.”

Stop.

A big price tag with no context is quite possibly the worst way to open a negotiation. It skips everything that’s come before it: prospecting, discovery, demo, and business case. It presents a price tag without any mention of the buyer’s pain points or the potential upside.

Effective negotiators frame the price in a narrative, wrap it in benefits, and reveal it carefully. At Ironclad, Brooke Adair asks her reps to recap their entire conversation with buyers:

“Hey, we’ve been working with you for nine months. I understand you’re losing tens of thousands of dollars on contracting inefficiencies every year. With Ironclad, we can reduce your contracting process from days to hours, reclaiming employee time and productivity. Now, here’s what we can do on price.”

In a couple of minutes, Adair’s rep has reminded their buyer why they’re here. The status quo is broken and it’s costing them money. Ironclad can solve their pain points. Here’s the potential outcome and saving, and this is what it costs.

“If you frame it up in the context of impact, the price should feel silly and insignificant,” says Adair. “Always pull back to value.”

Put your price up and stop talking

Silence is not your enemy. When you present your price and hear nothing, don’t immediately jump to defense and justification. Instead, put your price up and shut up.

"In a negotiation, you should be talking significantly less. Put the price up, stop talking, and get them to talk.”

It’s uncomfortable, especially the first few times. But think about it: what else can you add? You’ve recapped context, repeated pain points, and highlighted your buyer’s potential outcome. You’ve given them your best shot. Anything you add now will weaken your position.

Never discount without a trade

“If you get zero objections after you tell them the price, your price is too low.”

That’s Will Fraser, founder and CEO of loyalty marketing platform SaaSquatch. A couple of years ago, he revealed how he increased his pricing by 100% without losing a single lead. The gist is this: buyers should push back on price. A healthy objection isn’t necessarily a bad thing. (Although if every buyer is running away, that’s a good sign you’ve gone too far.)

What’s important is how you respond to discount requests or feature upgrades. Here, there’s one thing everyone agrees on: Never hand out freebies.

When a buyer requests something, Ranjay Matharu recommends highlighting it as a material change: “Hey, look, that’s going to change things.” It lets them know the contract details are important to you and stops them from treating things like seat count, contract length, and price as abstract numbers.

But Matharu doesn’t recommend stonewalling buyers. Instead, sellers should “give to get.” If a buyer wants to reduce their seat count for a product, what could change in the seller’s favor? Possible offers include:

• Earlier signature date

• Longer contract lengths

• Case study participation

Matharu even requests introductions to untapped accounts in exchange for contract tweaks. “Introductions are really helpful,” he explains. “I’ll look on LinkedIn and see who they know that I want to sell to. I’ve asked for introductions to people, teams, and executives.”

Have a hierarchy of trades before you go into a negotiation and always prioritize what’s most important to you.

Pick your medium carefully

During an interview with Dropbox, workplace communication expert Kim Scott described a “hierarchy of [communication] mediums." Face-to-face conversations are best, she said. Although she was talking about feedback, her advice holds true for negotiation, too.

Sitting across a table from someone, you can see the other person and read their body language. Are they open and honest? Are they cagey and closed? “Around 80 to 90 percent of communication is nonverbal,” explains Scott. Talking with someone in-person gives you the best chance of seeing, hearing, and feeling that non-verbal subtext.

But in-person conversations aren’t always possible or practical.

A video call is the next best thing. You lose some of the nuance of in-person but you retain most of it. You can see facial expressions and some of your buyer’s body language. In today’s world of remote and hybrid work, video calls are usually your best bet.

When video isn’t possible, phone calls are okay. While you can’t see your buyer roll their eyes or lean forward in anticipation, you can pick up a lot of nuance through their voice. You can hear their tone and gauge their attention, interest, and concentration.

At the bottom of the communication hierarchy are text-based mediums. Email, instant messaging, SMS — they all cross the line between acceptable and ineffective. There’s no body language to read or vocal tone to interpret. Text is vague and impersonal. It lacks emotion and nuance. In short, they’re not the right choice for negotiations.

When someone tries to negotiate via email or instant message, shut it down quickly. Send over your Calendly link and have them book time for an in-person, video, or phone conversation. As before, pitch your Calendly (and your push back) carefully:

“I want to be sure I understand where you’re coming from. Let’s set up some time to talk. Here’s my Calendly link for your convenience.”

“That’s a good question and I want to give you a great answer. Let’s jump on a call so I don’t miss anything. To avoid email ping-pong, here’s my Calendly link.”

“It sounds like we have a lot to talk about! How about we book a call? Here’s my Calendly link so you can grab a time that suits your schedule.”

When you get them to commit to in-person, video, or phone, it’s a huge boon to your negotiation. People make ridiculous asks and outlandish claims via email. When they’re looking at you face-to-face or holding a phone to their ear? Not so much. So remember Kim Scott’s communication hierarchy and climb as high as you can.