The Anatomy of an Effective Enterprise Sales Meeting

We asked seven top sales leaders what it takes to open and close a deal. Here’s what we learned.


Brian Kroopf flew home for Thanksgiving in 2018 with good news.

He had just been promoted to Director of Commercial Sales at G2, a Chicago-based technology marketplace. Kroopf ran his first team meeting from his family living room. As he videoconferenced with team members in San Francisco and Chicago, many of whom he was meeting for the first time, his dad walked by in the background. He was shirtless, with his hairy chest visible for everyone to see.

“I just laughed,” Kroopf recalls. “I said, ‘Everybody, meet my father!”

Modern meetings present unique challenges, whether it’s a team meeting or a sales call with a new prospect. In Kroopf’s case, having run literally thousands of meetings in his career as a sales leader, he knew to always expect the unexpected.

“Things are going to come up during meetings,” Kroopf says. “You just have to roll with it.”

While you can’t always predict what will happen in a meeting, there’s plenty you can do to be prepared. The best sales leaders know from experience what it takes to run great meetings, from how to find prospects and book calls to what to do when you’ve got them on the line.

☝️ That’s what this book is all about.

We spoke to sales leaders from companies like G2, Gong, Outreach, and others about what goes into a great sales meeting. First, we’ll dive into what needs to happen before the meeting, including prospecting, research, and outreach. Next, we’ll run through the nuts and bolts of what a successful meeting looks like. And finally – because sales is a long process, almost always with multiple meetings – we’ll show you how to follow up after a call.

One of the key lessons from everyone we spoke with is that the customer comes first. We’ll show you the importance of taking the time to understand your prospect and help them on their buying journey. By building trust and creating a solid relationship, you’ll be able to provide solutions to their pain points and ultimately close the sale.

“A modern sales meeting should feel like you’re chatting with a friend who’s knowledgeable on a subject you need help with,” says Collin Cadmus, VP of Sales at Aircall, a cloud-call center software company based in New York. “Modern salespeople should position themselves as industry experts, educators, advisors, and most importantly, helpers.”

Good meetings are the lifeblood of successful sales teams. Learn what it takes to be a master of meetings, and deliver value for your prospects, your team, and your bottom line.


Getting There: How To Book Sales Meetings

There’s a lot that goes into a successful sales meeting — and it starts long before you’ve got a prospect on the phone. As you’ll learn in this chapter, prospecting, research, and setting a clear strategy and agenda are just as important as shaking hands and getting down to business.

Start Prospecting

The best sales teams assign individuals to research and reach out to prospects who fit a set of criteria. Once known as “cold calling,” it used to be that sales reps would dial thousands of phone numbers a week in hopes of getting just a handful of leads. Later, that strategy was adapted for the email age.

In today’s landscape, neither strategy is effective.

“The era of mass emailing is impersonal and less effective than ever before,” says Al Hogan, Head of Enterprise Sales at Drift. People are just turned off by that. They know somebody’s trying to sell.”

Today’s sales teams need to get creative with how they research prospects. For Drift and other companies, one solution has been LinkedIn. Drift has BDRs responsible for researching “dream accounts,” identifying target buyers within those organizations, and contacting them via LinkedIn. An important part of the process involves understanding the company’s strategic goals and vision, and finding a way to frame how Drift can help them. They craft a personalized message, sometimes with a short video, to compel them to want to learn more.

“LinkedIn is an incredible channel for our team because it’s relevant, it’s short, personal,” Hogan says. “It shows that we took the time to research that person in their company and what they’re trying to do and how our technology can tie to that.”

When possible, it’s also extremely valuable to leverage the relationships members of your management team might already have with their counterparts at a prospect company. Outreach, for instance, strives for what it calls “executive alignment.”

“If any of our executives know a prospect’s executives, we’ll put them in front of each other,” says Scott Barker, Head of Partnerships at Sales Hacker, a subsidiary of Outreach.

And if they don’t have any relationships to leverage with a prospect, they employ another creative tactic: They invite their key executives onto one of Outreach’s two podcasts.

“It’s almost like a Trojan horse,” Barker says. “It plays up their ego a little bit, and everyone loves that exposure. Then naturally at the end of the recording, we can broach the subject of, ‘Hey, what are your sales engagement strategies looking like for the next year?’”

Do Your Research

Once a prospect meets your criteria, it’s important to get a sense of who they are, including the industry they’re in and the challenges they face. This will allow you to speak to them on their level and communicate your message in a way that resonates and feels familiar.

“It’s important to come to the call prepared with context about their business,” says Bryan Tucker, head of mid-market sales at Gong, a San Francisco-based sales-intelligence tool. “If you’re talking about software and you’re selling to someone who’s an industrial manufacturer of chemical tanks, obviously terminology, the way they run their business, it’s going to be different.”

It’s also crucial to have a command of what you want to get out of a meeting. Having a clear goal and strategy for each meeting, whether it’s a 15-minute phone call or two-hour face-to-face conversation, will set your sales team up for success. Setting that strategy ahead of time helps keep each meeting on track and move the prospect along the path to purchase.

“Prior to any meeting I have, I will set the goals I want to get out of the call,” says Jonathan Buhe, Enterprise Account Director at Demandbase, an account-based marketing company. “If you don’t lay out what you want next steps to be, those introductory calls can become a little convoluted and confusing. So you have to make sure you have a clear agenda to keep everything on the rails to drive things forward.”

Use A CRM Tool

Customer Relationship Management (CRM) platforms help sales teams research prospects and track clients. As the data warehouse for a sales team, a CRM stores information like a prospect’s title, company size, where they’re located, and what services they’ve used previously. This helps you construct an image of the prospect and be an advisor rather than simply a sales representative trying to sell something.

“The point of a CRM is to enable yourself to quickly get context about the person you’re about to speak with,” says Hogan. “It’s the central source of truth.”

CRMs also help you assess the health of a deal by integrating with data tools and call recording software that can help get your team up to speed on a prospect by enabling them to listen to and assess previous calls. You can keep track of the roles of the various people you’re in contact with and quickly see how long a prospect has been in the pipeline.

“I don’t know how we could go without a CRM,” says G2’s Kroopf. “I use it in combination with our other intelligence tools and our call recording software to look at the notes the rep has typed into the account record, to listen to the discovery call if I wasn’t on it, to look at the health of a deal, and to analyze closed deals.”

Publish Case Studies

In today’s digitized landscape, your website serves as not only a vital lead generator but proof of your company’s success. Almost all B2B buyers will do some form of online research before agreeing to a meeting. In fact, by the time a buyer arrives on your company’s website, they’re already 80% of the way down the road to making a buying decision. Making information about your success readily available on your website helps buyers cross the finish line to a sale. Publishing case studies and customer-success stories on your website lets you leverage your relationships with past and existing customers, enhancing your credibility with new prospects.

“Name-dropping other customers in the prospect’s industry is especially helpful,” Hogan says. “A lot of times in the beginning part of the process and then again at the end, we will direct prospects to case studies to validate that we are seeing success in their market.”

Demandbase includes about 20 different customer stories on its website that illustrate nearly every possible use case. Sales reps and account executives select appropriate cases to send to prospects, illustrating how similar companies have seen success with their solution.

“I think our customers find case studies really helpful because it shows, how did we build this strategy with our technology?” says Buhe.

Demandbase supplements case studies with videos from it’s annual Account-Based Marketing Innovation Summit. “Our customers tell their stories there,” explains Buhe. “And then we have those videos to rely on. It’s helpful to be able to send that through to a customer because they’re generally pretty recent. They speak to the same kind of pain points, and it allows us to give our customers visibility, not only for their organization but also as a thought leader.”

Save Time On Scheduling

Time spent bogged down in administrative tasks like scheduling calls is time not spent closing deals. But those administrative tasks are still crucial. The best salespeople make scheduling, confirming, and following up on meetings as streamlined and simple as possible, almost always with the help of an automated tool.

“Automation handles the monotonous, less-important tasks, freeing you up to spend time on the deep work and business consulting needed to get a complex enterprise deal done,” Hogan says.

Outreach uses a robust automation process that sends follow-up campaigns, prioritizes emails, and helps schedule meetings.

“For every email that I send, I can actually attach it to an automated campaign, that helps me bump that email back to the top of someone’s inbox until they respond,” says Feiten. “If I don’t have time on the calendar with someone for our next step, I will use automation to help drive that.”

Whether it’s Drift or another tool, find a technology that integrates seamlessly into your calendar so you can easily find and confirm times to meet and send out reminders.

Be Consistent

An otherwise good meeting can go off the rails when inconsistencies emerge. To combat this, Drift uses a “meetings book” to keep a list of questions, background data, and notes from sales reps. Every member of the sales team is able to see the book before they start a meeting, and use it to plan the call accordingly and keep their pitches straight. At Demandbase, the sales team uses email to get everyone in sync on talking points and then holds a quick 15-minute meeting before jumping on a sales call.

“Our job is to be the quarterback of the account,” Buhe says. “I say, ‘Hey guys, here’s this video of the account and here’s what I need your help with.’ And then I put together the agenda for the call or the onsite meeting to bring in those teams.”

Making sure the entire team is on the same page in advance of any sales meeting helps you avoid potential gaps in your team’s story and objectives. It’s easy to imagine that prospects won’t notice gaps like these, but they’re much more discerning than you think.

“If your story is not cohesive and your team is not talking on the same talk track, the customer is going to start to poke holes and see red flags,” Hogan says. “The best meetings happen when you’ve done your research, you own the process, and you’re really driving it and showing that you know what you’re talking about and that you’re there to help.”

Set Clear Objectives

Setting a clear agenda and having solidly defined objectives is a major part of keeping meetings on track. Whether it’s a product demo, a discussion about technical requirements, or an ROI analysis, you should know going into a meeting what you want to get out of it, as well as what the prospect needs to get out of it in order to continue on their buying journey.

The most important aspect of objective-setting, according to Collin Cadmus, is shifting the focus from you and what you’re selling to what your prospect needs help with.

“As a salesperson, the call is not about addressing my objectives, it’s about identifying my prospect’s objectives and helping to address them,” he says. “Forget about your quota, forget about your daily metrics goals, forget about yourself entirely and change your mindset to serving your prospects and helping them solve problems. This mindset results in more sales and happier customers in the long run, and your sales processes will be significantly easier.”

Feiten says she creates agendas for her prospects and customers and outlines them at the beginning of a meeting to confirm what they will be covering.

“Then, we revisit them at the end of the meeting,” she says. “We want to make sure that any action items are assigned to specific people, so everyone knows what they’re meant to do when they walk away.”

On The Call: How To Run Sales Meetings

Once you’ve researched your prospect, set a strategy, and laid out an agenda, you’re ready for the sales meeting. In this chapter we’ll walk through the anatomy of a successful meeting, as well as some considerations that can help you run better meetings.

Start With An Outline

No matter where your prospect is in the sales pipeline, every meeting should start with an outline of objectives you want to accomplish. Setting objectives and a clear agenda helps make the prospect feel heard and respected, and also facilitates a more productive meeting.

Sales teams should discover and confirm their prospect’s objectives upfront. For Aircall, Cadmus says this means starting the call by asking lots of questions to understand why the prospect is taking the call, what their objectives are, and what problems they have that Aircall can potentially solve.

Gong prefers to open with what Tucker calls a “strong, upfront contract,” which outlines exactly what both sides should expect to get out of the meeting.

“This is an agenda explaining the purpose for the call, the goals of the call, and our biggest concerns,” he says. “So, for example, if we go down a technical rabbit hole later on, we can lean on the expectations we set up front and get back on track in a non-confrontational manner.”

The start of any call is about level-setting and creating expectations. For a discovery call, getting to know the customer can take at least 30 minutes, so be upfront that your first goal is to get to know your prospect. The focus of these meetings is to learn more about the prospect and demonstrate your company’s value.

In later calls, the meat of the meeting may include a demo of your service. A loose rule among most sales leaders is that demos are typically tabled during the first call. Ideally, the demo is custom-tailored to the prospect to align your solution to their business needs, along with any challenges you identified earlier in the call or on a previous one.

Whether it’s a discovery meeting or a demo, let your prospect know what they’re in for.

Build Trust

Sales experts agree: a salesperson’s primary task is not to sell but, rather, to help customers along their path to purchase. With this in mind, building trust and listening to a prospect’s needs become extremely important – and it starts at the very beginning of your very first call. Every meeting should start with the idea that you’re going to have a broad, wide-ranging and interactive conversation with your prospect.

“It’s important to paint a broader vision for what you’re discussing to give the other person an opportunity to latch on to something that’s relevant for them, before you get hyper-focused around what you think is relevant,” Tucker says.

In other words, don’t go directly into “sales mode.” More often than not, an aggressive approach will turn off prospective customers. People don’t buy from people they don’t trust.

“The salespeople who struggle and don’t see success are the ones who get on an initial sales meeting and go right into selling mode,” adds Hogan.

Read The Room

Understand the prospect’s locality so you can match their energy and tone. Remember what we said about speaking to prospects on their level. In this case, try and adjust your speed to theirs. A client in Southern California will probably speak differently than one in New York City.

“You’re still going to push them down the path of what our best sales process can look like,” Hogan says. “But talking to two people from different parts of the country or world, you have to be aware of that and match your approach to their culture.”

Reading the room also involves learning about each person in the meeting. The more research you can do on meeting attendees beforehand, the better. If you know you’re going to be speaking to a room full of executives, you’ll want to adapt your approach accordingly.

“Preparation is extremely important,” says Rebecca Feiten, Senior Account Executive at San Francisco-based sales engagement platform Outreach. “Understand who is going to be in the room, learn what you think they care about, and then clarify that early on in the meeting.”

And don’t be afraid of getting something wrong Feiten says – your prospect will appreciate that you tried.

Ask Thoughtful Questions

The best questions are often the simplest: Can you tell me more about X? What does Y mean to you? If Z doesn’t get done in the next quarter, what does that mean for your business?

Questions like these help you begin to understand what a prospect is struggling with, what they want, and how you can help them. They also help to build trust, making the customer feel like a salesperson is invested in their success, and that they’ve done their research.

You can also go deeper.

Rather than simply asking “Walk me through a day in the life of your job,” do enough research before the meeting so you can ask more pointed questions, such as: “I spent 10 minutes before the call on your website doing a bit of research and I found what looks to the ideal customer journey path. Tell me more about what went into building that process.”

In an effort to get prospects to open up early in a meeting, one of Tucker’s favorite questions to ask is: “Unrelated to what we’re talking about today, if I were to sit down with your CEO, what are the top three things that he or she is thinking about next year?” Then, once he gets a better sense of his prospect’s business, later in the sales cycle when he’s trying to determine if a deal will actually close, he likes to ask: “Under what circumstances could we get this deal closed before the end of the month?”

“And then you just shut up,” he says. “And asking it that way, what I found is that people tend to think out loud and throw up kind of all the different steps along the way.”

Asking open-ended – as opposed to yes-or-no – questions is a great way to add value to a meeting. For example, asking “What else do you want to cover today?” at the end of a meeting is more likely to provoke additional thoughts and conversation than, “Is this everything that you wanted to cover?” Giving a prospective customer the opportunity to end a meeting before you’ve achieved your objectives is the easiest way to make sure that you never do.

Build Demand For Your Solution

Sales is less about simply making a deal than it is about showing prospective customers how your product can make their life better. By doing sufficient research and asking the right questions, you can identify the gaps in your prospect’s business that your solution solves.

“Our biggest challenge is helping people identify their own gaps, when they don’t always know what they are,” Feiten says. “A lot of people want to take a meeting about what they would consider cool new technology, but they don’t know how to fit it into their existing process.”

As a salesperson, you should expect to play the role of educator and advisor, building demand for your solution by illustrating a use case based on your prospect’s needs.

Pick Up On Prospect Cues

Feiten says one problem she encounters frequently during sales meetings is the dreaded “distracted meeting attendee.” Though she recognizes that everyone has a lot going on in their lives, she feels it’s her responsibility to keep their attention. Whenever she feels a prospect’s attention slipping away, she tries to engage them in the conversation directly.

“Everyone wants to talk about themselves,” she says. “If I feel like somebody’s not paying attention, I might ask ‘Hey, Joe, does what Rebecca said resonate with you as well? Can you see there being an opportunity to impact that for your team?’ Then I’ll repeat their names when I reference back what they said, and I’ll try to use their same words. I think it makes people feel good when other people use the same language they use. I’ll just reinforce that I’m hearing what they’re saying, and, as such, people are more willing to hear what I’m saying.”

Skepticism is another warning sign worth keeping an eye on. The best plan of attack, Feiten says, is to understand early why a prospect might be skeptical. That could come as early as the pre-meeting research phase, flagging potential concerns the prospect might have about your solution. Once she notices a buyer’s skepticism, Feiten tries to confront it head-on – especially because it can create opportunities to further explain an advantage over the competition.

“A lot of times, people tell you they got burned by similar technology,” she says. “‘It wasn’t well managed,’ or, ‘It wasn’t well run’ – they give you whatever you need to talk your way out of the objection. My first tactic would be to dig in and say, ‘Tell me more about that. Can you share with me your experience in the past that’s led you to feel like this might not be valuable?’”

Hogan adds that salespeople should have the courage to challenge their customers – respectfully, of course – when they sense skepticism about the value of a solution.

“If a customer asks you a question and you know it will not possibly benefit the evaluation process, it’s up to you as their professional consultant to let them know,” he says. “You could say, ‘Hey, really interesting question. I understand why you’re asking that. But based on where you guys are at in the process, if we do that, it might delay things.’”

Win As A Team

Bringing in team members to speak to various aspects of your solution can give prospects a fuller understanding of how it can help them. Your team should identify which part of the sales process is relevant to each team member, and then pull in resources accordingly.

For example, this may include bringing in an engineer to elaborate on the technical aspects of your product, or having an executive speak to add a layer of authority. At Outreach, Feiten assigns an executive sponsor to each account for this purpose.

“We try to align with whoever is most engaged on the project,” she says.

Don’t Hide Pricing

Buyers have many opinions about how and when they want pricing to enter the conversation. Some like to know before meeting with a provider how much the solution is going to cost. Others prefer to get that number during the first meeting. Some are even okay waiting until further down the line, as long as they know they’re in the right ballpark.

Whatever your prospect’s preference, if your company doesn’t show pricing on your website, they have likely done some research or consulted others in their network to at least make an educated guess as to how much your solution will cost them. So while you might not want to give a concrete number too early in the process, the prospect is probably wise to you.

Drift’s Hogan says it’s never advisable to hide your pricing structure from a prospect – especially when they ask directly – and that your pre-meeting research should uncover what their peers may have been willing to spend.

“You never want them to feel as though you’re hiding or trying to fleece them on anything,” he says. “If the customer’s asking for pricing, you should know enough and feel confident in what your value is and what similar types of customers have spent.”

Utilize Video

If the meeting is not in person, you should consider video conferencing. Once a luxury, video has grown into a necessity for any sales team. Now, 87% of sales teams use video on a regular basis, up from just 63% in 2017. Video closes more deals. In fact the latest research shows video  is used 41% more frequently in closed/won deals.

“Video has revolutionized the selling process,” Hogan says. “If we’re on video and seeing each other face to face, we’re developing a personal connection that will build trust over time.”

The one caveat: quality matters. A clear, voice-only call is always better than a patchy video connection, which can make it next to impossible to get your message across.

“If things are breaking up and it’s a bad connection, that’s super challenging,” Tucker says. “From time to time we’ve got spotty internet at our office, so we’ll ditch the video conference and just hop on a cell phone to have a productive conversation that isn’t full of technology troubles.”

Establish Next Steps

Most B2B sales, especially enterprise sales, take a long time. But you must be closing at every step of the process. Leave 10 minutes at the end of every meeting to discuss next steps, answer questions, and ensure that you nail down a firm future commitment with a time on the calendar (and stay on top of time management so you’re ready for that next call).

Tucker likes to end every meeting by putting another call on the schedule and solidifying who will attend. “That way, we’re engaging with you in a consulted manner as opposed to chasing you like an annoying used car salesman,” he says.

Keep Closing: How To Follow Up On Sales Meetings

The end of a sales meeting is an “end” in name only. Any enterprise sale is going to be a lengthy process, which means the conversation needs to keep going in between meetings. Following up is an art that the best salespeople have perfected, and it’s one that’s crucial to a good meeting flow.

Always Follow Up

Every sales meeting demands a detailed follow-up email that recaps everything that was discussed on the call. The follow-up should outline action items and define who is responsible for each one. It should also note any updates to the project plan, if necessary.

“It’s all about the follow-up,” Cadmus says. “When and how depends on the next steps that are decided at the end of each meeting, but a good AE always makes sure a follow-up is expected.”

Respond ASAP

Your prospect may send their own follow-up email that asks detailed questions about things that were discussed but not resolved during the meeting, or they may bring up new issues altogether. Response time is critical. Rather than try to resolve every issue immediately, respond as quickly as possible, even if it’s just to acknowledge their message.

“A prospect might send you an email at 9:00 p.m. on a Thursday night, and it’s a very technical question and you have to talk to your engineering team about it the next day,” Hogan says. “The worst thing you can do is wait until you have the answer, which might take two or three days.”

Hogan suggests responding immediately, as you might in a text message:

“Hey, thanks so much for the question. Really good one. I’m going to meet with my team in the morning and get you feedback as quick as I can.”

Responding quickly will make sure your prospect feels acknowledged and supported.

Disqualify Bad Leads

While it’s important to invest time in qualified prospects, it’s equally important to not waste time on unqualified ones. Tucker suggests acting “independently wealthy” and defensive of your time. In other words, value your time, and don’t be afraid to walk away from a lead that doesn’t feel right or productive. But how do you know when to disqualify a lead?

Every company, even a startup, once they have 10-20 customers, should get a sense of what their Ideal Customer Profile looks like. These characteristics typically include company size and industry. If a prospect doesn’t fit these criteria, they probably won’t buy.

In addition to these criteria, think about the person you’re speaking to, and listen to what they’re saying. If they aren’t a decision-maker or an influencer, or if they say there’s no budget for your solution, or if they don’t have time for you, it’s probably time to walk away.

Final Thoughts

As we’ve learned, a great sales meeting isn’t entirely about sales – at least not on the surface. Your primary aim should be to put the customer first. Do research, ask questions, and tailor your tone and talk to their attitude and needs. Show how your solution provides value by addressing their pain points. Use your team and every tool at your disposal so you can spend more time connecting with prospects. Close every meeting, and make an action plan for the next one.

Ultimately, more meetings mean more closed deals. But your sales team isn’t always available to talk. With Drift Meetings, you can schedule qualified meetings for your reps even when they’re sleeping. Drift Meetings shortens sales cycles, increases your SDR productivity, and improves the “handoff” experience to your buyers.

Ready to get started with Drift Meetings? Chat with our team now.

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We asked seven top sales leaders what it takes to open and close a deal. Here’s what we learned.