Friction kills sales. Email ping-pong slows your deal velocity. Missing Zoom links hurt your credibility. Piecemeal Salesforce records create confusing handoffs. Simple errors undermine the buying experience, frustrate your prospects, and ultimately cost you revenue.
This isn’t meant to put sales reps on blast.
The modern B2B buying journey is more complex than ever. Gartner has described the process as non-linear, with prospects jumping forward and backward, revisiting each sales stage at least once. They’re acting autonomously, too.
When considering a purchase, buyers spend just 17% of their time with potential vendors.
That’s all vendors, not just you.
Reps no longer deal with single buyers, either. The average buying committee contains six to 10 decision-makers, each armed with their own research. Every major player on the sales team needs to plan, schedule, and execute a lot of multi-person meetings. These meetings are the keystones in deals. If you streamline your meeting process and create a delightful buying experience, you’re more likely to close deals and increase revenue.
Finding the perfect time to schedule meetings with so many stakeholders involved can be a headache for even the most seasoned salespeople. Delays and no-shows can slow down—or even extinguish—entire deals. But it’s worth the effort: according to McKinsey, companies that deliver better customer experiences increase revenue, profits, and shareholder returns.
+%
Sales revenue
+%
Profitability
+%
Shareholder return
Thankfully, this nut has gotten easier to crack. In this guide, Calendly’s sales experts lay out what we’ve learned about how to get time on your side and simplify multi-person meetings. We’ll outline how SDRs can facilitate a smooth handoff to AEs, how AEs can satisfy the many (many!) needs and schedules that must be orchestrated to sign the deal, and how CSMs can use ongoing check-ins with customers to preemptively scope out and solve issues that stand in the way of expansion or renewal opportunities.
We hope you’ll come away from this guide feeling like you have the tools to make multi-person meetings easier than ever, so you can focus on closing more deals.
Make demos more effective
While it’s true that sales meetings tend to get more complex the further you move down the funnel, complexity is not reserved for AEs alone. Without the right controls in place, things can get sticky in the demo stage, too.
BDRs and SDRs have the tricky job of qualifying leads and giving their all in demo presentations. When this process is done poorly, it can lead to wasted time with no-shows or mismatched fits for the product. And it’s done poorly far too often; the demo stage is one of the most overlooked areas for optimization within the sales cycle.
"I was an absolute expert at the product I was pitching — I was presenting Monetate’s products day in and day out to some of the biggest brands in the country — but people still didn’t seem to really get it. It became abundantly clear that knowing your product doesn’t make a demo successful."
When you dig into what makes a successful demo, you discover that a winning process starts long before the demo itself.
Qualify leads before the demo
Sales leaders consistently report lead quality as a top challenge. Considering that marketers, SDRs, and BDRs are often evaluated on lead and meeting quantities, that’s not surprising. They prioritize volume because, to them, that’s what success looks like. The knock-on effect is that up to 50% of prospects turn out to be a poor fit.
“This doesn’t mean that they’re qualified prospects who end up disappearing on you,” says Marc Wayshak, founder of Sales Insight Lab. “Rather, it means that the majority of your prospects will never be qualified to buy from you—they’re just bad fits from the start.”
Qualifying and rejecting poor-fit prospects early is essential.
If you let them into your sales process, they eat up resources and decrease the time your sales reps have for high-quality prospects.
Implement automation at sign-up to qualify leads and keep SDRs and BDRs focused on opportunities that are a better fit for the business.
By building routing into your sales process, you can show demo scheduling pages only to leads who meet your qualifications, like prospects from specific industries or companies of a certain size. For example, Calendly Routing lets you qualify leads through your existing HubSpot, Marketo, or Pardot forms, or build new forms in Calendly.
This step helps pair prospects with the right rep and weed out anyone who isn’t an ideal customer. Take Givebutter, for example: By adding Calendly Routing to their HubSpot forms, Givebutter saw 70% of qualified leads booking demos directly from their website.
Schedule demos automatically
Time is the enemy of all deals.
x
Vendors who reply to prospect inquiries within an hour are seven times more likely to qualify the lead
%
of buyers choose the vendor who responds first
Don’t let a lengthy demo scheduling process derail deals in their early stages. Automated lead routing and distribution ensure that high-value leads can instantly book demos from your website.
Once a qualified lead fills out your website form, instantly route them to the right booking page based on their responses. From there, scheduling or CRM software with round-robin lead distribution can automatically assign new meetings to team members. With Calendly, for example, you can choose equal distribution, assign to the first available rep, or prioritize specific team members.
Round-robin distribution lets BDRs and SDRs respond to meeting requests faster and save time manually assigning leads.
What do automated lead qualification, routing, and distribution look like in action?
You might have separate demo booking pages for your enterprise sales team and mid-market reps. A lead marks their company size as 1,000+, so your scheduling automation software routes them to your enterprise sales team page. They book with the next available SDR based on your round robin distribution logic.
Getting the right leads into the pipeline and simplifying demo scheduling won’t just streamline your BDRs’ and SDRs’ day-to-day tasks. It also gives your reps more time to usher quality leads through to your AEs, setting them up for a successful sales cycle.
How High-Performing Teams Achieve Even More with Scheduling Automation
Learn more about how scheduling automation can help your team save time and hit your goals.
Learn more about how scheduling automation can help your team save time and hit your goals.
Streamline the BDR/SDR & AE handoff
The BDR/SDR to AE handoff is incredibly important. Once a prospect is in the AE’s hands, the deal enters the sales pipeline and has a real chance of contributing to revenue.
From the customer’s perspective, however, being passed from one rep to another can feel jarring. They’ve already spent hours of their precious time telling a BDR or SDR about their pain points and what they need. If the handoff isn’t well-orchestrated, this step can feel like starting over.
Making the handoff as smooth as possible
Great handoffs feel frictionless. They’re like an extension of an ongoing conversation, rather than the beginning of a new one.
“No prospect wants to feel like they’re being shuffled off to a different sales rep. Think about when your cable or phone provider transfers you to yet another department, only for you to be asked the same questions over again. This is the type of frustration you want to avoid during the SDR to AE handoff.”
Collin recommends SDRs be transparent about upcoming handoffs. Don’t introduce AEs unexpectedly, as this will cause confusion. Instead, use a simple statement early in the process to set expectations of a future handoff:
"As I learn more about your goals and needs, at some point I’ll be bringing in an expert who will be able to better address your situation and the ways we can work together."
Brief AEs before the handover meeting. Collin suggests running a separate meeting between SDR and AE to talk through the prospect’s pain points, challenges, and goals.
During the handoff call, the SDR should:
Introduce everyone
Recap pain points
Share the highlights of earlier conversations
Share the agenda for the meeting
At this point, the AE takes over and drives the conversation.
Making sure everyone is available
It's essential that the right people are present for the handoff to go well. This is a great time to leverage a feature like Collective scheduling to find the best time that works for the customer, SDR, and AE.
Sales teams can also keep things moving (and keep the customer engaged and accountable) with Workflows, which allow you to send out emails in an optimized cadence that primes the customer for the handoff talking points.
Workflows are a secret weapon for reducing customer no-shows and cancelations, which are more common in the early days of the sale. In fact, 88% of our sales customers reported a decrease in meeting no-shows by using automated reminders.
Stay in touch with an active, up-to-date plan that sets clear expectations and responsibilities. By asking the prospect to confirm their attendance, you increase their sense of urgency and encourage them to uphold their end of the relationship.
Deliver on the technical discovery meeting
The technical discovery call is another turning point in the sales cycle. It’s an opportunity for your solutions engineer (SE) to show off their technical expertise and walk the customer through a number of proposed solutions.
During the technical discovery call, it’s important to have both the AE and SE present. For customers, the AE is the thread that weaves the entire experience together. The AE is the main point of contact between meetings, and an anchor for the customer any time a new point of contact enters the funnel.
In the technical discovery meeting, the AE’s job is to provide context and color to — and sometimes translation for — what the SE is proposing, keeping the focus on customer pain points and goals. Importantly, AEs need to recognize their limitations. When a conversation veers into technical territory, they need to step back and allow their SE to take over.
"If the use case is more in the weeds and I need more technical support, I’ll include an SE to help with additional discovery. That way, they can ask all the questions they need to help prepare for the demo.”
The AE is also there to keep the solution rooted in the customer experience, so the SE knows exactly which problems they’re trying to solve and why.
The technical discovery call is an opportunity for alignment. Whereas the BDR/SDR and AE handoff is the event that makes a deal “real” for the seller, the technical discovery is often what makes the solution feel real to the customer.
Get SEs scheduled and up to speed
You can’t hold a technical discovery call without an SE, so getting one booked into a meeting quickly is priority No. 1. Using an automated meeting distribution feature like Calendly's Round Robin scheduling can help you find an available SE who can step in at the right time.
Prior to the discovery meeting, it’s critical for the AE to bring the SE up to speed on any need-to-knows. This doesn’t have to be done with a meeting; in the interest of keeping things moving at a quick pace, AEs can use the meeting invite as an opportunity to recap the discussions that have taken place so far, and prime everyone for what will be discussed in the upcoming meeting.
This is how you get that technical win. Your SE provides a technical play-by-play, and your salesperson translates it into problem-solving.
You’ll know you set up a technical discovery well if everyone leaves the meeting with a clear understanding of what was discussed, including next steps that cover both strategy and technical implementation. Keeping all stakeholders in the loop early and often is the key to making that happen.
Perfect the proposal
Once the technical details are worked out, it’s time to come back to the customer with a formal proposal. This stage is high-stakes: if the pitch isn’t in line with what the customer expects, they could shoot down the deal and erase weeks of hard work.
This is also typically the point at which more variables are added to the mix. It happens on both sides of the deal: stakeholders with the power to approve or reject deals join on the customer side, and from the seller side, a sales manager may join the conversation to field higher-level questions and help formalize the pitch.
In general, adding new players to the conversation means there are more opportunities for things to get derailed. New questions or objections from the customer may come to light, as well as considerations that may not have surfaced before.
Eliminate uncertainty pre-proposal
To keep things from falling apart at the proposal stage, do everything you can to keep communication focused and goal-oriented leading up to the meeting.
This starts after the technical discovery call. Once the AE and SE have a chance to reconnect after that call, the AE can send a thank you email to the meeting attendees, recapping what was discussed and which solutions were proposed, and asking the customer to send along any outstanding questions or concerns.
Once a proposal meeting is booked, you can leverage the list of attendees to aid with any prep work. Since there will likely be a number of newcomers in this meeting, AEs can use the attendee list to try to anticipate any questions or concerns that may be raised by new stakeholders during the pitch.
“You want to see who’s in the room and why they’re there. If your customer has added an IT manager, shift the agenda to make it more IT-focused. You don’t win deals by giving the same spiel over and over.”
Even if the customer still has unanswered questions leading into the proposal meeting, make the customer feel at ease by preemptively reiterating concerns and offering assurance that questions will be answered soon.
Make sure every decision maker can attend
The last thing an AE wants is to execute a pitch, only to have the proposal killed after the meeting by some unseen force on the customer side. Use Collective scheduling to find a time that works for all stakeholders.
AEs can then use meeting reminders to get confirmation that attendees will be present. If someone with approval power has a conflict, the meeting can be rescheduled to another time that suits everyone’s schedule.
Polish up procurement meetings
After a prospect accepts your proposal, it’s time to hammer out the finer details with a procurement meeting.
Like all other meetings in the sales cycle, it’s essential the AE is present for this one. In this scenario, the AE is there to balance the customer and seller needs, which are often at odds at this stage. It’s a delicate dance: it’s important for the AE to hear out any negotiations the procurement team puts on the table, and just as important to steer the conversation toward a solution that will help the customer achieve their goals.
“Procurement’s job is to try to negotiate discounts. You need people who have been a part of the whole process. The AE has a vested interest in getting the deal done and keeping price integrity.”
Procurement meetings can also be among the hardest to schedule. The customer often brings in external parties like lawyers, and if a critical stakeholder isn’t available, the deal can come to an abrupt halt until their schedule clears up.
Keep the focus forward-looking
The last place you want to deal with back-and-forth is at the procurement stage. Rather than painstakingly trying to find a time that works for the many parties involved, the AE can use Collective Scheduling to send out a link allowing the customer to select a time that works for everyone.
Emails to attendees before the meeting also go a long way. AEs can use this channel to distribute an agenda, outline important details, and get confirmation that every party will attend.
The procurement stage is, in many ways, the final push for the AE to close the deal. The more unknowns that can be eliminated early on, the better.
Plant a good seed with CSM
For AEs, getting a deal signed is cause for celebration. For the customer, things are just beginning. Now it’s up to the AE to execute a smooth handoff to customer success (CS) so the customer journey can start off right.
Much like the BDR/SDR and AE handoff, the AE and customer success manager (CSM) handoff highlights another critical point in the customer journey. Until now, the customer has invested a lot of time and resources to communicate their needs, negotiate a deal, and come to an agreement that satisfies their expectations. Once the customer is passed along to CS, a new phase begins, where the customer begins to evaluate whether the value they’re receiving matches what they feel they were promised during the sales cycle.
"If there’s a clunky handover and the client feels like it’s been a poor process, they’re going into the relationship with a bad taste in their mouth."
While presale friction leads to slower deal velocity and lost revenue, post-sale friction reduces expansion opportunities and the likelihood of retention. The consequence of both is the same: lost revenue.
On the other hand, a strong handoff sets up customers for success. It allows CSMs to learn about each customer’s specific challenges and goals, and tailor their onboarding process accordingly.
Make sure nothing gets lost in the shuffle
Because this part of the customer journey is so important, it’s smart to stick to what’s worked in the past. In other words, AEs shouldn’t be reinventing the wheel every time they gift a new client to the CS team.
Email templates are an excellent tool to use at this stage in the customer journey. There’s a tremendous amount of information the AE is passing over to the CS team prior to handoff, so creating a warm transition with a highly-structured (but easy to digest) email outlining everything that’s taken place so far, as well as specific client goals for the future, will both prime the CS team and put the customer at ease.
Integrate for a more automated handoff
SaaS integrations are another tool to help automate the exchange of information. For example, you can integrate your scheduling system with Salesforce or other CRMs so the AE’s customer meeting notes can be funneled directly into a multi-person meeting invite.
This way, the CSM can receive a direct download of everything that’s transpired, without any editorializing. They’ll know what to anticipate, what the customer expects, and how they can proactively address any challenges that lie ahead.
Simplify CSM onboarding
Once they’re officially in CS’s hands, the customer still has a long way to go. During onboarding, the customer gets clear on how the solution will be rolled out, what their critical success benchmarks will be, and whether the value they’re receiving is what they felt they were promised. It’s a time for many questions, recalibrating expectations, and reality checks.
This is a make-or-break period to set the tone for customer satisfaction. If customers are onboarded well, the stage is set for recurring revenue and expansion opportunities. If not, things can get risky, quick.
Keep the conversation going with Workflows
Once the CSM handoff has taken place, the ball is in the CSM’s court. The customer is waiting for the CSM to tell them what’s next, and they’re eager to get started and schedule some onboarding sessions. Calendly Workflows keep communication going in a way that’s attentive, but relatively automated.
Used well, Workflows can provide regular touchpoints to new customers, giving them tips and information they can work with before or between onboarding sessions. CSMs can also customize email sends to include recaps from past sessions, as well as an agenda for the next meeting.
Including a meeting link in each workflow is also a great way to let the customer know the CSM is just a click away. If the customer has any questions that can’t be answered over email, they can book a quick 15-minute call to work things out.
Workflows allow you to keep a conversational relationship between the customer and CSM without a heavy lift on the CSM’s part. Reminders and follow-ups also ratchet up your rate of communication. Instead of days or weeks of radio silence, your customers hear from you regularly, keeping the implementation top of mind.
Stay in touch with CSM check-ins
When onboarding is over, it’s up to the CSM to keep a finger on the pulse of customer satisfaction and look for risks that may hamper renewal or expansion opportunities.
The last thing a CSM wants is to learn too late about the customer’s challenges or doubts.
This is why regular check-ins are important. CS reps should be setting up a meeting at least every quarter to discuss success metrics, customer wins, and plans for the future. This way, when renewal conversations start, there’s a trail of check-ins revealing what needs to be addressed.
Bring AEs back into the fold
Expansion opportunities are among the biggest boons to recurring revenue. Redpoint venture capitalist Tomasz Tunguz suggests that upsells drive between 8 and 26% of new bookings.
"Mining the existing customer base for customer expansion seems very logical. Customers know your product and your sales team, so increasing the account value should be easier."
That’s why having an AE join quarterly check-ins is a great idea. During these check-ins, the CSM can introduce the AE to other buyers or stakeholders in the customer’s world and ask the right questions about expansion opportunities.
Throughout this process, it’s important to keep customer questions and concerns documented and visible so nothing falls through the cracks. CSMs can leverage email templates to build meeting recaps, outline action items, and propose next steps that come out of these conversations.
Keeping AEs in the loop and building a 360-degree view of your customers in a CRM can go a long way in managing everyone’s expectations throughout the year. This isn’t a place you want to falter; customers' needs are always growing and changing, and acknowledging and addressing those changes is critical to sustaining success and ensuring quarterly check-in meetings end on a positive note.
Simplify your sales meetings
The B2B buying journey has changed. The era of linear buyer journeys and simple relationships is long gone. Today’s salespeople must adapt their strategy and remove friction wherever possible.
In this guide, we’ve given you some surefire ways to streamline multi-person meetings, improve the buyer’s journey, and close more deals. We hope you’ve picked up some tips and tricks you can use to simplify your sales cycle.
As you can see, there are many ways to make multi-person meetings go more smoothly. With the right tools and strategic automation, you can eliminate the most time-consuming, tedious, and frustrating parts of the sales process, and focus on customer needs.
By turning the buying experience from a chore into a joy, you will strengthen relationships with prospects, accelerate your deals, and secure more revenue. More than 93% of sales teams achieve shorter sales cycles with Calendly, and 89% close more deals.
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