Let’s see if this scenario sounds familiar: You’ve been engaging with a prospect for weeks, perhaps even months, with steady momentum, and you’re this close to closing a big sale. And just as you’re finally about to cross the finish line—poof. They disappear. 

Thirty-six percent of salespeople say closing is the most challenging part of the sales process, according to HubSpot. While putting pen to paper—or mouse to button—should be a quick and painless process, it rarely is. 

There are plenty of reasons sales teams get stuck in the closing stages of a sale: the point of contact is waiting for final approval from their director, they’re still negotiating other options, or they simply just forgot—regardless, it’s crucial to keep your prospects engaged from start to finish. 

At ZoomInfo, we recognize the importance of multiple touchpoints throughout the buyer’s journey, as well as being an ally and support system for our potential customers—not just a pushy sales rep salivating over their business. We believe in nailing down the art of sales into a science.

“The art is relational to the specific opportunity constructive to the uniqueness of a buyer’s situation,” says Lou Wolf, vice president of new business sales at ZoomInfo. “The science is your step-by-step process to close the deal.” 

That’s why we operationalized a best-in-class email automation process to ensure consistent communication with prospects and increase closed-won opportunities, while decreasing tedious, manual processes that waste reps’ time and put revenue at risk.

Here’s how we did it—and how you can replicate the same success. 

Never Leave Their Side

It didn’t take long for us to recognize the powerful impact of email drips that offer support to prospective customers toward the end of the buying cycle. Now, at the end of every week, we review the DocuSign contracts we sent to potential customers that have had zero engagement for 48 hours.

Once we pull that list, we trigger an email that communicates:

  • how excited we are to work with them;
  • how dedicated we are to their partnership;
  • how we will support them by providing ourselves as a resource should they need any additional assistance prior to signing the agreement.

Here’s the kicker: This first touchpoint is signed by ZoomInfo Chief Revenue Officer Chris Hays. Here’s why: Up until this point, the potential customer has primarily only interacted with the sales team. Receiving an email directly from the CRO creates a sense of urgency, as well as lets them know their business is important to us. 

Here’s an example of an email template you could use: 

Subject line: [insert company name] [insert executive title] – need support ahead of the weekend?

[First Name],

I know you have been working with [insert name of sales rep], and we are super excited to have you partner with us. I wanted to make sure you have everything you need ahead of the weekend and offer myself as a resource to you if you need any additional assistance prior to signing your agreement.

I assure you that we are 100% dedicated to this partnership for the long haul and are excited to help you plan strategically for [insert timeframe]. Let me know if there is anything I can help with. 

With your success in mind,

[insert executive signature]

The overall message? We see you, and we value you—regardless of the size of your account. This offers an open avenue for customers or prospects to raise concerns or issues directly to a senior executive. While many automated sends can be considered less personal or less valuable, the reality, in this case, is we really care and we want to handle the reply. We would be sending this outreach even if it wasn’t automated. In fact, we did send it manually for a long time until we realized we should never skip this step, and we automated it. 

While automating an email from an exec is easy, what’s more challenging is actually following up. Hays sets aside time every day to respond to each reply he gets. So while someone on our team is automating his original email sends, he replies to any responses he receives himself. No bots here.

“A CRO reaching out to most anyone in a mid-market or SMB account…that’s going to make them feel unique and special and like their deal is important,” says Scott Sutton, vice president of revenue operations at ZoomInfo. 

While this email is sent on Thursday or Friday, a second touchpoint is sent on Sunday, two or three days after the first send. This one cc’s additional resources for good measure. While the general message stays consistent, this email provides a slightly stronger push to get the prospective buyer to sign.

Here’s another example of an email template you could use: 

Subject line: REPLY

CC: [include additional resources, such as your customer success and/or product leadership]

[First Name],

I hope this note finds you and your family well this weekend.

I wanted to check in again to make sure you have what you need to sign. My team and I are looking forward to partnering with you and are standing by to address any outstanding concerns about moving forward.

I am including [insert resource(s) name and title] on this note in case you have any questions about [insert use case(s)]. I assure you that we are 100% dedicated to this partnership for the long haul and are excited to help you [insert business objective] through [insert timeframe]. 

We’re here all weekend, please don’t hesitate to reach out.

Best regards,

[insert executive signature]

Tip: Getting buy-in from the C-suite to use their name and signature in automated emails can be tricky since executives tend to be particular about what they stick their name to and invest their time in. Dominique Catabay, manager of revenue generation at ZoomInfo, explains how to successfully frame your pitch:

“All you have to do is show the value. If you can get executives to [agree to a small pilot] and they see the positive responses that come in, they’ll see what’s holding up some of these deals and stopping people from closing,” he says. “That’s really valuable information to have.”

The Results 

When we looked at emails with similar messaging sent by a sales team member as opposed to our CRO, it was clear how much weight a C-suite name carries. 

Emails sent by our CRO to existing customers had a 19 percent increase in open rates and a 21 percent increase in reply rates. Similarly, emails sent by our CRO to prospects had a 12 percent increase in open rates and a 35 percent increase in reply rates

Response rate is the primary KPI to look at here. This means we’re re-engaging roughly 16 opportunities every week and accelerating their time to close. That revenue adds up fast. 

Tip: Your deliverability rate should be close to 100 percent. You’re reaching out to people you’ve already engaged with, so if you’re seeing anything lower, it could be a sign of a soft bounce or temporary failure (e.g., Someone is out of the office, and their inbox is full). Your email may go through if you try sending it another time.

On top of that, this automated email process gives our executives a few hours of their week back, which they can then allocate to other important projects. 

“If the average email takes about three minutes to write, our executives save 7.5 hours,” says Catabay.

It saves the time of sales reps and sales operations team members, too. On average, it takes an individual in sales ops between 10 to 15 minutes to manually pull the list of outstanding DocuSign contracts with zero engagement from the past 48 hours and trigger an email. 

Needless to say, 10 to 15 minutes for a single person to send out high-value touches to dozens of prospects who are already actively engaged in the closing process is very valuable. No individual can manually send 50-plus emails in 10 to 15 minutes in any easy manner. 

“The qualitative value of responses is the real win here as it has surfaced many stuck DocuSigns and helped us identify a path forward,” says Catabay.

We Made It Happen—You Can Too.

Arguably one of the toughest aspects of operationalizing any system is simply knowing what to automate. At ZoomInfo, our approach is simple: Look at what your sales reps are doing well. Oftentimes, it may just be a one-off email that saw great results—so don’t ignore those.

If you’re not sure what’s working well—ask your sales reps. They work with prospects every day, so they pick up on what does and doesn’t land. They’re a wealth of knowledge—use them to your advantage.

Once you’ve decided what to operationalize, consider implementing A/B testing, also known as split testing, to see what converts before locking down the automation in your CRM. A/B testing involves splitting your intended email list into two separate lists and sending a slightly different variation of an email to each. Consider testing variables such as subject lines, sender names, calls-to-action, and day or time of send.

“Our data team goes out to the data lake and pulls all of the necessary data. We’ll then go manually sequence it, and after a few times testing it, we put automation in place. So we have a nice process where we iterate, test, and automate,” says Sutton.

How do we do it? We use a trigger field in Salesforce. So, as soon as some conditions are met (such as the account type changes from customer to former customer), we populate the sequence selection of win-backs. Then, we use that field as a transitory light-up switch to light up sequences that are useful for hundreds of different sends, such as a trial follow-up email, 30-day welcome email, six-month check-in email, and much more.

“It’s kind of like a scientific method,” says Sutton. “We go out, we test different things, we have hypotheses, we prove them with data, and once we come to something compelling, we make the build decision.”

Research, test, automate is the name of the game. Keep the appropriate people in the loop, and don’t be afraid to make changes or take risks throughout the process.

“Look at what your team is doing and what your team thinks is the ‘art’ side of sales, and then go make that the ‘science’ side,” says Wolf. “Lock it in, do it in mass, and do it consistently.”

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