How to choose the best cold calling software for your sellers

For all the talk about cold calling being “dead,” there’s no shortage of evidence suggesting that cold calling is alive and well. Firstly, not every business can rely just on inbound calls from potential customers.

And yes, there’s also LinkedIn and other channels, but research shows that over 80% of buyers still accept meetings with sellers who reached out to them, and 57% of VP buyers actually prefer to be contacted by phone.

So how do you get the most out of cold calling and make it an effective prospecting or lead generation tactic for your business?

One of the most important things to do is invest in quality cold calling software—and no, I’m not just saying it because I’m biased and work at Dialpad. I oversee a team of SDRs who make cold calls all day, and it’s hard to imagine them being as successful as they are without the help of software. In this post, I’m going to show you a few ways we use cold calling software and how to choose a tool that fits your business and empowers your sales team.

What is cold calling?

Cold calling has been around a long time, as you probably know. “Cold calling” is simply when a salesperson contacts people over the phone about a product they’re likely unaware of or haven’t expressed interest in. There’s usually no established connection between the salesperson and the people they’re cold calling.

(Before the Internet, salespeople would go door-to-door selling products. Now, salespeople can still sell door-to-door technically, but it’s way easier—and much cheaper for companies—for salespeople to just cold call or cold email.)

So, where does that leave telephone cold calling today? Well, 41% of salespeople still say that the phone is their most valuable sales tool. But the days of having your outbound sales team flipping through a Rolodex or just reading off a call script are over.

Today, sales teams need tools that streamline the sales process in real time, deliver results, and allow reps to work from anywhere. I’ll show you what we look for as a sales org when we look for software in just a bit.

How does cold calling software work?

Cold calling software typically works in conjunction with a few tools, like your Customer Relationship Management (CRM) software like HubSpot, Salesforce, Zoho, or Pipedrive:

• Cold calling software: Typically has VoIP or telephony technology that lets you make the actual phone calls

• CRM: An essential lead management tool. It’s basically your directory of prospects and customers, where contact information and details about their interaction history with your business are logged

• A “contact info finding tool”: This is more of a nice-to-have. ZoomInfo is probably the most well-known one, though we’ve also tried LeadIQ and Seamless.ai in the past

This combination of tools will help your team both manage leads and make calls, as well as helping sales managers measure sales activity and train sales staff.

Let’s say you’ve collected a list of cold call opportunities and are ready to get your salespeople to start making calls. An automated phone system, sometimes called a dialler, auto-dialler, or power dialler automatically places the call and then moves on to the next one when the previous call finishes.

Dialpad’s Salesforce integration for example, embeds a power dialler right into Salesforce so that sellers don’t have to keep switching between windows or tabs:

The cool thing about this integration is that not only does it work perfectly on the mobile app, it also automatically logs activities for reps so they don’t have to manually take notes for each call—super important if your team is making a high volume of outbound calls every day. You want to have as many at-bats for your team, as quickly as possible.

And if your team doesn’t use Salesforce, Dialpad also integrates with other sales apps and CRMs like HubSpot:

Why use cold calling software? The benefits

When you get the magic combo of the right CRM software and the right cold calling software for your business, the benefits are enormous. With outbound sales especially, you can accrue a lot of data like activity notes, phone numbers, emails, and more.

Keeping track of all this could be a nightmare, but cold calling software combined with a powerful CRM can keep everything organised—and your sales activity humming.

Insights into every call

Most of the time, one-on-one cold calls are just black holes of activity—your sales reps make the calls, either someone picks up or doesn’t pick up, they try to set a meeting or make the pitch, and then they move on. It’s just a repetitive set of actions that don’t provide you with any valuable insight.

But if you have good cold calling software, you can uncover learnings in every call—even the “unsuccessful” ones.

For example, with Dialpad, we have the ability to record calls. This is essential, especially for training new team members (and even for helping out more experienced team members with challenging calls).

I can even create coaching playlists, where I can curate a collection of sales call moments and share with my team for training. If one of my reps handled an objection particularly well, I can add the call to, say, a “Best Objection Handling Learnings” playlist so that sellers can listen to these case studies and learn on their own time:

Dialpad can also transcribe each sales call—in real time!—thanks to its artificial intelligence, Dialpad Ai:

The neat thing about this is that managers and coaches can see running transcripts for every call in progress, for every agent or rep on their team. It means you can spend more time listening to recordings of actual live calls—rather than listening to your reps leave a voicemail or hear the phone ring (and also lets me provide more real-time coaching through messaging on Dialpad as a result).

The transcript also gets emailed to you automatically for review as part of a call summary after the call has ended—I don’t know about you, but I can scan and read transcripts in much less time than it takes to listen to the recordings. And I can click on a certain point in the transcript to instantly play the recording from that moment, which helps me hone in on the key moments more quickly:

For busy sales leaders, call transcripts are pretty much a must.

With this information gleaned from our sales calls, I can do another crucial thing as a sales leader: coach and train my sales team more efficiently. How?

Dialpad Ai not only transcribes calls, it also picks up on keywords that are spoken on calls—which means I can track specific keywords (like competitor names and features that prospects frequently ask about). All I have to do is create a "Custom Moment" with trigger words or phrases:

This will then track how frequently these Custom Moments occur on calls—if I notice certain topics coming up a lot, I can dig into those transcripts and recordings to get more context.

To go one step further, I can also create RTA (Real-time Assist) cards that automatically pop up when the prospect and/or the rep uses specific triggers or words (this is a popular feature with our Support team too):

RTA cards are great, especially for newer reps who aren’t super familiar with things like pricing and the competitive landscape yet—they’re essentially cheat sheets with notes on how to speak to any topic you want.

More at-bats (sales call opportunities) for your team

Cold calling isn’t easy. It’s a numbers game—the more calls you make and the more at-bats you get, the better chance you have of setting meetings and generating leads.

Not every business relies on cold calling, but for the ones that do, this is the number one reason to use cold calling software: to help your sales team make more calls, faster.

A CTI (computer telephony integration) feature basically turns your computer into a phone—which means you can do things like click to dial instead of manually entering phone numbers..

Dialpad also has another great feature that accelerates seller activity: voicemail drop. For many outbound sales teams, getting a pickup is not a guarantee. In fact, many cold calls go to voicemail. How much time is your sales team spending on reciting a voicemail script?

With Dialpad, if someone doesn’t pick up, my reps can “drop” a pre-recorded voicemail message and move on to the next call—which can save hours if you’re a high-volume outbound team:

What can your reps do with the extra time that they don’t have to spend on reciting voicemail messages?

Consolidated data

Many sales orgs have way too many tools. It’s no one’s fault—it’s often just a natural progression at the vast majority of companies. But it makes life harder for sellers, not only because they have to switch between tools constantly just to do different tasks, but also because information and important data end up being scattered in different places.

Cold calling software that integrates with your CRM can consolidate data to make your life easier, reducing the amount of copying and pasting your team has to do because it just syncs data between the tools automatically.

For example, when our sales team uses Dialpad to make cold calls, every interaction and call is automatically logged, along with transcripts and notes in Salesforce, so that reps are prepared with everything they need to maximise their chances of booking a meeting at all times.

6 essential cold calling features to look for in software

Power dialler

I’ve already talked about power diallers earlier, but I can’t overstate how important it is to have some kind of auto-dialling tool if you’re a high-volume outbound sales team.

Bottom line: If you can use sales automation to take “busywork” (follow-ups, data entry…) off your reps’ plates, do it. Their time is their most valuable asset—help them maximise it.

CRM integration (automations, basically)

The cold calling software you choose should integrate with the tools your team is already using—most importantly, a CRM integration. Again, the benefit of this is that it creates a streamlined workflow for your reps by automatically syncing insights and data.

It’s not just CRMs either—take a look at your team’s workflows and which tools they’re using. For example, if your sellers are also using Outreach to manage email outreach sequences, then your cold calling software should integrate with that as well. Here’s how Dialpad’s integration with Outreach looks:

Call recording

If you are a sales leader or work in sales enablement, then you’ll probably want to be able to record calls and play them back. That’s something your cold calling software should be able to help with.

Call recording is super valuable for me—it allows me to review calls, train new team members, and coach reps through difficult call scenarios.

My managers like it because they can listen to recordings of cold calls together with reps and other sales leaders, and get real-time insights during call blitzes.

In addition to recording calls, Dialpad’s call recording feature also records what’s happening on screen, which can help managers of both Sales and Support teams with training and development.

It’s easy to set up automatic call recording for inbound and outbound calls in Dialpad—just choose your settings and check a box (you can also turn this off and have your team record calls manually):

Real-time coaching and objection handling

Wouldn’t it be great if there was a magic tool that could tell reps when they’re saying “Um” too much on calls or speaking too quickly?

While this kind of thing doesn’t exist for everyday, real-life conversations, you can find this feature in some cold calling software. Dialpad’s real-time speech coaching capabilities can alert agents when they’re speaking too quickly, too slowly, talking too much, or using too many filler words.

Um, that’s awesome.

Dialpad Ai Contact Centre also has a live sentiment analysis feature that shows sales managers if phone calls are going positively (or negatively) in real-time, so they can listen in and jump on the call if extra support is needed. It’s a great tool to have when training new sales team members.

Together, functionality like real-time speech coaching, live sentiment analysis, and RTA cards (which I mentioned earlier) all help get new sales reps up to speed and working the phones effectively in less time.

Whether you’re running a small sales team or an outbound call centre, real-time coaching tools like these are essential.

Voicemail drop

I mentioned this one earlier as well—if your sales team leaves a lot of voicemails on a daily basis, this can be a huge time-saving feature to have. It’s an essential for my team.

Empower your sales team with cold calling software

From real-time metrics to coaching at scale, the benefits of using cold calling software are huge.

Many of these features also come with contact centre software designed for sales teams—just make sure that whichever one you end up going with will actually enhance the quality and number of your outbound calls.

Some might argue that “cold calling is dead,” but with the right tools, you can make cold calling your strongest sales strategy, whether you run an enterprise outfit or a startup business.