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#SellersBecomeMarketers - Sales Automation Like a Marketer

Liston Witherill
Liston Witherill
19 min read

Sellers today are still expected to have one-on-one conversations with clients, but they’re also expected to reach a lot of people in a personalized way to find clients in the first place. Start piling up all the little things you need to remember throughout the day and it’s no wonder tasks start slipping or falling behind.

Marketers have been using automation for a long time for this reason. And now, the tools exist to help you do the same with your sales process — saving time and improving your efficiency so you can get back to focusing on what you like to do best.

In this episode of Modern Sales, you’ll learn how automation can help you in your sales efforts across the funnel, what you can learn from marketers, and specific tools you can start using today to start selling more effectively. This is the last episode in our #SellersBecomeMarketers series where we’ve been diving into the huge shifts in sales and the critical marketing skills sellers need to get ahead today.

In this episode, you’ll learn:

The science behind why you want automation in your sales process

  • Automation is critical for two scientifically-backed reasons: the psychology of repetition and the neuroscience of productivity. 1) The more we hear something, the more we believe it, the more it matters to us. Some people need to get your message several times before they’re ready to respond. 2) Automation can reduce the loss of focus due to switching tasks all the time.

The core skills you need to get automated

  • Automation isn’t about executing the tool. It’s about executing the process. You need to understand the full spectrum of every step in the sales process, the basics of if/then logic, and how to do quality control with data in a spreadsheet. I’ll cover all of this.

Awesome automation tools to start using (as of Nov. 2019)

  • Ready for some juicy automation hacks? I tell you exactly how I use automation in my business, Serve Don’t Sell, and the tools I love to get the job done. Get ready to level up your emails, capture leads, enter data, prune lists for quality contacts, better connect with people on the phone, and send thoughtful cards or gifts — all automatically.


Subscribe to Modern Sales podcast on iTunes
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#SellersBecomeMarketers – Sales Skills We Learn From Marketers
#SellersBecomeMarketers – Being a Mind Reader with Sales Copy
#SellersBecomeMarketers – Product Differentiation: Why Different Is Better Than Best
#SellersBecomeMarketers – Content Marketing for Sales Teams
#SellersBecomeMarketers – How Content Is Shared (Inside Companies)

For more information on remote selling and a complete list of links mentioned in this podcast, visit this remote selling article on our website.

#SellersBecomeMarketers – Sales Automation Like a Marketer:

Full Transcript

Hey Siri, what’s the best sales podcast in the entire world?

Hang on, let me listen.

Not quite what I wanted, but I do love my Google assistant. I do love Siri. They both helped me do all kinds of things, and obviously they both have some work to do, but still the technology is amazing. Though it seems totally mundane now, automations like this one are all around us. Some people talk to Alexa. The heater in my house turns on and off based on when my wife and I are in the house. I have a bot email me whenever Pitchfork has a new highly reviewed album. And I have a bot that lives in my inbox flagging for me emails that haven’t received a reply.

But it wasn’t always like this. There was a time when an ox pulling a sled to plow a field was automation, at least compared to doing it with just your bare hands. Automation comes in waves, not all at once. A lot of people are worried about the coming automation displacement, including me, honestly. McKinsey predicts that up to a third of all jobs could be displaced by automation by the year 2030. And yes, automation may be coming for you.

But what is it anyway? Is it robots completely replacing people? Is it these really dumb, not AI at all, chatbots that ask you to choose one of three options before giving a response on a website? Well, it’s both, of course. Here’s the definition of automation from Oxford, the use of largely automatic equipment in a system of manufacturing or other production process. I want to draw your attention to that phrase largely automatic, which is to say two important things. Automation tends to happen in a stepwise fashion one small piece at a time. Someone has to set up the automation correctly for it to be useful.

The good news is you can do both right now. Automation can be used for good and it can be used to annoy the hell out of people. Around 50% of phone calls made right now are all spam calls. That’s a bad use of automation. On the other hand, surgeries are getting faster, more successful, and often have less complications with the use of robotics in the operating room. That’s good. What kind of automation are you using? In this episode of Modern Sales, you’ll learn how automation can help you in your sales efforts across the whole funnel, what you can learn from marketers and what to do to make your selling 1% more effective today.

Welcome to Modern Sales, a podcast for entrepreneurs, business owners, and salespeople looking to have more and better conversations with your perfect clients. You’ll get a healthy scoop of psychology, behavioral economics and sales studies to help you create win-win relationships. I’m your host, Liston Witherill, and I’m pleased to welcome you to Modern Sales.

This is the Hashtag Sellers Become Marketer series on Modern Sales where we’re talking about the skills you need to survive the giant shift in sales and skills that you can pick up from marketers. This is the last episode in the series, all about automation, so you can provide a better, more consistent experience to more people. Each of the episodes will have the Hashtag Sellers Become Marketers at the beginning of the title to help you find them quickly, so if you’d like to catch up on the series, just scroll back in the podcast feed. Now, let’s talk automation.

The problem is one of complexity and volume. On the complexity side. Selling is more complex because there’s huge amounts of data and information you need to balance in order to be successful. There’s research you need to do, insights you need to come up with, and tons of little things you need to remember to do throughout the day, every single day. Then there’s the volume of complex work you need to do. If you’re in a prospecting role, you’re probably expected to do 40 to 120 sales actions every single day. There’s no way you can remember all of that on your own. Add to that the deals you manage, the network you’re building and, any content efforts you’re undergoing. It’s a lot.

Meanwhile, marketers have been using automation for a long time, but sales has been a little later to the game, mostly because the tools haven’t been there before. Here’s the thing, sales is getting more competitive every day because of that little thing that I’m talking about, automation. And while automation is the solution, it’s also the problem. Really, it comes down to how it’s done.

I’m not advocating for you to put your whole sales process on autopilot, quite the opposite actually. What I’m pushing you to do is think strategically and systematically about everything that goes on in your sales process and figure out, not how can you automate the whole thing, but how can you automate very particular pieces of it.

See, marketers figured out how to automate things because they didn’t have the luxury of just doing one-to-one interactions the way we do in sales. They had to reach a lot of people and quickly, and often in a personalized way or at least somewhat personalized. But now, the game is changing and you’re expected to do both jobs as a seller. On the one hand, you’re supposed to reach a lot of people using personalization, just like a marketer would, and on the other hand, you’re also having those one-on-one conversations in a traditional sales process, which is why we’ve come full circle and I call this series Sellers Become Marketers.

Now, there are a couple of psychological factors at play here that I want to draw your attention to. One is repetition. The more we hear something, the more weight it holds for us, the more persuasive it is, the more convincing it is, and the more it matters to us. When our prospects hear something multiple times, they’re more likely to respond, they’re more likely to trust it, they’re more likely to be receptive to the message. Also, they are busy, just like you, just like me. They may need to be exposed to you and your message six, seven, eight or more times before they’re ready to respond. No worries. That’s fine, right? We expect that, but it’s hard to keep up with that level of volume without some kind of automation in place.

Then there’s a psychology for us, in particular, the neuroscience of productivity, and that is the cost of task switching is huge. One of the features of automation is it allows us to do things in bulk, set them up, and then let them run on their own so we don’t have to go from thing to thing and it saves us a lot of time. Research shows that it takes a full 25 minutes to regain focus after it’s lost due to switching tasks. Automation can help us reduce the loss of focus and also keep us involved in more of the things we actually like to do.

When it comes to automation and what we can pick up from marketers, there are three core skills that we need. Number one, we have to kind of think like an operations person, understanding the full spectrum blow by blow of all of the tasks that we need to execute throughout the sales process. The second thing is understanding the basics of automation, most of all, if-then logic, if this happens, then I want to do something else, and how it branches out. The third thing is how to work with data, specifically a spreadsheet and make sure you’re doing quality control on your data so it’s always right.

Then if you want bonus points you can start to learn a little bit about how APIs work. API stands for application programming interface, which is basically just how different pieces of software can talk to each other. Now, don’t worry, you don’t need to write any code. There is a wonderful app out there called Zapier which allows you to connect different pieces of software and have software triggered based on what’s happening in one place.

Now, I’m getting it specific for you about some automations that you can put into place right away and there’s one app in particular that I am very bullish on, I mentioned it on the podcast several times, and it requires absolutely no programming from you. But I do want to give you a quick note. I’m going to make some software recommendations here, and this episode was recorded in November of 2019. As you might imagine, specific software recommendations may become out of date. Software companies may get bought by other companies, they may go out of business, but the fundamentals of what we’re trying to achieve here, they don’t change all that much. Feel free to check out the tools that I’m recommending. No one paid me to recommend these. But I want you to know that getting the job done is much more important than the actual tool.

Finally, before I get into the tools, I want to cover something important here. You really have to have an intimate understanding of what needs to be done before you can effectively automate anything. I’ll give you an example. Right now, on this here podcast, on the Modern Sales podcast, I’m currently prospecting for sponsors who might want to advertise on the podcast and reach you, dear listener. I’m automating part of the outreach process in order to help me out. But in order to do that effectively, I needed to understand what I’m trying to achieve from start to finish.

And so, it goes like this. First, I need a list of viable prospects to target. That started by me making some assumptions and some guesses, really, about whose likely to be a better fit for a sponsor on this podcast. I looked at online listings, different types of sponsors, people already buying advertising. I had my assistant put together a list, which I reviewed line by line. She also went out, got each prospect’s information, all the way down to phone number, mailing address, email address, of course, LinkedIn profile, on, and on, and on. I then wrote a five part email series. For each prospect, I want to make sure I reach out to them, let them know what I’m working on and I want to send them at least several emails, in this case, five emails, to let them know, “Hey, this is what I’m doing.” And just in case they’re busy or I keep catching them in a bad time, it’s a good idea to repeat this process. Right? I went out, I wrote a five part email series that’s pretty customized to each individual recipient.

Once I get a response, the idea then is to send a special scheduling link for the people who are interested. That scheduling link allows them to book on my calendar. It automatically gives them a followup email with an agenda for the meeting so that they know what we’re going to talk about and they can prepare a little bit. And it also pushes their information straight into my CRM as an opportunity. I then also wrote a followup template, so that after my sales calls, I could send an email that was pretty much the same every single time, and I also put together a contract so that people could have a faster and easier buying experience from me.

There were quite a few moving parts, right? The main thing I automated here was the email sequence, but I also prewrote all of the copy that’s associated with this campaign. I Also have a sales deck, which is the process I’m using on the sales calls, where I’m learning a little bit first about the client and then I’m going through the deck to walk them through how does the podcast work and what would they get. Now, full disclosure, the sales deck took way longer than anything else. I mean, multiples longer than anything else I mentioned here. But I did need the full picture of what needed to be done long before I could automate anything, and that’s the thing I want to emphasize here, is that anything I’m recommending here, it’s not about the tool, it’s about executing the process. I hate to use the phrase, but doing more with less is the goal here, and that’s why I’m recommending some of these automations.

What I don’t want you to do is automate at the expense of delivering a useful and valuable experience to the person receiving it. Disclaimer over. By the way, if you know anybody, if you or your company want to advertise on this podcast, feel free to email me That’s my story. Also, if you’re interested in learning more about this campaign and how I am selling ads and the whole process I went through, I’ll probably post an article at least on Medium, but feel free to email me if you’re interested in hearing about that. Now, let’s move to tools.

The first thing that I recommend is automating as much of your email as you possibly can. Now, I’ve had this dream. Really, I think it’s a fantasy, that I could just log into my inbox and only see emails that actually mattered to me. The problem with email is it continues to ebb and flow. If you unsubscribe from a bunch of things, then you may not see some important things. There’s marketing emails, plus there’s emails from individuals. There’s all kinds of reasons why email is a challenge. I haven’t figured out how to automate only seeing the best emails in my inbox. You can of course outsource this to G Suite. If you’re on G Suite, it can sort your inbox for you. It does an okay job, not the best job. But in any case, I haven’t figured out how to do that. But there are several types of things that I recommend you automate in your email. The one app that I recommend, it only works with G Suite, for now, at least, is Mixmax, and that’s I’ve put my affiliate link below in the show notes here.

The thing I love about Mixmax is it has just as great suite of amazing ad-ons that work right there in your inbox with very little explanation needed. One thing it can do is it can automatically send a followup sequence of emails. If you write a generic followup sequence that’s just the standard nudge emails, “Hey, did you see my last email? Or what do you think?” Or whatever you want to say, maybe three emails over four weeks, something like that. You can add that on. You have reminders pop up in your inbox, so you can snooze a message for a predetermined amount of time, on a specific date, plus 90 days, however you want to say it. It can read just plain text and it’ll bring emails back to you. You can send emails later. I know a lot of these are now included in Gmail. The implementation by Mixmax is much better than what Gmail has done.

But three of the big things that I love about Mixmax, number one, is it makes inserting custom videos dead simple, and fewer clicks than any other solution I’ve seen. You can record a video for your prospects or even include videos in sequences that go out that maybe isn’t customized for every single prospect, but you have a video for a campaign. You can do that with Mixmax and it’s really, really easy to do that. The second thing I love is the meeting scheduling. Now, there are apps out there that do meeting scheduling a little bit better than Mixmax, but mostly it’s really good, and you can also set up an automatic reminder so that a day before or an hour before someone gets an email, and like I said a second ago, I like setting that up as the meeting agenda so people know what we’re going to talk about.

The third thing that I really love about Mixmax is sequences. What’s powerful is if you combine your meeting link with the sequences, Mixmax can automatically stop the sequence when someone books you on your calendar, which is amazing. It’s so great. It will also automatically stop the sequence just like all the other solutions out there when someone replies, and it has out of office detection. So if you’re looking to do campaigns, Mixmax Sequences are fantastic. One thing that I love about Mixmax Sequences, and we’re going to get a little bit into the weeds here, but I promise you there’s a reason for this.

Liston Witherill:
If you wanted to send someone a drip sequence, meaning they get all of the emails in the sequence, even if they reply, you can do that in Mixmax. A lot of the other solutions on the market are designed just to get replies, and I find that this flexibility that Mixmax gives me is really, really amazing. In any case, I’m a huge fan. Again, they haven’t paid me a dollar. Yet. I mean, I’d welcome them as an advertiser if they’re listening, but they haven’t paid me a dollar. I just love the software. It’s fantastic.

The next thing you probably want to think about automating as much as you possibly can is capturing leads and data entry. For this, there are a lot of good solutions out there. It depends on your particular workflow and it depends on your use case. I actually use several different solutions for my own prospecting, but here’s the bottom line. If you rely LinkedIn for prospecting, which I know is pretty standard nowadays, but if you rely on LinkedIn, and especially Sales Navigator for prospecting, Lead IQ is a great tool. What it allows you to do is when you’re looking at a results page on LinkedIn or when you’re looking at an individual profile on LinkedIn, it goes out and finds all of the information about those people on either that single profile page or on the results pages. You can then save their info and it will give you their business address.

It’ll give you, if you want, their mobile phone number. It gives you their business phone number, gives you their email address, just a ton of data, and pretty well organized, and I find it’s pretty reliable, as well. You can then export that into a CSV, which is just a very basic spreadsheet that just about any software database tool can read, including your CRM, including Mixmax. That’s how I upload my lists of prospects in bulk. Lead IQ is that tool also linked in the show notes.

The next thing I recommend is to prune your list, to make sure it’s high quality, to make sure you’re not going to get a bunch of bounces. Not much to say here other than if you send a bunch of bad emails, it’s going to affect your deliverability. It’s going to affect your company’s email deliverability, so don’t do that. I recommend never bounce for this. That’s all I have to say about that.

The next type of automation is called an autodialer. Now, if you spend a lot of time making calls during the day, and especially you spend a lot of time making calls that don’t connect. An autodialer will help you spend more time talking to people rather than just dialing into phone trees or hearing voicemails. Now, I don’t have a particular recommendation on autodialers because I don’t personally use one, but if you’re a manager and you don’t have one, or if you’re on a team that doesn’t have one, you may consider bringing this up at the company and looking into how autodialers can make you more productive. I know some CRMs have them built in. Then of course, there’s lots of third party options that work with Salesforce and other big CRMs, but an autodialer can really improve things if you spend a lot of your prospecting time on the phone.

Related to autodialers, there’s this feature called Voicemail drop, whereby you can prerecord a voicemail and it will only connect with people if they don’t pick up. I know that seems counterintuitive. But let’s say you wanted to treat voicemail sort of like another inbox and just leave a message for people, this feature, Voicemail drop allows you to do that. Again, I don’t use this, so it’s not something I personally have a recommendation for, but there are teams who do use this.

The last thing I want to recommend to you is, and I did mention in the last episode, is automated gifts and cards. I believe that every marketing and sales channel kind of waxes and wanes over time. Right now, email is terribly crowded, and I’m guessing it will never be uncrowded unless it gets more expensive to send email. But if you think about the phone, fewer people are talking on the phone these days, so actually the phone may be a better channel to use. And of course, this is very dependent on your market and who you’re trying to reach.

But as things change, right, as the phone becomes crowded, maybe people go to emails. As email becomes more crowded, people go back to the phone. As Facebook advertising gets more expensive, people go and put a lot of resources into LinkedIn. There’s a little bit of a shell game there, right? But one thing that’s true is things in the real world are more costly and more time consuming. One of the things that you can do to stand out is be in the physical world through automated gifts and cards. I have two recommendations here. One is from a company called Handwritten. That’s linked below in the show notes. What they do is send real pen and ink written cards. They look like they’re, as the name implies, handwritten, but they’re actually written by robots. But Handwritten lets you automate that.

Let’s say, back to my example, I’m out prospecting for sponsors for this podcast. I send a bunch of emails to people. Some people open those emails, some people reply, I have some meetings, right? What I could do is upload a list of everybody who doesn’t respond to the sequence to Handwritten and have handwritten cards sent to those people in an effort to get their attention, which I’m guessing would yield at least a few responses. Likewise, for the people who I actually did talk to, I could send them a handwritten card thanking them for talking to me and asking if and when they would be ready to sponsor the show. It’s pretty powerful, right? My objection historically to doing this myself is that it’s time consuming. It’s a pain. I just don’t like to do it. I’ll be honest. And so, Handwritten for a pretty low fee allows you to start to implement some direct mail into your prospecting, into your sales, into your client relations.

The next one is called Sendoso, and Sendoso is a database of gifts, and it works much the same way. I do want to point out both of these, I talked about understanding how API’s work, both Handwritten and Sendoso have direct integrations, but they both work with Zapier. I’ll give you an example. Let’s say after you have a sales call with any new prospect, it’s your first sales call. You move your deal in your CRM from initial call to schedule deep dive, whatever you call the next step in your sales process, and you’re actually moving that in your pipeline, in your CRM. Well, you could have that movement trigger a Handwritten call or trigger a gift from Sendoso sent directly to that contact who’s attached to that deal, and you can do that automatically without having to do anything else. Of course, assuming that your credit card is hooked up and in good standing, right? They have to charge someone.

But that’s the power of automation right there, is going through this process, really understanding what you want to happen at what points, and how you can advance people down your funnel, and then having things in the real world actually supplement that, but somewhat, at least automatically, turns out to be quite powerful. This is how marketers think. This is how we now as salespeople need to think as we enter a world that’s much more complicated and people honestly want a more and more personalized experience at the same time that we’re having to interact with way more prospects.

That’s it. We’ve done it. Thanks for listening to this final episode in the Sellers Become Marketer series. Next week, I’ll be kicking off a new series about something that costs us businesses $400 billion last year and takes up a third of your time. Funny enough, you think this activity is often a waste of your time, but you spend almost no time understanding how to do it better.

If you aren’t already subscribed to this podcast, please do so by clicking the subscribe button. You can also get notified of all episodes with some behind the scenes information, as well as other exclusive sales content I put out by signing up for the newsletter at It’s totally free and it’s linked in the show notes. And finally, if you’re looking for help training your team to sell more of your big, hairy, complicated products and services to big companies, I can help with remote and onsite training options. Just head over to, click the contact button, and you can fill out a quick form to begin the conversation.

Thanks so much for listening. I’m Liston Witherill of Serve Don’t Sell, and I hope you have a fantastic day.

Modern Sales Podcast