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Using a Cold Email Email Campaign to Monetize This Podcast

Liston Witherill
Liston Witherill
21 min read

Tools mentioned in this episode:
Google Slides
LinkedIn Sales Navigator

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

 Using a Cold Email Email Campaign to Monetize This Podcast:

Full Transcript

There’s a woman who sits outside my local Whole Foods with a cooler buy her side. Propped up against the cooler is a sign with tamales scribbled on it in big block letters. “Tamales, tamales,” she calls out as people walk by. And you know what? It works. People are often handing money over when I see her. The fact that she’s sitting in front of Whole Foods is genius because there are two things we can glean about most Whole Food shoppers. Number one, they are not price sensitive. They’re willing to pay more for food. And number two, they’re already thinking about food. That’s why they’re at the grocery store in the first place.

Now, I’ve never bought tamales from this woman, but plenty of people have and they swear that they’re delicious. What she understands about sales, though, is essential to any outbound campaign you may plan now or in the future. Sell food to people thinking about food. In this episode of Modern Sales, I’ll walk you through the process I used to bring the first advertisers onto this here podcast, from the initial strategy to the sales process itself to the adjustments I made along the way.

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.

Turning total strangers into buyers is just about the hardest challenge in sales. But when you’re going from zero to one, that’s exactly what you have to do. And that’s exactly what I did when I decided to seek advertisers for this podcast for the very first time. I started the campaign in November of 2019 and by January I secured my first two advertisers with many more interested in advertising on the show. What follows is the initial strategy, sales process, and results of the sales campaign.

One thing to note, I used an important tool in the campaign, and it’s called Mixmax. They are a paid advertiser on the show, but they haven’t contributed to this episode whatsoever, and I was using their tool before they paid me a dime. Just the opposite. I’ve been a paying customer of Mixmax for quite a while.

Now that that’s out of the way, I’d love to dig into the big problem I was facing going into the campaign. Sometimes this can seem insurmountable, and it was one that I couldn’t easily correct without the right strategy in place. That’s coming up after this short break.

First things first, I needed to start with a strategy. The first challenge with selling ad inventory on the podcast was that I’m not a household name. I’m not Joe Rogan. I’m not an NPR show. I’m not a Gimlet Media show. Although, I’m aspiring to be all of those things, but I’m not yet. And I’m certainly not the level of household name like the doctors from Botched or Dr. Pimple Popper are in my own home.

So here I am selling ad inventory on a podcast that a potential advertiser is unlikely to know about. They may not know about me, they may not know about the podcast. What I eventually learned, and I’ll cover later in the podcast, is that some potential advertisers don’t know all that much about how podcasts advertising works in the first place. What I do know, however, is that a hungry person somewhere will always gladly buy food. Which is to say, what kind of company is most likely to sponsor a podcast? Well, the first thing we need to understand is podcasts themselves. People mostly listen, as maybe you are right now, while they’re doing other things, and listeners are quite loyal. While they may be multitasking or distracted, they keep listening episode after episode, on average of course. And they didn’t ask to hear a specific ad when it plays. They only signed up to listen to the podcast. Maybe this sounds familiar. Most listeners know the advertising may be part of the experience and part and parcel of listening to a podcast just as seeing commercials on television is part of the experience, but they weren’t actively seeking it.

Compare that to a Google ad or a Facebook ad retargeting website visitors. That kind of advertising is very different. It’s served to people who voluntarily shown intent to buy something or at least explore it with their behavior. In a Google ad search, I type in the search that I want. And if I’m looking for a local plumber where I live in Portland, Oregon, then of course plumbers in Portland pay Google to advertise when you do that search, similarly on Facebook. If you visit a website and they have a Facebook retargeting pixel installed, you’re likely to see ads on Facebook, or Instagram, or any of their other various properties when you go there. That’s so different than the people listening to this podcast.

The big idea here is that podcasting isn’t a great direct response medium, especially on a niche B2B show like mine. It’s better for awareness and brand building for companies who want to access the curated audience that I’ve built. Once again, thank you for being here. Only people interested in actively improving sales strategy and skills would listen to my show. And what kinds of potential advertisers care about such things? Well, for one, it’s advertisers that would have high CLV, customer lifetime value, and are selling sales-related products and services. If a company has a CLV in the five figures or above range, they don’t need to see a lot of conversion for their bet to pay off. In fact, the risk reward is pretty obvious for them. They make a small bet with marketing dollars and worst case scenario get exposure to a group of listeners who become more familiar with them and are more or less the perfect audience for those advertisers.

Just like the woman selling tamales, the key to my campaign was selling food to the hungry people. You may know this concept as relevance. Pick a particular tactic and you can be sure that someone has already declared its downfall. Cold email’s dead. Cold calling doesn’t work. LinkedIn is over. You missed it. The moment’s gone. I say wrong, wrong, wrong.

Reaching prospects with a sales message is as old as civilized society, my friend. The only thing that’s changed is how we reach people. The key isn’t the channel. The key to it all is relevance. Doing the work first to understand your prospect and her motivations, her options, her opportunities, and of course her pain goes a long way to increase the potency of your message. So what did I do? I ultimately set my sights on companies with 50 to 500 people who are selling software for salespeople and have a strong online marketing presence and relatively high CLV. And that was the key to my campaign, selling food to hungry people, and that was my strategy.

Liston W.:
Now we need to get the ball rolling on execution. I got my strategy in place, and I needed a way to make this whole thing happen without taking over all of my time. After all, I have a podcast to write and produce, and I have a business to run outside of this. And the plan started with prospects. Where would I find these hungry people?

Before I get into the nuts and bolts of where I found prospects, I want to give you two notes. Note number one, the strategy of the campaign came from me, and the execution of the research and database building was done by my assistant. If you can divide the labor in this way, you will save yourself a ton of time and money and actually get the work done without losing the core learnings that come from it. If you’re in an SDR or BDR role, this could equally apply to you. Maybe you’re doing some of this research now. But once you figure it out, you can rinse and repeat and maybe outsource some of this.

Note number two, I spoke to two friends during the planning stages of this campaign. So before any of this stuff I mentioned about my theories about who I’m going to go after, and why, and who the hungry people are, I talked to friends who’ve done it. They both shared with me how they’d successfully sold advertising on their podcasts, and that’s a big deal. There’s no need to start from scratch when plenty of other people have already done it. Find them, ask them, and take a copious amount of notes. So those are my two notes.

Now, you’re probably wondering where did I find prospects. So to begin the campaign, I started with the hypothesis that companies already spending money on brand awareness marketing would be most likely to sponsor the podcast. I guessed that I would need about 200 prospects to begin to meet the goal of monetizing the podcast in Q1 2020, so we looked for sales conferences and their sponsors. After looking around at about 30 different conferences, we began to see the same companies come up again and again. Company names and the conferences that they sponsored were captured and saved on a spreadsheet. This yielded a list of about 150 companies.

With this list of 150, my assistant went out and found a C- or VP-level marketing person on LinkedIn Sales Navigator and save their contact information to a spreadsheet using LeadIQ. We then verified their emails using NeverBounce to minimize the chances of sending emails to bad email addresses. This cut the size of the list even further. And it’s so sad as you do all of this hard work to put prospects on the spreadsheet and see the numbers start dwindling quickly as you’re not able to find good contact information. But so it goes. It’s all part of the game here.

Now, I’ll get to the particulars of what I did to actually contact prospects later, but we have a more pressing problem at this moment. My original target was 200 prospects, but we had quite a bit less than that. We needed to add more prospects. Where would they come from? We’ve already looked at our sales conferences. That was the first hypothesis, and that group is already exhausted. So the next pool of prospects came from G2,, also G2 Crowd as it’s called. It’s just a software review site. The site has categories of software and one of those categories is sales. Under sales are sub categories like CRM, sales enablement, sales engagement, on, and on, and on.

One thing to know about G2 is that their business model is lead generation. Companies listed on G2 pay for leads that originate from their site. So why does that matter? Well, again, we want to sell food to hungry people. Companies that are invested in their G2 presence are almost certainly paying G2 to generate leads. G2 provides direct response marketing rather than brand awareness marketing, meaning the goal is to get conversions directly from the site. And that’s not exactly what I’m offering, but finding advertisers on G2 at least shows that a company is willing to try a variety of different marketing channels. And for the purpose of this campaign, I’d say good enough.

So using the lists on G2, another 200 or so leads were generated and added to the spreadsheet. Company names were then enriched with a key point of contact. Once again, email addresses were verified, bad emails were pruned from the list. Now, it’s worth noting here that your prospecting net should err on the side of being small, assuming you’re at least somewhat specialized and not a commodity. The original unedited list that came back from my assistant, they had well over 350 prospect companies. Each time the list came back, I reviewed, yes, I reviewed, each individual new prospect. I visited their website or their LinkedIn page to make a determination about fit. Nearly half of the companies didn’t make the cut, and I was able to establish richer guidelines for ideal prospects.

Now, I’m not going to lie to you. This is a pain. It really is. But this process, it’s also allowed me to get more clarity about who my prospect is and why. It also helped my assistant better understand who was a good lead and who wasn’t. And just like that, snap your fingers. It was nearly instantaneous to get to this point. We had a list of about 200 prospects in the campaign. So that’s how I found my prospects, and now I was ready to start contacting them.

I think of the mechanics of a sales campaign kind of like building a bookshelf from Ikea. With the right parts, and the right schematic, and the right steps taken in the right order, I’ll have my bookshelf. So here are my ingredients. I know what my strategy is. I know who I’m going to contact and more or less why I’m contacting them. I have a strong reason. Now I need a sales plan, a campaign plan, a way to put all of this together. And shouldn’t you plan a sales campaign with at least the same level of dignity as an Ikea bookshelf? Yes, I agree. We’re on the same page.

So I had four considerations in setting up the sales campaign. The first was buying style. How do people like to buy things like what I’m selling? The second is the sales process itself, which I want to align to their buying style. The third is what I had to make in order to execute the whole thing. And the fourth was all of the tools that I needed in place to make it run as seamlessly and as scalable as I possibly could.

So first up, buying style. I think of buying style as being a spectrum between transactional and relational. So on one end of the spectrum, transactional buying is what we do with simple, easy-to-understand, and relatively low priced products. A $9 Ikea lamp doesn’t need a pitch or an explanation. It’s there on the shelf. You just understand it, and you buy it or you don’t.

On the opposite end is the most complex and expensive buying style, the relational kind. It requires education, consultation, time, expertise, political and social maneuvering, compromise, and more. This is closer to what you and I do. Now, in many settings, advertising can be very transactional. You can log into Google or Facebook right now and purchase ads no problem, especially if I’m selling to people who are used to doing a lot of digital ads. But I didn’t want to take a transactional approach with the advertising on my podcast because, number one, I knew it would diminish my value proposition and, number two, I only wanted advertisers who I actually liked and felt good about promoting on the show. So I wanted to make the campaign as personal as I could while also keeping it efficient.

I figured two things. Prospects probably didn’t want to spend too much time with me, charming as I am, and enough volume would be critical in executing the campaign. I also knew that campaign would flop if my podcast advertising were presented as simple, you know, advertising. Some buyers would see the ads as transactional, a total commodity. My prices would suffer as a result. Plus, in my opinion, it’s absolutely the wrong metaphor. What I offer here is not just advertising, it’s an implicit endorsement, like a conference. So instead, I needed a process that didn’t include self-service and provided a different framing for the purchase. So I never framed it as podcast advertising. I framed it as weekly conference sponsorship in your ideal market. What sounds more valuable to you?

So now the process. If we envision the bookshelf fully built, we work backwards from there step by step. The process started with outreach over email and LinkedIn. The sole purpose of outreach was to make prospects aware of how I could help and generate replies. Once I had a reply, I transitioned from stranger to engaged prospect, and the sole purpose of that step is to book a meeting. Sometimes people would book a meeting with me directly, other times there was a quick email exchange or a phone call first. Once a meeting was booked, I ran in incredibly simple sales process. The reason for that, of course, advertising is pretty well understood. Plus, it’s not a huge purchasing decision. I imagined a single 20-minute call that would bring the prospect to a decision about whether there is a conceptual fit and how they wanted to proceed.

Now, that’s the process. Here’s what I had to make. I needed to make stuff to execute the campaign quickly and effectively. I always start with messaging. So I’m asking myself, “What story am I going to tell about this?” I already mentioned the framing of the podcast sponsorship opportunity, which was critical. I also had messages about the podcast itself and how it’s different. For instance, my shows are scripted and they’re solo shows, and I’m always trying to bring research, and psychology, and economics into the discussion. I want this to be a richer discussion rather than me just sitting here telling you my opinion about everything. And I also imagined what the prospects would be thinking and feeling, what questions they’d have, the level of knowledge they’d have, which I was largely wrong about, and their likely objections. Then I had to implement the messages by writing my email campaign, a LinkedIn welcome message, a video script to include a video in the first email, and the slide deck I’d used to present on the initial call. All total, that stuff took me about two full work days to create spaced out over a week. So that’s when I had to make. Now I needed some tools in place to make sure the whole thing ran effectively.

The good thing about tools is you can think of them as infrastructure for your business. Once they’re in place, yes, they need to be maintained, but they don’t need to be recreated. Where I live in Portland, there are 12 bridges that go over the Willamette River connecting the west side of the city to the east side. Once you build a bridge, you don’t need to do it again. You just have to maintain it. And that’s how I think of these sales tools. So a lot of this infrastructure I had in place already, but I do want to share with you what was there because I get asked all the time. So here’s what I used. And every resource that I’ve mentioned earlier in the show right here about my tools and later in the show is linked in the show notes. Some of those links are affiliate links so I will get credit or even some sort of payout if you buy something.

So here we go. These are the tools that I used. I first needed a way to send an email drip campaign directly from my inbox, so it had to be an email from me to someone else not going through an email marketing tool. So for that, I highly recommend Mixmax for this. It works with G Suite, which is important, and I do have an affiliate link below. And as I said earlier in the show, they are a paid sponsor, not of this episode, but of Modern Sales.

The second thing is I needed a way to embed video thumbnails and shoot custom videos for each prospect. I use Loom video for this. I love the high quality of the video. I love the way it looks. I love how you can interact with it. I love the compatibility with Slack, and LinkedIn, and all these other various tools that are important in sales. I also bought their pro plan so that I could add a CTA button, a call to action button, to each video allowing prospects to book a meeting directly on the video.

The next thing I needed was a slide-making tool. I use Google Slides because it allows me to send a live link to prospects so they’re always seeing the most up-to-date version of the slides as I make changes, whether that’s adding or subtracting information. Maybe I want to update the prices. I always want people to see the most up-to-date version, so I do have one single Google Slide deck that I use for everybody.

I also needed LinkedIn Sales Navigator to get data and message people. As I said earlier, I used LeadIQ to get the contact information of people, and I’d also use that to get direct dial numbers as I noticed that people are opening or interacting with the campaign. I needed a CRM to manage the whole darn thing and make calling a whole lot easier. So my CRM has built-in calling. That’s important. And finally, I have PandaDoc to manage contract signatures. Now, I know this sounds like a lot, but once it’s all in place, trust me, it is a breeze to use.

So those are the tools that I had in place, and now it was time to execute my campaign. Because with all of this, I had a clear picture of what it would take to bring advertisers onto the podcast. Back to my Ikea example, I knew what the bookshelf would look like, and I knew how to build it. Now it was time to finally go to work and execute.

The thing about that, though, as Mike Tyson once said, is everyone has a plan until they get punched in the mouth. When he said it, Mike Tyson knew that there’s a funny thing about plans. He’d actually just been beaten by Evander Holyfield right before he said this. And the thing about plans is that they’re useful in that they allow us to be strategic about choices. When we plan, we make decisions based on the best information we have right now.

So again, back to my core strategy. The big idea was I was going to reach out to companies selling software to help salespeople to see if they were interested in learning more about advertising on my podcast. The thing that was in it for them was that they could reach a curated sales audience who’s loyal and has some level of trust built up in me. Or maybe a better way to say that is I’ve built some level of trust with my audience. So instead of asking people directly when I went out to these prospects, I went with a question that assumed nothing. And all I asked them, the call to action in these emails, was, are you the person who handles podcasting advertising at insert name of company. Now, this yielded plenty of responses right away and it worked as a call to action. The subject line was also doing its job. I was pleased with the email open rate across the campaign. Initially, though, the reply rate looked a little bit too low for my taste so I made that change to the campaign I mentioned earlier. I added videos using Loom. Some of the videos were personalized to each recipient. Some people received a generic video I made for the campaign. In both conditions, the reply rate went up, but personalized videos seemed to have a slight edge.

The next thing is phone calls. And calls, obviously you must know this, make a huge difference. There were basically two kinds of email responses I received, people who would say, “Let’s talk about this,” or, “Send me some more info.” Now, I knew that people treating this as transactional would not be a good fit, and so initially I was hesitant to send information without a meeting because, honestly, I positioned the podcast as a little bit of a commodity because of the selling and buying style that we were following.

Eventually, I did start sending information with the assumption that a greater number of more educated prospects was a good thing, especially if it was my only chance to inform a particular prospect. The way I solved for that was I started sending custom-recorded videos to individuals who requested more information rather than the deck itself. The reason is because I learned, and I’m not surprised by this, this is what I thought going in, calls are the key to serious prospects. This is true in pretty much every setting. If someone won’t commit to a phone call, they’re probably not a real prospect. There are two ways to get them to commit, number one, over email or similar LinkedIn message and, number two, using the phone to set up a phone call. So yeah, you can call your prospects. It yields a much better conversion rate if you have a direct dial. And especially once you get a response from them, any response, I’m a big advocate of picking up the phone and calling.

Next thing is follow-up. The structure and quality of your sales meetings obviously is critical. And I’ve recorded a series on sales meetings if you want to go back and listen to that. It’s a big part of the book that I’m writing, so there’s more to say about it than I can possibly cover here. But what happens after those meetings is also critical. So initially, my follow-up was writing a custom email after every single meeting followed by a routine follow-up based upon the schedule the prospect shows. So if they said, “Let me think about it for a week,” or, “I need to talk this over with so-and-so, and that’ll be in two weeks,” I would send a note to follow up at that interval.

After about three or four of those calls, it became really clear that prospects all needed four things in the follow-up, and number one is a recap of their organizational goals and how the podcast could help them reach those goals, number two, a link to the slide deck, I presented, number three, links to representative podcast episodes. I am curious if anybody actually listened to those. Who knows. And number four, some information about next steps, which was also available in the deck. There isn’t really a sense in writing this email over and over again, so I created an email template. I saved it in Mixmax. That allowed me to standardize the follow-up of items two through four. And all I would have to do is write the recap of their organizational goals and anything that that particular prospect mentioned to me on the phone.

So that was the whole campaign. Now here are the results. I got to say, given that this campaign is only about two months old, I’m quite pleased with the results. Here’s a quick overview of the results. And by the way, I have articles that I’ve linked in the show notes that have graphics that I’ve produced about how the campaign was structured. I also have a table detailing what I’m about to say in the results. So if you like to see things and you want to read them and spend a little bit more time, those articles are linked in the show notes.

So I had 209 people enter the campaign. I had 125 total people opened at least one email, meaning 60% of the people opened an email. 10% of the people who opened clicked a link. 24% of the people who opened replied to my email, positive or negative. It didn’t matter. I got 10 meetings out of that group, and that gives me an effective meeting rate of 8%, which is pretty good. I’d like to see that number go up. But overall, I’m pretty happy with it given that this is the first exposure people have to what I’m doing.

Which brings us to plans for improving the campaign. This isn’t done. I’m going to continue to sell advertising on this podcast, and so I’ve been thinking about what to do to iterate on the campaign. One thing I’d recommend to you is to build this into your process at a regular interval. You should be making adjustments as you go. The biggest opportunities that I see to improve upon the campaign are adjusting the initial messaging and continue testing through to meetings, meaning my goal here is to actually meet with people. Whether or not they buy, I do have some control over that, but not a lot. I have a lot of control over the earlier parts, so I want to make sure that those are set up properly so that I can maximize the number of meetings I’m getting because I feel pretty confident once I get into those meetings.

The next thing I can do is find a new cohort or category of prospects. I use the sales conferences. I use G2. There’s a variety of other places I can go to find people who might want to reach you, dear listener. So I will go out and look for those.

The next thing is to find new contacts at existing accounts that haven’t engaged. So like I just said, 125 people opened an email, which means 84 of the 209 accounts never opened an email. Well, actually, technically what it means is 84 of those accounts didn’t report that the email was open. It’s another thing for another day. But basically, I know that they didn’t respond. So given that I got 30 replies out of 209 people, I have plenty of reasons to go back to those folks. So I can either find new contacts at existing accounts or even go back to some of those same contacts who haven’t engaged.

The next thing is to create a short follow-up campaign with existing prospects who did express some interest but the timing was just plain wrong. So that will be a separate campaign. And you can see that this is starting to branch out and get more and more complicated.

The next thing I’d do is create a short piece of educational content about the benefits of podcast advertising and how it works. The reason I want to do that is because I talked to several people who probably didn’t want to admit it but it was clear to me in the process that they didn’t know a lot about podcasts. They didn’t know a lot about what could be tracked or not tracked on podcasts. They didn’t know about the analytics. They just didn’t really have a good understanding of the landscape. So for people like that, I think I can follow up with some educational content and be a resource for them on how podcast advertising works, whether they advertise on my show or not, so that could help them get to a point of making a more informed decision about whether they want to advertise on a podcast.

So that’s it. We’ve reached the end. That’s my entire story of how the first podcast monetization campaign went. I know this is a bit of a longer episode, but obviously I’ve learned a lot. The campaign has been successful, and there is plenty of room for improvement. So that’s it for this episode of Modern Sales. In next week’s episode, I will be bringing you a short series on personality tests and what they can tell us, if anything, and the surprising origin of personality tests that may make me ask you, “What is your sign?”

If you aren’t already subscribed to this podcast, please do so by clicking the subscribe button. It would greatly help me get the word out about this podcast. If you are nice enough to go leave a review on Apple podcasts, or iTunes if you’re still dealing with that, but I’d love it if you left a review of this podcast that’ll help new people discover us. You can also get notified of all podcast episodes and get my daily, yes, daily, email newsletter with a custom hand-drawing every single time that I make just for you. All you have to do is go to Those daily sales insights are totally free. You can unsubscribe any time. And yes, I promise, you will stick around for the drawings. If you’d like to subscribe to that newsletter, you can get it in the show notes now.

Thank you to everyone who makes this podcast possible. Juan Perez is our editor. Mary Ann Nocum is our show assistant. The show theme, and ad music, and much of the music on today’s episode was produced by me, Liston Witherill, And some of the other show music is by Logan Nickleson at Music for Makers. 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