2022 Growth Trends: Personal Branding with Darryl Praill

Natalie Marcotullio
January 18, 2022

We spoke with Darryl Praill the CRO VanillaSoft, a sales engagement platform that gives your sales team the tools they need to engage, qualify, and close sales all in one place.

Darryl was also voted one of the top ten SaaS branding experts, top three marketers on LinkedIn, top 32 sales leaders on LinkedIn, top 50 sales keynote speakers and is the podcast host of Inside Inside Sales.

In this interview we discuss:

  • How to write a stellar email
  • Benefits of events beyond marketing
  • Building a social brand without gaming the algorithm

To start, give a high-level introduction of yourself

I’m the Chief Revenue Officer here at VanillaSoft. VanillaSoft is a sales engagement platform which just means we help your reps make a heck of a lot more touches with your prospects using lots of channels, phone, email, social, direct mail, etc.

By education, I’m a computer programmer, but over many years I slowly got into sales, sales engineer, product management, product marketing, and marketing.

Over the last 20 years, I’ve gone back and forth in senior leadership roles, from being a VP of Marketing or VP of Sales to being a CMO. And most recently, I’ve become a CRO. So basically, I get revenue.

What is a recent innovative marketing campaign that your team conducted?

There’s a LinkedIn bracket going on right now, there were 200 marketers at first that became 32. Then we bracketed off. And when you asked for my information, I was down to the top eight.

Now I’m top three. In fact, the contest is going on as we record this to figure out who’s number one.

How you respond in these circumstances is always interesting. It shows you the depth of your skills. Its opportunity is what it is, can you react fast enough?

I had progressed for the first two rounds, and I found myself up against Udi Ledergor, if you don’t know Udi, Udi is the CMO of Gong. Gong is only a multi-billion dollar valued company with hundreds upon hundreds of millions of dollars in funding.

And Udi is a legend, so I said to my team I’m screwed don’t even bother. Let’s go out quietly.

Then I went off to England for some work and my team totally ignored me. They did this campaign all on their own with no permission and sent an email blast.

This is a brilliant example of guerrilla marketing. They sent an email blast and followed all of the best rules behind the channel.

To start, let’s break down why emails work and why they don’t work. And then this will make sense why this actually worked.

Over 80% of emails are going to be deleted before they’re ever opened. It’s been researched. Over 80% of your emails are going to be viewed on a mobile device. That’s also been researched.

So why do people open an email at all? Because they’re deleting so much of it? They open it because of the subject line.

The subject line’s gotta be killer.

What makes a good subject line? Well, a good subject line is five words or less. Fewer words are better, a little bit of adoration or motion or personality in it is a good thing. It’s clickbait. You’re teasing them to want to know more. That’s the first thing.

The second thing about the email is it’s got to fit in two screens of your mobile device. Max one screen better. Typically, you’re going to have three to four paragraphs. That first paragraph has got to be a trigger or make it personable so that it prompts them to read more.

Think about LinkedIn when you see a post and it says … read more. What made you click on read more. Email is the same way, there’s gotta be a very clear call to action, a very clear next step, and it’s got to resonate and be personalized to them.

That’s what makes email work. Too many people try to say too much. They try to do too much.

They do feature pitches, and if you’re a growth marketer trying to get a product off the ground, you’re enamored with your product and you want to tell the world, but nobody cares. It doesn’t relate to them.

What my team did was they said, I’m basically screwed. Their subject line was three words and it had an emoji, which, by the way, emojis increase open rates.

The subject line was “I’m basically toast” and the emoji was a picture of toast, and that was it. We had huge open rates on it.

The email is literally two paragraphs and a big Giphy. And the big gif is this Asian fellow staring at the screen and all it says on it is, I’m screwed.

The text says:

“Look, it’s Friday, you and I both know you don’t want to be working, so take a break and vote for me as one of the top marketers on LinkedIn. I’m going to be honest with you. I’m up against Udi Ledergor the CMO of Gong. My chances of winning this round are slim. I’d love if you vote for me, so I lose with a little bit of dignity.”

I got so many votes from that. I had so many marketers come up to me to say this email was so funny, so relatable, I voted for you just because it was so well done.

Before they sent this email, I think it was like 70% had voted in favor of Udi, and less than 30% voted in favor of me because there’s a third option that says none of the above.

When we’re all said and done, I think the numbers had basically gone 60 40 in the end. For us, that’s the comeback that this campaign did, and I won.

That’s how I went from being top eight, which is what you announced, and now being in the top three.

Was it all the email that caused the success or also the work you put into your social branding?

The answer is all of the above, but I’ll be more specific.

This was the third round in the post. I had already gone to them twice previously. So this third round is an element of exhaustion for them, and they should not do anything.

Which is why I told my team not to bother. I’m like, I can’t keep going back to the well and taking advantage of the generosity of my community.

However, you’re spot on when you build a personal brand and you do that honestly by consistently adding value and educating or entertaining or informing or challenging in a way that connects and resonates with your target audience.

When you do that and they choose to intentionally follow you, there’s a bond there. That first following is saying that they like you and what you’re doing.

It’s kind of like, I’m going to date myself with these references, when somebody leaves the radio station or local newscast or your favorite show and you feel sad because you really like them, but you’ve never met them.

It shouldn’t have worked, but the email was done so well. Combined with that there’s a definite sense of loyalty and obligation that they view me as a peer and that’s something they want to lift up and support.

That’s an awesome lesson there. Build your community, folks because you never know you’re going to need it.

What is one marketing strategy or mindset that you’re really getting excited about in 2022?

It’s events. I tend to be the primary public speaker for the company. That means I get to be on stage, I love that. I can pace again, I can work the audience, I get reactions. I can look down at faces and they’re smiling at me.

But what was so interesting was the rest of my team said the same thing, and not all of them go to shows. They just help support the shows. When I talk to the staff, who have been working the booth, they love it.

The reaction after the one we just went to, it was a three-day event, they were like, I can’t believe three days has gone by.

Not only from a marketing point of view but also from a camaraderie point of view for the team to be together person to person, side by side, working together.

It builds the morale of the team. Which makes my team more productive and more effective, makes them more loyal, more dedicated, and keeps my turnover down. If there are times when I call upon them to do a little extra work, a little bit of overtime, they’re in it.

There are so many related benefits to live events that are not directly attributable to lead flow or revenue that it’s a brilliant investment for the organization.

What is one marketing mindset or strategy you’re ready to see end this year?

We got a variety of answers on this one when I pulled the team, but there was an overriding theme. There’s an exhaustion on LinkedIn in a couple of different manners, one being polls.

We’re just done with polls. Right.

And the second and related note is the gamification of the algorithm. So the content is being driven towards timeline, placement, and reach. And we’re tired of that.

You don’t need to use all 3000 characters to get your point across and my day is busy.

I know we’re trying to get dwell time because dwell time implies interest and interest gets more reach and therefore you get to a bigger audience, but enough already.

We’re kind of tired of the whole social media gamification that has taken place. We know that’s part of the process. We know it’s how you build the community, but we’d like to get back to something more substantial.

How can people be successful on LinkedIn while going against the algorithm?

I get asked that question a lot. People come to me and say, how did you get to where you were?

Because I started with nothing and I’ve done relatively well and I say times have changed, so it’s harder with full admission. I got in at a little earlier time, but what hasn’t changed is good engagement. Consistency goes so far.

I’ll get this all the time, “I do content Darryl and I get zero engagement”. You’re looking at the wrong metric.

What you need to understand is that 90% of the people on LinkedIn are lurkers. They never like they never comment. They just view so you may think you’ve got zero engagement.

The reality is hundreds of people have looked at your content and been influenced by you.

The second thing about LinkedIn is you actually make as much noise, sometimes more in the comments and not in the posts.

One of the things that I did that still works to this day to get notoriety and reach was I would follow the influencers in my space, the tier one influencers, and often the tier two influencers. In other words, the people who are most active on the tier one comments.

When they would post something, usually I would agree with 75% on what they said, and I might have a different opinion on 25%. That’s not uncommon.

Instead of my comment being preached at a boy, way to go, love it, which is all useless. I would add value by saying, I really appreciate here and here, but I disagree with you here. And this is why.

What was amazing is my comment was often unique in that thread of comments because everybody else was doing an Attaboy and mine was actually discussing.

Then that original poster who probably is a major influencer, responds to you. We’d end up getting into a conversation that was bigger in the comments than was in the original post, with more contributions from more people.

At that point in time, I would then reach out directly because I was already connected with them and say:

“Hey, Natalie, haven’t talked directly before. I’ve been following you for a while. Looks like we’re onto something with this conversation going on right now. Let’s say you and I do a webinar together on this topic. I’ll do all the work and you show up. I’ll share the leads, minimal involvement for you. But I think we got a winning topic.”

Never once did they say no, and these are major players. And the beauty of doing that is other people see you with those players and say, “oh, Natalie is hanging with Darryl. I love Natalie. Darryl must be great.”

That’s how it grows. You can still do all of this today. But the biggest thing is consistency.

Promote your services or how people can get in touch with you?

As you might imagine, LinkedIn is the easiest. But if you’re not sure, just Google my last name Praill. I’m all over Google. You can go right to my personal website, darrylpraill.com.

And as far as where I work, I work for a company called VanillaSoft. If you want your sales reps to double or triple their pipeline. Talk to me. I can show you how to do it.

What’s interesting is Gartner recently declared it an L one technology investment.

Meaning they’re going to say you need good data, you need a CRM, you need marketing automation, and you need sales engagement, so I can help you with the sales engagement side.

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