Episode #271 – Darryl Prail

Why You Must Hyper-Personalize Your Digital Sales Approach

Darryl Praill


Darryl Praill

Darryl Praill is the CRO at VanillaSoft, a Top 50 Sales Keynote Speaker, a Top 10 Branding Expert, a social media influencer, a category-leading podcaster, and a serial entrepreneur. He’s raised almost $100 million in funding, been an acquirer and acquired, and gone public. He’s only been fired once.

Darryl admits that digital selling is hard because there’s a lot of noise out there. The sales industry has a propensity toward reusing what’s been done before—the same emails, same LinkedIn sequences, the same ad layout, etc. and it becomes noise. So what do you need to do to improve? Hear Darryl’s thoughts in this episode of Sales Reinvented!

In this episode of @SalesReinvented, @ohpinion8ted shares why you must hyper-personalize your digital sales approach. Don’t miss it! #SalesReinvented #Sales #DigitalSelling #Personalize #Strategy #ThoughtLeadershipClick To Tweet

Outline of This Episode

  • [0:53] The difference between social selling and digital selling
  • [2:41] Understand your customer profile
  • [5:15] Darryl’s evolving digital selling strategy
  • [8:50] The attributes/characteristics of a great digital seller
  • [12:07] Tools, techniques, and strategies to improve digital selling
  • [16:17] Top 3 digital selling dos and digital selling and don’ts
  • [19:19] Build thought leadership on social media

Understand your ideal customer profile and personas

Who are you targeting? It can’t just be “anyone in high tech.” You have to be granular. Having 10+ granular customer profiles is fine. Then you develop your personas within those profiles. Darryl is the CRO of VanillaSoft and they target people who are the head of sales, head of marketing, head of operations, head of finance, and the head of IT. If you don’t know their world, you can’t create hyper-personalized messaging or content that resonates with them. Salespeople drop the ball by being too generic. You need to be specific to catch more fish.

Darryl’s evolving digital selling strategy

Darryl’s digital strategy starts with account-based marketing and selling. You identify your ICPs and personas and build lists. This can give you 50 unique lists with a specific message. Then you need to advertise where they live (Google, LinkedIn, industry forums, etc.). When they come to your website, you want to be able to track their IP to see where they’re coming from. You present content on the website related to that persona. It’s about building a collection of signals.

Then, you put programs in place to nurture and grow the leads. It takes 9–12 touches before someone responds. So you want to use a combination of social, email, SMS, and even a phone call to get them to engage. Make sure you have a sales enablement platform in place so you can see when they’ve opened the content, if they’ve shared it, if they’ve watched a video. All of these things are signals that help you have a hyper-personalized engagement attempt to get someone to a conversation.

What does @ohpinion8ted digital selling strategy look like? Why is it always evolving? He shares more in this episode of @SalesReinvented! #SalesReinvented #Sales #Personalize #Strategy #ThoughtLeadershipClick To Tweet

The attributes/characteristics of a great digital seller

A great salesperson logs into their CRM and looks for signs of engagement or conversion. If there is a signal, they use their digital tools to identify their top targets and get them in cadences to engage with them.

Secondly, they must schedule time to go to forums, discussion groups, or wherever conversations are taking place and engage without pitching. It’s about establishing your own brand and thought leadership. Darryl emphasizes that you must also plan engagement so that everything is hyper-personalized to a prospect’s personas and signals.

You can’t send people a generic template email or social touch. You can’t look for shortcuts and means to spam people because it’s a “numbers game.” If you aren’t converting, it doesn’t matter what your numbers are. People buy from people and if you don’t make it relational and relevant to them, they won’t trust you or find you credible. The buyer will walk away. You’ll have spent a boatload of money with no ROI because you tried to scale and take shortcuts.

Engage in your community and contribute to conversations without the expectation of receiving anything in return. It’s a long game to build your reputation and street cred. But Darryl emphasizes that it’s amazing the volume of deals that come to you when people like and trust you. It’s the lowest acquisition cost and highest conversion rate.

Build thought leadership on social media

When Darryl started at VanillaSoft in 2017 he had zero social media presence. LinkedIn was simply a vehicle for his resume. He recognized that he didn’t have a lot of budget, so he couldn’t compete on a digital spend strategy. So he took the route of LinkedIn. He saw traction within 6 months when he had a crowd around a trade show booth.

One year later, after continuously sharing content on LinkedIn, that same trade show booth was packed. People knew his name. This was happening around the world. Everyone came to the booth looking for him. That’s when he learned branded content and contribution to conversations was a powerful driver.

VanillaSoft got a ton of business they wouldn’t have gotten otherwise. Nothing else had changed at the company. The only change was a personal brand presence geared toward building a network.

Why does engaging in #ThoughtLeadership make you a great digital seller? @ohpinion8ted shares some tips in this episode of @SalesReinvented! #SalesReinvented #Sales #Personalize #Strategy #DigitalSelling Click To Tweet

Resources & People Mentioned

Connect with Darryl Praill

Connect With Paul Watts


Audio Production and Show notes by

More About Darryl Praill

Are there any great Digital or Social Selling books that you highly recommend?

Move: The 4-question Go-to-Market Framework – It’s moreso a GoToMarket framework but digital plays big in the overall strategy.

Platform: Get Noticed in a Noisy WorldThis book is showing it’s age a wee bit but the concepts and approaches remain very relevant

Annual LinkedIn Algorithm Report Edition 2021 by Richard Van Der BlomIt’s an eBook but it will tell you exactly what you need to do on LinkedIn to be successful for social selling.

What do you most admire in the sphere of Digital or Social Selling and why? I do not have a single person I admire the most. There are several that are incredible but for different reasons. Specifically: Daniel Disney – he is the master of creating content and community using humor and integrity. Brynne Tillman – if you need a LinkedIn Social Selling expert who will tell you what you need to hear, then this is the woman who can change your life. Michael Hyatt – he’s personally used both digital and social selling to build a family business online, after being a print book published for decades. What an amazing transition.

Are there any aspects of your own Digital or Social Selling skills that you are working on improving at the moment? Trying very hard to get more engagement without falling into the trap of “playing the game” simply to get clicks and likes. 

Hobbies, Interests? Family, Camping, time with my wife and dog, news junkie, all things gadgets

How can our listeners contact with you? darrylpraill.com, LinkedIn, or Twitter.