Welcome to Episode 24 of the Sales Influencer Series, a podcast featuring the brightest minds in B2B sales and marketing.

In episode 24, Ambition's Jeremy Boudinet welcomes TrustRadius Director of Business Development Dailius (Dail) Wilson, who brings a millennial focus to this episode - talking all things millennials in sales.

Ep 24. The Millennial Sales Ep with Dailius Wilson


Interview Topics 

Introductions 0:00 - 6:35.

Dail Wilson is a rising star in the tech sales world. He's an Australia-born lifelong entrepreneur and sales leader who's spent his whole life helping others learn the world of sales, marketing and technology.

Dail is the newly-christened VP of Business Development for TrustRadius. His strength has always been the ability to connect with the C-Level Suite and his goal today is to discuss innovative techniques for how millennials can break through to high-level prospects, build their own brands, and develop leadership skills fit for the new world of B2B sales. 

Dail's father was the VP of Sales for HP-APAC, so he was exposed at a young age to global technology sales. Early on, he developed a passion for technology, sales, marketing and working with young companies.

Dail's Core Drivers of B2B Lead Generation. 6:35 - 14:01. 

Driving leads in B2B is difficult, because you can never have the volume you can get with B2C. So there's less margin for error. Once you engage at a B2B level, that relationship lasts a lot longer than at a B2C level, so it's important to maximize those opportunities. One major area to focus on is in the way we prospect, find and engage leads - we have to engage them in a unique, creative way that elicits a response. 

A great way to do that is to find a point of mutual interest, for interest Harry Potter or a band, via social channels and mention that in the initial outreach. A mistake is to say, I stumbled on your LinkedIn and saw you like fishing. What Dail prefers to do is casually mention it in a way that doesn't let the prospect know he was doing research on them.

How Reps Should Think About Marketing. 14:01 - 20:00. 

You should also position yourself as a social leader - you should create some kind of brand identity to show you are an authority on the identity. People who say they're an expert often are not one. Writing material that the industry will be interested in and making sure it gets in the hands of media sites where your audience will be, then people believe that you're an expert and you no longer have to claim that yourself. 

How to Disarm and Engage Prospects. 20:00 - 32:53. 

A fundamental tenant of sales is confidence. With that said, you shouldn't mix confidence and arrogance. The best salespeople are people who are likeable and chameleon-like, in that they match their character for different audiences.

There's also something Dail likes to call the Zebra + Cheetah approach. Salespeople are typically perceived as cheetahs, in that they're hunters. Zebras, on the other hand, are unique and interesting to look at, but also a little bit strange.  The key is that you appear interesting and zebra-like to draw prospects in and open them up to initial conversations. Then, when it's time to close, have the cheetah mentality come out and close the deal. 

Dail also believes in nurturing your entire contact list over the lifetime of your experience. You want to prioritize your contact list and help people who can also help you over time. That includes existing customers and connections in the industry. When you're working with high-level people and building a contact list that is C-Level or close, you're helping yourself not only close deals but build a powerful network to help spur your career growth. People are too myopic and short-term - they need to see this as a medium-term strategy. "How do I get powerful people in my network over a longer period of time?" Dail does this by reaching out and complimenting people on something small. 

Dail's Go-To Hack to C-Level Cold Email. 32:53 - 40:30. 

Dail uses a controversial tactic to get through to C-Level executives that he swears by. He does two things. First, he tries cold email with a subject line about their family or some personal matter that - in the body of the email - admits the deceptive opening and asks for empathy by admitting that Dail is a young, hungry-to-the-point-of-desperate salesperson looking to make it.

The second tactic Dail uses is physical gifts. He prefers to research interests, send a well thought-out gift, often handmade, that's inexpensive, easy-to-make, but also impactful. He also believes in following up with clients he's closed by giving small gifts to everyone in the office with a personalized letter to the CEO.  Dail also brings something personal to in-person meetings as a gift to the CEO. And at all times, stay humble yet helpful.

How to Contact Dail and TrustRadius. 40:30 - 43:49. 

TrustRadius helps software companies centralize and showcase their customer success. Email Dail at dw@trustradius.com.  If you want to improve conversions, source social proof and build new case studies, sites like TrustRadius are a great place to start.

Lastly, we encourage you to reach out to Dail. He is one of the most enjoyable, genuine people in sales and he loves to meet new people. Contact him via email, LinkedIn or Twitter.

The Sales Influencer Series Library

To check out further episodes and see why CloserIQ has ranked the Sales Influencer Series as one of the very best sales podcasts of 2016, just click on the links below. 

Episode 1. John Barrows

Episode 2. Lori Richardson

Episode 3. Max Altschuler

Episode 4. Matt Heinz

Episode 5. Mark Leslie

Episode 6. Kyle Porter

Episode 7. Jon Bradford

Episode 8. Eks Anderson

Episode 9. Matt Hottle

Episode 10. Heather Morgan

Episode 11. Ilan Ferdman

​Episode 12. Ryan Jenkins

Episode 13. Tamara Schenk

Episode 14. Mike Weinberg

Episode 15. Scott Britton

Episode 16. Mark Kosoglow

Episode 17. Dionne Mischler

Episode 18. Ken Barton

Episode 19. Kevin Karner

Episode 20. Jill Rowley

Episode 21. Brandon Redlinger

Episode 22. Will Wickey

Episode 23. Drew Woodcock

Episode 24. Dail Wilson

Episode 25. Nathan Sexton

Episode 26. Tucker Max

Episode 27. Bruce Tulgan

Episode 28. Dallas Hogensen

Episode 29. Morgan J. Ingram

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