
019: Value of Industry Expertise and Leveraging Video as a Sales Rep with Nathan Leary
05/01/19 • 31 min
Nathan Leary is an IT & Cybersecurity Sales Pro based in Austin, Texas. He is the host of Security + Brews Chat, which is a video series about actual IT problems. He has conversations with IT professionals over coffee, which positions him as an industry expert and a content creator. We discuss his early sales career, how he accidentally fell into IT (and loved it), and how he thinks about video, personal branding, and sales teaming with marketing to really add value to his buyers in the sales cycle.
Show highlights:
- 05:00 - Nathan selling Cutco knives as first sales job to haphazardly applying for SDR jobs after college, looking for a start up. Accidentally ended up in IT sales.
- 08:00 - How Nathan came to know and love cybersecurity without a background in it. He learned from talking to customers about their problems and listening.
- 13:00 - Starting the "Security and Brews Chat". Content in the sales process and include the personal branding piece. Nathan's goal is entertaining and valuable.
- 20:00 - Resources to get started with trending sales, marketing, and prospecting tactics like video. Find frameworks to make your content, then sales reps can plug and chug versus reinventing the wheel.
- 22:00 - How sales can approach marketing and brand managers to do bottoms-up messaging, versus waiting for it to trickle down. Nathan recommends Jake Dunlap for enabling sales to be digital brand ambassadors.
- 25:00 - find a company that lets you take an idea and run with it, especially as a sales rep if you're already taking content that marketing made and make it digestible.
- 28:00 - Frequency of posting content in 2019, don't dilute your message. How do you balance it with your job? It's okay not to scale your brand at a fast rate.
Nathan Leary is an IT & Cybersecurity Sales Pro based in Austin, Texas. He is the host of Security + Brews Chat, which is a video series about actual IT problems. He has conversations with IT professionals over coffee, which positions him as an industry expert and a content creator. We discuss his early sales career, how he accidentally fell into IT (and loved it), and how he thinks about video, personal branding, and sales teaming with marketing to really add value to his buyers in the sales cycle.
Show highlights:
- 05:00 - Nathan selling Cutco knives as first sales job to haphazardly applying for SDR jobs after college, looking for a start up. Accidentally ended up in IT sales.
- 08:00 - How Nathan came to know and love cybersecurity without a background in it. He learned from talking to customers about their problems and listening.
- 13:00 - Starting the "Security and Brews Chat". Content in the sales process and include the personal branding piece. Nathan's goal is entertaining and valuable.
- 20:00 - Resources to get started with trending sales, marketing, and prospecting tactics like video. Find frameworks to make your content, then sales reps can plug and chug versus reinventing the wheel.
- 22:00 - How sales can approach marketing and brand managers to do bottoms-up messaging, versus waiting for it to trickle down. Nathan recommends Jake Dunlap for enabling sales to be digital brand ambassadors.
- 25:00 - find a company that lets you take an idea and run with it, especially as a sales rep if you're already taking content that marketing made and make it digestible.
- 28:00 - Frequency of posting content in 2019, don't dilute your message. How do you balance it with your job? It's okay not to scale your brand at a fast rate.
Previous Episode

018: Answering Questions for Buyers with LinkedIn Videos in IT and Telecom Financing with Seth Thompson
Importance of sales reps answering buyer questions, on video, and then distributing the video on LinkedIn to engage buyers in a way that builds trust and sets appointments over time. Show highlights:
07:00 - Seth Thompson's thoughts on majoring in communications studies. Also part of Powerlifting club. How University of Iowa and athletics made Seth the professional he is today. Valuing intellectual and physical strength and persistence. Not going to get quick wins because guaranteed results are never guaranteed. 13:00 - Idea of injury prevention in competitive fitness is similar to avoiding burn out in business. Doing the little, boring things right over time with discipline to get payoff. 16:00 - How Seth ended up in Sales. Why Seth enjoys customer facing. 21:00 - UCaaS (Unified Communications) as a service. Seth provides different ways for those that provide those services financial programs to help end customers to make purchases. SMB space is Device-as-a-Service, how do I have the latest and greatest and not go out of date. 26:00 - How Seth is acting as an advocate for his customers on LinkedIn. Using social media, not to sell customers but to educate them. Need to be using video because that's the trend to personalize to buyers. Answer questions in a non-biased way. You don't have to be an expert, just try to be helpful. 32:00 - Your personal branding content doesn't have to be perfect! Don't have to over-script, can't fear failure, it's okay to look away from the camera and sound dumb. Putting something out there imperfect is better than never putting anything at all. 36:00 - The internet didn't allow us to share video the same way. Sales people are so well suited in this new age of selling. 37:00 - Concern about not being an industry expert to not technobabble. How do you add value to a customer base without being technical in a technical industry? Seth says that you don't have to share groundbreaking stuff. Think of the top 10 questions your customers ask and "who is Seth?". Start asking questions. That's all you have to do and 80% of buyers will have the same questions. 42:00 - in 6 months you will start seeing return, Sales Navigator. You have to cold call and follow-up after sharing and engaging on LinkedIn. 45:20 - Seth's company wants him to get better at LinkedIn and supports him to do it. Takes it back to his business and makes a case. Virtual networking events. "LinkedIn is digital industry event our our time." 48:00 - Every lead you got at a tradeshow doesn't call you back, either...don't know how to do it without selling." I'm a person first, and then I happen to sell this, too. That buyer must believe in you first to buy from you. 50:00 - Company can take your tools, but they can't take your personal brand. 52:30 - Job hopping and documenting your story on LinkedIn. Protect career. 54:00 - Sales Leaders, you want these personal branding sales reps on your team because they will bring you customers. 55:00 - "I trust Aaron, he trusts his company, so therefore I trust his company." 56:00 - a lot of buyers aren't active on LinkedIn, and even if they are your still have to cold call and email. 57:00 - Final thoughts from Seth, driving the point home about being okay with failure and finding ways to help other professionals in personal development and their jobs.
Next Episode

020: Power of Storytelling in Software, Managing Perceived Value with Kyle Lacy
Kyle Lacy is the VP of Marketing at Lessonly, a high-growth, venture-backed enterprise learning software. He is the author of 3 books and he did over 100 speaking engagements around the world between 2012 and 2014 when he was at Exact Target (now Salesforce Marketing Cloud). We discuss ego, your perceived value, storytelling, and using event marketing and personal branding to build meaningful connections with both buyers and peers.
Show highlights:
06:00 - Kyle's music background made him love marketing. Playing in a band got him interested in applying marketing concepts to get shows and promote. Music also taught Kyle how to tell a great story.
09:00 - Ego and your perceived value are reflections of your truth. And, they help you move forward when you're a young professional. One thing that Kyle learned early in his career: if you can't execute and deliver on your perceived value then you're a liar, whether you mean to or not. Kyle started his early career with his own firm, Brand Swag, which was both successful and struggled because of Kyle's ego early in his career.
12:30 - Then, Kyle was on the global speaking circuit at Exact Target (now Salesforce Marketing Cloud). He learned the importance of balancing his personal-self with his professional-self. He felt that if he wasn't careful, there actually wasn't a lot of distinction between Kyle the speaker and Kyle the human. While it was fun for him, his profession got somewhat over-consuming.
14:30 - From speaking so much around the globe, Kyle learned how to tell a story better than his competitors in software. While they were dumping marketing tool feature sets on audiences, Kyle was focused on how lives changed from email marketing and shared those wins, relevant to the audience, whether that was in Germany, Asia, or the US.
15:30 - Kyle is more nervous in front of 50 people or small networking room, but can more easily get in front of a huge room of people. How can I control my personal brand better? In a 3,000 person setting they cannot question you, but in a small setting you can. 18:00 - Executives building a personal brand and network. All LinkedIn is doing is a place to cultivate the network. You can only handle 100 relationships well, how do you handle the rest?
22:00 - managing tech stack, Kyle things about if it's helping to hit goals or not and if it's a nice to have, probably won't buy it as a narrow "point tool"
25:00 - SDRs at Lessonly tying marketing to SDR activity. Doing a lot of direct mail sends. Marketing is good at continuous rapid improvement, which works for SDR team which is very process driven. When running a test, need a kick-off and a retro. SDRs feel more creative under marketing and more license to test.
29:00 - 5 Tradeshows and 14 field events per territory. No presentations, doing "Taste of Lessonly" where prospects come and talk and hangout, versus come and have content. Why does it work? Great customers and people are tired of being sold to. Instead, people just love meeting peers and learn from each other. Don't like when vendor tells them what to do. For paid, doing Google and Bing but no real banner ads. Spends focus with direct mail sends.
33:00 - Paid versus direct mail when thinking about Contact-based approach. Do you spend $300 to maybe put a banner ad in front of that person, or send $100 to get highly personalized direct mail to their desk, and with tracking you know they got it? Too easy to buy tech to scale and automate, but really we're just human. Feature sets are old news, so how do you win
35:00 - Comes back to focus and targeted, who are your lists? If you feel you need leads you're just going to thow money wherever. VERSUS we want 10 top call centers in US, we are going to create campaigns specifically for that. It depends on go to market, because MailChimp is doing something different because their contract values. Fundamentals: know your deal size, know how many accounts you're going after.
39:00 - Getting ready for annual event. NOT a product conference but it's all about learning, developing, and teaching people how to do better work. Most keynotes are customers. How do you have better conversations? How do you share products before you're ready?
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