Craft Beer and Conversation: Navigating Your Sales Career with John DiLeo

How to navigate your sales career in today’s ever-changing media landscape? We recently took on the topic in an evening of craft beer and conversation with sales leader, John DiLeo, VP of Sales and Marketing at DNAinfo, attended by over 30 individuals at all levels of their careers. Our very own Eugenia Neri Mini moderated a lively discussion with John in which he challenged the audience to consider a range of issues (including their greatest personal achievements and what comes to mind when they think of “sales people”) and offered advice, personal experiences, and suggestions for how to close a difficult sale.

A few key takeaways:

An interview is a sales presentation. When he’s interviewing for new members on his team, DiLeo always looks to candidates to sell themselves first—it’s a good indication of how they’ll sell the product. His top three qualities in a sales person are commitment, determination, and work ethic. DiLeo advises, “At the end of the day, if you don’t say it, the hiring manager can only infer from what’s on your resume.” In other words, your interview is not the time to be humble! Be ready to explain what makes you unique, and have anecdotes to support your statements.

DiLeo Pro-Tip: Do Your Research! You should never go into an interview without knowing as much as you can about the company. “Look for the right moments to show that you’re informed while still being conversational.” Remember, your interview preparation indicates how well you will prepare for a sales presentation once you’re in the position.

You control your brand. When asked what stereotypes come to mind for salespeople, the words sleazy, pushy, cheap, dishonest, and inauthentic filled the room. DiLeo warned that it’s important to remember what you’re up against. He emphatically reminded us that no matter what you are selling, you are your own brand. “You can be ethical, you can be honest, you can care about the customer, you can provide value and follow up. You can be the brand that you want to be. That’s your choice…. Be the person you would want to buy from.”


Always be responsive. You will always have difficult clients, and DiLeo stresses the importance of viewing your difficult clients not as a burden, but as your best opportunity. “They know they’re difficult, and they respect the people who hang in there with them, provide good service, and are responsive to their needs.” He suggests sending them relevant industry articles and links and continuously building your relationship with them. By building that trust, and staying top of mind, you’ll be much more likely to get or maintain their business when the time comes to buy or renew.

Know when to navigate. The digital media industry is particularly volatile and extremely competitive. When determining the right industry or the best move, be as well-informed and well-researched as possible.  “When you get to the point where your company isn’t making the changes necessary to stay relevant in a fast paced industry, it may be time to consider a move.” A top salesperson is one of the most valued assets in any organization, and demonstrated sales success will allow career leverage and flexibility should the time come.

John DiLeo also spoke to his personal management style: “I’m not a micromanager. I provide clear performance expectations in terms of quota, sales process, contacts per day and satisfactory job performance and I expect people to be motivated to get the job done. I think sales people have a lot of challenges. I try to help, to support, and to coach.” With a background in college football, DiLeo is a firm believer in the coaching approach to help his team learn from any mistakes, and to understand and apply the fundamentals of a successful sales process.  His vast amount of sales experience has enabled him to lead by example, and to understand and relate to what his team faces on a daily basis. A team member in attendance also pointed out that he maintains an open-door policy, which fosters an environment of collaboration and teamwork, particularly when facing challenges.


After a lengthy question and answer session, there was time for networking and we received some effusive feedback:

The 'Launching Your Career in Sales' event was not only a valuable opportunity to network with other young sales professionals, but also a fantastic chance to hear a seasoned and successful sales manager share his insights about the current landscape of the industry. It was particularly valuable to hear his words of wisdom about career growth and development, told through the lens of his own career history. 

The event with John DiLeo was super insightful in how to break into sales! I learned so much from the event but the biggest take away for me was remembering that you are your own brand. While lying to get the sale might be great in that moment, in the long term it will tarnish your reputation. 

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