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The Sales Evangelist

Cold Calling, Omnichannel Outreach, Fred Diamond, Donald C. Kely

I sat down with Fred Diamond at Podcast Movement 2019 to discuss the keys to helping your sales team perform their best. Fred is the host of Sales Game Changers Podcast and today he turned the microphone on me and allowed me to share the things I’ve learned during my career in sales. 

The Sales Evangelist

This podcast resulted from my own struggle as a B2B seller. Because of my own struggles, I wanted to help new and struggling sellers improve their sales game. I wanted to educate people who were in the same shoes and help elevate their performance. 

As The Sales Evangelist podcast grew, people in our community of sellers reached out to me for sales coaching. I started with one-on-one coaching for reps, and then those reps took their training back to their companies, and I started hearing from entrepreneurs and other business owners who needed to replicate themselves so they could scale their companies. 

I launched into the consulting side and helped businesses set up their sales teams. Eventually, that led to speaking opportunities and other things, so in 2015 I left my full-time job to do The Sales Evangelist full time. 

The podcast didn’t make money on its own, but it did generate leads and coaching opportunities and speaking and consulting gigs. Now, though, it generates its own income. 

Sales career

I got into sales before college, partly because my entire family was involved in sales. As a Jamaican boy, I grew up in a setting where everyone sold something. I didn’t see it as sales, necessarily. I simply saw it as the family business. 

I’m naturally outgoing, so people told me I’d be perfect in a sales career. That continued through college where I struggled to find a sales program. 

Eventually, I got a couple of sales jobs in timeshares and door-to-door that involved B2C selling. I made about $20,000 in three months selling door-to-door over the summer during my first year. 

When I transitioned to the professional world of selling, though, I struggled. 

Lessons learned

One of the things I learned selling door-to-door was the value of working smart. I saw people who worked hard but who weren’t effective, so they got burned out because they continued doing things that were ineffective. Those who hustled, on the other hand, worked efficiently and they practiced their messaging and they stopped doing things that didn’t work. 

I learned that I had to be willing to move on when a sale didn’t work out. 

Eventually, I moved into a BDR role in a B2B company, and I brought that need to work efficiently and plan my activities because it was a full-commission job. 

Time is money, and I needed to pay rent. 

During my time at the IT training company, Steve Hatch took me under his wing. He was the CEO of the company, and he taught me both the sales and the business sides of his company. In several cases, he did that by throwing me into the deep end. 

We were trying to work a deal with a local NPR station and he helped me learn to lead the deal and negotiate the deal. He helped me see who I could eventually become. 

Sales challenges

Current sales reps face a number of challenges that are unique to the kind of setting they operate in. Most of the ones I meet with struggle with prospecting, and with prospecting effectively. 

Many learn that cold calling is dead, for example, but they work for companies that were built by cold calling. Their leaders want them to engage in cold-calling but others tell them it’s ineffective, so they feel pulled in different directions. 

At the same time, many sellers struggle with the idea of social selling in which they engage with people on social media. They often don’t have the confidence to do it effectively, so they wait for inbound leads to come, and though they do often come, it simply isn’t enough. 

I constantly give training on how to use LinkedIn and how to take advantage of cadences and flow processes for outreach. 


Multichannel outreach, sometimes called omnichannel, matters the most in prospecting. When I work with sales reps, I encourage them to begin their interactions on social media. Make a genuine connection with people as a starting point. 

Understand that genuine connection doesn’t mean you simply “like” something that they posted or shared. Instead, engage with that person. If someone comments on something you share, take that conversation to the inbox next and tell him how much you appreciate his comment. Then, once you’ve built that connection, you can move the conversation to a phone call. 

Now you’ve created a warm, engaging connection. 

Then, for enterprise sales, you can even take advantage of snail mail to send them something to grab their attention. We created a Willy Wonka style ticket and invited them to join us for our demo. We sent sodas and snacks and a Starbucks gift card. We spent about $12 for each of three boxes and landed about $100,000 worth of deals. 

Sales tips

I read a lot of books in an effort to improve my game, and one of my recent favorites is Mike Weinberg’s Sales Management. Simplified. because he focuses on fundamentals. For me, mastering those fundamentals is the key to moving to the next level. Aside from prospecting, asking appropriate questions makes a big difference as well. 

For sellers who know nothing about their buyers, pipelines won’t matter at all. We’re skipping the discovery process and we’re missing a chance to ask meaningful questions and demonstrate our expertise. 

Related to that topic, time management presents a big struggle for sellers right now. I attribute my continued success to planning. In fact, I’ve created a selling planner because I couldn’t find one that I liked. 

I read a book by Kevin Kruse called the 15 Secrets Successful People Know  and another called The 12 Week Year related to time management. A lot of sales reps throw as many things as they can on a calendar in hopes that they can maximize their time. 

Instead, I break my day down based on categories to measure my effectiveness. I separate sales activities, marketing activities, and operations. I tracked those activities for a week to see where the commonalities are and which tasks I’m repeatedly doing. Then, I eliminated tasks that my team could do for me so I could focus on sales-related tasks. 


Do a three-minute prep prior to each sales call. If you have a focused list of clients, consider hiring someone to do research on each of those clients. Find out the following:

  • How does this company make money?
  • What challenges do they have that they aren’t even necessarily aware of?
  • What common challenges are they facing?
  • How does this person I’m going to call help the company make money?

If you can help your customer achieve his goals, you’ll be so much further down the path. The process isn’t about you.

Someone is going to solve your customer’s problem. Why don’t you figure it out first and be the first to provide the solution?

“Helping Your Sales Team Perform” episode resources

Connect with Donald on LinkedIn. Also check out the Sales Game Changers Podcast.

 If you’re a sales rep looking to hone your craft and learn from the top 1% of sellers, make plans to attend the Sales Success Summit in Austin, Tx, October 14-15. Scheduled on a Monday and Tuesday to limit the impact to the sales week, the Sales Success Summit connects sellers with top-level performers who have appeared on the podcast. Visit Top1Summit.com to learn more and register! 

You can also connect with me at donald@donaldk4.sg-host.com or try our first module of  TSE Certified Sales Training Program for free. This episode has been made possible with the help of  TSE Certified Sales Training Program, a training course designed to help sellers in improving their performance. We want you guys to go out each and every single day to find more ideal customers and do big things.

I hope you like and learned many things from this episode. If you did, please review us and give us a five-star rating on Apple podcast or in any platform you’re using – Google Podcast, Stitcher, and Spotify.  You can also share this with your friends and colleagues. 

Audio provided by Free SFX and Bensound.

About the Author The Sales Evangelist

Donald is the host of the popular sales podcast,"The Sales Evangelist". He is the founder of The Sales Evangelist Consulting Firm where he helps small companies develop killer sales process to scale their business and increase growth.

Donald is also an award-winning speaker, sales trainer, and coach. He's a big fan of traveling, South Florida staycations and high-quality family time. Donald has a belief that “anyone” can sell if they have the desire and receives the proper training.

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