An Interview With James Buckley: Winning Deals by Selling with Heart

By: Teresa Weirich

November 18, 2018

James Buckley, Enterprise BDM at Cirrus Insight

When looking back at his career, James Buckley never really figured he’d end up in sales, which is a common thread among sales professionals.

“During my years spent in the culinary industry, friends and family would constantly tell me I would be great in sales,” James said. “I originally wanted to be a reporter, but quickly realized that it’s more profitable to write persuasively.”

After following up on a friend’s Facebook post about a job opening, James entered the world of sales and never looked back. Now, he’s the Enterprise Business Development Manager at Cirrus Insight, the world’s leading Salesforce and inbox integration platform.

In the following conversation, James discusses the importance of selling from the heart, how to build strong relationships with prospects, and ways sales reps can break through the ‘red tape’ of enterprise sales. We hope you enjoy the following conversation with James!

What does ‘selling with heart’ mean to you?

The phrase ‘selling from the heart’ is from a book written by my good friend Larry Levine, but it’s really shaped the way I approach sales and prospects. For me, it means selling to the relationship you have with a prospect and to the context of the conversation; all while establishing mutual trust.

So many sales reps want to push features as hard as they can, but being able to establish an emotional connection is what sets a true sales professional apart from a sales rep. Larry calls this ‘being your most authentic self’ and it’s really about stripping away the ‘sales guy’ and being heartfelt with your prospects.

At Cirrus, selling from the heart means addressing the root emotional issues behind a sale. When you think about it, we’ve spent the last 25 years relating our inboxes to our work, which has given it a negative stigma. So for us at Cirrus, we’re trying to untangle that emotional connection and rebuild the narrative. I reach out to people through channels associated with warmth, friendship, and personalization, such as Twitter and LinkedIn and even Instagram. Then, once we have a conversation going, we can expand to email and introduce features when the time is right. It’s all about realizing your customer and connecting on a level playing field. Cirrus Insight is an inbox and Salesforce integration after all.

What can reps do to sell from the heart during cold calls?

Honestly, I think sales reps, in general, try way too hard to push facts and features on prospects. We have a terrible habit of making every conversation about ourselves when we haven’t earned the right to barge in like that. On cold calls, there needs to be some element of emotional attachment, which is hard to establish at first. When we’re calling someone who’s never heard of us and doesn’t know anything about our company or product, our first thought should be about their time and productivity. I always start conversations by asking ‘Is this a good time?’ and then direct the conversation from there.

Cold calls can be made ‘warm’ by laying the groundwork for curiosity and connection. People are always going to be intrigued with things they’ve learned, so you need to make your features pitch about learning and exploring. Plus, when it comes to cold calling, practice definitely makes an impact. It’s all about consistency, but it really is impossible to become a pro.

I always tell our reps that the secret to being a good cold caller is to actually take cold calls from vendors yourself. Being on the other end can help show you what not to do. In my opinion, the worst trend out there is feature regurgitation. It comes off so scripted and harsh that there is no longer any conversation at all — just an onslaught of information. The best sales reps are constantly practicing their craft and learning from others along the way. You can always learn something from somebody.

Can you walk us through your personal sales framework?

Although I don’t personally subscribe to a formal methodology, I do believe in a pragmatic approach to sales. It’s important to know your product, your customer, and their industry for every single deal — regardless of size. Being yourself is my framework and my customers appreciate that I’m being honest and fair with them. You can’t rehearse success, and if it’s not happening, you’re just not trying hard enough. It’s a “no excuses” mentality. You have to own it.

One sign of success that I see when I receive cold calls is research. People who view my profile and actually know what problems our company is trying to solve are much better prepared. If you know who I am, what I stand for, and what I do, then it’s a call I want to take. It’s also a call I want to give you information on. That’s the goal, isn’t it?

How can teams leverage ‘heart’ to break through the red tape in enterprise deals?

It’s no surprise that enterprise deals are often long, arduous processes that require multiple levels of decision making, but I think that salespeople as a whole target these decision makers too often. When you’re constantly looking for the ‘right’ person, you can let potential champions slip through your fingers. I talk to anyone who will listen, and while it does take time and effort, I work hard to establish personal relationships with as many people as possible.

If you have a solid relationship with your prospects, they will help you overcome the hurdles and introduce you to the right people. I recommend being responsive and making it easy for people to find and contact you personally. I call this an “open channel of business,” and it’s a fluid cycle of communication between your team and your prospects. With this philosophy in place, your hard work will pay off in the end.

Do you have any advice for sales leaders who want to help their reps sell from the heart?

It may sound silly, but it all starts with sales leaders realizing that they are unique and beautiful butterflies. Nobody can ever be an exact replica of a sales leader, which is why leaders can’t simply train their reps to be like them. Sales leaders can only show their team the pathway to success and give them the tools and resources they need to capitalize on the opportunities at hand. There can’t be any hand-holding or, worst of all, expectations. Expectations kill everything: excitement, metrics, goals, and morale. End expectations for a truly heartfelt sales team.

I’ll also recommend that sales reps look to LinkedIn to network with like-minded professionals. I am a part of a group of 5 or so sales leaders on LinkedIn that shares ideas and strategies to build motivation. Also, reading is a huge plus, but reading a book itself isn’t enough. You must read and internalize what you’ve read to truly make it your own. You must internalize the words to start selling from your heart. I recommend Selling from the Heart by Larry Levine, and Gap Selling by Keenan.

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    Teresa Weirich

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