Boost Your Average Deal Size By 68% with Personalized Sales Training & Coaching—For Real

I studied Sales at Purdue, started my career as an SDR in Silicon Valley, and since then have always pursued sales roles at B2B startups because I love them. Some roles have felt fairly similar, but here’s what’s varied from place to place: sales training techniques. These employers not only differed in sales training ideas, but also in culture, mission, vision, values, you name it. Each one wanted to sell, close business, grow, and make that money, but training was consistently different.

After experiencing such a mix of sales training courses, I couldn’t help but wonder, “What sales training really helps reps close a sale?” 

No magic sales sauce, just my story

Now I’m not one to say that this blog post will carry the key to the magic sales sauce and solve your training problems, but here is my story and what led me to find my answer to this question. Read on to find out!

It was January 2016, my first day at my first real job, and I was getting ready to go through my first official sales training. Ah, the innocence! The naivety! A precious, but aloof soul was about to embark on her remarkable journey of the corporate world. It’s beautiful, ain’t it?

As a Sales major at Purdue, I went into this job with bright eyes, a full heart, and what I thought was a mind full of sales expertise. The first month was packed with all types of sales training programs, sales training methods, and even a sales training certification—the whole works!

Before I knew it, the sales training material had come to an end, and I was ready to hit the ground running… at least so I thought.

I was a couple months in and, to my surprise, I was stuck wondering, “Can I do this?” I was truly wondering if I was capable and cut out for this.

Had I not explored enough advanced sales training topics or learned enough sales training tips in school? What more could I do? Why wasn’t it clicking?

Ring, ring! changed everything

It wasn’t until June, six months in, when a sales leader passed by me one day after work. Let’s call him Evan. At this point, I was staying late five days a week, trying to improve, exploring different B2B sales training topics, jotting down scripts, recording myself and listening back, cold calling just for practice! Yet I was still falling short.

Evan asked: “How’s it going?” I replied, “Umm, in life or with work?” Knowing that at the time, both were miserable because of my consistently poor work performance. I had no life to live because I was spending every waking moment “trying so hard to be good at my job!” He got the long winded, messy answer that eventually led me to asking him, “Wait, what was your question again?” I was struggling… clearly. 

He was unphased by my pity party and said with a smile: “Role play with me. Ring, ring!”

He took the time to hear my pitch and how I was calling on prospects, and with just a few minor personalized tweaks, my job was seen in a whole new light. It was soon after this conversation that things finally clicked. It was simple, but necessary for me to start performing.

In sales training, they said: ask these questions and be you! Now, go! From the moment I decided to pursue a career in sales, it was my energy and enthusiasm in making connections that had me thinking I’d be good at sales. And hey, these may be assets, but only when used properly. I was working hard, that’s for sure, but was I working smart?

After this, my career took off! I started booking meetings, hitting or exceeding quota, and flying from the very bottom to the tip top of the charts. So, what sales training really helps reps close a sale?

Two words: personalized coaching

The proof is in the pudding. Take, for instance, two sales reps, each with different skill gaps that still need to be addressed after they attended a training session. Once you combine training with coaching, these skill gaps turn into results like an increase in first calls or the increase in deal size. Think about how much time managers dedicate to coaching today.

Is it personalized?

Minitab found there was a 68% increase in average deal size with personalized coaching and training instead of the status quo, one-size-fits-all training.

Had that sales leader not taken the time to understand where I excelled and where I lacked, who knows where I’d be today. Probably still attempting to come in way too hot on a cold call. 😉


Lessonly helps sales leaders deliver personalized coaching at scale

Is your team growing? Want to boost your average deal size by 68%? If you answered no to that, are you feeling okay? Regardless, we’d love to partner with you and hear more about your training strategy and see if Lessonly’s enablement and coaching software might help. Book time with us here if you’re interested.

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