How Todd Caponi, Founder of Sales Melon, Sells: The Power of Transparency

When I opened Todd Caponi’s LinkedIn profile, the first thing that caught my attention was the first two words of his headline: Transparency Nerd. That was definitely an attention grabber, but the next two lines were equally interesting: Sales Historian.

Here’s the double click on both. When it comes to transparency, he’s a standout authority. He’s the award-winning author of The Transparency Sale and his latest release, The Transparent Sales Leader. Beyond his achievements as an author, he’s also a podcaster, channeling his passion for sales history into a popular show aptly named The History of Sales. He also has a thriving consulting business and is regularly on the speaker circuit, too, now.

Needless to say, there are so many universal truths and practical ways to build trust packed into this one. Follow me, Amanda Van Nuys, Head of Thought Leadership in LinkedIn Sales Solutions, and let me know what insights you found most valuable.

Without further ado….

1. ? Let’s dive in. You’ve been in sales and studying sales history for a long time. Why do you love it and what keeps you going?

Absolutely, let’s dive into a bit of history to set the stage.

Imagine stepping back 120 years, right at the dawn of the 20th century. Sales was a profession not only trusted and respected but genuinely admired. This was a time when salesmanship was celebrated, taught in universities and even high schools. However, by the 1950s, that respect had waned significantly, and today, sales often ranks near the bottom in ethical standings, alongside politicians, according to Gallup’s annual survey.

I’ve been deeply connected to sales for as long as I can remember—my first sales job was in college, inspired by my father, who was a sales leader. I’ve always been passionate about this profession, and I believe we have an opportunity to revive its former prestige. While I may not be able to overhaul the entire industry, I can certainly work to uplift the individuals and teams I interact with, one at a time.

2. Transparency is such a simple and powerful way to build trust with a buyer. Tell us more about it.

At its heart, the foundation of effective sales is this: transparency sells better than pretending to be perfect. It’s simple but profound—being open and honest far outweighs the facade of perfection.

I want to share two of my favorite sales quotes to illustrate this point. The first is from Arthur Sheldon’s 1911 book, The Art of Selling. He said, “True salesmanship is the science of service. Grasp that thought firmly and never let go.” This captures the essence of sales as a service profession—one where helping others is at the core of what we do.

The second quote comes from Arthur Dunn’s 1919 book, Scientific Selling and Advertising. In a bold move, Dunn included a blank page with just one sentence on it: “If the truth won’t sell it, don’t sell it.” It’s a powerful reminder that honesty and transparency are crucial to sales success.

So, if we were to distill these ideas, it would be this: transparency outperforms perfection. A salesperson’s role is fundamentally about service, and if the truth won’t close the deal, then it’s not worth pursuing.

3. Can you share why transparency is so important and what it really means in the context of a deal?

Let me share a bit of my story with you. A few years ago, I was the Chief Revenue Officer at a company in Chicago called PowerReviews. As you might guess from the name, we were in the reviews space. If you’ve ever checked out ratings and reviews on a site like Crocs.com, that was us collecting and displaying feedback for them and many other brands.

A few years back, we partnered with Northwestern University to study how websites—acting as digital sales people—affect consumer behavior. The results were eye-opening and had a profound impact on me. In fact, so much so that I quit my job and wrote a book—yes, I went a bit overboard!

Here are the three key data points we uncovered:

1. ? The first finding was fairly straightforward: Most people consult reviews before making a purchase, with 96% of us doing so for items we haven’t bought before.

2.? The second finding was a game-changer for me. Over 85% of people, when considering medium to high-ticket items they haven’t bought before, actually read the negative reviews first. We’re talking about skipping the five-star reviews and diving straight into the fours, threes, twos, and ones.

3.? The third finding revealed that products with an average review score between 4.2 and 4.5 have the highest conversion rates. Surprisingly, products with negative reviews convert at a higher rate than those with only perfect five-star reviews. In fact, a product with all five-star reviews sells at the same rate as one with a 3.25 average score.

When I first saw these results, my initial reaction was more about how they affected our clients. But then my inner geek took over, and I started to question why people seek out negative reviews first. Why do we need to see the negative before we can fully appreciate the positive?

So, I did some digging and consulted with a neuroscientist at DePaul University. We discovered that this behavior isn’t just confined to online shopping. It applies to B2B and human-to-human interactions as well. It turns out we subconsciously know that perfection doesn’t exist, and we need to see the negative to fully process the positive. We aren’t just buying based on persuasion; we’re making predictions about whether the value we get will outweigh the potential downsides. We seek the negative for context, not necessarily to talk ourselves out of a purchase, but to understand if the trade-offs are acceptable.

This insight led me to redefine transparency in sales. To me, transparency means showing your cards face up and letting customers see what you might be sacrificing to be great at your core. It means being upfront about what you’re not the best at before diving into the benefits, building trust early on.

When we started embracing this approach at PowerReviews, it transformed our sales process. We became Chicago’s fastest-growing tech company from 2014 to 2017, despite often being the inferior solution in the market. The key was that by being transparent and genuine, we built trust and differentiated ourselves in a meaningful way.

In today’s world, with reviews and feedback everywhere, customers will uncover the truth regardless. Embracing transparency not only makes you a better human being but also leads to better sales outcomes.

4. Let’s switch gears and talk about technology and the rapid rise of AI. How are you approaching AI in sales and how do you think it will transform selling as we know it?

Let’s take this one in three parts.

1: Buyers Know More Nowadays

Thomas Herbert Russell, in his 1910 book Salesmanship, said, “Buyers know more nowadays.” Back then, people worried that mail order catalogs and advertising would make salespeople obsolete. I even have a 1908 Sears Roebuck catalog in my collection—like Amazon in print, you could buy almost anything from it, from human hair to modular homes. Despite these concerns, the sales profession continued to thrive.

Fast forward to 2015, and Forrester’s report predicted that millions of B2B sales jobs would disappear by 2021 due to the rise of e-commerce. Yet, the opposite happened. More information hasn’t simplified the buying process; it’s made it more complex.

Again, my argument is and always will be that access to more information hasn't made it easier on buyers and AI can be used to create more information or help curate it so that buyers get to the right decision faster.

2: Salespeople Are? Sherpas

A salesperson who acts as a guide—doing the homework, presenting both pros and cons—makes the buyer’s journey easier and more valuable. Even if we don’t close a deal immediately, a thoughtful, helpful approach can lead to future opportunities.

Think about it this way: if you’re at the airport and have to talk to someone, something went wrong. The same applies to buying—if you need to interact with a salesperson, it’s often because something hasn’t gone smoothly. Ideally, buyers should be able to handle most of the process themselves and only need salespeople for final steps.

A good salesperson provides guidance, much like a Sherpa on a mountain. For complex purchases like enterprise CRM systems or tools like LinkedIn Sales Navigator, buyers need that expert help to navigate the process. In contrast, simple transactions don’t require as much hand-holding.

3: Salespeople Need to Use AI Thoughtfully

Salespeople have a knack for turning every new technology into a double-edged sword. The telephone, invented by Alexander Graham Bell in 1876, was a game changer for sales. Yet, it wasn’t long before we misused it so badly that technologies like caller ID and the Do Not Call Registry were created to combat it.

Email, too, started as a brilliant tool thanks to Ray Tomlinson in 1971. But we quickly turned it into a spam haven, leading to blacklists and the CAN-SPAM Act, which still doesn’t fully solve the problem.

Now, AI is the latest tool with potential for good—like researching buyer perspectives and tailoring solutions. But there’s a risk we’ll misuse it too. I’ve seen startups planning to send out tens of thousands of “personalized” emails daily using AI, which just feels like a repeat of past mistakes.

The key is using AI thoughtfully. While it can help us prepare better and match clients effectively, we must avoid falling into the trap of scaling it mindlessly. If we’re not careful, we’ll end up needing new technologies—and maybe even government intervention—to fix the issues we’ve created once again.

5. Switching gears here. You’re a very busy consultant so what’s your secret to staying balanced?

I spent years as a sales leader, including a number of sales leadership roles at ExactTarget, where I participated in the company’s growth through its IPO and eventual $3 billion sale to Salesforce. My next role was the Chief Revenue Officer of PowerReviews, which was an exciting ride, but it took a toll on me. My commute was an hour and 20 minutes each way, and I carried that stress home, affecting my health and family life.

With two kids and a house full of rescue pets—three cats and two dogs—I wasn’t my best self. A kidney stone attack and subsequent surgery made me realize how badly I needed a change. Writing my first book, something I’d never done before, seemed like a crazy idea, but it was exactly what I needed. It helped me reconnect with my family, get healthy, and find joy again.

Now, six years later, I’ve no intention of going back to my old life. I’ve learned to value my time and prioritize what truly matters. Using tools like virtual assistants, not for prospecting but to free up time for my family and personal life, has been transformative.

When I decided to leave and write a book, my CEO was torn between hugging me and hitting me with a bat. What I thought would be a brief hiatus turned into a fulfilling six-year journey. It wasn’t just about escaping a demanding role; it was about following my passion and making a meaningful impact.

6. Here comes everyone’s favorite How I Sell question. What was your biggest fail and what did you learn?

Back in 2003, I was at Hyperion, selling financial consolidation tools. I found myself dreading each day. I was stuck talking about the same dull topics with the same uninspiring people. No offense to accountants and finance folks, but I just wasn’t feeling it.

Then, a sales trainer from ValueSelling came in, and I was truly inspired. A friend told me, "Todd, you'd be great at this. You should teach and train." So, I dove in and bought a sales training franchise—every dollar I had went into it. Unfortunately, it was a disaster. After three years and nearly $100,000 lost, the franchise failed miserably.

I often think of that experience as my version of an MBA. It was an expensive lesson, but it taught me so much. People see the success I have now and think it came easily, but it took a significant failure to get here. That painful experience, driving a clunky car and scraping by, shaped me.

The lessons I learned from working with various sales organizations, understanding processes, and building confidence to speak to hundreds of people have fueled my leadership career. It wasn’t just about making a comeback; it was about applying those hard-earned lessons to thrive in my career.

7. Last question. Looking into your crystal ball, how do you think B2B sales will evolve in the next 1-2 years and what do other sales leaders need to do now to prepare?

Here’s my rant: everyone keeps saying sales has changed. But honestly, it hasn’t changed as much as people think.

What has changed in the last 15 years are two big things. First, the rise of the as-a-service economy. Back in the day, making the sale was the endgame. Today, the sale is just the start of a relationship where we need to keep customers engaged, buying more, and advocating for us. That’s why we’ve seen the rise of roles like CRO and customer success. The sale is no longer the peak; it’s just the beginning.

Second, the explosion of reviews and feedback. In the 1990s, a bad experience meant writing a letter or calling an 800 number. Now, your peers’ opinions are everywhere, and the truth about your product or service is broadcast loudly and persistently. This means that the long game in sales, focusing on lasting customer relationships and doing right by your clients, not only wins in the long term but also in the short term.

So here’s the punchline: if you’re investing in tech or crafting your sales strategy, don’t just think about scaling up. Think about doing right by your customers and playing the long game. The winners will be those who embrace this approach, making their companies not just profitable but enduringly successful.

It’s a reminder that while tech and tactics evolve, the core principles of building genuine, lasting relationships with customers remain timeless.

Todd, thank you so much for sharing your wisdom with us. It’s fascinating to delve into our historical roots as a function, explore the latest innovations like AI technologies, and be reminded about timeless truths: relationships are the cornerstone of successful selling, and transparency is a powerful way to build trust and strengthen those relationships.

Also, I want to extend a big thank you to Sam McKenna who recommended that I speak to Todd! Great recommendation!

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