How Founders Can Overcome Their Sales Fears with AJ Cassata


You probably didn’t become a founder to send cold emails. You wanted to solve a problem and create something of your own.

But sales always seem to follow you like a wintry draft.

While there are rare stories of customers and clients flocking to a business from Day One, in reality, if you build it, they won’t necessarily come.

So how do you sell without sacrificing the reason you became a founder in the first place?

“I think most entrepreneurs just wing it with sales, especially if they’re charismatic,” AJ Cassata says. “You can rely on your network and rely on referrals, but you can’t control that. You’ll kind of eventually hit a plateau.”

Cassata is a B2B sales consultant who helps entrepreneurs grow their businesses fast with his straightforward, systematic, and scalable approach to sales growth. His company, Revenue Boost, helps clients create a system for lead generation instead of just winging it. He’s also the instructor behind Foundr’s course, Find Your Dream Clients.

Cassata’s formula helps entrepreneurs embrace sales as a system to grow their businesses instead of a hassle that eats into other projects.

It all begins with a having process.

Cold Calls and Emails

In 2018, Cassata left his sales manager job and hit the road.

He started a digital agency called Magic Clicks from a Sprinter van. He traveled across the United States, hitting major cities along the way to build a client base.

While the miles racked up, his client list remained stagnant.

“I had all this confidence coming out from the job and just being really good at sales at that point. And I thought it was gonna be a breeze,” Cassata says. “But for the first three to four months, it was an absolute struggle.”

Even though Cassata worked 60 to 80 hours per week, his bank account dwindled with each new stop. Soon, he’d run out of money for gas.

“[Then], everything just clicked. All of a sudden, the next week, it was like something out of a movie, you know?” Cassata says.

“[Then], everything just clicked. All of a sudden, the next week, it was like something out of a movie, you know?”

One of his prospects called him back and committed to a few grand per month. The next week two more clients signed up. Within a month, Magic Clicks went from zero to $10,000 in sales.

“It was just all the compound interest from the past efforts and repeating that sales process of getting leads, having meetings, [and] pitching our offer,” Cassata says.

That compound work taught Cassata the importance of patience. This trait is not shared by sales pros but one Cassata believes all founders need.

“People do both ends of the spectrum. They’d either follow up too much where it’s spammy, or they don’t follow up at all,” Cassata says. “Stick with it and play the long game.”

As Cassata worked with clients, he narrowed his niche to email prospecting, which he reminds us isn’t dead.

“People always ask me, ‘Does cold email still work? Does LinkedIn still work?’” Cassata says. “Assuming everyone in the world has an email, it works for sure.”

“Assuming everyone in the world has an email, it works for sure.”

In 2019, Cassata returned from the road and then decided to travel abroad and work remotely. While he was living in Vietnam in 2020, the COVID pandemic struck. The period forced him to restart his business because his clients, mostly small companies, lost their marketing budgets. Thankfully, building his new business, Revenue Boost, was easier than the first time. It took him less than six months to reach $50,000 in sales.

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AJ Cassata’s Simple Sales Process

That’s thanks to the prospecting process he perfected over his career. And it’s surprisingly simple.

Step one: Identify your ideal clients.

Cassata says the simplest way to do this is to get a piece of paper and write down the qualities you admire in a perfect client.

“If you’ve been doing business already, just think back to your past clients […] the most profitable, the easiest to sell to in the first place,” Cassata says.

Use LinkedIn to start researching, Cassata says. It’s the largest accessible business database online. Find out what the company does, how big the company is, and what the job title is for each decision-maker. Build a list of at least a few hundred prospects.

Step two: Send it.

Write an email template and customize the first two lines for a personal touch.

Cassata says the mistakes he sees in cold emails are trying to sell to everybody and sounding like everybody else.

“It’s like, ‘Hey, sorry to bother you, my name is this, I work at this company, I do this, our product has this,’” Cassata says. “And when you say that, it just sounds like everybody else. So you just got to be a little bit more unique than that to stand out.” (Keep reading to learn Cassata’s tips for crafting a standout email.)

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Step three: Convert.

Cassata says you need to find a middle ground between following up with prospects and annoying them.

“Try to find that sweet spot between staying on top of their mind but not being super desperate,” Cassata says.

At Revenue Boost, on average, they send prospects four messages in two weeks. If they get a response, the next step is to confirm the lead is a qualified match for their services because wasting time for you and a prospect is a lose-lose.

“Plenty of people will be willing to take a meeting if they think they’ll get some free information out of it,” Cassata says.

To whittle down qualified prospects, Revenue Boost uses an automated survey tied to Calendly to filter prospects based on their goals, revenue, and costs for service.

A better fit produces better results. Cassata says a healthy booking rate is 0.5 to 3 percent on average. It’s a reminder that prospecting (and sales in general) is a quantity game. Meaning for 1,000 cold emails sent, booking 30 calls is above average. That’s why Cassata believes his process requires constant attention and nurturing.

“If I look at the theme to success in all the businesses I’ve been in, it’s just having that very consistent, very repeatable sales process,” Cassata says.

But getting a prospect’s attention is more than rinse and repeat. You need to become a standout in an inbox.

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The post How Founders Can Overcome Their Sales Fears with AJ Cassata appeared first on Foundr.



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