Selling to Fortune 500 companies isn’t the same as pitching to a small business owner who can make decisions on the spot. These deals take months, involve countless stakeholders, and can die and resurrect multiple times before closing. Tariq Amassyali learned this the hard way, but his unconventional background gave him an edge that most enterprise sales professionals lack. Starting at flea markets as a kid, he developed skills that now help him navigate complex corporate hierarchies.
Learning Sales by Observing People
Most enterprise sales reps didn’t learn their craft selling at weekend markets, but Amassyali’s story starts there. His father immigrated to the United States in 1980 and built a retail business based on negotiation skills. Every weekend, young Amassyali found himself observing customers and learning to read their needs. “At a young age, I was forced to learn the behaviors of who was in front of us, who that client, that customer was, the end user,” he recalls.
English wasn’t his first language, which actually became an advantage. When you can’t rely on perfect communication, you get better at reading people. His mother also struggled with English but developed sharp instincts for understanding what customers wanted. “She relied on senses, feelings, and listening,” he explains. “Because of those experiences, it forced me to listen, understand who my audience was in that moment.” Those early years shaped everything that followed. From elementary school through early adulthood, Amassyali spent weekends at the flea market, constantly refining his approach. The goal was simple: make sure every customer left happy with exactly what they needed.
Understanding People in Enterprise Sales
Here’s what Amassyali figured out that many sales professionals miss: enterprise sales and retail aren’t that different at their core. “The correlation between retail sales at an early age to enterprise sales and managing enterprise relationships at a very high level with the largest brands in the world, fundamentally, it’s the same,” he says. “It requires listening, and it’s a skill a lot of professionals do not have.” Too many salespeople focus on selling solutions without understanding the real problem. You might have the perfect product, but if you can’t communicate in a way that resonates with your audience, you’re going to struggle. Amassyali puts it bluntly: “You may have the best product, but if you can’t cater to your audience or communicate in a way that they can comprehend and understand, and create a safe place for them to say, ‘this may be a dumb question,’ you’ll struggle.”
He has developed his own way of cutting through typical corporate politeness. At the start of every relationship, he asks a direct question: “How do you want this to go? We can dance or we can get right into business.” The dance means the usual sales presentation with all the bells and whistles. Getting to business means honest conversation about pros and cons. The response is always the same. “Every time I’ve asked this question, 100% of the time they said I don’t want to dance, I want to get to business.” This approach opens up frank discussions where clients feel comfortable expressing what they don’t understand. It creates space for productive friction without damaging the relationship.
Navigating Long Enterprise Sales Cycles
The biggest difference between enterprise and smaller companies isn’t just budget size. “Enterprise has time,” Amassyali explains. “So naturally there’s a longer sales cycle. They have to get it right the first time.” These organizations are dealing with multi-million or billion-dollar problems. They can’t afford to rush decisions in the same way as smaller businesses that are operating month to month. This fundamental difference changes everything about how you approach the sale. Mid-market companies are chasing enterprise-level success, but they don’t have the luxury of extended evaluation periods. Enterprise clients have the power and the time to be thorough.
One particularly challenging deal taught him an important lesson about enterprise complexity. The solution his company offered was clearly the best option, but some individuals at the client company tried to fast-track the decision. This actually backfired when other leaders caught wind of the shortened process and demanded a more thorough evaluation. The deal kept dying and coming back to life. Personnel changes, reorganizations, and new stakeholders kept appearing. Amassyali received some valuable advice during this process: “This thing will die three times, but you have to bring it back to life every time.” Understanding the organizational chart became critical. You need relationships across multiple departments because you never know who might influence the final decision.
Despite all the talk about AI and automation changing sales, he believes relationships will remain king in enterprise sales. Technology might handle more transactional processes, but complex B2B relationships still require human connection. “As enterprise sales reps, it’s going to be incredibly critical to reach those decision makers, to be creative on how you stand out from a relationship standpoint.” Amassyali proves this point in unexpected ways. During our interview, he was shirtless after a yoga class, and he plans to tell his enterprise clients about it. These real moments create connections that no CRM system can replicate. It’s about being memorable, authentic, and human in a world that’s becoming increasingly digital.
Follow Tariq Amassyali on LinkedIn for more insights on mastering complex B2B relationships.
