Building an A-List Sales Team: Strategies for Enterprise Success

Good vibes all around

On Rehman’s team, there’s a zero tolerance for toxic behavior. “At the founding of this team, we created a strict no assholes policy.” We embrace being kind, smart, and intelligent. We keep out the bad vibes, focus on collective advancement, and never forget that a successful team is a collective effort. Because it's a team climb, each team member must ask themselves, "How do I want to level up?" Then they need to figure out how to bring the team along for the ride. Forget the lone wolf strategy. If you're aiming for 500% attainment, you can't get there without your pack.

“At the founding of this team, we created a strict no assholes policy.”

"Sales reps alone almost never close the deal, especially in enterprise sales," Rehman says. You need a cohesive team, from sales reps to solution engineers, all delivering their A-game to close deals. Team success isn't an optional extra; it's the core ingredient.

Another cornerstone of his philosophy: sales leaders can't forget that they're in a service role. "Your job is to serve the team," he emphasizes. The road to a winning culture is peppered with more than just high-flyers. It requires A-list players who not only excel in their roles but also contribute to a synergistic work environment. And let's not forget, A-listers aren't desperate. They can find another job faster than you can say “vacancy.” So, if you're a sales leader, your task is cut out for you. Ensure that you treat your A-list players in a way that makes them feel not just valued, but indispensable.

‍Ready for the hustle? 

So how does one build a team of A-list players? Rehman admits that while it’s incredibly hard, it is doable. First, it isn't about hiring someone who's already a superstar. It's about spotting those with the raw material to become one. "Don't just focus on who they are. Zero in on who they could become." Rehman doesn't scan a resume. He takes a deep dive into the individual's motivations and ambitions. It's crucial that the candidate is genuinely thrilled to join your ranks. A passive candidate? Not a chance. They need a nudge? Give it to them, but make sure that excitement becomes palpable.

"Don't just focus on who they are. Zero in on who they could become."

But what about red flags? What tells Rehman that someone might be a dud in disguise? The secret is less in the answers and more in the questions you ask. "Where do you see yourself in five years?" is a tired and ineffective question. Rehman cuts straight to the chase: what's the biggest challenge you've faced in the past two years? How did you overcome it? Your motivation is what? These questions don't skim the surface; they dig deep into the core of a person. It's about past behavior, but it's even more about future potential. Are they ready to hustle? Have they faced adversity and come out stronger? If the answer is yes, congratulations, you've got a future A-lister on your hands.

Landing the first big whale 

How do you pivot from SMB to enterprise without tumbling? Once you've bagged a couple of big fish, the enterprise market seems a lot less impenetrable. But how do you land that first whale? It's not about the product features. Instead, it's in your ability to deeply understand and articulate the customer's problem. You're not just selling a solution; you're building a business case.

Features are a dime a dozen; everyone can rattle those off. The game-changer is your ability to tell a compelling story around the customer's problem. Educate them on the size of their challenge, quantify the cost of inaction, and illuminate the path to a better future. It's not about making a better offer. Your value isn't in your software or your service. It's in your storytelling ability to translate problems into palpable needs.

Paint the picture of the status quo and show them what's possible with your solution. That not only opens doors but cements your credibility, giving the enterprises the confidence to say, "These guys get us." And once you've got that, you're not just in the game—you're a force to be reckoned with.

The right frameworks and tools 

Navigating the sales landscape without a proper methodology is like sailing without a compass. You might get somewhere, but not necessarily where you want to be. What are some of the tools Rehman has used to guide his team to success? MEDDPICC (Metrics, Economic buyer, Decision criteria, Decision process, Paper process, Identify pain, Champion, and Competition) has been a particularly effective tool for guiding sales conversations.

Why MEDDPICC? Because it forces sales reps to reflect on their deals critically. If you can dissect their decision-making process, identify their key challenges, and clarify what it takes to move from point A to point B, then you're not just another salesperson. You're a consultant they can trust. If Rehman had a do-over, he'd put in place MEDDPICC sooner to enable better thinking and sales execution.

Bart reminds us that whatever methodology you choose, consistency is key. The same language should resonate throughout the company. The methodology isn't just for the sales team; it's an organizational mantra. Imagine a scenario where the head of marketing and the head of support are asking the same questions, aligned with the sales methodology. It amplifies the quality of discussions, keeping everyone, from leadership to frontline reps, on the same page.

“Always ask, hey, who else should I be talking to? Who else should I be solving this? Problem for. You'd be surprised how many answers you get.” 

Even the most advanced sales stack can't replace fundamental sales skills. When Rehman joined his organization, they started with rudimentary Google Sheets for tracking. As they matured, they used tools like Salesforce for CRM and various enablement platforms like Showpad and Highspot. But, the game-changer was not the high-tech arsenal. It was the sales team's ability to articulate and solve the customer's problem. “Always ask, hey, who else should I be talking to? Who else should I be solving this problem for? You'd be surprised how many answers you get,” he says.

While digital outreach is a part of their strategy—through LinkedIn, emails, and cold calling—their real strength lay in being problem solvers. They do their homework to understand the issues facing their potential clients. They frame conversations around solutions rather than pitching product features. The preparation they put into understanding client issues gives them the edge. It turns even a cold call into a warm opportunity.

The power of presence

Remember the airplane? Rehman’s team is always traveling, interacting directly with customers, which no digital tool can truly replace. Once you've established credibility and know your strength in solving specific problems, leveraging that to connect with more people is the key. Ask for referrals in the last five minutes of a call. Engage people at industry events rather than passively waiting at the booth. The human element in sales can't be underestimated.

When you have zero leads in the pipeline, Rehman suggests, "Go to that country. Message everybody." A strategy as simple as inviting potential clients to dinner can work wonders. It helps establish initial credibility and paves the way for more substantive discussions. In-person meetings serve many purposes across different stages of the sales cycle. Whether it's for opening doors, expanding deals, or reducing time-to-close, sitting across the table from someone is invaluable. Sales pitches and presentations may not be the decisive factors in closing deals. But, the candid conversations that unfold over a dinner table influence the client's decision.

Salespeople have unique personalities that are best conveyed in person rather than over a video call. Such interactions provide an unfiltered view into what drives the client, what their pain points are, and how they perceive competition. Discovery should happen at every stage of the sales cycle. Nothing facilitates that better than an in-person conversation.

The intersection of work and personal life 

Looking inward, what are the most desirable traits a salesperson can have? According to Rehman, humility tops the list. The reason is twofold. First, humility helps the team navigate the highs and lows inherent to sales. This often involves handling rejection. Second, humility allows for self-reflection: another trait Rehman deems crucial for anyone on his team. Being able to introspect and identify areas of failure facilitates personal growth. It also enriches the team's collective learning. 

“If you're successful in your work life, you're happier in your personal life. And if you're unhappy in your personal life, your work life suffers.”

Rehman takes a moment to ponder the intersection of work and personal life. He rejects the idea of a strict separation between the two realms, arguing that one invariably influences the other. People spend a significant portion of their lives working. It's almost impossible to compartmentalize completely. “If you're successful in your work life, you're happier in your personal life. And if you're unhappy in your personal life, your work life suffers,” Rehman says. He has focused on creating a culture where team members can share their concerns and challenges—whether they originate at work or home. By fostering an empathetic environment and genuinely aiming to help individuals realize the best versions of themselves. Rehman believes that he's been able to create a work setting where people are not only happier but also more productive.
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