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The Shift to Upmarket: Empowering Sales Teams to Go for €150K+ deals

Even a Formula 1 driver needs a crew and a clear path to race to victory. What does it take to empower an entire sales team to speed toward more lucrative opportunities? Recently, Jakub Hon and Bart Omlo from SALESDOCk  were joined by sales industry leader Rehman Abdur for a webinar entitled “How to Empower Your Sales Team to Go for Upmarket Deals.” Continue reading as we share the key takeaways.

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It starts with a solid foundation

Rehman recalls his early days at MessageBird, "We were using good old Google Sheets instead of a CRM.” At that time, MessageBird was a startup. It showed promise with its Series A funding, but lacked essential sales infrastructure. To steer the company to a multi-million euro operation required making pivotal choices. It required an entire strategic overhaul that extended beyond the sales team to involve the whole company.

“You need a different setup to close a €10 million deal. You have to redefine what an enterprise sale is. It's more than just selling a product; it's selling value.”

Transitioning to enterprise sales isn’t merely a strategy shift. It requires a multifaceted transformation involving every aspect of a sales operation. It involves rethinking onboarding processes, developing post-sales support for high-value customers, and adjusting the mindset of the sales team. As Rehman points out, “You need a different setup to close a €10 million deal. You have to redefine what an enterprise sale is. It's more than just selling a product; it's selling value.” Salespeople often limit themselves with their mindset. They restrict what they believe they can achieve. Overcoming this barrier forms a critical part of a successful transition to enterprise sales.

From sales tactics to sustained partnerships

Rehman underscores the critical role of a wider circle of influence in order to close deals. He shares a hard lesson from his past. A powerful champion like a CTO on your side doesn't guarantee a done deal. Two days before closing what would have been the biggest deal of his career, the CTO informed him that the CEO hadn't approved it. The takeaway? Salespeople shouldn’t place blind trust in any one contact within the buyer's organization. Verification is key, he advises, emphasizing the need for due diligence.

Rehman likens effective salespeople to "glorified project managers." It's not about aligning your stakeholders; you must ensure that the buyer is also aligned on their end. What’s the surest sign of an impending successful deal? When the buyer shares the same forecasts and implementation plans with their stakeholders is a good indicator. This mutual alignment brings a deal closer to fruition.

"Successful salespeople are glorified project managers."

In Rehman’s view, a sale is not an isolated transaction but the beginning of an ongoing dialogue. He details the importance of setting mutually agreed-upon milestones and metrics, both pre and post-sale. These can range from demos and proof-of-concepts to metrics that are scrutinized at three, six, and twelve-month intervals. And as part of an evolving relationship with the client, more products and services should be introduced. For Rehman, the first sale opens the door. Over the following months and years, a successful salesperson will keep selling. It turns that first sale into the opening lines of an extended conversation.

Rehman encourages us to rethink what sales can be. Expanding strategic influence requires meticulous verification and long-term relationship building. It’s an evolution  from sales tactics to sustained partnerships built on mutual alignment and trust.

Sales is the ultimate team sport

A Formula 1 driver depends on engineers, strategists, and pit crew. Similarly, a salesperson needs an array of organizational support to navigate the complexities of enterprise sales. For Rehman, a salesperson's preparation is as crucial as execution. He emphasizes that “sales leaders should measure the team a hell of a lot more based on preparation and a lot less on execution." Preparing adequately for every stage of the sales process may result in losing some deals, but it prepares the salesperson for long-term success. He believes that the sales leader doesn’t need to be the smartest person in the room. This leads to bottlenecks, which he alleviates through knowledge sharing.

“Sales leaders should measure the team a hell of a lot more based on preparation and a lot less on execution."

To help educate salespeople, Rehman recommends structured onboarding. During his 16-week program, each salesperson writes about a new topic every week. This  concept of “narratives” originated at Amazon. Open to team feedback, the write-ups aim to clarify thoughts. His teams also role-plays customer meetings—offering a safe space for constructive criticism. This approach allows the team to develop a shared body of knowledge and expertise.

Weekly peer review sessions for discussing major deals in the pipeline play an important role. These are not cursory reviews. They're in-depth discussions where every team member is invested in each other's success. From the first discovery call with a potential big client like IKEA to solution presentations, peer reviews provide an invaluable opportunity for identifying gaps and strengthening strategies.

Changing the KPI of success for sales teams

At most companies, onboarding and sales training consists of initial introductions. These include presentations, value propositions, and targeted personas. Rehman’s structured onboarding complements the official corporate introduction. A key difference: his onboarding program aims to mold the "best version" of a salesperson. He avoids passive learning from slides. Instead, new hires in his team are thrust into an interactive learning environment. Feedback flows freely. He reminds us that people learn better through active participation than passive observation. Instead of learning about the product or company, the team members engage deeply with each other. This creates a strong foundation for a culture of active learning and continuous improvement.

Rehman doesn't shy away from admitting the revenue-centric focus of sales teams. Numbers are what sales industry folks wake up and go to bed thinking about. In an environment where the pressures of hitting targets and generating revenue loom large, how does one make time for onboarding new hires? Start with team values he recommends."Who are we as a team? What do we stand for?" These are questions Rehman uses to challenge his teams. They aren’t just a sales unit. They are a community bound by shared values of psychological safety, empowerment, and mutual growth.

For a completely remote team, this kind of cohesion is vital. They meet quarterly to discuss performance as well as reflect on these core values. It takes team building to the next level. By keeping everyone grounded in their collective mission, Rehman ensures that the short-term pressures of hitting numbers doesn't compromise the long-term health and unity of the team.

How do they find the time for onboarding when under pressure? Rehman attributes it to the team's value-based foundation. The team recognizes its broader mission beyond closing deals. Thus, making time for something as fundamental as onboarding becomes a natural extension of their shared values. He believes that the quality of the team's interpersonal dynamics will leave a more lasting impact than any single deal they close. It's a culture where each member actively contributes to making others the "best version of themselves."

“When people like myself or anyone else leaves the organization, we're not going to remember each other by the number of deals we've closed.”

Rehman has changed the KPI of success for his sales team. While revenue remains crucial, it's no longer the sole yardstick by which the team measures itself. They assess their success also by the strength of their community, their commitment to shared values, and their ability to bring out the best in each other. This is the real key to building a high-performing, resilient sales team. He ends with a poignant remark: “Ultimately, when people like myself or anyone else leaves the organization, we're not going to remember each other by the number of deals we've closed.” 

No assholes, what? Yes, you read that right. In our next article, you’ll find out about Rehman’s strict “no assholes” policy as a cornerstone for assembling a powerhouse sales team. Feeling inspired by Rehman? Check out our previous interview with him entitled “How the Hungry Huners Eat.” 

And if you’re in the neighborhood, come chat with us in Amsterdam on 15  November. You can find here. Stay connected with us on LinkedIn for event updates and to find out when the next article in this series is available.

 Westley Overcash | Content creator at SALESDOCk

Westley Overcash | Content creator at SALESDOCk

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