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Keith Orlean’s Tips for Building a Winning Sales Team

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At the epicenter of any successful business, from Main Street to Wall Street, lies in its ability to build a sales process (and sometimes, depending on the business team). Building a sales org is a daunting task no matter what size business you have or which industry you’re operating in, but especially if you’re a small business owner.

Keith Orlean, the New York-area entrepreneur who writes a blog describing his experience in business called A Path to Sales Success, has overseen the beginning of a sales team time and time again. In a recent post, Orlean shared his five most important things to plan for when building a sales team.

1. Lead Generation and Sales Pipeline Development

One of the foundational elements of building a successful sales team is understanding where your sales leads come from. Are they provided to your sales team, or should the sales team be responsible for sourcing their own leads? The answer to this crucial question often lies somewhere in the middle. Perhaps your new sales lead knows where to acquire quality leads but expects the business to invest in lead generation tools or resources. No matter what the answer is, Keith Orlean emphasizes the need to communicate fully about this critical step, as it is one of the ways that time and resources can be wasted.

In today’s competitive business landscape, generating leads is not just about numbers; it’s about the quality of those leads. Therefore, a well-thought-out strategy that includes a mix of inbound and outbound lead generation, online and offline methods, and leveraging technology, is essential. Make sure your sales team understands the importance of lead qualification and how to nurture these leads throughout the sales pipeline. This clarity will set the stage for a productive and results-driven sales team.

2. Structured Onboarding Process

It’s vital to recognize that salespeople, even experienced sales leaders, are not simply “plug and play.” Implementing a structured onboarding process is key to expediting the learning curve, especially when it comes to keeping the sales team updated on product knowledge, industry trends, and effective selling techniques specific to your industry.

A well-structured onboarding process ensures that your new sales team members become productive as quickly as possible. This process should include comprehensive training, mentoring, and continuous feedback. Ensure that your team not only understands your products or services inside out but also the unique value propositions that set your business apart from the competition. Moreover, ongoing education is critical, as sales tactics and market dynamics evolve. Encourage your sales team to stay up-to-date with industry trends and invest in their professional development.

3. Emphasize Communication

Effective communication is a cornerstone of a successful sales team. Encourage open and transparent communication among your sales team members. Ensure they are comfortable sharing their challenges, successes, and ideas. Regular team meetings and one-on-one discussions can help identify bottlenecks in the sales process and provide an opportunity to address them promptly.

Additionally, communication between the sales team and other departments, such as marketing and product development, is equally important. Sales feedback can help marketing refine its lead generation strategies, and it can also influence product development by highlighting customer needs and pain points.

4. Metrics and Performance Tracking

To build a winning sales team, you need to measure and track performance. Implement a system for tracking key performance indicators (KPIs) that align with your business goals. These KPIs may include metrics like conversion rates, average deal size, sales cycle length, and customer satisfaction scores.

Regularly review these metrics with your sales team and use the data to make data-driven decisions. It’s essential to recognize and reward high performers and provide additional support and training to those who may be struggling.

5. Adaptability and Continuous Improvement

The business landscape is dynamic, and what works today may not work tomorrow. Encourage your sales team to be adaptable and open to change. Foster a culture of continuous improvement where feedback and innovation are embraced.

Invest in ongoing training and development to keep your team updated on the latest sales techniques and tools. Moreover, stay attuned to market changes and evolving customer preferences. Your ability to adapt to these changes will ensure that your sales team remains effective and competitive.

In conclusion, building a winning sales team is a multi-faceted endeavor that requires careful planning, effective communication, and a commitment to ongoing improvement. By implementing these key strategies, you can lay the foundation for a successful sales organization that drives growth and revenue for your business.

For more of Keith Orlean’s insights and tips on constructing a successful sales team, head to Top 5 Things to Plan for When Building a Sales Team at

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