Enabling Sellers with the Winning Edge
Sales Management 10.20.2022

Enabling Sellers with the Winning Edge

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In this episode of Sunny Side Up, Uttam Reddy joins the conversation to talk about sales enablement in the IT and SaaS space. Listen as Uttam discusses strategies to break the digital barrier when nurturing customer relationships. He dives deeply into the importance of onboarding and setting sales reps up for success. Uttam also shares key industry secrets on how to turn an economic downturn into a win.

About the Guest

Uttam Reddy is currently the Global Vice President of Sales Enablement & Strategy at Rackspace Technology. Additionally, he chairs global deal governance for large transactions and leads the bids & proposals team. Before joining RXT in 2020, Uttam held leadership roles at DISCO, DoubleHorn, Accruent, Centurylink, and Dell. He started his career at IBM as an industrial engineer. He holds an MBA from Duke’s Fuqua School of Business and a BS in Industrial Engineering from New York University.

Connect with Uttam Reddy

Key Takeaways

  • To keep up with the changing sales landscape due to COVID, drastic decisions needed to be made quickly. Rackspace’s decision to go fully remote and pour its resources into onboarding and equipping sales reps was investment worthy of making. 
  • Onboarding is one of the key steps in creating a successful employee. Rackspace follows a process of “ever-boarding” its employees by constantly providing new training and up-to-date resources.   
  • Providing bite-sized information is vital when equipping sales reps without information overload. This way, reps can quickly take action on what’s important to them without feeling overwhelmed. 


“Economic downturns can be a windfall for technology. As customers are having challenges with budgets and resources, having a reliable solution provider like Rackspace is an advantage.” – Uttam Reddy


Highlights from the Episode

Talk about your role at Rackspace

Uttam’s two main goals are helping sales and customer success teams be more effective with their conversations with customers and minimizing risk on deals. In addition to training and support, his job includes helping to set global win strategy and pressure testing deals to make sure they are as successful as possible while working on proposal responses and collateral delivery to customers.

How has Rackspace had to change in the landscape of COVID now that people are primarily digitally connected instead of having person-to-person interactions?

Covid has dramatically changed how Rackspace engages with customers. One of the key changes made was taking its sales onboarding completely remote to speed up the process and increase efficiency. They also augmented their curriculum to provide resources to help their salespeople better connect with customers and prospects.

How do you ensure that your sellers are up to date on the product, but at the same time are not overburdened with information overload?

Rackspace has evolved its onboarding process to focus on “ever boarding.” This means they are constantly providing new training and support to their reps to be productive and keep up with the latest changes. One way they do this is by holding a global call called the Weekly Sales Academy every Monday morning. During these calls, reps get updates on new offers, capabilities, and other important news.

How do you train your sellers to engage with prospects/ customers remotely? Do you have a framework that you could share with our listeners?

Rackspace spends a lot of time and effort making sure their new employees are up to speed on all the vital information, tools, and procedures that they will need to be successful. After the first week of training, reps move on to more practical exercises so that they can start using the tools and techniques they have been taught. Beyond the first 90 days, they continue to receive support and training. 

How are you and your organization adapting to the current economic downturn?

Rackspace encourages its customers to lean in during difficult economic times by offering support and assistance. This allows customers to still access the company’s technology services when they need them most.

Is there a book, blog, newsletter, website, or video that you would recommend to our listeners?


Walter Rogers – President and CEO of Baker Communications

Brian Souza – NYT Bestselling Author

Mark Friedman –  Chairman of Advantive

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