People.ai

In every organization there are unsung heroes. Many times these heroes are the men and women that fuel the engine of the enterprise – sales leaders. This series is an attempt to share written portraits of these amazing humans that bring together a passion for moving the business forward with data, technology, and a few other ingredients that might surprise you.

There are companies that leave an indelible mark on our careers and on our lives. Red Hat was one of them for me, so I was especially thrilled to chat with Austin Dickerson, Senior Sales Director at Red Hat. Read on to learn about the mindset of a data-driven sales leader that not only consistently drives results, but builds winning teams centered around a culture of collaboration and solving customer problems.

Austin and I start our Zoom chat reminiscing about some of our favorite people within Red Hat, but I am curious to learn more about him and ready to dive in. We begin with going back in time – it’s always so interesting to see where people get their beginnings and how that shapes who they are today. Austin recalls his first sales role at Enterprise-Rent-A-Car. He realized then that he has a knack for sales; the combination of knowing how to strike up a conversation, make a connection with people, and share his passion. He realized he wanted to hone that skill and set out to build a career in sales. He found his way to tech sales with a data storage company, NetApp. 

He started as a cold caller, which meant he had to quickly learn how to understand what people wanted and needed, how to overcome objections, and win people over with his passion. Here he began learning about technology sales and honing his craft. Austin, then took on an account executive role, handling customers one on one with a massive LA territory consisting of 600 accounts. Within the next year, he stepped into a leadership role where he fine-tuned his management style and learned from some of the best in the business. He describes his phenomenal leaders, his manager Peter Terry and sales director, Joe Santamorena. He credits them and his peer leaders for inspiring him to embark on the journey of becoming the sales leader he is today.

As he looks back, he reflects on how many people touched his career and shaped his philosophy on leadership and on sales. Today, Austin brings all of his energy to his team and to Red Hat. His passion comes through Zoom and he speaks about how much he loves to jump into the seat, strategize how to grow the business, how to overcome any obstacles in their way. He brings a lot of energy and focus to the team, I think in big part because he loves what he does – the excitement of every customer problem being something new and different and the pleasure of seeing his team go through the process of becoming better sellers, and in the end achieving their goals and receiving promotions. All of it coming together is clearly what makes Austin tick.

Austin’s reputation as a data-driven sales leader preceded him when he joined Red Hat, so I am curious to know what are the core data points he uses to manage his book of business. I discover that his mind is very methodical when it comes to how he runs his business and how he leads his team. He lays out one of the clearest descriptions of how to use sales data I’ve heard in some time. He talks about “multiple buckets” of data. “Each bucket is leveraged in different ways for each account set but tells a story about how we are performing against the customers expectations and how we can tell the Red Hat story in different ways that will help solve a business challenge.”

The first set of indicators are all account focused: leveraging the different tools used internally to help paint the picture of areas of opportunity within an account and the ability for the team to solve broader customer challenges. 

The next is focused on individual sales reps and the leading indicators that show whether they’re driving the right conversations with the right set of accounts. It’s these data points that Austin feels are the most important in telling him how to help the sales team and where opportunities lie to streamline productivity. These data points are meant to be reviewed on a daily or weekly basis so the rep can judge themselves and have a blueprint for success. Some of the initial data points reviewed are around pipeline density— how many touch points does the team have with a customer, what types of deals per product family, and lots of focus on propensity data. 

The final set of data is focused around the team’s execution on the opportunities they have within their pipeline. Austin uses multiple data points to understand how his team is performing in their sales campaigns. This allows him and his leadership team to be involved in the strategy of the sales campaign and simplify the overall process. I ask Austin what is key to his team’s success? His answer is simple: “It’s important to be honest with ourselves on how we are truly doing”.

It’s clear that Austin has a well oiled machine and a solid recipe for success. Now I want to understand his problem areas – I ask Austin about his frustrations and I love his response. He turns the question around. He doesn’t think in terms of frustrations, but in terms of what is difficult that needs to be solved. I find that to be a profound distinction. I asked him what he considered difficult and he shared about how his challenges are a result of COVID and the impact it had on his people. “The crux of the problem lies with knowing how to address the needs of your people – how do you really know what’s going on and how you can help. How do you recreate in-person training with a whiteboard? So many new employees join without ever meeting, and the question of how do you build relationships comes up regularly. How do you substitute going for lunch, being the office, being a part of the team, and experiencing the Red Hat culture – all contribute to setting up the individual for success.”

Austin challenges himself to rethink how things have been done and recreate the connections made on the sales floor in new ways, whether a call or IM, that keep everyone connected and letting them know he’s there for them. Knowing where to focus and how to act on the awareness of a challenge has been what he has had to overcome as a leader – and he admits, it took some time to adjust.

I can see that Austin clearly cares about his team, so when I ask what is the most rewarding part of his job, the answer is no surprise. He talks about the impact he can have on people, the goals that are achieved, the career journey that can be cultivated and spearheaded within Red Hat. It goes beyond the promotions for Austin (which is rewarding) but having an impact on people’s lives and their career trajectory is the ultimate goal. On the customer side, flexing the muscle of understanding customer needs and being able to translate how Red Hat can help them with the impact of COVID on their business.

As I speak to Austin, all the pieces of the puzzle start falling into place. The love of data, the passion for the craft of sales, solving customer problems, and the desire to see his people succeed. I am curious what Austin sees next for sellers. I ask him what he thinks of when he sees the words “sales transformation”. The answer?  Data.

“The ability to leverage AI – leveraging data that you have to find new ways to interact with customers on their journey”. I dig deeper on what that means and he proceeds to describe the “imperfect” sales funnel, one where customers look for information significantly before they speak to a seller. This is where Austin believes we can leverage AI to connect with people wherever they are in their buyer journey. Austin chuckles that this is the fun part — letting people try Red Hat technology, see how it works, and rely on the seller to help in the process.

My favorite part of the interview – I get to ask Austin to picture himself a year from now on a SKO stage. What will be his greatest accomplishment?

“My team and I stepped into the journey of accomplishing our 2-3 year vision. We have addressed our customers’ needs. We have found a way to overcome and stay connected as a team and drive a common goal. We have cultivated the Red Hat culture and provided our reps the tools and the support they needed to be successful.”