Kristie Wilson, former senior director of IT at Walmart, is one of our most veteran advisors and the current Emissary of the Month.

Over the years she’s helped countless salespeople improve their strategies, and has personally mentored her fair share of IT leaders to boot. We spoke with Kristie about the role of technology in business in 2019, as well as how salespeople should prepare if they actually want to impress their prospects.

Leading digital transformation at Walmart

After graduating with degrees in both criminology and psychology, Kristie landed a job at Walmart where she worked in asset protection. Her intention was to pursue a master’s degree in industrial psychology, and she started the job to gain experience and apply some of the skills she’d learned in the meantime. Walmart’s emphasis on the professional development of its employees saw her promoted to a regional senior manager role—where she immediately excelled. From there, it wasn’t long before she took her management talents the retail giant’s IT team.

In a large, complex organization like Walmart, being able to adapt swiftly to technological change became a major priority, and improving agility became a primary focus for Kristie. She managed a team of 24 and oversaw a budget of $236M within the office of the CIO, where she contributed to the modernization of the company’s traditional processes.

“If we think about how quickly organizations are changing, if you’re waiting 18 months for an overhaul, you’re going to be outdated,” Kristie said. “If it’s taking you 20 weeks to create a new product, it may no longer be relevant due to a competitor’s ability to get it done in eight weeks.”

Bringing business and tech together


While becoming more agile is critical, improving synergy between the commercial functions and IT leadership is equally important.

“Technology permeates everything we do, so a tech leader now has to be able to identify what is best for the entire company—not just their own team,” Kristie said. “You have to be a holistic thinker and plan with the big picture in mind.”

Kristie’s unique background and an understanding of human psychology helped her empathize with the divergent interests of leadership personnel across all the teams she was trying to unite. She also came to master the delicate balancing act of meeting the needs of all departments while still contributing to the overall business goal.

Pain points are only the beginning

But it’s not only tech leaders who could use a better understanding of business goals. According to Kristie, salespeople could also benefit from digging deeper into their prospects’ organizations and their main needs.

“The salespeople who were most successful—the ones I looked forward to working with—were the ones who understood the pain points and really ‘got’ the business and were then able to point out things that I hadn’t seen yet or challenge my thinking in some way,” she noted. “They truly became partners.”

That’s the key differentiator: Understanding a prospect’s pain points is an important first step to building a successful relationship, but it’s not the end-all-be-all.

“Someone just coming in to tell me about what I’m missing or what my pain points are will just sound like all the other meetings I took from competing vendors,” she said.

To truly differentiate yourself and your offering, she stressed that you need to go beyond the obvious to demonstrate the value you could bring to a prospect’s organization. The salespeople who did their homework were always apparent, she said. They could speak fluently about their products, and they didn’t skirt issues of scale or relevance.

“The best sellers were fluent in all the current industry trends,” she said. “They were able to answer my technology questions with a clear understanding of who would be making the buying decision and what was important to the business.”

To get that information, Kristie recommends an approach that features digging for data and leveraging your professional network to get insight from experts.

“If you need to speak more fluently about your technology, who in your organization could help you?” Kristie said. “Look at your buyer’s annual report, too. That’ll help you determine what’s most important to the company at the moment. Then approach someone on the inside who may be missing a piece that’s preventing them from contributing to that goal, and show them how your solution can help.”

Evolving for Success

In helping drive digital transformation at Walmart, Kristie experienced almost all the common challenges IT leaders face today. And while there’s no shortage of resources that espouse the abstract virtues of sound leadership, very few provide actionable advice on how to get there. To address this gap, Kristie founded Evolving for Success in 2017.

“You’ll see all these articles about how leaders need to be collaborative, innovative, entrepreneurial, adaptive, etc. There’s a lot of talk about it, but there’s very little action. Leaders need a framework to help them actually work in the way that’s being so highly touted.”

Each of the leaders Kristie mentors have different experiences and use cases, but the general philosophy behind her approach to leadership success is based on three things: action, resilience, and drive.

“Really hone in on your vision and move toward it,” she said. “You have to take action. Leaders get pulled into reactionary black holes where they’re reacting to different interests, but nothing is moving forward.”

Leaders, she believes, ultimately have to make tough decisions, but the best ones balance it all with a good heart. If you can be resilient, know how to manage stress (she suggests meditation), and employ agile strategies when tackling new initiatives—like creating a checklist of achievable goals along the way—you’ll be halfway there.

Kristie the Emissary

When Kristie’s not helping leaders with Evolving for Success, she’s busy helping sales teams with Emissary. Kristie was initially attracted to the idea of working with Emissary because she saw it as an opportunity to add value—not only to the salespeople she was assisting, but to her former employer, as well.

Buyers stand to gain just as much as sellers when Emissaries enter the equation. As former leaders within the organizations sellers are targeting, Emissaries know what’s best for their businesses and can help ensure that salespeople deliver both a positive selling experience and a product that meets their former employers’ needs.

“I love having the ability to form relationships with salespeople and being able to help them through the sales process, “ Kristie said. “I’m also able to add value to the client—my former company—and myself. I love learning about all these vendors, their solutions, and staying on top of all the different technologies out there.”

Some of the most common advice she gives to tech vendors looking to break into new accounts harkens back to her own work generating synergy between business and IT teams.

“Business partners are going to become savvier with the technology they are purchasing, and they’re going to ask more specific questions,” she said. “Being viewed as a partner who doesn’t understand the technology or as a technology offering that isn’t applicable to the business won’t help.”

Executive Insights

Kristie Wilson, former senior director of IT at Walmart, has more than 24 years of leadership experience and plenty of insight into the current role of IT within the retail organizations. She’s used her background in psychology to facilitate better collaboration between business and IT teams to get them focused on the same goals. She has a lot of advice for salespeople, too, on how they can improve, namely: Do your homework, challenge your prospect’s thinking, and open their eyes to new solutions to forge stronger partnerships.

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