Ep. 19 Ross Gilbertson - Senior VP of Information Technology


Ross is currently the Senior VP of information technology at Northern Tool + Equipment. He is a results-driven business and technology leader with 25+ years of experience managing complex information systems and technology environments both domestic and international.

He has broad-based technology and business skills, with an extensive history of successfully partnering with both internal and external customers to deliver organizational growth and high-value returns.

Episode Summary

Ross Gilbertson is a long-time Information Technology manager. He worked his way up from the director level to Chief Information Officer and Senior VP of technology.  Along the way, he’s worked across a variety of industries, ranging from banking to eCommerce to coffee and publishing!

When starting out, Ross recalls “a lot of the jobs were more along the programming bent”, but Ross was more of a business guy with an interest in technology. He attributes curiosity as a major part of his successful career. Curiosity not only for learning new skills, but also a curiosity for understanding people.

For other tech roles and descriptions click here.

In this episode we’ll also cover:

  1. Why ‘what does better look like?’ is a great unifying question
  2. What Ross looks for when hiring?
  3. The mindset of digital natives and current trends in technology
  4. The importance of setting clear expectations when managing employees
  5. Traits that will help you become successful across multiple industries

Key Milestones

Key Quotes

“I started on the path in the direction of finance and accounting when an opportunity presented itself for me to pivot and move down the technology path. I’ve never looked back.”

“When computing hit the mainstream a lot of the jobs were more along the programming bent, developing software and writing software systems. Whereas I came at it from more of the business systems perspective.”

“I had a jaded view of marketing as a department that seemed to get unlimited funding for whatever they want but there was no justification or quantification for the value they provided.”

“I had a mix of technical interests but also a strong interest and passion for understanding business in general.”

On becoming a manager in information technology (IT)

“You’re now being measured based on what a group is producing and so you have to tap into other skills around mentoring and motivating and coaching and guiding people to get the most out of them.”

“Being an active listener and asking good, open-ended questions is important to really draw people out of a shell they might be in or a skeptical position they might have towards something.”

“I truly believe that I was able to make those transitions from industry to industry because of that curiosity, that interest in innovating and making things better, and a true genuine desire to build relationships with people that maybe didn’t have all the exact same interests that I did.”

On leading people

”’ What does better look like?’ is an important question.”

“There’s a way to instruct someone or provide someone with information without making them feel like you’re talking down to them or that they’re ignorant in some way.”

On hiring

“I like to say I hire for talent, not for position.”

“You’re typically not going to find someone that checks all the boxes that you’re looking for. Often times, you may find someone who maybe checks some different boxes that could really add value or cover some gaps that you have within your organization.”

“Different roles meld better with different personalities. You need to understand what is the personality makeup that’s going to fit best within a team.”

On staying current with technology

“Quite frankly, I spend a lot of time with my kids understanding the technologies that they’re using, why they’re using them, and how they might differ from what might be my go-to technology to solve a particular problem.”

“Be a lifelong learner. Find ways to relate to whatever demographic or generation it is. Whether its a customer you’re trying to relate to or whether its a co-worker or employee you’re trying to relate to.”

“Making that shopping experience as ‘friction-free’, or as seamless as possible, is a lot more challenging than you might expect.”

“I like to make it all about the team. I don’t need it to be about me and I think that’s important. Its almost never an individual that drives the success, it’s always a group of people.”