Develomentor

Ep. 19 Ross Gilbertson - Senior VP of Information Technology

December 30, 2019 Grant Ingersoll / Ross Gilbertson
Develomentor
Ep. 19 Ross Gilbertson - Senior VP of Information Technology
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Develomentor
Ep. 19 Ross Gilbertson - Senior VP of Information Technology
Dec 30, 2019
Grant Ingersoll / Ross Gilbertson

Ross Gilbertson is a long-time IT 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 full episode show notes click here

Show Notes Transcript

Ross Gilbertson is a long-time IT 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 full episode show notes click here

Speaker 1:

[inaudible]

Speaker 2:

welcome everyone to the development or podcast, your source for interviews and content on careers in technology. I'm your host grant Ingersoll. For those new to the show, we have two simple goals. We want to showcase interesting people in technology across a variety of roles and highlight all the different paths people take in their careers in technology. Today's guest is a long time an it manager, having worked his way up from the director level to CIO and SVP of technology along the way. He's worked across a variety of industries ranging from banking to eCommerce to publishing. And I believe even if I read correctly, the coffee business, please welcome to the show Ross. Gilbertson. Ross, great to have you here.

Speaker 3:

Thanks grant. Great to be here.

Speaker 2:

Hey Ross. So why don't we just start off by having you introduce yourself and your career in your own words?

Speaker 3:

Certainly. Uh, well, I'm, I'm going on probably 30 years now, uh, in, in my profession of it didn't think I was going to be a, an it professional when I, I was in college and going down that path, transitioning from a high school to post secondary education. But uh, at that time, so the technology industry was starting to take off the internet was an attempt to see and, and um, technology was, was beginning. It's, it's uh, it's boom. And so, um, started down the path actually in the direction of finance and accounting and, uh, you know, opportunity presented itself for me to, to pivot, move down the technology path and I've never looked back.

Speaker 2:

Wow. So, so actually coming out of high school you were thinking, Oh, I'm going to go be an econ or I'm going to work at a bank or, or something along those lines and then got into it. W was it a mentor or was it just a job opportunity? How did you, how did you find yourself making that shift?

Speaker 3:

No, I would say through high school and then into college. And through my accounting courses I was getting more and more exposure to computers and technology. And, uh, my first role actually, it was in somewhat of a data processing position that had a technology component [inaudible] but the company at the time was starting to expand their use of computer systems and they were looking for talent internally that could help. I support that process and that a growth of utilization of computing within their organization. And uh, they quickly discovered that I had a knack for it and I had an interest in it. And one thing kind of led to another and more and more of my, uh, job started to, to drift in the direction of, uh, computer systems management.

Speaker 2:

Ah, interesting. Yeah. And you know, it's funny cause I think, uh, you know, when you think of the, like, like my son's age and his generation, people who grew up as digital natives, this notion that computers were just coming into the workplace is, is perhaps a bit foreign yet. Like folks like me, I know like, and I think what I'm hearing from you is there's this, Hey, you know, I was good at good at math, good at some of these, you know, things like accounting and et cetera. And so there's kind of this natural, a way of lending itself into it because especially back then it tended to gravitate towards people who were more, shall we say, inclined that way towards math and numbers. Is that a, is that fair for you?

Speaker 3:

Yeah, I would say so. And you know, some might say that I took a little bit of a nontraditional approach, uh, in the infancy of, I guess when computing hit the mainstream. A lot of the jobs were more around the programming bent and developing software and writing software systems. Whereas I came at it more from the business systems perspective, you know, from an accounting perspective in a word processing and a graphics design perspective. I'm more on the business side than on the engineering side or the computer science side. And I think that's what's helped make me successful throughout my career is that, uh, I had a mix of technical interests and uh, and passion to some degree, but also a strong interest in passion and understanding business in general. And, uh, throughout my career as I've made moves from, uh, organization to organization, I think that combination has really served me well.

Speaker 2:

Yeah, that's interesting. And that's actually a great segue into, I want to, you know, as I was digging into your background, I mean, you know, you've, you've been pretty successful working across a lot of different industries. I think. Uh, you know, I counted finance and I mentioned publishing. Uh, I think he did a stint at a coffee company there for awhile. You know, what are, what do you see as some of the key lessons you've learned as you've taken this skill of, uh, being pretty technical, but then understanding the business. What do you see as kind of some of the key things that have helped you really dig in across those roles?

Speaker 3:

Know, I would say above all, it's curiosity. Um, interest in really listening and understanding and learning and observing, uh, what's going on around you. And then you know, that the innovation side, which then takes that curiosity and those learnings and causes you to search for solutions or better ways forward. Um, but along with that, and I guess surrounding all of that would be relationships. It's all about developing relationships and not just in your core area of expertise, but all across an organization. And you bring those three together. I think you find that you can have success in just about any organization you go to. And if you look at my career path, you're right, I didn't focus on a specific industry. It wasn't manufacturing, it wasn't retail, it wasn't banking, it was some of each of those. And 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.

Speaker 2:

Yeah, no, that, that's great. I mean, wow, there's a whole lot of packed in there. And I want to unpack a little bit on the relationship side because you know, as I've done a number of interviews for this podcast, I mean this, this theme keeps coming up time and time again. And I think especially like if I look back at 18 year old grant, getting into tack the relationship part of it was the least of the things I cared about. I couldn't wait to get working on technology writing code, like digging in on, on the tech side and, and now, you know, what I'm hearing from you is, yeah, that's important and you've got to be naturally curious there, but you also have to develop this, this relationship to the business that that is really what carries you, you know, so perhaps, you know, unpack that a little more. What are some examples where the relationship aspect really, you know, has been some of the key parts of your career?

Speaker 3:

Okay, well for one thing I would say it's really opened doors for me, you know, earlier in my career as I was still learning the business. Um, for example, I looked at marketing and some of my early exposure to marketing was the observation of a tide logo on the hood of a race car. And I remember thinking to myself, there is no way that that sells more laundry soap. And so I kind of had this jaded view of marketing as, as a, 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. Similarly for sales, I found that when I, earlier in my career I was in a technology consulting, uh, organization and I felt that as a presales engineer, I was the one who was ultimately telling the customer now what the technology would do in the value would bring.

Speaker 3:

And I, and I didn't have a great appreciation for, for the work that the sales rep was doing. But as, as my career kind of continued to progress, I got to know those individuals better and understand, you know, what it is that they did to try and even get their foot in the door so that we could have that meeting with the customer to show them what our technology was that we were trying to sell them, or that marketing department leader and all the work that they were doing to try and understand who their customer was so that they could even [inaudible] this marketing opportunity in front of them. Because of that, I started to gain a better appreciation for all the work

Speaker 2:

that they do. While it was different than me, and I maybe didn't understand it enough to fully appreciate it, that it was still important to the overall goals of the organization. Yeah. That notion, it takes the village. And boy, I tell you one area in my own career where it's [inaudible] where it's hit home is, uh, when you see the salespeople dealing with the legal and procurement after you've done all the technical stuff, and then in your mind as a sales engineer that the work's done, right? Like they're sold and then you're like, Oh yeah, we need to talk about contracts and language. And then you're like, wow, that's, that's a whole nother level of work that you just had no clue even existed.

Speaker 3:

Exactly.

Speaker 2:

So, you know, so see, you've kind of shifted and grown. You shifted through some industries and you've, you've grown in, in title, you've had titles like CIO and, uh, and I think in your current position is SVP of technology. What shifts for you, you know, what's shifted in terms of going from that individual contributor role into being a leader of an it organization? And how do you think about that role as a leader of an it organization?

Speaker 3:

You know, I think one of the big things is really coaching and mentoring. Uh, when you transition from being responsible for solely responsible for the work that you're producing, and maybe you're a part of a team, but that's end of the day you're being judged by what you individually produce to where you're now supervising or leading people. Um, the role really changes to that of you're now being measured based on what a group is producing. And so you have to start tap into other skills around, uh, uh, mentoring and motivating and coaching and guiding, uh, people to, uh, get the most out of them and to leverage their skills, uh, to their greatest, uh, greatest possibilities.

Speaker 2:

Yeah. And then, and you know, and I would imagine, you know, as you know, so what are some of the lessons you had to learn along the ways? Cause I think, you know, many of us on the tech side, you know, we're not always, let's say the most outgoing, uh, I can't speak for you of course, but I know that's, I've met plenty in this industry. You aren't. And yet you have to shift to this being a leader of people. Like, what were some of the things you really had to learn that you just like, you know, I don't even know how to do that or, or I don't even know where to start.

Speaker 3:

Okay. No, I think one is just being a, an active listener and asking [inaudible], you know, good open ended questions to really [inaudible] you know, draw people out of the shell. They might be [inaudible] or the skeptical position they might have towards something. Mmm. You know, questions like what does better look like? To me it's an important question because a lot of times people can quickly say, I don't like it, but they don't always come right forward with and here's what I would do differently. And so sometimes you need to respond to that, uh, point of view with what does better look like and what better looks like might be different from one person to another. And so then you need to try and understand their point of view. Why does that make it look better for them? And that might be different for the next, for the next person in the room. So you really have to have good, Mmm, carefully planted questions to try and draw out the information to make sure you have full context for what it is you're trying to accomplish or what is the perspective of the individual. That's what you're there to serve.

Speaker 2:

Yeah. And I imagine too, in, in your leadership role, you're all better, it goes across a lot of different roles, right? You like you, you hit on already marketing, sales and then obviously your own it constituency and, and keeping an eye on the big picture. How do you think about balancing what you know is technically possible with where the business ultimately needs to be?

Speaker 3:

Okay. Oh, that's a great question. I think it's a challenge that, that I've, you know, I've faced throughout my career and that really hasn't changed from organization to organization. Um, technology can sometimes be very complicated and hard to understand. And because of that there could be expectations for how easy or how quickly or how inexpensively it might be able to be deployed. And you know, my role I guess is really, Hmm. Oftentimes as an educator and you know, just like just like a teacher, there's, there's a, there is a way to kinda instruct someone, uh, or provide someone with information they may not, or knowledge that they don't have without making them feel like you're talking down to them or that, you know, they're ignorant in some way on a specific topic. And so, you know, it's, it can be tricky sometimes to um, try and help people understand that there's more to a situation than what they might, uh, have anticipated. Um, but do it in a way where you're, you're working towards a mutual or a common goal, you still want them to have the outcome they're looking for, but helping them understand that there's a path to get there and that you're going to walk down that path with them together.

Speaker 2:

Yeah. Wow, that's great. Wow. Two, I mean two really good nuggets in there. This notion of what does better look like? I'm going to steal that for, for my own day to day cause I love, I love that question. And then this walking down the path together and, and, and building the case together. I think a lot of us in it, we always just, Oh well let's go deploy the latest tech. And that's not always the right answer. And I think you, you hit that nicely. Uh, you know, Ross, whenever I have a, a manager of people on the show, I really like to take a step back and, and not just be about your career but, but you know, because this, this podcast is targeted at people who are new to this field or are coming in and want to be hired in a technology role in a, in a company perhaps like yours is, you know, what do you look for as a hiring manager in people to bring onto your team?

Speaker 3:

Okay. You know, I like to say that a hire for talent and not for position, um, when you post a position or a job requisition, you don't know what you're going to get in terms of applicants. And I think you need to be prepared to go into with an open mind. Um, you're typically not going to find somebody that checks all the boxes that you're looking for. Oftentimes you'll find somebody that maybe check some different boxes. It could really add value or, or cover some gaps that you have, uh, within your organization. So I think you need to really go into that with an open mind. Um, I also look for aptitude. Uh, you know, someone may not have all the skills I'm looking for, but if they've demonstrated to me the aptitude to learn and take on a new new skills and new new capabilities, uh, that's, that's gold for me.

Speaker 3:

Um, but above all, I would say attitude, um, people's attitudes and their personalities and their styles. Mmm. You know, those are things that are, that are developed over years and years. [inaudible] yeah. Typically a couple of decades before they even get into the professional workforce. And those things don't, they don't change overnight. So, um, based on the role, different roles, you know, meld better with different personalities and you need to understand what is, what is the personality makeup that's going to be fit best within a team, uh, and make sure that you're looking for that because that's something that, uh, if you trade off on, on, um, you know, they're, they're a work ethic or they're, um, relationship skills or, or, or interpersonal skills. Those aren't things that can easily be, uh, molded or fixed once they're onboard.

Speaker 2:

Yeah, I know a lot of great advice in there, uh, uh, is so many nuggets as well. I love, I love that a phrase you said hiring for talent, not position then you know, obviously once you've hired somebody, you, you, you bring them on in their, in your Oregon. And I imagine that a key part of your role also is helping nurture and giving feedback to people and, and helping them grow in their career, which is, you know, especially as a leader is often as important as anything else you do, you know. How do you think then about the people once they're in the fold? In terms of growing, uh, and, and giving feedback and all of those kinds of things.

Speaker 3:

Well, I think clear expectations are, are number one, if you haven't set clear expectations, it's really hard for somebody to meet your expectations. I often tell a new employees that join my team that, you know, if, if you make a mistake on something and we haven't established a shared expectation about it, uh, it's going to be, uh, an expectation setting conversation. It's not going to be, um, you know, a performance credit criticizing type conversation because we haven't established shared expectation about what I was looking for from a performance perspective. Everybody likes honest, constructive feedback, including myself. And so, you know, I think you need to be prepared to, to offer that, um, a on a regular basis, both when things are going great as well as when things maybe aren't meeting expectations. And I think if you approach that, you know, based on behaviors, uh, demonstrated rather than, you know, the person themselves, uh, they're generally received better if you can, if you can tell someone that this is the outcome I'm looking for and the approach and the actions that I think can, can get us there, uh, it becomes much less personal and more about just actions that they can perform to, to meet expectations.

Speaker 2:

Yeah. So, so very true. So very true. A lot of great things to unpack there for our listeners and Ross and interest time. I want, I want to move forward and, and talk a little bit about the role is kind of, it's developing these days and thinking about the opportunities and challenges of, of being an it leader and, and one of the things that's really struck me that's happening right in, and I hinted at this earlier with this, this notion of digital natives is that, you know, business users are more tech savvy than ever and techies are probably more business savvy than ever. And you've even hinted, that's been one of the things that propelled your career forward. How do you then see, you know, the it field in it management evolving as, you know, kind of everybody comes in with this base level of expectations of, you know, the modern era of technology.

Speaker 3:

Okay. Oh, that's a great question. Um, you know, one thing that immediately comes to mind is, is really to, to know your customer and make sure that your employees know your customer. And I think that kind of goes back to my earlier comment about having 'em, you know, shared expectations. Well, it's not just shared expectations for what we provide to each other as a, as a supervisor and an employee. But what are we here to provide to the organization? Maybe it's an internal, uh, business stakeholder. What are we here to provide to the customer in the case of, you know, a retailer, which, which is, is the industry that I'm in today. And if you can, you know, establish kind of what that common ground is, uh, and, and work from that. Um, you know, I think that that kind of takes away the opportunity for, you know, a conflict or, or, or misunderstanding in terms of what, what the goal is to your point about, you know, the current, the current generation of digital natives.

Speaker 3:

Um, you know, I, I'm, I'm not, uh, I'm not a digital native and so I've had to [inaudible], you know, work very hard, I would say, to maintain my understanding of technologies as it's changed over time. Um, quite frankly, I spend a lot of time with my kids, understand the technologies that they're using, why they're using them, uh, and, and how they might differ from, uh, what I, what might be my go to algae to solve a particular problem and just, you know, be a, be a lifelong learner. Find ways to relate to whatever a demographic or generation is. Whether it's a customer that you're trying to relate to or whether it's a, it's a, it's a coworker or an employee that you're trying to relate to, that it is a, in a different, um, you know, generational perspective than you are. So I think it's just continuous learning. Um, seeking to understand and, and, and constantly exploring, uh, those around you.

Speaker 2:

Yeah. I think that notion of learning, I think you hit the nail on the head in technology, right? Is that, you know, at the end of the day technology is all about change. So if you, if you don't want to be in a learning mode, then technology probably isn't the right field. It often reminds me of my grandmother who had nineties, like I want to learn this iPad thing, you know, and she went in all wholehearted into it. I'm glad. You know, maybe one last question along this theme of opportunities and challenges and I, and I'm glad you brought up this, you know, the idea that you are the fact that you work at a retailer and I think, you know, one of the big challenges facing, you know, let's call them traditional retailers. I don't particularly love that term, but you know, brick and mortar is what is collectively called digital transformation. And you know, it's one of the big challenges I think many companies are facing. How do you think about that challenge of modernizing a company? That's probably been perhaps been doing business for, you know, 20, 30, 40, 50 or a hundred years.

Speaker 3:

Okay. Yeah. Well, in the situation I'm in right now, I think that is one of the key challenges we face. We're a 35 year old business that um, you know, has been very successful over that period of time. And um, because of that though, we do have some systems that have been around for in some cases a couple of decades in the retail space today, the consumer expectations are changing very rapidly with the, with the, uh, the, the new expectations that are being set around delivery, uh, by the likes of Amazon, uh, or for uh, omni-channel retailers or those that sell, you know, both online as well as through a brick and mortar store and maybe over the phone. Making that shopping experience as what they call or as seamless as possible is, is a lot more challenging than you might expect. You know, what we're doing to try and address that is look for opportunities where rather than trying to, uh, adapt what we have, how do we maybe replace it with something that is more new and modern, uh, still covering off on all those base needs that we, that we had 10, 12 years ago.

Speaker 3:

But also bringing along, uh, the newer modern capabilities that, you know, our digital natives have come to expect through, you know, mobile devices and social media and, uh, you know, even technologies like, uh, like drone delivery technology. It's something we're not using, but it's something that we obviously you need to keep up, keep our eyes on because it's coming.

Speaker 2:

Yeah, no, and again, it probably all comes back to this fundamental theme you, you've had throughout your career, which is you just gotta you just gotta always be learning. Right. Hey Ross, you know, I mean, so many good things. I'm sure we could continue on this conversation for quite some time because I think there's a lot we could unpack in terms of both the here and now of, of being an it leader in the retail space as well as your, your career. Looking back, I wanna I want to finish up though with a question I ask all of my guests, which is just, you know, as you reflect back on what got you to where you are now, what are some of the key bits of advice, uh, you know, you hinted at the always be learning. What are some other key pieces that really have helped propel your career forward?

Speaker 3:

Uh, you know, I think it just be genuine. And for me, you know, one way that that shows up is being humble. Uh, take responsibility when I mess up. Um, but also share the credit when things go right. You know, when, when I'm, uh, you know, seeing progress or when we, when we have a big win within our teams, I like to make it all about the team. Um, you know, I don't need for it to be about me. And I think, I think that really that really matters. Um, people need to know that, um, it wasn't an individual. It's almost never an individual, uh, that drives the success. It's always a group of people. And so I think as long as people feel like, you know, while you may be the top level, maybe you're in an executive position, uh, the company could not accomplish what it accomplishes without the contributions of everybody within the organization at some level. So, you know, really just staying humble, um, acknowledging where you've made mistakes, uh, acknowledging where you can do better. Uh, one of the things I often ask new departments when I come into an organization is, um, where do you think we can do better? And are we really being open and honest about that and letting them know that, that it's, that they can be vulnerable and they can, they can feel safe and where

Speaker 3:

we're not as good as we need to be. And that's okay. As long as we acknowledge it and plot a path to fix it, make it better.

Speaker 2:

Yeah, some very wise words in there. And I think that goes back to what, uh, that a question that is still in my mind, the summary of this, this whole interview in many ways, which is what is better look like. Ross, I wanna I want to thank you so much for your time, for joining us here today on, on develop mentor.

Speaker 3:

Absolutely. Thanks for having me. Grant.

Speaker 1:

[inaudible].