Tech Sales is for Hustlers Podcast

Campus Series: Caitlyn Gill – Sales Require Stamina

Guest-At-A-Glance

Name: Caitlyn Gill

What she does: She’s the Director of Oregon State Sales Academy at Oregon State University.

Company: Oregon State University

Noteworthy: She is an award-winning sales educator and global sales leader with extensive industry experience.

Where to find Caitlyn: LinkedIn

Key Insights

⚡ Professional sales can open doors for you. Professional sales is not like retail or other types of traditional sales. Most students don’t see the difference, so they usually don’t see themselves as fit for sales jobs. Caitlyn says that one of the first things she does in her classes is showing her students the vast pool of possibilities that sales can offer. “We’ll do that for a couple of different companies, and then all these light bulbs start going off — ‘Oh, I didn’t even realize that that’s what professional selling was.’ The people in the company get to build relationships with other people, set up partnerships with other people, and earn revenue for the company. That’s the sales force.”

⚡ The importance of believing in the product you’re selling. Believing in your product is not a must-have in sales, but it does make you more persuasive. When you believe in the product you’re selling and are passionate about your company, you have a better chance of thriving in sales.

“I stood behind those products like they were my children. I didn’t have children [then]; I have children now. But at that point in time, those were my babies. And I’m like, ‘Don’t call my kid ugly.’ […] So I think it does matter. You have to be passionate about the products that you’re selling and about the company and the company culture. I think that it’s not only a product fit when you work for a company, it’s a culture fit.”

⚡ Sales is the quickest path to the C-suite level. Unlike what some students think, sales is one of the most promising jobs. Caitlyn says that sales is your ticket to executive and C-level positions.

“What I tell my students is that basically every single person that I’ve ever met in the C-suite has gotten there through some path that has coincided with sales. So if you ever want to be in an executive position, be in the C-suite, or run a company, sales is your quickest path there, honestly. It takes a lot of self-discipline. It takes a lot of training, and it has high highs and low lows. It takes a lot of mental and physical stamina, but the rewards are immense. And as a salesperson, you have the privilege to help people every day of your life.”

Episode Highlights

Active listening is an essential component of being a salesperson. 

“I loved that consultative part of sales. I loved being a good, active listener. So all of these things that I was doing as a very entry-level retail salesperson are actually building blocks for professional salespeople as well. So I teach these things to my students all the time — how to be an active listener and how to do discovery with your clientele and learn about their pain points before you ever go into selling your product or service.”

Sales require stamina, but it also comes with a lot of excitement.

“I believe that she will probably leave my class and not go into sales. I just don’t think it’s for her, and that’s totally fine because there is a certain amount of stamina that you need to pursue a professional sales career. But with that stamina comes a lot of excitement. It’s like a rollercoaster ride. There are big highs and there are big lows, but I’d rather be on the rollercoaster than on the choo choo train that is slowly chugging around the track.”

Always approach things with a beginner’s mindset.

“I’m thinking of all the different sales tools we have to record your calls and allow you to analyze everything that you said. And we had nothing like that. So it does remind you that although we have all these tools now, what it takes is being that lifelong learner and having that beginner’s mindset always. I think that the one thing that I try to kind of hone in for myself is to always approach things with a beginner’s mindset.

Even with 15, 20 years of experience, even [though I’m] teaching sales, I’m still a learner first — before I’m a teacher, before I’m a salesperson.”

Transcript:

[00:01:13] Kristen Wisdorf: Welcome back, hustlers, to another edition of our podcast. I am your host, Kristen Wisdorf joined by Libby Galatis. 

[00:01:21] Libby Galatis: Hello, hustlers. Excited to be here today.

[00:01:24] Kristen Wisdorf: And today

[00:01:25] we have Caitlyn Gill who is the Director of the Sales Program at Oregon State University which is really exciting. Go, Beavers. Caitlyn, welcome to the podcast. 

[00:01:37] Caitlyn Gill: you so much for having me. I’m incredibly excited to be here.

[00:01:40] Kristen Wisdorf: Yeah, we’re excited to chat with you. You have some really unique experience. You, you know, have some experience in your sales career, in software sales and in technology, which is obviously what we focus on here at memoryBlue and you also work with students, which is, you know, our target demo for the folks that we hire into our SDR role.

[00:02:01] So, we kind of are from the same world, which is really exciting. Caitlyn, we want to get started by talking to you about, asking the question that we ask all of our students that we actually interview. So, while it is an interview question, it should be a pretty easy one. If you can take 60 seconds to tell us about you, essentially, what would be your highlight reel?

[00:02:23] What would be on that highlight reel to share us a little bit about your background? 

[00:02:28] Caitlyn Gill: Yeah. Great question. It’s, it’s actually really funny that you asked that because my students are preparing right now for an elevator pitch competition through our sales academy, so we talk a lot about how to, you know, how to describe yourself in an elevator pitch and how to kind of package everything together in a, in a 30 to 60-second pitch.

[00:02:48] So, incredibly relevant. So, to describe myself, what I would say at this point in my career, I am an award-winning sales educator, I’m a global sales leader as well in the tech space and I teach currently personal and professional selling at the Oregon State College of Business. I’m the Director of the Sales Academy, which is, we’ve actually been named one of the top collegiate sales programs by the Sales Education Foundation

[00:03:11] and our goal at the academy is to educate students on the principles of professional selling, all students at Oregon State, so not just students in our college of business. I’m very proud to say that in the two and a half years that our academy has been around, we have earned national championships,

[00:03:28] most recently we are in the second-place title at the International Collegiate Sales Competition, but outside of my responsibilities at Oregon State I do, still do some consulting in the tech space, helping companies with sales enablement, sales transformation. I’m doing some training and my industry expertise is really around financial reporting and business intelligence.

[00:03:49] Caitlyn Gill: So, to package myself up, I would just say that I am a combination of academic sales experience as well as tech sales executive and with all of that I, I am certainly a lifelong learner, so my goal now is to educate, but also continue to learn myself.

[00:04:09] Kristen Wisdorf: Okay. That is amazing and there’s a lot to dive into there. Thank you so much. So, let’s take it back to college, right? What did you go to school for? I see you went to school in North Carolina, you also used to live in North Carolina, so talk a little bit about your time at ECU, what you went to school for and how you transitioned from school into sales. 

[00:04:29] Caitlyn Gill: Yeah. Great question. So I, you know, I honestly think that many of my students say before they take my class, they say, “Well, you know, I guess I’ll go into sales if I don’t figure out anything else,” right? Which, after they take my class, they are like, “We want to go into sales because this is the best career in the entire world,”

[00:04:48] so I think there’s a lot of education that happens there, and when I was in school, especially an undergrad at East Carolina, there was no sales program, there was no sales track within a business degree, so my, my degree was in business, specifically in public relations and I, in my time in college, I honestly didn’t really know what I wanted to do, but I knew I wanted to do something sales-related,

[00:05:10] Caitlyn Gill: so I wasn’t really sure if I wanted to go into tech or to medical device sales, but I was pretty sure that I wanted to go into sales because I, prior to college had a job in sales, I worked at a jewelry store, while I was in college I supported myself by working as a bartender and, you know, honestly, it could be argued that any, any career that you have has a sales component, but I definitely was very interested from an early age in pursuing a sales career because I knew that you could essentially have uncapped salary potential with commission,

[00:05:44] and I learned that at an early age selling jewelry. I wanted to come out and go into sales, and I knew that, and I think that that’s really different than a lot of students that end up kind of taking a job out of college and then eventually find sales because they realize it’s the best job out there,

[00:05:59] but a lot of them start in a different position and make their way there a couple of, couple of years down the road. And then, it was, it was interesting by the time I went to grad school, so I went to East Carolina for undergrad and then I went to University of North Carolina for grad school,

[00:06:14] I was, at that point, you know, 12 years into a sales career so it was really interesting being able to experience education from a professional sales perspective and experience a degree program and how it can kind of help build you as a business person once you’ve had that, that length of time of sales experience.

[00:06:38] Libby Galatis: Wow. We’ve, you just seem, you’re such a decorated professional in this industry and to be speaking with a woman who’s been able to climb the ladder so quickly and early in their career I think this is an incredible opportunity that, you know, I appreciate you taking the time to sit and meet with us.

[00:06:53] I want to take a step back and talk about this experience that you’ve kind of pointed to a couple of different times, that first sales position that taught you about commission, that gave you some perspective and enlightenment into sales as a profession, was that something that you had stumbled upon?

[00:07:08] Libby Galatis: Did you have influencers in your life that were whispering, you know, “Pursue sales, you should start in a sales role, you can make a ton of money here,” and, and catch us up a little bit about that experience and sort of what it provided you as far as that defining, “This is something that I’m really good at and something that I want to be part of it and pursue.”

[00:07:26] Caitlyn Gill: Yeah, that’s a great question. I actually love to take it back to that time of my life because, you know, you don’t know what you don’t know when you’re a kid and a teenager, but, but the interesting thing about that first job, and I worked, I worked at a jewelry store and prior to working at that jewelry store, I worked at a sandwich shop across the street,

[00:07:45] Jersey Mike’s actually and the folks from the jewelry store would always come over and have lunch and I would make their sandwiches, and I was just kind of impressed with the fact that they were dressed nicely. They all seemed very professional, and so I would always chat it up with them and I used to, like, write their name and mustard on their sandwich buns,

[00:08:08] and so I, one day, one of the gentlemen that worked over there, he asked if I had any interest in working and selling jewelry and I was thrilled, oh my gosh, I was, I was 16 and I was like, “This is amazing,” I, I really thought, like, “This is the most professional job I’ve ever been offered and I’m so excited.”

[00:08:27] Caitlyn Gill: And so, so I got the interview and started working there and I just loved it. I loved people coming into the store, I love talking to them about, you know, why they were there and what they were buying jewelry for and really trying to fill a need, fill a need in their life with something that we could provide,

[00:08:47] and so I loved that consultative part of sales. I loved just really being a good, active listener. So, all of these things that, that I was doing as a very entry-level retail sales person are things that actually are building blocks for professional salespeople as well, right? So, I teach these things to my students all the time, how to be an active listener, how to do discovery with your, with your clientele and learn about their pain points before you ever go into selling your product or service

[00:09:14] and I was doing all that in a retail-type situation selling jewerly, right? And then the plus side of all of that was that I did get paid an hourly rate, but I also got made commissions. I was super motivated to pick up extra hours and work late and work over holidays because I had that earning potential,

[00:09:34] Caitlyn Gill: and so I learned that at a pretty young age and then luckily through my parents and just other professionals I would meet through them, I realized that, “Oh, sales can actually be a career-career, like, you could go into business-to-business sales after college and do this at a much higher level.” So I, I, 

[00:09:52] kind of went into college knowing that or thinking that that was what I was, what I was interested in pursuing.

[00:10:00] I just think that’s so interesting because you had mentioned earlier that part of what you love about what you’re currently doing is sort of shifting that, you know, “Oh, I’m stumbling into sales because I am really late to the game, and now I’m realizing through experience it’s where I want to be, 

[00:10:13] Libby Galatis: I’m intentionally pursuing this,” which is something that you kind of identified through this first experience that you just shared with us. So, what do you think, like, resonates most with students in your classes, whether it’s the first sales course that they take, or, you know, certain elements of those kind of more intense sales classes that you might be teaching?

[00:10:29] Like, what, what starts that process of where those light bulbs start to go off? Like, “Hey, this is actually really great and a lot of people can do it,” just kind of walk us through what your process is like.

[00:10:40] Caitlyn Gill: Sure. Well, I think it actually starts with explaining what business-to-business sales is, right? A lot of students that come into my class, the first thing we talk about on, on day one is what professional sales is, so I asked them, “You know, what do you think professional sales is?” Because most students’ experiences at this point are retail sales,

[00:11:01] home sales and car sales, right? So, that’s what everybody thinks professional sales is. If I’m going to go into professional sales, I’m going to be selling in retail, I’m going to be selling houses or I’m gonna be selling cars, and there’s nothing wrong with selling houses or selling cars or selling retail,

[00:11:15] those are all great business-to-consumer sales situations, but they don’t have any idea what business-to-business sales is, right? And so, we kind of start there with, “Let’s look at all of these companies that you would ideally work for.” So, we’re here in Oregon, in Corvallis really close to Nike headquarters and 99.9% of my students are like, “I want to work for Nike after college,”

[00:11:40] right? And so, we kind of explore, “Okay, let’s look at, let’s build a list of the 10 companies you want to work for, and then let’s take a look at the types of jobs that you would want to have in that company,” and when we really kind of dive in to what these students would want to do, so, “I want to work for Nike.” “But, what do you want to do at Nike?”

[00:11:59] “I want to be in a, you know, kind of a business-to-business situation at Nike, or I want to help build new clientele at Nike, or I want to build brands at Nike or, you know, reach, connect new markets at Nike,” all of those are sales roles, right? And so, we’ll kind of do that for a couple of different companies,

[00:12:17] Caitlyn Gill: and then all these light bulbs start going off and saying, “Oh, I didn’t even realize that that’s what professional selling was”, you know, the people in the company that get to build relationships with other people, set up partnerships with other people, earn revenue for the country. That’s the sales force,

[00:12:36] right? So my classes fall under the marketing department at OSU, and a lot of my students do, do want to go into marketing and they do go into marketing, but I have actually seen students, a lot of students in, in my, in my 15 years in software, see a lot of folks that come in through marketing that end up in sales anyway, because they realized, “I really want more of 

[00:12:56] a client-facing role,

[00:12:58] I want more of a relationship-building role,” in those are all sales roles. 

[00:13:03] Kristen Wisdorf: Absolutely. What a good exercise to open up a student’s minds to the way that they can break into these companies that they really want to work for rather than just saying, “Oh, you’re most likely going to end up in a sales role,” it’s actually walking them through a company they actually want to work for,

[00:13:20] and then it becomes something that they’re excited about versus they feel grudgingly that they have to get into. 

[00:13:25] Caitlyn Gill: Right. Absolutely. Absolutely. And, you know, and I also always tell students, “Sales is, it’s not for everybody,” right, just because you go through this class, I mean, I had, I had a student this term who, from the beginning of class she was like, “Nope, never going into sales.” And I probably, I believe that she will probably leave my class and not go into sales,

[00:13:43] like, I just don’t think it’s for her, and that’s totally fine because there is a certain amount of, of, stamina that you need to pursue a professional sales career. But with that stamina comes a lot of excitement, right? It’s like the rollercoaster ride. There’s, there’s big highs, there’s big lows but I’d rather be on the rollercoaster

[00:14:02] than on, like, the choo-choo train that slowly chugging, chugging around the track, right, in a circle. So I think it’s, 

[00:14:09] I just think that 

[00:14:10] you have to honestly be honest with yourself 

[00:14:12] if this is the right career for you based on what you’re looking

[00:14:15] for in your 

[00:14:16] career. 

[00:14:16] Kristen Wisdorf: Yeah, and also props to that student for taking the class anyway, because there’s still a great foundation to have 

[00:14:21] whether she, he or she stays in sales or not, so that’s amazing. There are a lot of listeners that we have who have maybe, like, a similar background as you when it comes to being in retail sales, being a bar tender in college, you know, being in the business school, whether they know for certain they want to be in sales role or not, that’s a really good kind of background and first foray into sales and what, what a lot of our listeners know as, you know, business-to-consumer sales. Let’s talk about

[00:14:50] your first B2B selling role or that first, you know, professional role post-college. What was the most surprising thing to you when you got into that role and you really started your professional sales career?

[00:15:07] Caitlyn Gill: Yeah, that’s a great question. So, I started my professional sales career with a company called Sageworks. It was a software startup in the RDU, Raleigh-Durham area and so they, they had a product called Profit Sense and what it did was translated financial statements into kind of readable reports and I was so excited when I got hired for this job.

[00:15:28] I just was so excited to be in the tech industry. I thought we had the coolest product on the market and in those days we didn’t have the luxury of LinkedIn. So, you were given a book of about a thousand numbers and you were just told to start calling, right? So I made 150 calls a day every day to accountants and analysts.

[00:15:44] I was, I was told everything in the book, every swear word you can imagine, probably hung up on about 50 times a day which, you know, some people say that builds character, I would say it’s part of the journey, but I was, I was just thrilled, honestly to have that suffer job and be working with other, is a very young company,

[00:16:04] Caitlyn Gill: so a lot of other young people that were all really excited about our product, and so I would say the startup culture was really perfect for me because it was fast-paced. There was an easy acceleration from SDR to AE. I moved into a consulting role and finally kind of settled in more of a sales engineering role which I think is

[00:16:20] personally the best job, best sales job on Earth, and I was able to kind of work with our clients to develop a new product, which was called Sageworks Analyst. I trained the first 150 banks who use the product and that product was ultimately part of a product suite that kind of moved the company forward.

[00:16:37] I moved on to a different company before that company, before Sageworks was acquired, but it was still an incredible experience to spend the first couple years of my career in this really fast-paced, fast-paced upper trajectory into the sales industry.

[00:16:55] Libby Galatis: I love this experience that you’re sharing with us so much, because I think you, I mean, you started from the ground level where, I mean, 500 calls a day, that’s a very high number 

[00:17:05] Kristen Wisdorf: 150.

[00:17:06] 

[00:17:06] Libby Galatis: and you’re dialing using, like, a regular telephone, which now we have our dialers and all that stuff, so we take a lot of that stuff for granted, but you were doing the tried-and-true grunt work, business development type, type role, that’s, that’s exciting and you have a unique kind of perspective when you entered kind of that sales engineering environment, and you said that was one of the best, if not the best kind of sales role that you can get into,

[00:17:30] and I think a lot of our listeners probably don’t even know about what sales engineering is and how beginning in, you know, an entry level business development or sales development role can provide a gateway into those types of opportunities and it would resonate with a lot of listeners I feel and kind of open up this whole new world of what the profession looks like,

[00:17:49] just getting that insight. Do you mind walking us through how you came into that position? Any reservations you may have had and sort of what you were doing and why you loved it so much? I’d love to learn more there.

[00:18:01] Caitlyn Gill: Yeah, no, I’m absolutely thrilled to talk about that because, like I said, you know, moving into a sales engineering role, a pre-sales role was one of the best moves of my career and it’s something that I hope more women pursue. So, so, sales engineers, technically what they do is they’re the liaison between the salesperson and the customer and the product, right?

[00:18:25] So it’s kind of a specialty sales job that brings together technical knowledge, sales training and it, it creates kind of hybrid role where you’re always involved in this sales cycle, but you’re involved in the sales cycle from a a demonstration or demo perspective and implementation perspective.

[00:18:44] So, sales engineers really specialize in being technically, technical experts on their product or service, so they use their technical skills to kind of explain the benefits of the product or services to the customers and then they show, show how the products or services work and then a lot of them have a hybrid training role,

[00:19:00] so you’ll also kind of be on both sides of the equation where you’re, in the sales cycle, doing the demos and implementation cycle, doing the implementation and training. So I was able to kind of move into that role at Sageworks, the first company, first startup that I worked with, and as we kind of built this new product for this new market, I was the only sales engineer or sales trainer on that product initially,

[00:19:25] so every single new bank that we brought on I flew out to train them or I would do the demos to get them on board. And then, when I moved to insight or what was then global software, which turned into insightsoftware I moved, I made that move specifically to be in a sales engineering role. So, the, the first boss that I had there, and I was so lucky to have all female bosses at Global Software and Insightsoftware really kind of took me under her wing and taught me a lot.

[00:19:53] So at Sageworks I taught myself a lot. I had some really incredible leadership there, but it was, in the startup culture there is a lot of self-development and then moving into Global, which became insightsoftware the first boss I had there, her name is Ms. Sherri Barham, she was really able to take me under her wing and, and teach me a lot of 

[00:20:12] business acumen and develop me into a much more refined sales engineer. 

[00:20:18] Kristen Wisdorf: Kind of walking through, you know, training and 

[00:20:20] working with customers and traveling what I think a lot of young people view as, like, their perfect, like, career path, right, in the future, but it takes work to get there and it takes this foundation and you making 150 dials a day to, like, to get there,

[00:20:37] so how do you work with your current students and the, the folks taking your classes to prepare them, like, “That is a great goal and here are the steps to get there and you have to put in the work,” like, how do you remind them of that or train them or get them prepared for that? 

[00:20:52] Caitlyn Gill: Yeah, that’s a great question, Kristen. So, a lot of the work that we do in our sales academy prepares them for exact, for these exact tasks and challenges, right? So I don’t ever want to sugar coat the fact that SDRs are going to have to make cold calls and students that have graduated from our sales academy and now are in sales development roles,

[00:21:13] they, they know that, but they were ready for it, right? So, the way that we train them for that, we have a lot of sales competitions that we participate in, in these sales competitions students actually have to go through the process of learning how to prospect, right? They don’t have to make 150 cold calls a day, but they know that, that, and, and honestly, I don’t think a lot of companies do that anymore,

[00:21:34] it’s, you know, I think that we have found many more efficient ways to prospect than that, but they do know that prospecting is a part of the, the job that they will have coming out, and they know that, you know, “We can utilize LinkedIn for that or combination of LinkedIn and calling and emailing, and there’s lots of great tools out there that can help us with that,”

[00:21:52] help us in ways that, I mean, when I started, we didn’t, we certainly didn’t have help, but through a lot of the sales competitions that we do our students actually sell products and services and they sell them to real-life professionals, and they compete against other schools that are doing the same exact thing,

[00:22:08] so they feel the pressure of being in a real sales scenario, right, and having to move through prospecting and discovery and presenting a product and closing and the pressure that they feel around that, and they have to do that over and over and over again. So, when we go to a sales competition, we’ll prepare for

[00:22:26] weeks, sometimes months to, to go to these competitions and that preparation involves a lot of role-playing and a lot of cold-calling and a lot of preparing with our discovery and a lot of preparing for presentations and a lot of, you know, on the fly objection handling, and so, the students that come out of our program, they’re, they’re ready to do the job and they know what the job is.

[00:22:51] Libby Galatis: And that, I think that that fact, students don’t realize how much it puts them ahead of the pack of those of those people that do just stumble upon sales or find it a little bit later in life or maybe start a job that doesn’t quite work out for them or isn’t living up to the expectations that they had when they first began it as their first step, as a recent grad,

[00:24:07] and that’s our specialty at memoryBlue. I mean, that’s almost exclusively what we hire, those individuals so early in their career that are looking to break into this space. Taking kind of a further step back into, you know, you shared your story with us and, and sort of how you came about and stumbled into sales or, you know, identified that’s what you wanted to pursue,

[00:24:25] Libby Galatis: and you mentioned that when you graduated undergrad from ECU, then you were trying to decide, you know, do you want to go into tech or med device sales? And, oh my gosh, if I had a dollar for every student that wants to go into med device sales, or, I mean, the tech space obviously is a booming space, but what are your thoughts on the importance of product?

[00:24:42] When you’re a recent grad and you’re kind of weighing out your options there’s so many different aspects and attributes of an opportunity that you have to take into consideration when you’re defining and identifying what you want to pursue. Like, how, how significant is the product or what you’re actually selling,

[00:24:57] and are there other aspects of roles and opportunities that should outweigh, you know, the importance of the product? I’m just interested about your perspective.

[00:25:05] Caitlyn Gill: Yeah, I think that’s, that’s a great question, Libby, and to be honest, I think the product is really important, but if you asked my 22-year-old self when I was coming out in my first sales role, I would’ve probably taken any, any job. And so, I will, I will be honest with you in the fact that I had a family friend of mine who was in medical devices share a position with me coming out of undergrad and I did interview for it

[00:25:32] and they, they said, “Come back when you’ve had some sales experience,” so I feel really lucky actually that that happened because I was hired not long after by Sageworks, which is the first tech company I worked for and I spent 15 years in tech before moving to academia, and I was incredibly lucky that both companies I worked for had amazing products,

[00:25:54] you know, Sageworks, the profits product and the analyst products were incredible, and I stood behind those products like they were my children. I didn’t have children then, I have children now, but at that point in time those were my babies, and I’m like, “Don’t call my kid ugly,” right? So it was, it was, I was very passionate about the products and then, moving to global, we sold a product called Spreadsheet Server which I still a hundred percent believe is

[00:26:18] Caitlyn Gill: best, number one reporting an analytics tool that you could use in the market, because it’s just so simple and so easy to use. And so, it’s, it, I think it does really matter, you do have to be passionate about the products that you’re selling and passionate about the company and the company culture. So, I talked to my students a lot about that too, you know, and I think that it’s, it’s not only a product fit when you go work for a 

[00:26:43] company, it’s a culture fit,

[00:26:45] and so I always tell them, really ask those questions when you’re going in for an 

[00:26:49] interview and 

[00:26:50] see if you can 

[00:26:51] get a feel for what the company culture is like, because that, that can really kind of make or break a job.

[00:26:58] Kristen Wisdorf: Absolutely. It’s so interesting. So, you got into startup and startup 

[00:27:02] life and now it’s, 

[00:27:04] especially in 

[00:27:05] the last year since the pandemic, startups and tech companies are, they’re more open to hiring people right out of college without experience, but even 5, 10+ years ago that wasn’t the case.

[00:27:17] So, you got into tech after college, your school didn’t have a sales program and you were in, like, banking and FinTech. How did you learn everything that you needed to know to have the success that you did? Like, how did you pick up? It’s not like you went to school for, for technology, right? Like, you weren’t like a tech wizard,

[00:27:37] I certainly wasn’t, like, how did you transition to high tech and learn what you needed to know to be successful in that first gig? 

[00:27:45] Caitlyn Gill: Yeah, that’s a great question, Kristen, because it was really intimidating, I will tell you, especially with the technology that I sold at both companies. It was accounting technology, and I didn’t have to, I did not have a degree in accounting at all, so I think that, and you could probably talk to a lot of people that are around my age about their first kind of jobs in tech,.

[00:28:06] I think that you just kind of do it the old-school method of, I read a lot, I read books on accounting, I actually got a textbook on accounting to try to teach myself the basics of accounting when I was in this job, because I knew I was going to be talking to accountants and I needed to understand, you know, what a P&L was, what a balance sheet was, you know, how to create a cashflow statement.

[00:28:27] So I, I was self-taught in a lot of ways and I was lucky when I went to grad school and got my MBA that I was able to take classes in all those areas because it was so helpful to actually take a class in accounting or a class in finance and, you know, learn this from an academic perspective or learn those subject matters from academic perspective,

[00:28:45] Caitlyn Gill: but I was self-taught in a lot of ways and then in terms of the technology it’s just practice, so I’ll tell you one thing I did, and this is, will date me technologically, but I had a little mini recorder and so when I first started at Sageworks and at Global Software, I would record people doing demos and then I would go home and I would type out the script, like, line for line,

[00:29:11] and I would just say it over and over and over again until it was so 

[00:29:16] ingrained in my brain that I could say it in my sleep and with my, you know, without looking at the script. And so, I essentially created

[00:29:22] a script 

[00:29:23] for 

[00:29:23] myself to help myself really learn the products and learn the industry, and then kind of, I built 

[00:29:29] from there. 

[00:29:30] Kristen Wisdorf: I think that’s so 

[00:29:32] important, and that 

[00:29:33] really resonates with a lot of 

[00:29:35] our listeners who, especially if you’re in school and you want to get into technology, because why wouldn’t you, it’s a booming industry, but it can be a little bit intimidating if you feel like you’re not,

[00:29:44] you know, a technological person, right?

[00:29:46] Kristen Wisdorf: And, you’re not super tech-savvy, so it’s a good reminder that you can learn these things and you can learn enough to be dangerous and still be very successful in the industry, and I love that you recorded demos because, I mean, that’s a tenant of memoryBlue. We record our calls, we do call evaluations and we break them down and that’s how you get better

[00:30:05] and that’s how you learn, is by doing things like that. So, a good reminder, yeah, you can be successful if you are willing to be a sponge and coach yourself essentially. 

[00:30:15] Caitlyn Gill: Yeah. Oh, it’s, it’s so crazy, Kristen, honestly, all the tools in the market now that do this for you, right? Like, let’s say hi, and I’m, like, thinking of all the different sales tools we have the record your calls and allow you to analyze everything that you, you know, everything that you said, and, like, we had nothing like that,

[00:30:34] so it really does, it really does kind of remind you that, that, yes, although we have all these tools now, really what it takes is being that lifelong learner and having that beginner’s mindset always, so I think that that’s, that’s one thing that I, I really try to kind of hone in for myself, is to always approach things with a beginner’s mindset.

[00:30:55] Even with, you know, 15, 20 years of experience, even teaching sales, I’m still a learner first before I’m a teacher before I am a sales person, I am, like to put myself in the seat of either the student or the prospect, because I think that’s what makes you successful. 

[00:31:12] Kristen Wisdorf: Absolutely, and it just goes to show that ultimately it’s the same foundation, the technology, the tools, that may change, but it really comes down to the core of, like you said, being 

[00:31:23] a lifelong learner and a sponge and there’s no such thing as perfect in sales. You can always learn and apply new techniques and develop your skills,

[00:31:31] so I love that. Talking a little bit more about developing skills and teaching yourself, you mentioned earlier that you had some really impactful leaders in your own career, specifically women leaders. I want to learn a little bit more about that. Like, what what are some of the best moments you’ve had with leaders and mentors in your career and how do you use what you experienced to apply it to your students today? 

[00:31:58] Caitlyn Gill: Yeah. Yeah. That’s a great question, and I’ve been so lucky to have, I don’t know, so many mentors that have really believed in me, honestly, at the end of the day and, and invested, invested in my wellbeing and given me opportunities to grow. So, you know, at the first company I worked for, Sageworks, because we were small,

[00:32:19] I was able to kind of have a lot of contact with our CEO, with our VP of Sales. So, our CEO, his name was Brian Hamilton and then Scott Ogle was one of one of our VPs and, and they really just gave me a lot of opportunity based on self-interest to move into these other areas, which was, which was really neat,

[00:32:37] and I, I remember I had an opportunity one time to go on a trip with Brian, it was kind of a cross, not cross country, but, like, a multi-day trip to go visit a couple of our clients and spend a lot of time in the car with my laptop open, taking notes. Right, as we were kind of driving these multiple hours on the road to go visit the clients

[00:32:54] which, which was really neat and it was all based on developing this new product, and, and then when I moved from there to Global, I had just, I mean, I can’t even begin to start to name all of the incredible mentors I had there. So, the first boss I had there, her name was Sherri Barham, and she was really the first one that took me under her wing,

[00:33:12] Caitlyn Gill: she taught me how to be a really good sales engineer. She taught me how to listen, she taught me how to ask good questions, she taught me how to really push myself to, to learn new products and to push myself to, to be more tech, what’s the right word, just technical, right? So I consider myself more of a sales person,

[00:33:32] and when I went there, she went, when I moved to Global, she really challenged me to be a technical expert, right? So, think of yourself as IT versus think of yourself as a salesperson, and so I started to see myself in that, in that role, and then I, so Sherri Barham unfortunately passed away, she was quite young.

[00:33:52] and then the, the new boss that I had come in after her, her name was was Sherry Puckett, so I had two wonderful Sherries in my life and Sherry Puckett also was, you know, she had an incredible background in finance, so I was able to learn a lot more about finance from her, and as well as a product background and she was very into kind of flexing the product if you will.

[00:34:14] Caitlyn Gill: So, she really taught me, “Hey, if you want to change something, like, you gotta go in there and break it yourself and change it and learn how to code a little bit more and learn how to build SQL a little bit more.” So, again, pushed me kind of beyond my limits of, of where I felt my, I felt my wall was, technically, she kind of pushed me over that and said, “Just try it, you know, try something new,”

[00:34:35] and I think, you know, at the end of the day, with, with both of the Sherries, they, they really just kind of pushed me to, to think that I could do anything in these companies, in the company itself I worked for and, you know, at Global, we also had a really incredible CEO. So Spencer Kupferman was the CEO of the company and actually it was two brothers when they started, Matt Kupferman was the one that hired me and also was very supportive and believed in me,

[00:35:01] I think, you know, Spencer ultimately took the company to acquisition and he was always such a great mentor and a really just positive light and really kind of pushed a lot of young people into, into leadership roles there, which was, it was really exciting, it was a great company to work for.

[00:35:20] Libby Galatis: That’s an incredible experience and I, I’m, I’m curious because, you know, we’ve talked a lot about the importance of sales skills and I mean, you yourself, you’ve been able to build, build that strong sales foundation and progress into so many different roles and, and excel in those different roles from what you were able to establish initially, and kind of, and obviously you’re still learning,

[00:35:42] everybody’s still learning and continuously building off of that, but that initial step that offered the sense of direction that you were able to kind of climb that ladder I think it’s, it’s incredible, and, you know, we at memoryBlue will hire individuals that see themselves selling tech forever, you know, they start here and they come here intentionally because they want to pursue the tech space,

[00:36:01] and that’s solely where they see themselves moving. You know, others see this as an opportunity to build up some strong takeaways and sort of figure out after this experience where they see themselves progressing. What are some the key takeaways that sales roles can provide anybody regardless of if they decide sales forever or maybe this experience provides them a different path to pursue? When it comes to that, that initial sales role, thinking back again to that first job that you had, what did you learn about yourself and what did you take away from that experience that you still can point to today, or that assisted that kind of elevation into where you are today?

[00:36:41] Caitlyn Gill: Yeah, no, it’s such a great question because a lot of my students do ask that question as well. They were like, “Well, sales seems like a relatively flat role, right? Then, you know, I can become a sales person, then what am I going to do?” And what I tell my students it’s basically, every single person that I’ve ever met in the C-suite has gotten there through some path that has coincided with sales,

[00:37:02] so if you ever want to be an executive, in an executive position, be in the C-suite, run a company, sales is your quickest path there, honestly. It takes a lot of self-discipline, it takes a lot of training, and it has high highs and low lows, right, it takes a lot of mental and physical stamina, but the rewards are really immense,

[00:37:20] and as a sales person you have the privilege to help people every day of your life, right? So, I think that, I think that that’s the biggest thing for me, is that when I think about what I really want to do with my life and I realize what I’ve had the opportunity to do in the sales roles that I’ve had,

[00:37:35] Caitlyn Gill: I’ve helped thousands of customers change the way they do business and that is incredibly empowering to me as a person, but it’s a career that you can be really, really proud of, and my career hasn’t been flat in any way, shape or form. You know, I went from an SDR to an AE, to a sales engineer, to a director role, to an academic role,

[00:37:57] so lots of different curves in the path, name a lot of my colleagues that have had very similar curvy paths in sales, but I can also name several of my close friends and colleagues that are in the VP or C-level roles at this point, 15 or 20 years into their career that started out with me as an SDR.

[00:38:17] Caitlyn Gill: So, I think that at the end of the day, success is really dependent on how you yourself define it, right, and so I think that folks that go into sales roles they really do have to, have to kind of define that success and define what success looks like for them, but I’m, I’m so incredibly grateful that I had the insight that I did as a young person to, to start in a sales career because it took me to places

[00:38:44] I never thought were possible, right? I was 

[00:38:47] able to travel all over the world, again, you know, interact with, with thousands of different people 

[00:38:53] before 

[00:38:53] Caitlyn Gill: I moved into academia and now I have the privilege of, of teaching sales to students and starting them on 

[00:38:59] their path. 

[00:39:01] Kristen Wisdorf: That’s really exciting. You, kind of change, you said you changed the way 

[00:39:05] so many of your

[00:39:06] customers do business, and now you’re changing the career and the life trajectory of hundreds 

[00:39:11] of students which is

[00:39:12] really exciting. You mentioned that success is how you define it. So, you’ve been at Oregon State for just over two years

[00:39:21] it looks like in the sales program, the marketing department, what are some of your goals and what’s next for Oregon State Sales? 

[00:39:29] Caitlyn Gill: Yeah, that’s a great question ’cause I, I have big ones. So, right now in our program and again, we’re, you know, two and a half years in at this point we’ve had a little over 250 students that have participated in the sales academy at this point and we are, we’re still kind of defining a lot of things with sales academy and how we want to build the program moving forward,

[00:39:53] but what I would like to see is our programs continue to grow outside of the college of business, so right now over 60% of our students are college of business students, but our program is open to every single college at Oregon State University and it’s free, so our program is backed by industry sponsors,

[00:40:11] so students don’t have to pay for this program. They can take part in the Oregon State Sales Academy, earn a certificate in professional selling at no cost to them. So, and I imagine that memoryBlue this would probably be something that would be exciting for you guys if you saw a student that was applying that had a certificate of professional sales on their 

[00:40:29] resume. 

[00:40:29] Kristen Wisdorf: Oh, yes. 

[00:40:31] Caitlyn Gill: That’s what we always try to tell our students. So, what I would like to see is that, that number shift. So, instead of having, you know, over 60% of our students coming from college business, it’s more of, you know, 40% of our students coming from college business, more students coming from engineering, more students coming from forestry, more students coming from all of these other areas that are going to go into sales-related careers or that want to go into sales-related careers.

[00:40:55] We’re also obviously building, building our portfolio of sponsors, so we want to continue to, to connect with industry. We have 10 industry sponsors that are absolutely fantastic, that are onboard with us right now, so I’ll give a shout-out to all of those companies. We have Pacific Office Automation, American International Forest Products, Aflac, Gallo, PAP Materials Handling Company, Beacon Hill, Insight Global, the partners group pay common tech systems.

[00:41:20] We’d like to see that number continue to grow so we can give our students more experiences because those, those companies are the ones that are coming in and doing workshops for our sales academies, so they’re teaching our students how to sell, right? So we kind of build the competitions, we build the online content,

[00:41:37] we work with a partner called Skylytics that has a sales simulation that our students run through to achieve a certain level of sales mastery, so it kind of tests them on every stage of the sales process from their approach to discovery, to presenting, to closing, to handling objections, and I would like to see our partners continue to grow.

[00:41:55] Caitlyn Gill: Maybe memoryBlue can become a partner one day. And so, that way our students can continue to be exposed to all kinds of different companies and, and learn how, how you guys are selling rather than, you know, how we’re teaching them how to sell. One of the big goals I have this year is to, or in the next two years is to have a physical sales lab with recording technologies,

[00:42:16] so our students can actually record themselves, we can play back those recordings in a physical location, so that’s a big goal of mine. But we’ve, you know, we’ve done a lot already. Honestly, we have placed in many national competitions, won a national championship, so in the short two and a half years we’ve been around, we have definitely, you know, we’ve definitely tried to make a name for ourselves.

[00:42:40] Libby Galatis: And clearly you have. I mean, the success that you guys have seen and I mean, ranking number two at the International Collegiate Sales Competition, that is incredible what you guys have been able to accomplish. I can’t say this enough. I mean, the number of sales professors that we’ve had on this podcast that have that tried-and-true sales experience, they’re industry leaders, they have, you know, true experiences that they can point to and, and share with their students so that they don’t have to go through the trial and error of, you know, the

[00:43:09] traditional way of, of going through your professional life and they can really identify their why and their end goal. So, with that said, you know, if you had to summarize one piece of advice or, you know, one anecdote that you could share with anybody that is about to embark in that first entry-level sales development, business development role, regardless of industry, what do you think that would be and why?

[00:43:34] Caitlyn Gill: Oh, gosh, that’s, that’s a tough one. You know, I think, so, so I am a long-distance runner as well, and I feel like there’s so many parallels between, you know, doing ultra marathons or marathons in sales, right? And so, I think, honestly, really the, the biggest parallel between the two is mental focus

[00:43:57] and the fact that you can really do anything that you put your mind to, right? So, at the end of the day, if you believe in what you do and you work hard at it, you’re going to be successful, but it takes that belief in yourself, that belief in yourself to really realize that you can, you can do that,

[00:44:14] Caitlyn Gill: your body will move you forward, right, but you have to believe in yourself. You have to believe in what you do. So, I think that sales is kind of the most beautiful long-distance race I’ve ever taken part of, so I hope to hope I can continue it as long as my legs keep moving me forward. But I think that if, if you want a job that allows you to truly 

[00:44:33] change the lives of people around you, then go into sales because, because that’s it. That’s it. It’s, it’s a beautiful, beautiful 

[00:44:40] career

[00:44:41] that is ever-changing and will always 

[00:44:43] challenge you, but will, will be the most 

[00:44:46] exciting 

[00:44:46] thing 

[00:44:46] you ever do.

[00:44:48] Kristen Wisdorf: Well, on that note, that was absolutely beautiful and we are so lucky we’ve got to spend some time with you today discussing your career. I know that your students are very lucky to have your wisdom and experience and I’m really excited to work closely with OSU. You know, we hire a lot of students in our California and our Seattle offices who go to school in Oregon.

[00:45:10] So, we appreciate the time, Caitlyn, and really excited to see OSU at all these competitions. 

[00:45:17] Caitlyn Gill: Absolutely. Well, thank you so much, Kristen and Libby, it’s been my pleasure and we are super excited to see memoryBlue at a lot of competitions and we hope that you hire a lot of our beavers, so that’s my goal.