Introduction
Today on the podcast we’re joined by Courtney Schickel, who brings unique and unparalleled expertise to the podcast as a Chief Revenue Officer with over 20 years of experience leading successful sales and RevOps teams at startups like Ingenious Med, and most recently Assuresign, who was acquired by NinTex in June of 2021. In this episode, we’ll do a deep dive into core nice lessons and learnings of leading and scaling multiple sales teams, the importance of alignment within internal sales and executive functions, and how to leverage cross-functional relationships internally and externally to augment your sales process. And we’ll also touch on navigating impostor syndrome while ascending in your career. We also touch on advice for early-stage founders when it comes to building ReVOps functions and how establishing clear communication channels can be the differentiating factor between success and shortcomings as a startup. Thanks to Courtney for her brilliant insights on the conversation today. And now we’ll jump right into today’s episode.
William Leonard
Hey everyone, welcome to the Atlanta Startup podcast. Today I’m joined by Courtney Schickel, who is one of the premier minds when it comes to building out early-stage sales and revenue ops functions. Courtney, welcome to the podcast.
Courtney Schickel
Good morning!
William Leonard
I’m excited for you to share your brilliance today as a former CRO of multiple acquired or exited startups. But I think the level setting and giving our audience the Courtney story in your background and journey of navigating multiple VP of sales and CRO roles would be the ideal place for us to start. So, I’ll turn it over to you to share more about your background.
Courtney Schickel
Thank you for the lovely introduction. Hopefully, my interview supports that praise there. My background is interesting. It wasn’t where I thought I would go or what I would do, but I was originally an art major and then ended up graduating with a marketing background. The first couple of years out of school, a few jobs here and there, and didn’t really know what made the most sense, but I landed in a startup company out of a physician’s kitchen with four other people, which was a little scary at the time. I think the biggest thing for me is I just never really understood what I didn’t know. I think that was a huge benefit when you had a group of four or five rookies at the first startup. We didn’t know any better so there weren’t a lot of preconceived or what works, what doesn’t work, and how are you supposed to do things. It was just kind of an open opportunity and figured it out and it worked out really well. Great story with the first company I was with which was Ingenious Med and that grew significantly over the years. I actually didn’t start with the intention of being in sales, it just happened. It was one of those things where you start with a limited number of people and resources and people just start doing things and learning things and then you figure out how can you build upon that. Moving forward from there, that was a long journey and it was all in healthcare. The next opportunity that I went to was slightly bigger, starting with five, and I think when we exited there were maybe 200-plus employees. Miss a little bit of that early-stage size but the good thing is I found another company where it was revenue-wise, more established, but the size of the company was a little bit smaller. It’s still that fun, fast-moving, able to get things done quickly and that was really where I enjoyed staying for a while. And then my last venture, I left healthcare, which I think a lot of people, should or shouldn’t, I had such a history and knew the landscape but made the jump and couldn’t be happier. It was a nice refreshing change and it was a little bit of a faster pace. It was a little bit of a challenge for me too. I like the fact that it was something different. I wasn’t kind of doing the lather-rinse-repeat of working with the same type of clients and going back after 15 years of being in the same industry. It was good to have a change. So sometimes challenging yourself by mixing it up is a great way to keep your energy up and take on a new challenge. So that was a fun one and that was significantly smaller than where I was. I did jump back to a really early stage and it was fun just to go through the different phases. I think for me, when you grow from 5 to 200, you kind of figure out which parts you like the most, and then you try to recreate that. But then obviously if you’re doing your job well, you’re going to leave those stages, which is very rewarding, but at the same time, it’s not going to stay that way. So then you can kind of find your next venture and figure out, okay, did I miss really having my hands in the mix and having things in such an early raw scenario? Or did I like it when I had a lot more resources and you can kind of jump around and figure out where you’re happiest and where you really can make your mark?
William Leonard
That’s such a fascinating start. You began in college as an art major, graduated, and then obviously started in sales with a healthcare focus. I would love for you to sort of walk us through and talk to us about finding your feet in the sales function at a startup so early on in your career when you admitted you were a bit just naive and you didn’t know.
Courtney Schickel
I think a lot of it was just we had one salesperson. I was actually coming in to help with marketing, just watching and learning. They would have presentations and a lot of it was the founder in the early days doing the majority of the sales pitches, but he was a physician and we had a very great salesperson as well. Just watching people’s reactions, what’s working, but more importantly, what’s not working in the end. We’ll talk about it a little bit, too. How sales as a whole has changed and developed over time, but in the end, it’s a person making a decision and you got to learn how to read the room and you can have the greatest product out there, but if you’re not understanding what their need is. A lot of it was just watching the interactions and to me, just not knowing any better. Sales in my mind, like sales training, sales whatever, if you can listen to people, you can figure this out and get pretty far. I think that was my biggest thing was just not knowing and not caring what was the sales process or what were the different ways I know as we started to grow and develop, salespeople would come in and look at different sales methodologies, but at the same time it’s people, it’s interactions, it’s going to be different every time. You just got to figure out what works or how can you connect with them.
William Leonard
As your perspective matured from just, one, doing the job, and two, observing senior leaders on the job, talk to us more about some of the lessons and learnings of being a part of an organization that grew from 5 to ultimately, 200 people and beyond that. Some of the takeaways as an early sales leader that maybe some of our listeners today can extract from your point of view.
Courtney Schickel
A couple of things. You do learn. There’s only so much I can do, so you got to figure out how to build a team. Even if you’re the most effective person, at some point, whether it’s your territory or the number of people that you can talk to in a day, there’s only so much that you can do. So you’ve got to figure out how to build a team. Which parts and pieces can you hand off? How can you guys work together to make people more efficient and more effective? It’s going to depend on just what you’re selling and who you’re selling to. There are going to be different ways that you can do it. I think the other big learning was what works amazing for me, might not work for other salespeople. Being open to people, figuring out different ways to do things, and then as you grow, there are things in early-stage companies that I know don’t make sense. Once you have a sales team of 20, you would never do it that way. But at the time, there’s a lot of really short-term creative things you can do that if you’re going to be in kind of this early stage, fast growth world, what I would do for a company if we have a team of 25 or in a certain scenario, I get it. It seems odd, it’s a strange commission plan or whatever it is, and it’s an incentive, but it’s just designed to jump-start things. It’s not going to be long term and it won’t work once you get to a certain stage. But there are things that you can do to be creative and you’ve got the liberty to do that. When you’re small, you can make fast changes, you can do things differently, and you’ve got the ability to try things. I think be creative. The other thing that I did learn is we did have a couple of different sales leaders before I eventually moved up. One of my biggest pet peeves is we had someone that came from a competitor. I think that was like the drawing factor initially, but every answer, everything that he wanted to do was because that’s how our competitor did it and that made no sense to me because why would we do it the same? You’re trying to beat them, right? You have to find your differentiator. Even if it was just their proposal or their pricing or whatever it was, be different. Particularly in the early stages, there’s always going to be competition or something similar in the market. Figure out a way to find one or two things that you can just do differently and run with it. I think a lot of times people are afraid to do stuff that changes or mixes it up and it won’t always work. Some people may want it to look vanilla and what they’re used to, and some people may really bite on an alternative. Trust your team. If they’re talking to potential prospects on the phone or the customers daily, give them some opportunities to try different things. You never know what’s going to stick or what will work.
William Leonard
True. that’s interesting insight there, Courtney. I’ll ask you to answer this next question from the perspective of your time with Ingenious Med and then secondarily, your time with AssureSign as well. When you first started at Ingenious Med in 2004, what did you believe to be true of building out a revenue or sales organization that you sort of had as a preconceived notion, but now you look retrospectively and you’re like, that’s not true. I wish I would have thought about this differently.
Courtney Schickel
I would say in 2004, I don’t know that I had much preconceived. I mean, I was fairly new, just a few years out of school. I can say, though, the importance of getting your leadership team all on the same page. So particularly in Ingenious Med, especially in the later years, it’s very common to have a kind of finance versus sales. If they’re not on the same page, it’s going to be a struggle, right? Like, you want your incentive plans, you want everything to be very sales friendly, very positive. I think that’s something that you can’t build a sales organization within the sales team. It has to be your whole leadership team on board and it’s got to be from the start. Like, you’ve got to do it together as a team. It can’t be something where you come up with like, here’s how I want my plans to be, or here’s how I think this is going to go. That would be one thing.
William Leonard
What processes or internal guidelines you should set for making sure alignment is always in conjunction with these executive teams because oftentimes you work in silos? I want to ask you what are some of the best practices that you saw and maybe didn’t see for making sure there was a consistent and constant alignment of vision.
Courtney Schickel
I think it can be as simple as a weekly standing Monday meeting. Sometimes the meetings can be short and everyone gets busy. If there’s not a lot to go over or if you have other meetings, make it a priority. Make sure that it happens. Sometimes they might be fast and easy, sometimes they might go on much longer, but make it happen and then come up with some type of process for it. Keep a rhythm or a flow of the meeting that you repeat every time and sometimes it can be like no updates here, no updates there, but keep it standardized so that you don’t forget or miss anything and there’s not a surprise or there isn’t something that we forgot to cover we thought somebody was in the loop on. Just keep it standardized and stick to it.
William Leonard
I love that. Now I’ll fast forward a bit to your time with AssureSign and I’ll ask you what’s one thing that as a CRO is easier now than it was, let’s say, 5 or 10 years ago when you were operating? Obviously, technology has significantly advanced from a 50,000-foot view. What has become more simplified and even more complicated on the other side of the coin?
Courtney Schickel
I think so much automation has happened, right? And there’s more analytics, there’s more automation, there’s all these things but it does also create noise in some ways. Easier in ways because you have a lot more information. Easier in ways because I do think this concept of early-stage companies and it’s a lot more common now. The world of software sales has really blown up and that’s the standard, that’s what everyone’s doing on a daily basis now. I think there’s a lot more understanding and acceptance of the ups and downs, the growth, and the stages. I think 15 years ago and maybe it’s just because I was new to it, but I feel like now there’s just a better understanding of startup companies and what it takes, the different stages, and how you can move through it. I just think it’s a lot more open and accepted and I think the peaks and the valleys are a lot more open and accepted. You’ve got to allow some people a little bit of longevity, not to the point where it sinks, but some flexibility to try things and do things differently. I don’t think ten years ago were as creative and open as many companies are today. The harder part, though, is that there’s just so much more noise.
William Leonard
How can one block out that noise, right? You think about all of the different platforms and software that are being thrown at you and pitched in your inbox as a CRO sales leader. I think you mentioned just blocking out the noise because the customer journey is ever-evolving. I think that’s what you really have to focus on and how technology can sort of intertwine and align with your goals of driving revenue as an organization. It’s probably almost impossible to block out the noise, but there are some things that you can do and put your blinders on.
Courtney Schickel
I think you can just do your best to simplify it. I mean, that’s my number one thing with sales as a whole, right? Do not overcomplicate it. Do not try to over-process it. Keep it simple, particularly for people on the other side too, right? Like, you want it just to be easy and fast. If I am interested, how do I get from point A to it’s up and running, and just make it as easy as you possibly can? Don’t complicate it, don’t add to it. I think for me, I created my own dashboard. And yes, there’s probably a lot more information and other parts and pieces and I would have people give me reports or updates. I didn’t use all of it. There were pick your two or three key metrics that you really own and understand. If something starts to go awry, then you can go dig into the rest but I think don’t overdo it. Have it all funnel into something and then just pick your simplified dashboard to where you can keep a quick temperature check and catch anything. But overanalyzing, I think is a problem that you can have today. And again, it still goes back to people, right? There’s data and there’s tons of data, and it can tell you trends, but in the end, it is usually a live person making a decision and they may just go with the other person one day because they liked their hair better. There are elements of that, it’s still people and I think just not getting lost in how it’s all managed in the different processes. There was a company, I won’t say the name because I don’t know how it turned out, but initial results were good, but they actually shifted. I, as a salesperson would have hated it. I don’t know that I could do it, but they changed from a traditional commission model to where they were just bonusing people based on productivity. Because the belief was when you look at your pipelines and you’re trying to build out a sales team or your quotas and all this stuff, like most salespeople look at it to where it’s like, okay, if I need to close 100,000 a month to be on track, I probably need 2.5 to 3.5. In my later stages, you work backward, right? This means that you probably needed five meetings or five in this stage and you go backwards through it. And so I think the model was, we believe that the product is good and it’ll sell itself and the company is there. So if we just incentivize people on the activity, the results will happen. The results initially, according to the person that I was talking to, were good. I don’t know long-term and how that panned out. I, as an old-school salesperson would have hated that model though, because I was also super competitive and you want the wins. You want the incentives on the wins. But if you think about it, that is a little bit of taking a step back and just trying to simplify it. I think there are things you can do where is that too much data. Is it relying on data enough? It’s hard to say what the answer is, but I think every organization will be different. I think a quick sales process versus the long complex one, what works in one versus the other, are going to be very different. I think I had the luxury of dealing with both with the AssureSign. That was kind of the first time that I moved into a much faster sales process, which I enjoyed after spending healthcare. They’ll tell you a year-long sales process, but it can be two if not three. I think in one case five. A little bit of fun where you can do different things depending on the environment that you’re in.
William Leonard
How does RevOps have to differ or be adjusted when it comes to the overall sales cycle? You mentioned with Ingenious Med was a little bit longer, but AssureSign was shorter, faster, and more robust. How does the RevOps function have to align with both sides of the coin there?
Courtney Schickel
It’s tricky. I mean, you’ve got to find a balance and I think we’re able to kind of separate. For a short time, the majority of it was more fast, like call it 30 to 60-day sales process, which is a lot faster and easier. That is where something does start to look more at activity and that is a scenario to where that can really help you encourage. When we talked about the metrics and the different things, make sure you’re rewarding in the right areas, right? It could be something where not a traditional just commission for the close, but some type of activity things would keep those funnels going and do it differently. In a longer sales process, that’s more difficult. Because if you’re working on something for a year, you might have activity for twelve months with nothing to show for it. I think making sure too when you’re looking at your plans, I kind of separated deals over a certain size amount. I put them in kind of a different bucket for AssureSign because they did become longer processes. It was a different sales team than the people that are doing the quick turn. We kind of had one person that handled more of like a partnership type, large deal. I separated the two because I did need them to be tracked differently and compensated differently. It’s just different. I divided it, but also AssureSign was a lot smaller so I could do it. I mean, I had a team of six and I can manage it that way. If I had 30 people, that probably would be a mess.
William Leonard
I can only imagine. But no, that’s fascinating insight because of company size, contract, those types of things, ACV. As we sort of move forward past AssureSign now, you’ve been doing this for over 20 years successfully and as you sort of think about modern-day company building, what is your advice and best practice for a CEO building out a revenue ops function or sales function today at the early stage?
Courtney Schickel
I think make sure to go back to that leadership team and that everyone is on the same page. Make sure it’s a good fit. You might have multiple candidates with proven track records but figure out who’s going to mesh with the company best, obviously. And then when you bring someone in the early stages, you often have a founder that’s still very involved or certain people that have had their hands in different departments because of simply the size and lack of expansion. Yet once you start to build out these teams and bring people on board, let them run with it. Give them some leeway. Don’t be afraid to make mistakes. I think doing things differently and being creative and figuring out fail a few times, right? And see what you learn from it. I think that is the biggest thing. My advice would be even anyone that has a process, I can tell you things that I would do or things that I’ve repeated, but I don’t know that would work in the next one. You’ve got to be open to understanding and constantly shifting and changing. I mean, look at how much the sales process has changed just with automation. And then we’re all on Zoom for all of COVID and stuff, right? If you used to have a model to where you were an in-person salesperson or that face-to-face was really the model, you’ve got to shift and change. You’ve got to figure out different things. I think be creative and be willing to make mistakes along the way.
William Leonard
I love that. I think that’s applicable advice. Almost everything in life is to get creative as you can. Don’t be afraid to fail. Embrace change. Those are great insights, Courtney. As we wrap up the conversation here, we talked a lot about the evolution of sales and RevOps functions from 2004 when you started and when you worked with Ingenious Med, helped them successfully grow, and helped AssureSign successfully exit as well. I’m sure at that point you worked and led a lot of teams and dealt with a lot of younger, newer, fresher talent that came into the industry. What were some of the common misconceptions that they had while you were leading them? Or preconceived notions that just simply weren’t true and you tried to dispel those notions for them?
Courtney Schickel
I think with a lot of the greener salespeople that came in, and in both cases, their resume basically had their GPAs on it and maybe an intern. I do think the younger salespeople are greener, I should say not younger, but in this last week, AssureSign, I do think there was a concept of, well, I’ve taken these sales classes or I’ve read these things, and I think there’s just a huge difference in training and then actually getting your feet wet and doing the job. I think that there’s always a learning curve with that. Helping earlier stage salespeople to figure that out and what you’ve read in a sales book, they’re guides, and there’s a lot of great ones out there, and there’s some that I think are terrible. Figure it out, right? Use it all as a way to create your own version or your own menu of what works for you. I think the other thing that was interesting for me, more so at Ingenious Med when we grew significantly bigger, my concern or preconceived notion is I thought some experienced salespeople or people that had 10 or 15 years on me would not respond well to me as their leader. But when you get the right salespeople and a true salesperson really is just there because they want to make money. Like they want to go and sell. And if I can help them do that, there wasn’t really an issue with being younger or having less experience from a longevity standpoint on my resume overall. What I was doing was different at that point, right? If it was salesperson to salesperson, like, yes, they had 15 years on me in healthcare, and I was five years in and moving into a leadership position. But I do think part of that’s with the interview process and everything, getting a team that just really works well together, and maybe one or two salespeople on the way, but for the most part, I would say I did a really good job on getting some fun teams together, and they enjoyed it. Many of them are in leadership roles now to where they’re not just a salesperson anymore, but they have graduated and moved up and one or two of them have gone back to sales, which happens right.
William Leonard
Did you deal with impostor syndrome at that point of your career when you were having to lead people who had 10 or 15 years of sales experience on you?
Courtney Schickel
No, because they came from established companies. In the case of Ingenious Med, the first year there were five of us, right? I knew how to log into the back of the system, add users, tweak, and change things. I knew that company inside and out. I knew the program inside and out in a way that nobody could ever catch up to me. I understood our organization. I understood our early customers because when you were a salesperson in the early days, you also answered the phone and took tech support calls, and did the training. There was an element of understanding our company that someone with 40 years of sales experience couldn’t catch me on how to navigate and how to do certain things. There was a huge advantage to that. I had a great track record. I think if you talk to any of the clients or when they were starting to build out and work with existing customers at one point, I think 75% of them were sold by me. There was some clout that helped but just having an understanding of the inner workings of the company from the start was a huge advantage.
William Leonard
That’s awesome. You touched on how some of the greener, newer sales individuals, account executives, whatever their position may be, had some preconceived notions from classes that they may have taken in undergrad, things like that. Maybe they heard from elders in a pipeline, whatever it may have been. But are there any resources for founders, AEs, VPs of Sales, or anybody in these RevOps functions that you’ve successfully leveraged over the years of your career that have turbocharged you or augmented your learning?
Courtney Schickel
I had a mentor that I worked with for a while but she was actually more from a marketing perspective and that was something that, I think, when all the automation and all these different parts and pieces change, and then I did take on a lot of the rebranding with Ingenius Med when we’re going to market and looking to have our first exit. I would say there’s a lot more of that available today. I think you can use your resources and your network. I know who mine are personally. I can tell you Gary would be somebody that I would leverage and find out who he works with or other people that he has. I think a lot of these places around Atlanta, you’ve got Atlanta Tech Village, you’ve got these little incubators and places where they’re collecting all the early startup and like minds and the entrepreneur programs there, utilize them. There are some great resources within that and they’re very easy to find. I know our building used to have like a Friday lunch thing and they had pitch practice, right? Your salespeople could pitch to other people in the building because they were also trying to get practice as well. We’re at the ATV, which does a really good job of providing some opportunities like that. I think there are multiple scenarios in Atlanta and I think everyone kind of has some access to that. But use your network.
William Leonard
It sounds like you found maybe a gold mine in leveraging cross-functional relationships within an organization and external to the organization to augment your ability as a sales leader.
Courtney Schickel
Absolutely. Other people’s experience and expertise, I know what I’ve been exposed to, but when you’re going to something else, absolutely reach out to the people that you know that you respect or enjoy or you know that they’re in a company that’s doing well or you think that their job sounds interesting, or you know that they’re trying new things, use that. And then I think a lot of early-stage companies, you’re going to have your portfolio, teams, and the other companies that are in and around you work with each other. We used to do that. We had kind of like a sister company when we were at Ingenious Med and if they got a hold of some new marketing software that was helping them get leads, we hopped right on over, looked at it, and understood it. Will it work for us? What can we do there? But you should easily be able to just with a quick phone call, email, reach out, and find people that you can leverage. It’s a big plus because I think we all have our own way of looking at things and you can get really stuck in your own status quo. Branch out, look at something differently, and figure out how other people are doing. It sounds horrible to me, but the sales commission plan where changed to just the productivity, as a salesperson I would have been livid and started looking to leave because that wouldn’t make sense to me and that just was a new model. But I was intrigued by it and I am talking about it a couple of years later because it’s completely in left field or out of the box of anything that I would have thought of to do. But there’s a huge opportunity to learn from it.
William Leonard
Courtney, this has been a really interesting and insightful conversation from the early-stage founder perspective who is looking to accelerate their organizational growth. You shed a lot of insights and dropped a lot of gems around the importance of alignment of internal sales and executive teams and how to assess fit when building out these RevOps and sales teams. And then I think that the last point you touched on, of leveraging cross-functional relationships to augment your capabilities as a salesperson. I appreciate the insights that you shared today, Courtney, and look forward to hopefully some founder or investor listening to this conversation to help augment their ability as a sales function within their startup.
Courtney Schickel
Will, this is fun. Thank you for having me.
William Leonard
Of course. Take care.
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